ORD record viewer · decoder definitions: ord-schema 0.8.3
Table numbers are rounded to 7 significant digits; decoded details retain full precision.
McDonald et al. 2025, MF-BO HDAC inhibitor discovery: automated syntheses (ACS Cent. Sci.)
Dataset description
Automated multistep syntheses run by an autonomous platform (liquid handler + HPLC-MS) during two iterations of multi-fidelity Bayesian optimization (MF-BO) for HDAC inhibitor discovery, from M. A. McDonald, B. A. Koscher, R. B. Canty, J. Zhang, A. Ning, K. F. Jensen, ACS Cent. Sci. 2025, 11, 346 (doi:10.1021/acscentsci.4c01991). One reaction per executed well in SI Tables S2 (iteration 1, 6 plates) and S3 (iteration 2, 4 plates): 268 wells. Reactants, reagents, catalysts and solvents are the platform's conditions from the Zenodo queue files (10.5281/zenodo.13983042, platform_queue_scripts.zip; ASKCOS-recommended, rule-adjusted conditions). Outcomes are qualitative HPLC-MS detection of the target (retention time and m/z of the most abundant product ion as reported in the SI); no yields. Amounts, temperatures and times are not reported per reaction and are left unmeasured; each well had a 500 uL total volume. Later plates use products of earlier plates as reactants (multistep routes); those inputs carry a SYNTHESIZED preparation naming the source well. Both iterations are kept together in this one dataset.
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 | CATALYST: copper(I) oxide REACTANT: Nn1cnnc1 REACTANT: COc1ccc(B(O)O)cc1 SOLVENT: dimethyl sulfoxide | Not reported | COc1ccc(Nn2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.COc1ccc(B(O)O)cc1>>COc1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[O-2].[Cu+].[Cu+]"
},
{
"type": "NAME",
"value": "copper(I) oxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 0): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward COc1ccc(N(c2c(C)noc2C)n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.380000114440918,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
232.08999633789062
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[1] | Record 2 | CATALYST: copper(II) acetate monohydrate REACTANT: Nn1cnnc1 REACTANT: COc1ccc(B(O)O)cc1OC SOLVENT: N,N-dimethylformamide | Not reported | COc1ccc(Nn2cnnc2)cc1OC · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.COc1ccc(B(O)O)cc1OC>>COc1ccc(Nn2cnnc2)cc1OC"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2].O"
},
{
"type": "NAME",
"value": "copper(II) acetate monohydrate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(B(O)O)cc1OC"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A10",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A10 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 17): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward COc1ccc(N(C(=O)CCCBr)n2cnnc2)cc1OC (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Nn2cnnc2)cc1OC"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.309999942779541,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
262.1000061035156
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[2] | Record 3 | REACTANT: Nn1cnnc1 REACTANT: Clc1ccc2[nH]ccc2c1 REAGENT: potassium tert-butoxide SOLVENT: dimethyl sulfoxide | Not reported | c1cc2cc(Nn3cnnc3)ccc2[nH]1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.Clc1ccc2[nH]ccc2c1>>c1cc2cc(Nn3cnnc3)ccc2[nH]1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2[nH]ccc2c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A11",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A11 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 18): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=S(=O)(c1cccs1)N(c1ccc2[nH]ccc2c1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cc2cc(Nn3cnnc3)ccc2[nH]1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.319999933242798,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
241.08999633789062
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[3] | Record 4 | REACTANT: Nn1cnnc1 REACTANT: O=Cc1ccc(F)c([N+](=O)[O-])c1 REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.O=Cc1ccc(F)c([N+](=O)[O-])c1>>O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(F)c([N+](=O)[O-])c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A12",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A12 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 19): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccccc2)c([N+](=O)[O-])c1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.9100000858306885,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
275.04998779296875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[4] | Record 5 | REACTANT: Nn1cnnc1 REACTANT: Cc1ccc(Cl)cc1 REAGENT: potassium hydroxide SOLVENT: dimethyl sulfoxide | Not reported | Cc1ccc(Nn2cnnc2)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.Cc1ccc(Cl)cc1>>Cc1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(Cl)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[OH-].[K+]"
},
{
"type": "NAME",
"value": "potassium hydroxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 2): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward Cc1ccc(N(c2c(F)c(F)c(F)c(F)c2[N+](=O)[O-])n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 4 queued routes. AMBIGUOUS: the queue holds more than one route to this well's product on this plate; the first (file order) is recorded. Alternatives: Nn1cnnc1.Cc1ccc(B(O)O)cc1>>Cc1ccc(Nn2cnnc2)cc1 [[\"\"], [\"[OH2--].[Cu+].[Cu+]\"]]"
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[5] | Record 6 | CATALYST: copper(II) acetate REACTANT: B(C1=CSC=C1)(O)O REACTANT: Nn1cnnc1 SOLVENT: dimethyl sulfoxide | Not reported | c1cc(Nn2cnnc2)cs1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "B(C1=CSC=C1)(O)O.Nn1cnnc1>>c1cc(Nn2cnnc2)cs1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "B(C1=CSC=C1)(O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A3",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A3 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 4): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward c1ccc(N(c2ccsc2)n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 5 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cc(Nn2cnnc2)cs1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.130000114440918,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
208.02999877929688
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[6] | Record 7 | CATALYST: copper(I) oxide REACTANT: Nn1cnnc1 REACTANT: O=C(O)c1ccc(B(O)O)cc1 SOLVENT: dimethyl sulfoxide | Not reported | O=C(O)c1ccc(Nn2cnnc2)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.O=C(O)c1ccc(B(O)O)cc1>>O=C(O)c1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[O-2].[Cu+].[Cu+]"
