patil_2025_acrylamide_ugi.pb.gz

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Table numbers are rounded to 7 significant digits; decoded details retain full precision.

Ugi-4CR (aldehyde/NH3/isocyanide/acrylic acid) precipitation-first acrylamide library, 2551 reactions

Dataset description

Patil, Ingenito, Fusco et al., Green Chem. 2025 (doi:10.1039/D5GC04440E). 2551 parallel Ugi four-component reactions of an aldehyde, aqueous ammonia, an isocyanide and acrylic acid in TFE (0.5 mmol, rt, 18 h, 96-well glass plates) with isolation by precipitation/filtration only. Every reaction the paper reports is included: 1235 'Green' (precipitated, 1H NMR consistent, >80% purity, isolated), 377 'Red' (precipitated, NMR inconsistent, discarded) and 939 'Black' (no precipitate). Outcomes are qualitative: the category label (CUSTOM product measurement) plus, for Green products, acoustic-ejection MS extracted-ion areas (all 1235) and UPLC-MS-UV areas (384-compound Plate1 subset) measured on the stored DMSO stocks after ~2 years (stability profiling); an area of 0 means the target ion / UV peak was not detected. No yields are reported in the source. Source tables (Zenodo doi:10.5281/zenodo.15496516, Supporting_Scripts.zip): product structure and label from Patil_Plates.csv (Green) and Black_Red.csv (Black/Red, column SMILES); aldehyde (R1) and isocyanide (R2) from the authors' R-group decomposition table FULL_DF_RGD.csv, each checked by regenerating the Ugi product with RDKit; MS outcomes from EchoMS_Plate1-4(.csv/_NEG.csv), matched on Plate_ID + 384-well position (Injection = WELL; 3 Plate4 wells D12-D14 without an assigned compound omitted) and UPLC_Plate1.csv matched on compound code. The derived EXP_DF.csv was not used (it only covers Plate1 and is a merge of the same source files). Amounts, conditions and workup are from the general procedure (ESI section 4), not per-row records; building-block stock volume (0.1 or 0.2 mL of 5 or 2.5 M TFE solution) was not recorded per reaction. Synthesis-plate positions are not in the sources; the identifiers give the compound code and, for Green compounds, the 384-well analysis-plate position. Repeat syntheses of the same product under different codes are kept as separate reactions. Structure checks: for 2478 reactions the authors' R1/R2 regenerate the reported product exactly. For 19 glycinamide products (2 Green, 17 Black) the R-group table is wrong (it moves the amide N-substituent into R1 and gives an invalid R2 'C#[N+]C'); their building blocks were derived from the product by retro-Ugi (formaldehyde + the isocyanide, which in every case is in the ESI isocyanide list). For 53 primary-amide products (52 Black, 1 Red) no listed isocyanide gives the reported structure; the authors' R2 is read as methyl isocyanide (ESI Iso_72) and the product is kept as reported, so these reactions are not atom-balanced and are flagged in procedure_details. One Green product (PHP-4492) had a diradical [CH][O] in the source SMILES, corrected to a formyl group (building blocks then also taken by retro-Ugi: isophthalaldehyde + 1-naphthyl isocyanide). Per-row details are in structure_check.csv in the sources archive.

Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.

Location	Record	Inputs and roles	Temperature	Reported measurements	Source
reactions[0]	Record 1	REACTANT: acrylic acid REACTANT: CCCCC=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · CUSTOM: Green [1H NMR] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · IDENTITY: — [1H NMR] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · PURITY: 80% [1H NMR] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 1170.127 [AEMS] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 1741.888 [AEMS] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 872.0651 [AEMS] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · IDENTITY: — [AEMS] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 4114546 [UPLC-MS-UV] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 1499105 [UPLC-MS-UV] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 194163.7 [UPLC-MS-UV] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · AREA: 1896.745 [UPLC-MS-UV] C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl · PURITY: 93.74% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[0] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CCCCC=O.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4688" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A1" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243229" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(CCCC)C(=O)NCc1c(F)cccc1Cl" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A1)", "float_value": { "value": 1170.1268310546875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A1)", "float_value": { "value": 1741.88818359375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A1)", "float_value": { "value": 872.0650634765625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 872.06506). Patil_Plates.csv mass-error confidence: Green, peak area 170545.0862" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 4114545.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1499105.25 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 194163.734375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1896.7451171875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 93.73999786376953 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[1]	Record 2	REACTANT: acrylic acid REACTANT: O=Cc1ccc(C(F)(F)F)cc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 3073.919 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[1] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccc(C(F)(F)F)cc1.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5401" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A2" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243346" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccc(C(F)(F)F)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(F)(F)F)cc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A2)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A2)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A2)", "float_value": { "value": 3073.91943359375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 3073.9194). Patil_Plates.csv mass-error confidence: Green, peak area 5499.5464" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[2]	Record 3	REACTANT: acrylic acid REACTANT: Cc1cccc(C=O)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OCc2ccccc2)c1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 1351.659 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 1022.362 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 2588.404 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 6322907 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 972467.7 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 430170.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · AREA: 3190.296 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1 · PURITY: 91.7% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[2] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "Cc1cccc(C=O)c1.N.[C-]#[N+]Cc1cccc(OCc2ccccc2)c1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4691" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A3" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243230" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Cc1cccc(C=O)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OCc2ccccc2)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OCc2ccccc2)c1)c1cccc(C)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A3)", "float_value": { "value": 1351.6593017578125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A3)", "float_value": { "value": 1022.3624877929688 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A3)", "float_value": { "value": 2588.404052734375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2588.404). Patil_Plates.csv mass-error confidence: Green, peak area 227690.7116" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 6322907 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 972467.6875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 430170.09375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 3190.296142578125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 91.69999694824219 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[3]	Record 4	REACTANT: acrylic acid REACTANT: O=Cc1cccc(Oc2ccccc2)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 447.2585 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 171.9054 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 688.7941 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 2157123 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 459192.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 294967.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · AREA: 1578.296 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1 · PURITY: 93.65% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[3] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(Oc2ccccc2)c1.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5402" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A4" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243347" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(Oc2ccccc2)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(Oc2ccccc2)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A4)", "float_value": { "value": 447.2585144042969 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A4)", "float_value": { "value": 171.90542602539062 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A4)", "float_value": { "value": 688.7940673828125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 688.79407). Patil_Plates.csv mass-error confidence: Green, peak area 54633.5131" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 2157123 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 459192.8125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 294967.0625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1578.29638671875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 93.6500015258789 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[4]	Record 5	REACTANT: acrylic acid REACTANT: O=CC1CCCC1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)c1ccc2c(c1)OCO2 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 307.7359 [AEMS] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 765.3614 [AEMS] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 3042.259 [AEMS] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[4] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=CC1CCCC1.N.[C-]#[N+]C(C)c1ccc2c(c1)OCO2.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4693" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A5" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243231" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=CC1CCCC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)c1ccc2c(c1)OCO2" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)c1ccc2c(c1)OCO2)C1CCCC1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A5)", "float_value": { "value": 307.7358703613281 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A5)", "float_value": { "value": 765.3613891601562 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A5)", "float_value": { "value": 3042.258544921875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 3042.2585). Patil_Plates.csv mass-error confidence: Green, peak area 57188.5956" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[5]	Record 6	REACTANT: acrylic acid REACTANT: CC(C)c1ccc(C=O)cc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 1480.041 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 1523.166 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 1998.418 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 1019329 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 448554 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 66601.41 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[5] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)c1ccc(C=O)cc1.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5404" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A6" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243348" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)c1ccc(C=O)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(C(C)C)cc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A6)", "float_value": { "value": 1480.041259765625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A6)", "float_value": { "value": 1523.1658935546875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A6)", "float_value": { "value": 1998.418212890625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 1998.4182). Patil_Plates.csv mass-error confidence: Green, peak area 358025.796" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1019329.1875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 448554.03125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 66601.40625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[6]	Record 7	REACTANT: acrylic acid REACTANT: COc1cccc(C=O)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1ccc(Oc2ccccc2)cc1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 477.0286 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 463.0459 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 6867.58 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 3476461 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 516899.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · AREA: 5342.495 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1 · PURITY: 94.36% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[6] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1cccc(C=O)c1.N.[C-]#[N+]c1ccc(Oc2ccccc2)cc1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4694" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A7" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243232" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1cccc(C=O)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1ccc(Oc2ccccc2)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1ccc(Oc2ccccc2)cc1)c1cccc(OC)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A7)", "float_value": { "value": 477.0285949707031 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A7)", "float_value": { "value": 463.0459289550781 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A7)", "float_value": { "value": 6867.580078125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 6867.58). Patil_Plates.csv mass-error confidence: Green, peak area 80929.5461" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 3476460.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 516899.84375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 5342.4951171875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 94.36000061035156 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[7]	Record 8	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1Cl SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 658.7393 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 280.7533 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 616.7214 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 38172.31 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 89424.59 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[7] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1Cl.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5405" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A8" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243349" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1Cl" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A8)", "float_value": { "value": 658.7393188476562 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A8)", "float_value": { "value": 280.7533264160156 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A8)", "float_value": { "value": 616.721435546875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 616.72144). Patil_Plates.csv mass-error confidence: Green, peak area 70922.4192" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 38172.30859375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 89424.59375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[8]	Record 9	REACTANT: acrylic acid REACTANT: O=Cc1cc(F)ccc1Cl SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 3063.079 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 1415.817 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 5366.691 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 53935.32 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 136176.9 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 10531.44 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[8] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cc(F)ccc1Cl.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4801" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A9" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243233" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cc(F)ccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(F)ccc1Cl" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A9)", "float_value": { "value": 3063.07861328125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A9)", "float_value": { "value": 1415.817138671875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A9)", "float_value": { "value": 5366.69140625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 5366.6914). Patil_Plates.csv mass-error confidence: Green, peak area 421961.8459" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 53935.32421875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 136176.9375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 10531.439453125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[9]	Record 10	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1C(F)(F)F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 580.5906 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 366.0202 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 1700.249 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[9] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1C(F)(F)F.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5406" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A10" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243350" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1C(F)(F)F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1C(F)(F)F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A10)", "float_value": { "value": 580.5906372070312 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A10)", "float_value": { "value": 366.0202331542969 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A10)", "float_value": { "value": 1700.249267578125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1700.2493). Patil_Plates.csv mass-error confidence: Green, peak area 118209.2746" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[10]	Record 11	REACTANT: acrylic acid REACTANT: CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 3621.42 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 1120.127 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 3952.319 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[10] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4803" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A11" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243234" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)(C)OC(=O)n1cc(C=O)c2ccccc21" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cn(C(=O)OC(C)(C)C)c2ccccc12" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A11)", "float_value": { "value": 3621.420166015625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A11)", "float_value": { "value": 1120.1273193359375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A11)", "float_value": { "value": 3952.319091796875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 3952.319). Patil_Plates.csv mass-error confidence: Green, peak area 584378.8423" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[11]	Record 12	REACTANT: acrylic acid REACTANT: O=Cc1cccc(F)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 519.9585 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 454.7451 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 5105.885 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[11] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(F)c1.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5407" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A12" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243351" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(F)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cccc(F)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A12)", "float_value": { "value": 519.95849609375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A12)", "float_value": { "value": 454.7450866699219 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A12)", "float_value": { "value": 5105.88525390625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 5105.8853). Patil_Plates.csv mass-error confidence: Green, peak area 113773.2121" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[12]	Record 13	REACTANT: acrylic acid REACTANT: O=Cc1cccc(Cl)c1Cl SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 2975.658 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 1040.106 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 6054.74 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[12] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(Cl)c1Cl.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4805" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A13" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243235" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(Cl)c1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(Cl)c1Cl" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A13)", "float_value": { "value": 2975.658447265625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A13)", "float_value": { "value": 1040.10595703125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A13)", "float_value": { "value": 6054.740234375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 6054.74). Patil_Plates.csv mass-error confidence: Green, peak area 307020.1182" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[13]	Record 14	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 513.8182 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 667.4811 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 1264.416 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[13] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1F.