},
{
"type": "NAME",
"value": "copper(I) oxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)c1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 5): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=C(O)c1ccc(N(c2ccc(C(F)(F)F)cc2)n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)c1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[7] | Record 8 | REACTANT: Nn1cnnc1 REACTANT: Nc1ccncc1Cl REAGENT: potassium tert-butoxide SOLVENT: dimethyl sulfoxide | Not reported | Nc1ccncc1Nn1cnnc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.Nc1ccncc1Cl>>Nc1ccncc1Nn1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccncc1Cl"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 6): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward N#Cc1ccc(N(c2cnccc2N)n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccncc1Nn1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.179999828338623,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
218.0800018310547
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[8] | Record 9 | REACTANT: Nn1cnnc1 REACTANT: OC(c1ccccc1)c1ccccc1 REAGENT: sulfuric acid | Not reported | c1ccc(C(Nn2cnnc2)c2ccccc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.OC(c1ccccc1)c1ccccc1>>c1ccc(C(Nn2cnnc2)c2ccccc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OC(c1ccccc1)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=S(=O)(O)O"
},
{
"type": "NAME",
"value": "sulfuric acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A6",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A6 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 7): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=C(CO)N(C(c1ccccc1)c1ccccc1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(C(Nn2cnnc2)c2ccccc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.8499999046325684,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
292.1199951171875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[9] | Record 10 | REACTANT: Nn1cnnc1 REACTANT: Clc1cnc2ccccc2n1 REAGENT: potassium tert-butoxide SOLVENT: N,N-dimethylformamide | Not reported | c1ccc2nc(Nn3cnnc3)cnc2c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.Clc1cnc2ccccc2n1>>c1ccc2nc(Nn3cnnc3)cnc2c1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1cnc2ccccc2n1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A7",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A7 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 9): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=[N+]([O-])c1cccc(N(c2cnc3ccccc3n2)n2cnnc2)c1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 3 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2nc(Nn3cnnc3)cnc2c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.369999885559082,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
254.0800018310547
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[10] | Record 11 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: CNc1ccc(Cl)cc1C(=O)c1ccccc1 REAGENT: potassium carbonate SOLVENT: N,N-dimethylformamide | Not reported | CN(c1ccc(cn1)[N+]([O-])=O)c1ccc(Cl)cc1C(=O)c1ccccc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.CNc1ccc(Cl)cc1C(=O)c1ccccc1>>CN(c1ccc([N+](=O)[O-])cc1)c1ccc(Cl)cc1C(=O)c1ccccc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CNc1ccc(Cl)cc1C(=O)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well A9",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well A9 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 16): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 1 toward CN(c1ccc([N+](=O)[O-])cc1)c1ccc(Cl)cc1C(=O)c1ccccc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well). DISCREPANCY: the SI reports product CN(c1ccc(cn1)[N+]([O-])=O)c1ccc(Cl)cc1C(=O)c1ccccc1 for this well, which matches no queue target on this plate. Inputs are taken from the unexecuted queue entry targeting CN(c1ccc([N+](=O)[O-])cc1)c1ccc(Cl)cc1C(=O)c1ccccc1 (pairing confidence: medium); the inputs actually used may differ."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(c1ccc(cn1)[N+]([O-])=O)c1ccc(Cl)cc1C(=O)c1ccccc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[11] | Record 12 | CATALYST: copper(II) acetate REACTANT: C1=CN=C(N=C1)N REACTANT: OB(O)c1ccsc1 REAGENT: pyridine SOLVENT: toluene | Not reported | c1cnc(Nc2ccsc2)nc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "C1=CN=C(N=C1)N.OB(O)c1ccsc1>>c1cnc(Nc2ccsc2)nc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1=CN=C(N=C1)N"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccsc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccccc1"
},
{
"type": "NAME",
"value": "toluene"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 21): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=S(=O)(c1cccs1)N(c1ccsc1)c1ncccn1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc(Nc2ccsc2)nc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[12] | Record 13 | REACTANT: Nn1cnnc1 REACTANT: O=[N+]([O-])c1ccc(Cl)nc1 REAGENT: cesium carbonate SOLVENT: dimethyl sulfoxide | Not reported | O=[N+]([O-])c1ccc(Nn2cnnc2)nc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.O=[N+]([O-])c1ccc(Cl)nc1>>O=[N+]([O-])c1ccc(Nn2cnnc2)nc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Cl)nc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[Cs+].[Cs+]"
},
{
"type": "NAME",
"value": "cesium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 22): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)n2cnnc2)nc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Nn2cnnc2)nc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.309999942779541,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
248.05999755859375
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[13] | Record 14 | CATALYST: copper(II) acetate monohydrate REACTANT: OB(O)c1cc2ccccc2o1 REACTANT: Nn1cnnc1 SOLVENT: N,N-dimethylformamide | Not reported | c1ccc2oc(Nn3cnnc3)cc2c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "OB(O)c1cc2ccccc2o1.Nn1cnnc1>>c1ccc2oc(Nn3cnnc3)cc2c1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2].O"
},
{
"type": "NAME",
"value": "copper(II) acetate monohydrate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1cc2ccccc2o1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B3",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B3 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 23): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward c1ccc(N(c2cc3ccccc3o2)n2cnnc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2oc(Nn3cnnc3)cc2c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.6500000953674316,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