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5408" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A14" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243352" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccccc1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A14)", "float_value": { "value": 513.8182373046875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A14)", "float_value": { "value": 667.4810791015625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A14)", "float_value": { "value": 1264.4163818359375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 1264.4164). Patil_Plates.csv mass-error confidence: Green, peak area 141736.9673" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[14]	Record 15	REACTANT: acrylic acid REACTANT: COc1ccc(C=O)cc1OC SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 2767.837 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 1443.266 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 4403.786 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[14] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1ccc(C=O)cc1OC.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4807" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A15" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243236" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1ccc(C=O)cc1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OC)c(OC)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A15)", "float_value": { "value": 2767.837158203125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A15)", "float_value": { "value": 1443.2657470703125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A15)", "float_value": { "value": 4403.78564453125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 4403.7856). Patil_Plates.csv mass-error confidence: Green, peak area 735052.7371" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[15]	Record 16	REACTANT: acrylic acid REACTANT: CCCC(C)C=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 1384.437 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 2058.919 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 2241.471 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[15] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CCCC(C)C=O.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5409" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A16" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243353" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC(C)C=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(C)CCC" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A16)", "float_value": { "value": 1384.4365234375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A16)", "float_value": { "value": 2058.9189453125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A16)", "float_value": { "value": 2241.470947265625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 2241.471). Patil_Plates.csv mass-error confidence: Green, peak area 196129.1231" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[16]	Record 17	REACTANT: acrylic acid REACTANT: COc1cc(C=O)ccc1OCc1ccccc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 3461.679 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 1200.499 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 3863.176 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[16] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1cc(C=O)ccc1OCc1ccccc1.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4809" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A17" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243237" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1cc(C=O)ccc1OCc1ccccc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(OCc2ccccc2)c(OC)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A17)", "float_value": { "value": 3461.679443359375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A17)", "float_value": { "value": 1200.4990234375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A17)", "float_value": { "value": 3863.17626953125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 3863.1763). Patil_Plates.csv mass-error confidence: Green, peak area 555492.6524" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[17]	Record 18	REACTANT: acrylic acid REACTANT: CCC(C=O)CC SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 935.4244 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 1422.896 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 1568.912 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[17] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CCC(C=O)CC.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5410" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A18" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243354" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCC(C=O)CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CC" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A18)", "float_value": { "value": 935.4244384765625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A18)", "float_value": { "value": 1422.8961181640625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A18)", "float_value": { "value": 1568.9119873046875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 1568.912). Patil_Plates.csv mass-error confidence: Green, peak area 135549.8947" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[18]	Record 19	REACTANT: acrylic acid REACTANT: O=Cc1ccc(Cl)c(Cl)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 1734.078 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 601.4082 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 12131.13 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 6349682 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 641960.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 761251.3 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · AREA: 10129.72 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1 · PURITY: 86.65% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[18] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccc(Cl)c(Cl)c1.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4810" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A19" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243238" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccc(Cl)c(Cl)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc(Cl)c(Cl)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A19)", "float_value": { "value": 1734.0775146484375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A19)", "float_value": { "value": 601.408203125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A19)", "float_value": { "value": 12131.1298828125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 12131.13). Patil_Plates.csv mass-error confidence: Green, peak area 176252.6133" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 6349681.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 641960.125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 761251.3125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 10129.724609375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 86.6500015258789 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[19]	Record 20	REACTANT: acrylic acid REACTANT: O=Cc1c(F)c(F)cc(F)c1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 1431.467 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 11295.49 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[19] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1c(F)c(F)cc(F)c1F.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5411" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A20" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243355" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1c(F)c(F)cc(F)c1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1c(F)c(F)cc(F)c1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A20)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A20)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A20)", "float_value": { "value": 1431.466552734375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 1431.4666). Patil_Plates.csv mass-error confidence: Green, peak area 10043.0313" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 11295.4892578125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[20]	Record 21	REACTANT: acrylic acid REACTANT: O=Cc1cccc(OCc2ccccc2)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 2533.979 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 938.9083 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 2166.071 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1 · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[20] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(OCc2ccccc2)c1.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4811" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A21" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243239" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(OCc2ccccc2)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cccc(OCc2ccccc2)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A21)", "float_value": { "value": 2533.978759765625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A21)", "float_value": { "value": 938.9083251953125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A21)", "float_value": { "value": 2166.070556640625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2166.0706). Patil_Plates.csv mass-error confidence: Green, peak area 404507.3695" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[21]	Record 22	REACTANT: acrylic acid REACTANT: CCCCC(C=O)CC SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 670.7279 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 523.9176 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 853.5298 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 205829.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 11039.31 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC · PURITY: 0% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[21] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CCCCC(C=O)CC.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5412" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A22" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243356" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC(C=O)CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)C(CC)CCCC" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A22)", "float_value": { "value": 670.7279052734375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A22)", "float_value": { "value": 523.9176025390625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A22)", "float_value": { "value": 853.5298461914062 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 853.52985). Patil_Plates.csv mass-error confidence: Green, peak area 93561.3075" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 205829.59375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 11039.3056640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 0 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[22]	Record 23	REACTANT: acrylic acid REACTANT: O=Cc1ccc2[nH]ccc2c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 2835.135 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 1522.371 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 2579.73 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 18130.73 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · AREA: 465.2341 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[22] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccc2[nH]ccc2c1.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4814" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A23" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243240" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccc2[nH]ccc2c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1ccc2[nH]ccc2c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A23)", "float_value": { "value": 2835.134521484375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A23)", "float_value": { "value": 1522.370849609375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A23)", "float_value": { "value": 2579.729736328125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2579.7297). Patil_Plates.csv mass-error confidence: Green, peak area 497720.8746" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 18130.732421875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 465.23406982421875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[23]	Record 24	REACTANT: acrylic acid REACTANT: O=Cc1cc(F)c(F)cc1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 2376.78 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 975765.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 443799.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 267938.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · AREA: 1880.984 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[23] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cc(F)c(F)cc1F.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5413" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 A24" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243357" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cc(F)c(F)cc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1cc(F)c(F)cc1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well A24)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well A24)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well A24)", "float_value": { "value": 2376.780029296875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 2376.78). Patil_Plates.csv mass-error confidence: Green, peak area 6150.651" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 975765.0625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 443799.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 267938.375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1880.98388671875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[24]	Record 25	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1C(F)(F)F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1ccc(Br)cc1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 592.8522 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 271.4112 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 12100.72 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 6814782 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 808531.5 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 1425652 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · AREA: 11194.94 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F · PURITY: 92.55% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[24] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1C(F)(F)F.N.[C-]#[N+]Cc1ccc(Br)cc1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5561" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B1" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243442" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1C(F)(F)F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1ccc(Br)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1C(F)(F)F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B1)", "float_value": { "value": 592.8521728515625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B1)", "float_value": { "value": 271.4111633300781 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B1)", "float_value": { "value": 12100.71875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 12100.719). Patil_Plates.csv mass-error confidence: Green, peak area 78855.8369" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 6814781.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 808531.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 1425652.375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 11194.9365234375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 92.55000305175781 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[25]	Record 26	REACTANT: acrylic acid REACTANT: COc1ccc(C=O)cc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1ccc(C)cc1F SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 161.9116 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 220.8841 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 804.6605 [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 886023.7 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 897923.7 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 219801.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · AREA: 4383.076 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[25] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1ccc(C=O)cc1.N.[C-]#[N+]c1ccc(C)cc1F.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5714" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B2" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243538" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1ccc(C=O)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1ccc(C)cc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1ccc(C)cc1F)c1ccc(OC)cc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B2)", "float_value": { "value": 161.91159057617188 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B2)", "float_value": { "value": 220.88414001464844 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B2)", "float_value": { "value": 804.6604614257812 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 804.66046). Patil_Plates.csv mass-error confidence: Green, peak area 32715.3339" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 886023.6875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 897923.6875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 219801.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 4383.076171875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[26]	Record 27	REACTANT: acrylic acid REACTANT: O=Cc1cccc(F)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1ccc(Br)cc1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 10443.78 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 2543405 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 561339.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · AREA: 6286.539 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1 · PURITY: 88.23% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[26] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(F)c1.N.[C-]#[N+]Cc1ccc(Br)cc1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5562" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B3" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243443" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(F)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1ccc(Br)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(F)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B3)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B3)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B3)", "float_value": { "value": 10443.779296875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 10443.779). Patil_Plates.csv mass-error confidence: Green, peak area 9514.1743" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 2543404.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 561339.375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 6286.5390625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 88.2300033569336 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[27]	Record 28	REACTANT: acrylic acid REACTANT: O=Cc1ccc(F)cc1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 156.4142 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 101.5136 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 1828.945 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 986505.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 661233.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 300823.5 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · AREA: 1700.549 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[27] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccc(F)cc1F.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5718" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B4" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243539" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccc(F)cc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccc(F)cc1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B4)", "float_value": { "value": 156.4141845703125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B4)", "float_value": { "value": 101.51361083984375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B4)", "float_value": { "value": 1828.94482421875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1828.9448). Patil_Plates.csv mass-error confidence: Green, peak area 59086.8371" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 986505.4375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 661233.0625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 300823.46875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1700.54931640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[28]	Record 29	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1ccc(Br)cc1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 338.1575 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 234.9877 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 7881.968 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 4501332 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 702338.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 599399.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · AREA: 9793.206 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F · PURITY: 95.65% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[28] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1F.N.[C-]#[N+]Cc1ccc(Br)cc1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5563" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B5" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243444" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1ccc(Br)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1ccccc1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B5)", "float_value": { "value": 338.157470703125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B5)", "float_value": { "value": 234.98765563964844 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B5)", "float_value": { "value": 7881.96826171875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 7881.9683). Patil_Plates.csv mass-error confidence: Green, peak area 55856.2789" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 4501332 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 702338.125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 599399.8125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 9793.2060546875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 95.6500015258789 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[29]	Record 30	REACTANT: acrylic acid REACTANT: Cc1ccccc1C=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 3967.488 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 2488.095 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 1619.828 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 4221222 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 2137972 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 270759.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · AREA: 5362.473 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[29] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "Cc1ccccc1C=O.