242.07000732421875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[14] | Record 15 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: CC(N)c1ccccc1 REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.CC(N)c1ccccc1>>CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(N)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 24): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward COC(=O)c1nc(N)ccc1N(c1ccc([N+](=O)[O-])cc1)C(C)c1ccccc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 5.289999961853027,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
284.1099853515625
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[15] | Record 16 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: CC(C)CN REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | CC(C)CNc1ccc([N+](=O)[O-])cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.CC(C)CN>>CC(C)CNc1ccc([N+](=O)[O-])cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CN"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 25): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward Cc1ccc(S(=O)(=O)N(CC(C)C)c2ccc([N+](=O)[O-])cc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CNc1ccc([N+](=O)[O-])cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.519999980926514,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
236.11000061035156
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[16] | Record 17 | REACTANT: Nn1cnnc1 REACTANT: Fc1cc(Br)cc(Br)c1 REAGENT: potassium hydroxide SOLVENT: dimethyl sulfoxide | Not reported | Brc1cc(Br)cc(Nn2cnnc2)c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.Fc1cc(Br)cc(Br)c1>>Brc1cc(Br)cc(Nn2cnnc2)c1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1cc(Br)cc(Br)c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[OH-].[K+]"
},
{
"type": "NAME",
"value": "potassium hydroxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B7",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B7 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 28): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=C(Oc1ccccc1)N(c1cc(Br)cc(Br)c1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 3 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(Br)cc(Nn2cnnc2)c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.510000228881836,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
357.8999938964844
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[17] | Record 18 | CATALYST: copper(II) acetate REACTANT: Nn1cnnc1 REACTANT: CC1(C)OB(c2cnc3ccccc3c2)OC1(C)C SOLVENT: toluene | Not reported | c1ccc2ncc(Nn3cnnc3)cc2c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.CC1(C)OB(c2cnc3ccccc3c2)OC1(C)C>>c1ccc2ncc(Nn3cnnc3)cc2c1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1(C)OB(c2cnc3ccccc3c2)OC1(C)C"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccccc1"
},
{
"type": "NAME",
"value": "toluene"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 1, well B8",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 1, well B8 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_0_79_101_queue.json (entry 31): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=S(=O)(c1cccs1)N(c1cnc2ccccc2c1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2ncc(Nn3cnnc3)cc2c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 3.640000104904175,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
253.08999633789062
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[18] | Record 19 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: Nc1c(Cl)cccc1Cl REAGENT: potassium tert-butoxide SOLVENT: dimethyl sulfoxide | Not reported | O=[N+]([O-])c1ccc(Nc2c(Cl)cccc2Cl)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.Nc1c(Cl)cccc1Cl>>O=[N+]([O-])c1ccc(Nc2c(Cl)cccc2Cl)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1c(Cl)cccc1Cl"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 0): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)c2c(Cl)cccc2Cl)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Nc2c(Cl)cccc2Cl)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.820000171661377,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
324
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[19] | Record 20 | REACTANT: Cc1ccc(Nn2cnnc2)cc1 REACTANT: N#Cc1ccc(Cl)cc1 REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | Cc1ccc(N(c2ccc(C#N)cc2)n2cnnc2)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Cc1ccc(Nn2cnnc2)cc1.N#Cc1ccc(Cl)cc1>>Cc1ccc(N(c2ccc(C#N)cc2)n2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(Nn2cnnc2)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A2 of this dataset (not detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "N#Cc1ccc(Cl)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A10",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A10 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 11): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward Cc1ccc(N(c2ccc(C#N)cc2)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(N(c2ccc(C#N)cc2)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[20] | Record 21 | REACTANT: c1ccc2nc(Nn3cnnc3)cnc2c1 REACTANT: CS(=O)(=O)Nc1ccc(B(O)O)cc1 REAGENT: N,N-diisopropylethylamine REAGENT: propylphosphonic anhydride SOLVENT: 1,2-dichloroethane | Not reported | CS(=O)(=O)Nc1ccc(N(c2cnc3ccccc3n2)n2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1ccc2nc(Nn3cnnc3)cnc2c1.CS(=O)(=O)Nc1ccc(B(O)O)cc1>>CS(=O)(=O)Nc1ccc(N(c2cnc3ccccc3n2)n2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2nc(Nn3cnnc3)cnc2c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A7 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)Nc1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
},
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1"
},
{
"type": "NAME",
"value": "propylphosphonic anhydride"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "ClCCCl"
},
{
"type": "NAME",
"value": "1,2-dichloroethane"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A11",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A11 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 12): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward CS(=O)(=O)Nc1ccc(N(c2cnc3ccccc3n2)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)Nc1ccc(N(c2cnc3ccccc3n2)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 6.820000171661377,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
423.1000061035156