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5726" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B6" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243540" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Cc1ccccc1C=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccccc1C" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B6)", "float_value": { "value": 3967.48779296875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B6)", "float_value": { "value": 2488.095458984375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B6)", "float_value": { "value": 1619.82763671875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1619.8276). Patil_Plates.csv mass-error confidence: Green, peak area 743846.5791" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 4221222 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 2137972.25 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 270759.4375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 5362.47314453125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[30]	Record 31	REACTANT: acrylic acid REACTANT: O=Cc1cccc(C(F)(F)F)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1ccc(Br)cc1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 12740.85 [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 3517985 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 967954.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · AREA: 6074.163 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1 · PURITY: 94.14% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[30] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(C(F)(F)F)c1.N.[C-]#[N+]Cc1ccc(Br)cc1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5564" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B7" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243445" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(C(F)(F)F)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1ccc(Br)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1ccc(Br)cc1)c1cccc(C(F)(F)F)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B7)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B7)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B7)", "float_value": { "value": 12740.8466796875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 12740.847). Patil_Plates.csv mass-error confidence: Green, peak area 4047.8527" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 3517984.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 967954.8125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 6074.16259765625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 94.13999938964844 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[31]	Record 32	REACTANT: acrylic acid REACTANT: Cc1cccc(C=O)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 1595.26 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 862.6847 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 497.9307 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 2212628 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 1471022 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 128498.9 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · AREA: 2345.68 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[31] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "Cc1cccc(C=O)c1.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5727" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B8" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243541" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "Cc1cccc(C=O)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(C)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B8)", "float_value": { "value": 1595.26025390625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B8)", "float_value": { "value": 862.6846923828125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B8)", "float_value": { "value": 497.9306945800781 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 497.9307). Patil_Plates.csv mass-error confidence: Green, peak area 303507.678" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 2212628 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1471022.125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 128498.90625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 2345.679931640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[32]	Record 33	REACTANT: acrylic acid REACTANT: CC(C=O)=Cc1ccccc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C1CCN(C(=O)OCC)CC1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 1013.292 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 249.4588 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 4409.033 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 6468432 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 1066127 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 503500.5 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · AREA: 5129.442 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[32] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C=O)=Cc1ccccc1.N.[C-]#[N+]C1CCN(C(=O)OCC)CC1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5565" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B9" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243446" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C=O)=Cc1ccccc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C1CCN(C(=O)OCC)CC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)=Cc1ccccc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B9)", "float_value": { "value": 1013.2916259765625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B9)", "float_value": { "value": 249.45880126953125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B9)", "float_value": { "value": 4409.033203125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 4409.033). Patil_Plates.csv mass-error confidence: Green, peak area 178271.1118" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 6468431.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1066126.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 503500.53125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 5129.4423828125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[33]	Record 34	REACTANT: acrylic acid REACTANT: O=CC1CCCC1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 3511.539 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 4239.479 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 1935.005 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 5513256 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 2831518 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 141987.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · AREA: 4500.694 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[33] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=CC1CCCC1.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5729" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B10" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243542" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=CC1CCCC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)C1CCCC1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B10)", "float_value": { "value": 3511.53857421875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B10)", "float_value": { "value": 4239.47900390625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B10)", "float_value": { "value": 1935.0045166015625 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 1935.0045). Patil_Plates.csv mass-error confidence: Green, peak area 690842.6642" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 5513256 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 2831517.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 141987.84375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 4500.6943359375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[34]	Record 35	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1Oc1ccccc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C1CCN(C(=O)OCC)CC1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 1110.47 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 312.0708 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 1167.05 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 4434078 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 770745.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 378685.3 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · AREA: 3304.693 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[34] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1Oc1ccccc1.N.[C-]#[N+]C1CCN(C(=O)OCC)CC1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5566" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B11" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243447" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1Oc1ccccc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C1CCN(C(=O)OCC)CC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1ccccc1Oc1ccccc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B11)", "float_value": { "value": 1110.4697265625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B11)", "float_value": { "value": 312.07080078125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B11)", "float_value": { "value": 1167.049560546875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1167.0496). Patil_Plates.csv mass-error confidence: Green, peak area 187552.4916" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 4434077.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 770745.375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 378685.3125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 3304.692626953125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[35]	Record 36	REACTANT: acrylic acid REACTANT: COc1cccc(C=O)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 2628.293 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 1143.021 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 1690.728 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 2976710 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 1424903 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 263882.5 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · AREA: 4333.083 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[35] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1cccc(C=O)c1.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5730" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B12" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243543" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1cccc(C=O)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc(OC)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B12)", "float_value": { "value": 2628.292724609375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B12)", "float_value": { "value": 1143.02099609375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B12)", "float_value": { "value": 1690.728271484375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1690.7283). Patil_Plates.csv mass-error confidence: Green, peak area 513892.2699" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 2976710 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1424903 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 263882.46875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 4333.08251953125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[36]	Record 37	REACTANT: acrylic acid REACTANT: CC(C)(C)C=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C1CCN(C(=O)OCC)CC1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 418.1482 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 139.1396 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 3119.21 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 5185308 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 2148915 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 552479.7 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · AREA: 4249.261 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[36] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)(C)C=O.N.[C-]#[N+]C1CCN(C(=O)OCC)CC1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5568" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B13" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243448" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)(C)C=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C1CCN(C(=O)OCC)CC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)C(C)(C)C" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B13)", "float_value": { "value": 418.1482238769531 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B13)", "float_value": { "value": 139.13955688476562 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B13)", "float_value": { "value": 3119.210205078125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 3119.2102). Patil_Plates.csv mass-error confidence: Green, peak area 78551.7079" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 5185308 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 2148914.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 552479.6875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 4249.2607421875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[37]	Record 38	REACTANT: acrylic acid REACTANT: O=Cc1ccco1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 4252.561 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 6872.589 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 2735.355 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 5207315 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 3308980 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 195809.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · AREA: 9660.325 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[37] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccco1.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5731" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B14" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243544" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccco1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1ccco1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B14)", "float_value": { "value": 4252.560546875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B14)", "float_value": { "value": 6872.58935546875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B14)", "float_value": { "value": 2735.354736328125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 2735.3547). Patil_Plates.csv mass-error confidence: Green, peak area 829576.0827" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 5207314.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 3308980.25 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 195809.78125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 9660.3251953125 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[38]	Record 39	REACTANT: acrylic acid REACTANT: O=Cc1cccc(C(F)(F)F)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C1CCN(C(=O)OCC)CC1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 172.3087 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 13771.24 [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 7073684 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 714613.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 894141.2 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · AREA: 4747.463 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[38] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc(C(F)(F)F)c1.N.[C-]#[N+]C1CCN(C(=O)OCC)CC1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5573" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B15" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243449" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc(C(F)(F)F)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C1CCN(C(=O)OCC)CC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC1CCN(C(=O)OCC)CC1)c1cccc(C(F)(F)F)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B15)", "float_value": { "value": 172.30870056152344 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B15)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B15)", "float_value": { "value": 13771.236328125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 13771.236). Patil_Plates.csv mass-error confidence: Green, peak area 48999.1932" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 7073683.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 714613.8125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 894141.1875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 4747.462890625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[39]	Record 40	REACTANT: acrylic acid REACTANT: O=Cc1cccc2ccccc12 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]C(C)(C)C SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 6430.18 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 2198.581 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 2373.081 [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 8059715 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 1530522 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 430711.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · AREA: 18030.4 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12 · PURITY: 97.97% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[39] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cccc2ccccc12.N.[C-]#[N+]C(C)(C)C.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5732" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B16" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243545" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cccc2ccccc12" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]C(C)(C)C" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NC(C)(C)C)c1cccc2ccccc12" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B16)", "float_value": { "value": 6430.1796875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B16)", "float_value": { "value": 2198.5810546875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B16)", "float_value": { "value": 2373.0810546875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2373.081). Patil_Plates.csv mass-error confidence: Green, peak area 1208509.5746" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 8059714.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1530521.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 430711.8125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 18030.40234375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 97.97000122070312 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[40]	Record 41	REACTANT: acrylic acid REACTANT: CC(C)CC=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1cc(OC)cc(OC)c1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 0 [AEMS] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 0 [AEMS] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 0 [AEMS] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 1536382 [UPLC-MS-UV] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 756333.2 [UPLC-MS-UV] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 522553.7 [UPLC-MS-UV] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · AREA: 5811.696 [UPLC-MS-UV] C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[40] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)CC=O.N.[C-]#[N+]c1cc(OC)cc(OC)c1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5582" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B17" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243450" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)CC=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1cc(OC)cc(OC)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(CC(C)C)C(=O)Nc1cc(OC)cc(OC)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B17)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B17)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B17)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass not detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 0). Patil_Plates.csv mass-error confidence: Yellow, peak area 988.2885" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1536382.375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 756333.1875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 522553.71875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 5811.6962890625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[41]	Record 42	REACTANT: acrylic acid REACTANT: O=Cc1ccccc1Oc1ccccc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1c(C)cccc1CC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 2686.474 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 1293.836 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 2851.77 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 8595715 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 1201360 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 585273.1 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · AREA: 11676.16 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[41] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1ccccc1Oc1ccccc1.N.[C-]#[N+]c1c(C)cccc1CC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5734" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B18" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243546" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1ccccc1Oc1ccccc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1c(C)cccc1CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)c1ccccc1Oc1ccccc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B18)", "float_value": { "value": 2686.473876953125 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B18)", "float_value": { "value": 1293.836181640625 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B18)", "float_value": { "value": 2851.770263671875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2851.7703). Patil_Plates.csv mass-error confidence: Green, peak area 455832.88" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 8595715 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1201359.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 585273.0625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 11676.1640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[42]	Record 43	REACTANT: acrylic acid REACTANT: O=Cc1cc(F)c(F)c(F)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1cc(OC)cc(OC)c1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 0 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 18625.69 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 2577864 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 804604.5 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · AREA: 9495.635 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1 · PURITY: 93.91% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[42] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cc(F)c(F)c(F)c1.N.[C-]#[N+]c1cc(OC)cc(OC)c1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5583" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B19" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243451" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cc(F)c(F)c(F)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1cc(OC)cc(OC)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1cc(F)c(F)c(F)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B19)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B19)", "float_value": { "value": 0 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B19)", "float_value": { "value": 18625.6875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=false, best adduct target_NA; negative area 18625.688). Patil_Plates.csv mass-error confidence: Green, peak area 4028.7863" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 2577863.