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[21] | Record 22 | CATALYST: copper(I) acetate REACTANT: c1ccc(C(Nn2cnnc2)c2ccccc2)cc1 REACTANT: COc1ccc(B(O)O)cc1 REAGENT: pyridine SOLVENT: toluene | Not reported | COc1ccc(N(C(c2ccccc2)c2ccccc2)n2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1ccc(C(Nn2cnnc2)c2ccccc2)cc1.COc1ccc(B(O)O)cc1>>COc1ccc(N(C(c2ccccc2)c2ccccc2)n2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].[Cu+]"
},
{
"type": "NAME",
"value": "copper(I) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(C(Nn2cnnc2)c2ccccc2)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A6 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccccc1"
},
{
"type": "NAME",
"value": "toluene"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A12",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A12 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 13): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward COc1ccc(N(C(c2ccccc2)c2ccccc2)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(N(C(c2ccccc2)c2ccccc2)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 5.25,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
398.1600036621094
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[22] | Record 23 | REACTANT: COc1ccc(Nn2cnnc2)cc1 REACTANT: Cc1noc(C)c1B(O)O REAGENT: oxygen SOLVENT: N,N-dimethylformamide | Not reported | COc1ccc(N(c2c(C)noc2C)n2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "COc1ccc(Nn2cnnc2)cc1.Cc1noc(C)c1B(O)O>>COc1ccc(N(c2c(C)noc2C)n2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Nn2cnnc2)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A1 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1noc(C)c1B(O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=O"
},
{
"type": "NAME",
"value": "oxygen"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 2): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward COc1ccc(N(c2c(C)noc2C)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(N(c2c(C)noc2C)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.880000114440918,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
327.1199951171875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[23] | Record 24 | REACTANT: CC(C)(C)O REACTANT: CS(N)(=O)=O REAGENT: sulfuric acid | Not reported | CC(C)(C)NS(C)(=O)=O · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "CC(C)(C)O.CS(N)(=O)=O>>CC(C)(C)NS(C)(=O)=O"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(N)(=O)=O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=S(=O)(O)O"
},
{
"type": "NAME",
"value": "sulfuric acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A3",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A3 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 3): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward CC(C)(C)N(S(C)(=O)=O)S(=O)(=O)c1cccc(Br)c1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)NS(C)(=O)=O"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.730000019073486,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
193.07000732421875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[24] | Record 25 | REACTANT: N#CN REACTANT: Clc1cnc2ccccc2n1 REAGENT: triethylamine SOLVENT: N,N-dimethylformamide | Not reported | N#CNc1cnc2ccccc2n1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "N#CN.Clc1cnc2ccccc2n1>>N#CNc1cnc2ccccc2n1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "N#CN"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1cnc2ccccc2n1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(CC)CC"
},
{
"type": "NAME",
"value": "triethylamine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 4): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward CC(C)(C)c1ccc(S(=O)(=O)N(C#N)c2cnc3ccccc3n2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "N#CNc1cnc2ccccc2n1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 6.929999828338623,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
212.05999755859375
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[25] | Record 26 | REACTANT: CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1 REACTANT: COC(=O)c1nc(N)ccc1Cl REAGENT: cesium carbonate SOLVENT: 1,4-dioxane SOLVENT: acetonitrile | Not reported | COC(=O)c1nc(N)ccc1N(c1ccc([N+](=O)[O-])cc1)C(C)c1ccccc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1.COC(=O)c1nc(N)ccc1Cl>>COC(=O)c1nc(N)ccc1N(c1ccc([N+](=O)[O-])cc1)C(C)c1ccccc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(Nc1ccc([N+](=O)[O-])cc1)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well B4 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)c1nc(N)ccc1Cl"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[Cs+].[Cs+]"
},
{
"type": "NAME",
"value": "cesium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1COCCO1"
},
{
"type": "NAME",
"value": "1,4-dioxane"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 5): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward COC(=O)c1nc(N)ccc1N(c1ccc([N+](=O)[O-])cc1)C(C)c1ccccc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)c1nc(N)ccc1N(c1ccc([N+](=O)[O-])cc1)C(C)c1ccccc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.25,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
434.1499938964844
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[26] | Record 27 | CATALYST: copper(II) acetate REACTANT: B(C1=CSC=C1)(O)O REACTANT: Cn1nnc(N)n1 REAGENT: 2,2'-bipyridine SOLVENT: tetrahydrofuran | Not reported | Cn1nnc(Nc2ccsc2)n1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "B(C1=CSC=C1)(O)O.Cn1nnc(N)n1>>Cn1nnc(Nc2ccsc2)n1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "B(C1=CSC=C1)(O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1nnc(N)n1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCOC1"
},
{
"type": "NAME",
"value": "tetrahydrofuran"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A6",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A6 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 6): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward Cn1nnc(N(c2ccsc2)S(=O)(=O)c2ccccc2)n1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). Negative m/z in the SI is read as a negative-mode ion."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1nnc(Nc2ccsc2)n1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.03000020980835,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion, negative mode",
"eic_masses": [
180.0399932861328