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 804604.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 9495.634765625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 93.91000366210938 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[43]	Record 44	REACTANT: acrylic acid REACTANT: CC(C)C=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1c(C)cccc1CC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 847.1307 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 1710.867 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 9398.585 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 1832557 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 1562407 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 860755.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · AREA: 6112.857 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[43] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)C=O.N.[C-]#[N+]c1c(C)cccc1CC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5735" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B20" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243547" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)C=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1c(C)cccc1CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)C" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B20)", "float_value": { "value": 847.1306762695312 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B20)", "float_value": { "value": 1710.8670654296875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B20)", "float_value": { "value": 9398.5849609375 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 9398.585). Patil_Plates.csv mass-error confidence: Green, peak area 161073.2669" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1832556.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1562406.875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 860755.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 6112.85693359375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[44]	Record 45	REACTANT: acrylic acid REACTANT: O=CC1CCC1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1cc(OC)cc(OC)c1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 537.8697 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 383.0066 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 9604.542 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 1934932 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 797495.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 704777.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · AREA: 10170.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1 · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[44] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=CC1CCC1.N.[C-]#[N+]c1cc(OC)cc(OC)c1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5589" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B21" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243452" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=CC1CCC1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1cc(OC)cc(OC)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)C1CCC1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B21)", "float_value": { "value": 537.8696899414062 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B21)", "float_value": { "value": 383.006591796875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B21)", "float_value": { "value": 9604.5419921875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 9604.542). Patil_Plates.csv mass-error confidence: Green, peak area 101601.1027" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1934931.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 797495.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 704777.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 10170.6025390625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[45]	Record 46	REACTANT: acrylic acid REACTANT: CC(C)(C)C=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1c(C)cccc1CC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 599.3944 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 1367.336 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 8902.252 [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 1278297 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 1200136 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 853068.8 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · AREA: 6060.993 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C · PURITY: 95.34% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[45] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CC(C)(C)C=O.N.[C-]#[N+]c1c(C)cccc1CC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5736" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B22" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243548" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CC(C)(C)C=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1c(C)cccc1CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1c(C)cccc1CC)C(C)(C)C" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B22)", "float_value": { "value": 599.3944091796875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B22)", "float_value": { "value": 1367.335693359375 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B22)", "float_value": { "value": 8902.251953125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 8902.252). Patil_Plates.csv mass-error confidence: Green, peak area 108732.1357" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1278297.125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 1200135.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 853068.75 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 6060.9931640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 95.33999633789062 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[46]	Record 47	REACTANT: acrylic acid REACTANT: O=Cc1c(F)cccc1F SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1cc(OC)cc(OC)c1 SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 619.2261 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 462.8087 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 2224.599 [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 3716505 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 636144.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 332250.3 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · AREA: 13836.31 [UPLC-MS-UV] C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F · PURITY: 95% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[46] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1c(F)cccc1F.N.[C-]#[N+]c1cc(OC)cc(OC)c1.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5590" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B23" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243453" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1c(F)cccc1F" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1cc(OC)cc(OC)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)Nc1cc(OC)cc(OC)c1)c1c(F)cccc1F" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B23)", "float_value": { "value": 619.22607421875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B23)", "float_value": { "value": 462.8086853027344 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B23)", "float_value": { "value": 2224.598876953125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 2224.5989). Patil_Plates.csv mass-error confidence: Green, peak area 106178.5117" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 3716504.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 636144.5625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 332250.28125 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 13836.3056640625 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 95 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[47]	Record 48	REACTANT: acrylic acid REACTANT: CCCC=O SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]c1c(C)cccc1CC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · CUSTOM: Green [1H NMR] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · IDENTITY: — [1H NMR] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · PURITY: 80% [1H NMR] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 207.101 [AEMS] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 347.8997 [AEMS] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 2764.87 [AEMS] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · IDENTITY: — [AEMS] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 460574.1 [UPLC-MS-UV] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 891796.9 [UPLC-MS-UV] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 370778.4 [UPLC-MS-UV] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · AREA: 1607.073 [UPLC-MS-UV] C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC · PURITY: 100% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[47] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "CCCC=O.N.[C-]#[N+]c1c(C)cccc1CC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5738" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 B24" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243549" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCC=O" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]c1c(C)cccc1CC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(CCC)C(=O)Nc1c(C)cccc1CC" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well B24)", "float_value": { "value": 207.1010284423828 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well B24)", "float_value": { "value": 347.8997497558594 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well B24)", "float_value": { "value": 2764.870361328125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_NA; negative area 2764.8704). Patil_Plates.csv mass-error confidence: Green, peak area 37741.5854" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 460574.09375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 891796.875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 370778.4375 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1607.0726318359375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 100 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[48]	Record 49	REACTANT: acrylic acid REACTANT: O=Cc1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1cccc(OC)c1OC SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 2768.716 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 702.716 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 1769.801 [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 1472332 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 0 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 67079.92 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · AREA: 1626.428 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1 · PURITY: 32.47% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[48] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "O=Cc1cc(OCc2ccccc2)cc(OCc2ccccc2)c1.N.[C-]#[N+]Cc1cccc(OC)c1OC.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-4815" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 C1" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243241" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "O=Cc1cc(OCc2ccccc2)cc(OCc2ccccc2)c1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1cccc(OC)c1OC" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1cccc(OC)c1OC)c1cc(OCc2ccccc2)cc(OCc2ccccc2)c1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well C1)", "float_value": { "value": 2768.715576171875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well C1)", "float_value": { "value": 702.7160034179688 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well C1)", "float_value": { "value": 1769.8006591796875 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1769.8007). Patil_Plates.csv mass-error confidence: Green, peak area 402180.7672" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 1472331.5 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 0 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 67079.921875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 1626.4281005859375 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 32.470001220703125 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }