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[27] | Record 28 | REACTANT: c1cc(Nn2cnnc2)cs1 REACTANT: O=[N+]([O-])c1ccc(Cl)cc1 REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | O=[N+]([O-])c1ccc(N(c2ccsc2)n2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1cc(Nn2cnnc2)cs1.O=[N+]([O-])c1ccc(Cl)cc1>>O=[N+]([O-])c1ccc(N(c2ccsc2)n2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cc(Nn2cnnc2)cs1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A3 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Cl)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A7",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A7 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 7): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=[N+]([O-])c1ccc(N(c2ccsc2)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(N(c2ccsc2)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.150000095367432,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
329.04998779296875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[28] | Record 29 | CATALYST: copper(II) acetate REACTANT: Nn1cnnc1 REACTANT: O=C(O)CCC(=O)Nc1ccc(B(O)O)cc1 REAGENT: oxygen SOLVENT: dimethyl sulfoxide SOLVENT: water | Not reported | O=C(O)CCC(=O)Nc1ccc(Nn2cnnc2)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.O=C(O)CCC(=O)Nc1ccc(B(O)O)cc1>>O=C(O)CCC(=O)Nc1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)CCC(=O)Nc1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=O"
},
{
"type": "NAME",
"value": "oxygen"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A8",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A8 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 8): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=C(O)CCC(=O)Nc1ccc(N(n2cnnc2)S(=O)(=O)c2cccc(Br)c2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)CCC(=O)Nc1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[29] | Record 30 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: Nn1cnnc1 REAGENT: dimethyl sulfoxide REAGENT: sodium hydride | Not reported | O=[N+]([O-])c1ccc(Nn2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.Nn1cnnc1>>O=[N+]([O-])c1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "[H-].[Na+]"
},
{
"type": "NAME",
"value": "sodium hydride"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well A9",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well A9 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 9): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward CC(C)(C)OC(=O)n1cccc1N(c1ccc([N+](=O)[O-])cc1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.380000114440918,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
247.05999755859375
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[30] | Record 31 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: NS(=O)(=O)C(F)(F)F REAGENT: potassium carbonate SOLVENT: dimethyl sulfoxide | Not reported | O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.NS(=O)(=O)C(F)(F)F>>O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)C(F)(F)F"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 14): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)S(=O)(=O)C(F)(F)F)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 4 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.269999980926514,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
311.989990234375
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[31] | Record 32 | CATALYST: copper(I) acetate REACTANT: c1ccc2oc(Nn3cnnc3)cc2c1 REACTANT: OB(O)c1ccccc1 REAGENT: pyridine SOLVENT: 1,2-dichloroethane | Not reported | c1ccc(N(c2cc3ccccc3o2)n2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1ccc2oc(Nn3cnnc3)cc2c1.OB(O)c1ccccc1>>c1ccc(N(c2cc3ccccc3o2)n2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].[Cu+]"
},
{
"type": "NAME",
"value": "copper(I) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2oc(Nn3cnnc3)cc2c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well B3 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "ClCCCl"
},
{
"type": "NAME",
"value": "1,2-dichloroethane"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 18): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward c1ccc(N(c2cc3ccccc3o2)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(N(c2cc3ccccc3o2)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.269999980926514,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
318.1000061035156
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[32] | Record 33 | REACTANT: Nn1cnnc1 REACTANT: CC(=O)OCC(=O)O REAGENT: 1,1'-carbonyldiimidazole | Not reported | CC(=O)OCC(=O)Nn1cnnc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.CC(=O)OCC(=O)O>>CC(=O)OCC(=O)Nn1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)OCC(=O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(N1C=CN=C1)N1C=CN=C1"
},
{
"type": "NAME",
"value": "1,1'-carbonyldiimidazole"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B3",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B3 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 19): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward CC(=O)OCC(=O)N(c1cccnc1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 3 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)OCC(=O)Nn1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 2.4800000190734863,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
226.05999755859375
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[33] | Record 34 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: Nc1ccccc1-c1ccccc1 REAGENT: potassium tert-butoxide SOLVENT: dimethyl sulfoxide | Not reported | O=[N+]([O-])c1ccc(Nc2ccccc2-c2ccccc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.Nc1ccccc1-c1ccccc1>>O=[N+]([O-])c1ccc(Nc2ccccc2-c2ccccc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccccc1-c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 22): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=[N+]([O-])c1ccc(N(Cc2ccc(Cl)cc2)c2ccccc2-c2ccccc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 6 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(Nc2ccccc2-c2ccccc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.820000171661377,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
332.1099853515625
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[34] | Record 35 | REACTANT: Brc1ccccc1 REACTANT: CC1(C)OB(c2ccc(N)cc2)OC1(C)C REAGENT: potassium carbonate SOLVENT: water | Not reported | Nc1ccc(-c2ccccc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Brc1ccccc1.CC1(C)OB(c2ccc(N)cc2)OC1(C)C>>Nc1ccc(-c2ccccc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1(C)OB(c2ccc(N)cc2)OC1(C)C"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 28): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 3 toward CC(C)(C)c1ccc(S(=O)(=O)N(c2ccc(-c3ccccc3)cc2)c2ccsc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 8 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(-c2ccccc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.769999980926514,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
211.08999633789062
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[35] | Record 36 | REACTANT: Nn1cnnc1 REACTANT: O=Cc1ccc(F)cc1 REAGENT: cesium carbonate SOLVENT: dimethyl sulfoxide | Not reported | O=Cc1ccc(Nn2cnnc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.O=Cc1ccc(F)cc1>>O=Cc1ccc(Nn2cnnc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[Cs+].[Cs+]"
},
{
"type": "NAME",
"value": "cesium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B6",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B6 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 36): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccc(Br)cc2)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). Negative m/z in the SI is read as a negative-mode ion."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(Nn2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.25,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion, negative mode",
"eic_masses": [
187.07000732421875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[36] | Record 37 | REACTANT: c1cc(Nn2cnnc2)cs1 REACTANT: O=C(O)CS REAGENT: triethylamine SOLVENT: water | Not reported | O=C(CS)N(c1ccsc1)n1cnnc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1cc(Nn2cnnc2)cs1.O=C(O)CS>>O=C(CS)N(c1ccsc1)n1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cc(Nn2cnnc2)cs1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A3 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)CS"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(CC)CC"
},
{
"type": "NAME",
"value": "triethylamine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B7",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B7 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 37): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=C(CS)N(c1ccsc1)n1cnnc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(CS)N(c1ccsc1)n1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 7.429999828338623,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
282.010009765625
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[37] | Record 38 | REACTANT: Nn1cnnc1 REACTANT: N#Cc1ccccc1Cl REAGENT: potassium tert-butoxide SOLVENT: dimethyl sulfoxide | Not reported | N#Cc1ccccc1Nn1cnnc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.N#Cc1ccccc1Cl>>N#Cc1ccccc1Nn1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "N#Cc1ccccc1Cl"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[O-].[K+]"
},
{
"type": "NAME",
"value": "potassium tert-butoxide"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "dimethyl sulfoxide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B8",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B8 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 38): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward N#Cc1ccccc1N(C(=O)c1sc2cc(F)ccc2c1Cl)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "N#Cc1ccccc1Nn1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[38] | Record 39 | REACTANT: O=[N+]([O-])c1ccc(F)cc1 REACTANT: CN(N)C(N)=S REAGENT: potassium carbonate SOLVENT: N,N-dimethylformamide | Not reported | CN(Nc1ccc([N+](=O)[O-])cc1)C(N)=S · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(F)cc1.CN(N)C(N)=S>>CN(Nc1ccc([N+](=O)[O-])cc1)C(N)=S"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(N)C(N)=S"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 2, well B9",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 2, well B9 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_1_58_79_queue.json (entry 39): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward CN(C(N)=S)N(c1ccc([N+](=O)[O-])cc1)S(=O)(=O)c1ccc(C(C)(C)C)cc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(Nc1ccc([N+](=O)[O-])cc1)C(N)=S"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[39] | Record 40 | REACTANT: CC(C)CNc1ccc([N+](=O)[O-])cc1 REACTANT: Cc1ccc(S(=O)(=O)Cl)cc1 REAGENT: pyridine | Not reported | Cc1ccc(S(=O)(=O)N(CC(C)C)c2ccc([N+](=O)[O-])cc2)cc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "CC(C)CNc1ccc([N+](=O)[O-])cc1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)N(CC(C)C)c2ccc([N+](=O)[O-])cc2)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CNc1ccc([N+](=O)[O-])cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well B5 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(S(=O)(=O)Cl)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well A1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well A1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 0): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward Cc1ccc(S(=O)(=O)N(CC(C)C)c2ccc([N+](=O)[O-])cc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(S(=O)(=O)N(CC(C)C)c2ccc([N+](=O)[O-])cc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 6.28000020980835,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
390.1099853515625
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[40] | Record 41 | REACTANT: B(C1=CSC=C1)(O)O REACTANT: COc1nccc(N)n1 REAGENT: sodium hydride SOLVENT: tetrahydrofuran | Not reported | COc1nccc(Nc2ccsc2)n1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "B(C1=CSC=C1)(O)O.COc1nccc(N)n1>>COc1nccc(Nc2ccsc2)n1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "B(C1=CSC=C1)(O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1nccc(N)n1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[H-].[Na+]"
},
{
"type": "NAME",
"value": "sodium hydride"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCOC1"
},
{
"type": "NAME",
"value": "tetrahydrofuran"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well A2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well A2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 9): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward COc1nccc(N(c2ccsc2)S(=O)(=O)c2ccc(C)cc2)n1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1nccc(Nc2ccsc2)n1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 5.179999828338623,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
249.0500030517578