reactions[49]	Record 50	REACTANT: acrylic acid REACTANT: COc1ccc(C=O)cc1 SOLVENT: 2,2,2-trifluoroethanol REACTANT: ammonia SOLVENT: water REACTANT: [C-]#[N+]Cc1c(F)cccc1Cl SOLVENT: 2,2,2-trifluoroethanol SOLVENT: 2,2,2-trifluoroethanol	25 CELSIUS	C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · CUSTOM: Green [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · IDENTITY: — [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · PURITY: 80% [1H NMR] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 1855.843 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 809.5943 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 1387.406 [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · IDENTITY: — [AEMS] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 5547379 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 869289.6 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 321469.7 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · AREA: 11329.69 [UPLC-MS-UV] C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1 · PURITY: 91.06% [UPLC-MS-UV]	10.1039/D5GC04440E
Decoded fields · reactions[49] Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. { "identifiers": [ { "type": "REACTION_SMILES", "value": "COc1ccc(C=O)cc1.N.[C-]#[N+]Cc1c(F)cccc1Cl.C=CC(=O)O>OCC(F)(F)F.O>C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1" }, { "type": "CUSTOM", "details": "compound code", "value": "PHP-5414" }, { "type": "CUSTOM", "details": "384-well analysis plate and well (Patil_Plates.csv)", "value": "Plate1 C2" }, { "type": "CUSTOM", "details": "LEM code (Patil_Plates.csv)", "value": "LEM00243358" }, { "type": "REACTION_TYPE", "value": "Ugi four-component reaction (ammonia / acrylic acid variant)" } ], "inputs": { "acrylic acid": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)O" }, { "type": "NAME", "value": "acrylic acid" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 35 uL neat" } }, "aldehyde": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "COc1ccc(C=O)cc1" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 2, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "ammonia": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "N" }, { "type": "NAME", "value": "ammonia" } ], "amount": { "moles": { "value": 1, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "O" }, { "type": "NAME", "value": "water" } ], "amount": { "volume": { "value": 0.05700000002980232, "units": "MILLILITER" }, "volume_includes_solutes": true }, "reaction_role": "SOLVENT" } ], "addition_order": 3, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette; 30% aqueous ammonia; mixture stirred 5 min at rt afterwards" } }, "isocyanide": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "[C-]#[N+]Cc1c(F)cccc1Cl" } ], "amount": { "moles": { "value": 0.5, "units": "MILLIMOLE" } }, "reaction_role": "REACTANT" }, { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.10000000149011612, "precision": 0.10000000149011612, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 4, "addition_device": { "type": "PIPETTE", "details": "multichannel pipette" } }, "solvent": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "OCC(F)(F)F" }, { "type": "NAME", "value": "2,2,2-trifluoroethanol" } ], "amount": { "volume": { "value": 0.30000001192092896, "units": "MILLILITER" } }, "reaction_role": "SOLVENT" } ], "addition_order": 1 } }, "setup": { "vessel": { "type": "VIAL", "details": "2 mL glass vial in a 96-well glass reaction plate", "material": { "type": "GLASS" }, "volume": { "value": 2, "units": "MILLILITER" } }, "is_automated": false, "environment": { "type": "CUSTOM", "details": "open-bench parallel synthesis in 96-well plates" } }, "conditions": { "temperature": { "control": { "type": "AMBIENT" }, "setpoint": { "value": 25, "precision": 5, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR", "details": "magnetic stirring bar in each vial" }, "conditions_are_dynamic": false, "details": "General procedure (ESI section 4): building-block stock solutions in TFE (2.5 M or 5 M depending on solubility, so stock volume 0.1 or 0.2 mL per 0.5 mmol); final concentration ca. 0.6-0.9 M. Stirred 18 h at room temperature." }, "notes": { "is_heterogeneous": true, "forms_precipitate": true, "safety_notes": "isocyanides are malodorous and toxic; acrylic acid is corrosive", "procedure_details": "To a 96-well glass plate with stirring bars, TFE (0.3 mL) was added, then the aldehyde stock in TFE (0.5 mmol, 1.0 equiv; 5 M 0.1 mL or 2.5 M 0.2 mL), then 30% aqueous ammonia (57 uL, 1 mmol, 2.0 equiv); stirred 5 min at rt. The isocyanide stock in TFE (0.5 mmol, 1.0 equiv) and acrylic acid (35 uL, 0.5 mmol, 1.0 equiv) were added and the mixture stirred 18 h at rt. Workup: Et2O (1 mL), 0 C 15 min (+0.5 mL petroleum ether and 15 min more if no solid), filtration on a metal 96-well filtration plate, washes with Et2O (1 mL) and 50% petroleum ether/Et2O, drying in vacuo. ESI section 4." }, "workups": [ { "type": "ADDITION", "details": "diluted with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "TEMPERATURE", "details": "stirred at 0 C; wells without free-flowing solid were scratched with a small spatula", "duration": { "value": 15, "units": "MINUTE" }, "temperature": { "control": { "type": "ICE_BATH" }, "setpoint": { "value": 0, "units": "CELSIUS" } }, "stirring": { "type": "STIR_BAR" } }, { "type": "ADDITION", "details": "only for wells where no precipitation occurred: petroleum ether added and stirred a further 15 min at 0 C", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "FILTRATION", "details": "transferred with multichannel pipettes (modified tips) to a custom metal 96-well vacuum filtration plate", "keep_phase": "solid" }, { "type": "WASH", "details": "solid washed with diethyl ether", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 1, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "WASH", "details": "solid washed with 50% petroleum ether in diethyl ether to remove unreacted acrylic acid", "input": { "components": [ { "identifiers": [ { "type": "SMILES", "value": "CCCCC" }, { "type": "NAME", "value": "petroleum ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" }, { "identifiers": [ { "type": "SMILES", "value": "CCOCC" }, { "type": "NAME", "value": "diethyl ether" } ], "amount": { "volume": { "value": 0.5, "units": "MILLILITER" } }, "reaction_role": "WORKUP" } ] } }, { "type": "DRY_IN_VACUUM", "details": "dried under vacuum on the filtration assembly for 30 min to 1 h; solids pushed into a collection plate", "duration": { "value": 45, "precision": 15, "units": "MINUTE" } } ], "outcomes": [ { "reaction_time": { "value": 18, "units": "HOUR" }, "products": [ { "identifiers": [ { "type": "SMILES", "value": "C=CC(=O)NC(C(=O)NCc1c(F)cccc1Cl)c1ccc(OC)cc1" } ], "is_desired_product": true, "measurements": [ { "analysis_key": "1H NMR", "type": "CUSTOM", "details": "outcome category (paper Fig. 3): Green: solid precipitated and 1H NMR consistent with the target product (purity >80%); isolated and retained in the library.", "string_value": "Green" }, { "analysis_key": "1H NMR", "type": "IDENTITY", "details": "1H NMR consistent with the target structure" }, { "analysis_key": "1H NMR", "type": "PURITY", "details": "lower bound: the paper reports purity >80% by 1H NMR for every Green compound", "percentage": { "value": 80 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+H]+ area (Plate1 well C2)", "float_value": { "value": 1855.842529296875 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES+ EIC [M+Na]+ area (Plate1 well C2)", "float_value": { "value": 809.5942993164062 } }, { "analysis_key": "AEMS", "type": "AREA", "details": "AEMS ES- EIC [M-H]- area (Plate1 well C2)", "float_value": { "value": 1387.405517578125 } }, { "analysis_key": "AEMS", "type": "IDENTITY", "details": "target mass detected by AEMS (positive: Overall Presence=true, best adduct target_H; negative area 1387.4055). Patil_Plates.csv mass-error confidence: Green, peak area 255307.2324" }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+H]+ area, summed over peaks", "float_value": { "value": 5547379 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES+ EIC [M+Na]+ area, summed over peaks", "float_value": { "value": 869289.625 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UPLC-MS ES- EIC [M-H]- area, summed over peaks", "float_value": { "value": 321469.6875 } }, { "analysis_key": "UPLC-MS-UV", "type": "AREA", "details": "UV (PDA, selected window) area of the target peak", "float_value": { "value": 11329.6904296875 } }, { "analysis_key": "UPLC-MS-UV", "type": "PURITY", "details": "UV area% of the MS-matched target peak (Peaksel 'UV sel Area%'); 0 = no UV peak matched", "percentage": { "value": 91.05999755859375 } } ], "texture": { "type": "POWDER", "details": "solid precipitate" }, "reaction_role": "PRODUCT" } ], "analyses": { "1H NMR": { "type": "NMR_1H", "details": "1H NMR (500 MHz) of each isolated precipitate; purity / identity check against the target product", "is_of_isolated_species": true, "instrument_manufacturer": "Bruker Avance 500" }, "AEMS": { "type": "MS", "details": "Acoustic ejection MS (SCIEX Echo MS+ with ZenoTOF 7600) of the isolated product after ca. 2 years storage as a 10 mM DMSO stock at rt, reformatted to 384-well plates and diluted to 100 uM in DMSO; carrier 0.1% formic acid in MeOH, 300 uL/min, 60 nL ejections; TOF MS 50-650 Da, positive and negative mode. Extracted-ion areas for [M+H]+, [M+Na]+ and [M-H]- from Peaksel processing (EchoMS_PlateN.csv / EchoMS_PlateN_NEG.csv). Raw data: Raw_AEMS.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "SCIEX" }, "UPLC-MS-UV": { "type": "LCMS", "details": "UPLC-MS-UV of the isolated product after ca. 2 years storage (0.7 mg/mL in 50% MeCN/water, 2 uL): Waters ACQUITY UPLC, PDA 200-400 nm, Xevo TQ-S Cronos MS (ESI+/-, m/z 100-1000); C18 1.7 um 2.1 x 50 mm, 40 C, 0.6 mL/min, 10-100% MeCN (0.1% HCO2H) over 6 min. Summed EIC areas and selected-UV peak area / area% for the target from Peaksel (UPLC_Plate1.csv). Raw data: Raw_UPLC.zip, doi:10.5281/zenodo.15496516", "is_of_isolated_species": true, "instrument_manufacturer": "Waters" }, "visual": { "type": "CUSTOM", "details": "visual check for precipitate after Et2O (and, if needed, petroleum ether) addition at 0 C" } } } ], "provenance": { "city": "Olomouc, Czech Republic", "doi": "10.1039/D5GC04440E", "publication_url": "https://doi.org/10.1039/D5GC04440E", "record_created": { "time": { "value": "2026-10-14" }, "person": { "name": "Jordan (Tokens for Progress), curated with the Claude agent", "email": "ord-curator@example.org" }, "details": "Built by build_dataset.py from Zenodo doi:10.5281/zenodo.15496516 Supporting_Scripts.zip (CC-BY-4.0) and the article ESI general procedure" }, "is_mined": false } }