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[41] | Record 42 | CATALYST: copper(II) acetate REACTANT: CC(=O)OCC(=O)Nn1cnnc1 REACTANT: COc1ccc(B(O)O)cc1 REAGENT: pyridine SOLVENT: dichloromethane | Not reported | COc1ccc(N(C(=O)COC(C)=O)n2cnnc2)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "CC(=O)OCC(=O)Nn1cnnc1.COc1ccc(B(O)O)cc1>>COc1ccc(N(C(=O)COC(C)=O)n2cnnc2)cc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)OCC(=O)Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 2, well B3 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(B(O)O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "ClCCl"
},
{
"type": "NAME",
"value": "dichloromethane"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well A4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well A4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 34): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward COc1ccc(N(C(=O)COC(C)=O)n2cnnc2)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(N(C(=O)COC(C)=O)n2cnnc2)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[42] | Record 43 | CATALYST: copper(II) acetate REACTANT: B(C1=CSC=C1)(O)O REACTANT: Nc1ncc([N+](=O)[O-])cn1 REAGENT: pyridine SOLVENT: dichloromethane | Not reported | O=[N+]([O-])c1cnc(Nc2ccsc2)nc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "B(C1=CSC=C1)(O)O.Nc1ncc([N+](=O)[O-])cn1>>O=[N+]([O-])c1cnc(Nc2ccsc2)nc1"
}
],
"inputs": {
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Cu+2]"
},
{
"type": "NAME",
"value": "copper(II) acetate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "B(C1=CSC=C1)(O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ncc([N+](=O)[O-])cn1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "ClCCl"
},
{
"type": "NAME",
"value": "dichloromethane"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well A5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well A5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 43): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 3 toward O=[N+]([O-])c1cnc(N(c2ccsc2)S(=O)(=O)c2ccc(-c3ccc4c(c3)OCO4)cc2)nc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1cnc(Nc2ccsc2)nc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.900000095367432,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
264.0199890136719
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[43] | Record 44 | REACTANT: COc1ccc(Nn2cnnc2)cc1OC REACTANT: O=C(Cl)CCCBr REAGENT: potassium carbonate SOLVENT: dichloromethane | Not reported | COc1ccc(N(C(=O)CCCBr)n2cnnc2)cc1OC · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "COc1ccc(Nn2cnnc2)cc1OC.O=C(Cl)CCCBr>>COc1ccc(N(C(=O)CCCBr)n2cnnc2)cc1OC"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Nn2cnnc2)cc1OC"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A10 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(Cl)CCCBr"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "ClCCl"
},
{
"type": "NAME",
"value": "dichloromethane"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well A6",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well A6 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 51): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward COc1ccc(N(C(=O)CCCBr)n2cnnc2)cc1OC (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(N(C(=O)CCCBr)n2cnnc2)cc1OC"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[44] | Record 45 | REACTANT: Nn1cnnc1 REACTANT: C=CC(=O)O REAGENT: diethyl cyanophosphonate REAGENT: triethylamine SOLVENT: N,N-dimethylformamide | Not reported | C=CC(=O)Nn1cnnc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nn1cnnc1.C=CC(=O)O>>C=CC(=O)Nn1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nn1cnnc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C=CC(=O)O"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOP(=O)(C#N)OCC"
},
{
"type": "NAME",
"value": "diethyl cyanophosphonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(CC)CC"
},
{
"type": "NAME",
"value": "triethylamine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B1",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B1 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 1): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 1 of 2 toward C=CC(=O)N(c1ccc(NS(C)(=O)=O)cc1)n1cnnc1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C=CC(=O)Nn1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 2,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
180.0500030517578
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[45] | Record 46 | REACTANT: O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1 REACTANT: OB(O)c1cc2ccccc2o1 REAGENT: triethylamine SOLVENT: toluene SOLVENT: chloroform | Not reported | O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)S(=O)(=O)C(F)(F)F)cc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1.OB(O)c1cc2ccccc2o1>>O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)S(=O)(=O)C(F)(F)F)cc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(NS(=O)(=O)C(F)(F)F)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 2, well B1 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1cc2ccccc2o1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(CC)CC"
},
{
"type": "NAME",
"value": "triethylamine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccccc1"
},
{
"type": "NAME",
"value": "toluene"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "ClC(Cl)Cl"
},
{
"type": "NAME",
"value": "chloroform"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported; total well volume 500 uL (queue total_volume)"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B2",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B2 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 11): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)S(=O)(=O)C(F)(F)F)cc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=[N+]([O-])c1ccc(N(c2cc3ccccc3o2)S(=O)(=O)C(F)(F)F)cc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[46] | Record 47 | REACTANT: Nc1ccc(-c2ccccc2)cc1 REACTANT: O=S(=O)(Cl)c1cccs1 REAGENT: pyridine | Not reported | O=S(=O)(Nc1ccc(-c2ccccc2)cc1)c1cccs1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Nc1ccc(-c2ccccc2)cc1.O=S(=O)(Cl)c1cccs1>>O=S(=O)(Nc1ccc(-c2ccccc2)cc1)c1cccs1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(-c2ccccc2)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 2, well B5 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=S(=O)(Cl)c1cccs1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccncc1"
},
{
"type": "NAME",
"value": "pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B3",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B3 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 19): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 3 toward O=C(CBr)N(c1ccc(-c2ccccc2)cc1)S(=O)(=O)c1cccs1 (queue final_product flag 'no'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=S(=O)(Nc1ccc(-c2ccccc2)cc1)c1cccs1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[47] | Record 48 | REACTANT: c1ccc2ncc(Nn3cnnc3)cc2c1 REACTANT: O=C(O)c1ccc(O)cc1 REAGENT: 4-(dimethylamino)pyridine REAGENT: EDC hydrochloride SOLVENT: N,N-dimethylformamide | Not reported | O=C(c1ccc(O)cc1)N(c1cnc2ccccc2c1)n1cnnc1 · CUSTOM: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "c1ccc2ncc(Nn3cnnc3)cc2c1.O=C(O)c1ccc(O)cc1>>O=C(c1ccc(O)cc1)N(c1cnc2ccccc2c1)n1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2ncc(Nn3cnnc3)cc2c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well B8 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(O)c1ccc(O)cc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccncc1"
},
{
"type": "NAME",
"value": "4-(dimethylamino)pyridine"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=C=NCCCN(C)C.Cl"
},
{
"type": "NAME",
"value": "EDC hydrochloride"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B4",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B4 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 35): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=C(c1ccc(O)cc1)N(c1cnc2ccccc2c1)n1cnnc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(c1ccc(O)cc1)N(c1cnc2ccccc2c1)n1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "CUSTOM",
"details": "NOT DETECTED: target not observed by automated HPLC-MS (SI retention time -1.00 min)"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[48] | Record 49 | REACTANT: Brc1cc(Br)cc(Nn2cnnc2)c1 REACTANT: O=C(Cl)Oc1ccccc1 REAGENT: sodium hydride SOLVENT: N,N-dimethylformamide | Not reported | O=C(Oc1ccccc1)N(c1cc(Br)cc(Br)c1)n1cnnc1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "Brc1cc(Br)cc(Nn2cnnc2)c1.O=C(Cl)Oc1ccccc1>>O=C(Oc1ccccc1)N(c1cc(Br)cc(Br)c1)n1cnnc1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(Br)cc(Nn2cnnc2)c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well B7 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(Cl)Oc1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[H-].[Na+]"
},
{
"type": "NAME",
"value": "sodium hydride"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B5",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B5 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 44): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=C(Oc1ccccc1)N(c1cc(Br)cc(Br)c1)n1cnnc1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well)."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C(Oc1ccccc1)N(c1cc(Br)cc(Br)c1)n1cnnc1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 6.369999885559082,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
477.9200134277344
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||
| reactions[49] | Record 50 | REACTANT: O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1 REACTANT: O=S(=O)(Cl)c1ccccc1 REAGENT: potassium carbonate SOLVENT: N,N-dimethylformamide | Not reported | O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccccc2)c([N+](=O)[O-])c1 · IDENTITY: — [LCMS] | 10.1021/acscentsci.4c01991 |
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",
"details": "queue reaction_smiles (planned transformation)",
"value": "O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1.O=S(=O)(Cl)c1ccccc1>>O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccccc2)c([N+](=O)[O-])c1"
}
],
"inputs": {
"reactant 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(Nn2cnnc2)c([N+](=O)[O-])c1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT",
"preparations": [
{
"type": "SYNTHESIZED",
"details": "made on the platform in MF-BO iteration 1, plate 1, well A12 of this dataset (detected by HPLC-MS there); crude/purified state before use not reported"
}
]
}
],
"addition_order": 1
},
"reactant 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=S(=O)(Cl)c1ccccc1"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction; platform tasks are of the form 'react 15 umol of A and B' (SI p. S25)"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"reagents": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])[O-].[K+].[K+]"
},
{
"type": "NAME",
"value": "potassium carbonate"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "not reported per reaction"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C=O"
},
{
"type": "NAME",
"value": "N,N-dimethylformamide"
}
],
"amount": {
"volume": {
"value": 500,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "MF-BO iteration 1, reaction plate 3, well B6",
"volume": {
"value": 500,
"units": "MICROLITER"
}
},
"is_automated": true,
"automation_platform": "MIT autonomous chemistry platform (Koscher et al., Science 2023): liquid handler with well-plate reactors, robot arm, HPLC-MS"
},
"notes": {
"procedure_details": "Automated reaction, MF-BO iteration 1, plate 3, well B6 (SI Table S2). Conditions are the platform's selected conditions from the Zenodo queue file iteration1/new_2_20_38_queue.json (entry 52): ASKCOS condition recommendation adjusted by human-curated platform rules (SI p. S8). Reagent/catalyst amounts, temperature and time are not reported per reaction; total volume 500 uL. Route context: step 2 of 2 toward O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccccc2)c([N+](=O)[O-])c1 (queue final_product flag 'yes'; the flag's meaning is not documented and is not an outcome of this well). This well's product is an intermediate shared by 2 queued routes."
},
"outcomes": [
{
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc(N(n2cnnc2)S(=O)(=O)c2ccccc2)c([N+](=O)[O-])c1"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "target detected by automated HPLC-MS (qualitative; no yield reported)",
"retention_time": {
"value": 4.78000020980835,
"units": "MINUTE"
},
"mass_spec_details": {
"type": "EIC",
"details": "most abundant product ion",
"eic_masses": [
415.04998779296875
]
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Automated HPLC-MS of the crude reaction; outcome determined automatically. SI Tables S2/S3 report retention time (-1.00 = failed) and the m/z of the most abundant ion of the product of interest. Raw data: Automated_HPLC_data.zip on Zenodo, by iteration/plate/well."
}
}
}
],
"provenance": {
"city": "Cambridge, MA, USA",
"doi": "10.1021/acscentsci.4c01991",
"publication_url": "https://doi.org/10.1021/acscentsci.4c01991",
"record_created": {
"time": {
"value": "2026-10-14T05:15:22Z"
},
"person": {
"username": "ord-curator",
"email": "ord-curator@example.org"
},
"details": "Curated from SI Tables S2/S3 and Zenodo 10.5281/zenodo.13983042 platform_queue_scripts.zip (CC-BY-4.0)"
}
}
} | |||||