ORD record viewer · decoder definitions: ord-schema 0.8.3
Table numbers are rounded to 7 significant digits; decoded details retain full precision.
Parallel Groebke-Blackburn-Bienayme reaction library (Govor et al., BJOC 2024)
Dataset description
Parallel Groebke-Blackburn-Bienayme three-component reactions (2-amino-azine 1 + aldehyde 2 + isonitrile 3 -> 3-amino-imidazo[1,2-a]azine 4) from E. V. Govor et al., 'Generation of multimillion chemical space based on the parallel Groebke-Blackburn-Bienayme reaction', Beilstein J. Org. Chem. 2024, 20, 1604-1613, doi:10.3762/bjoc.20.143 (Enamine). All 2052 entries of SI File 2 are included, kept together in one dataset and distinguished in each reaction's conditions/notes: (a) 580 preliminary experiments with TsOH (entries 1-580), (b) 580 preliminary experiments with Sc(OTf)3 (entries 581-1160; 24 products appear in both screens), (c) the 892-member library run with Sc(OTf)3 (entries 1161-2052). Each reaction: 0.270 mmol of each reactant, 10 mol % catalyst, MeOH 0.5 mL, rt, 16 h (iPr2NEt 1 equiv when the amine was a salt), evaporation, DMSO, filtration, prep. HPLC. Isolated yields (mg and %) as reported; 0% entries (failed syntheses) are kept as negative results. Products purified with a TFA additive may have been isolated as trifluoroacetate salts (not specified per entry); the reported % yields are consistent with the free-base molecular weights.
Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.
| Location | Record | Inputs and roles | Temperature | Reported measurements | Source |
|---|---|---|---|---|---|
| reactions[0] | Record 1 | REACTANT: Cc1cc(CO)cc(C=O)n1 REACTANT: Cl.Nc1cc(ccn1)c2ncon2 REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: Cn1nnc(C[N+]#[C-])n1 SOLVENT: methanol | Not reported | CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1 · AMOUNT: — [isolated] CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1 · YIELD: 84% [isolated] CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[0]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cl.Nc1cc(ccn1)c2ncon2.Cc1cc(CO)cc(C=O)n1.Cn1nnc(C[N+]#[C-])n1>Cc1ccc(cc1)S(=O)(=O)O.CO>CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1cc(CO)cc(C=O)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cl.Nc1cc(ccn1)c2ncon2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{28}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1nnc(C[N+]#[C-])n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{4}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) and iPr2NEt (1.0 equiv, 0.270 mmol; amine used as the salt) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #1, product 4{28,7,4}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CN1N=NC(CNC2=C(N=C3C=C(C=CN23)C2=NOC=N2)C2=CC(CO)=CC(C)=N2)=N1 |c:2,11,13,21,28,31,33,t:7,9,18,24|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{28,7,4}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8786958949"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 94.4000015258789,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 84
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
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"reaction_role": "PRODUCT"
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"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[1] | Record 2 | REACTANT: COCc1nocc1C=O REACTANT: CC(C)(C)OC(=O)N1CC(C1)Oc2ccc(N)nc2 CATALYST: p-toluenesulfonic acid REACTANT: COCCC[N+]#[C-] SOLVENT: methanol | Not reported | COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC · AMOUNT: — [isolated] COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC · YIELD: 72% [isolated] COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[1]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CC(C)(C)OC(=O)N1CC(C1)Oc2ccc(N)nc2.COCc1nocc1C=O.COCCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCc1nocc1C=O"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{8}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)OC(=O)N1CC(C1)Oc2ccc(N)nc2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{29}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{5}"
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],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
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"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
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{
"type": "SMILES",
"value": "CO"
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],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #2, product 4{29,8,5}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COCCCNC1=C(N=C2C=CC(OC3CN(C3)C(=O)OC(C)(C)C)=CN12)C1=CON=C1COC |c:10,25,33,t:6,8,30|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{29,8,5}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8801681836"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 94.80000305175781,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 72
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[2] | Record 3 | REACTANT: O=Cc1ccsc1 REACTANT: Cc1ccc(cc1)c2cccc(N)n2 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1 · YIELD: 71% [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[2]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1ccc(cc1)c2cccc(N)n2.O=Cc1ccsc1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccsc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{9}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(cc1)c2cccc(N)n2"
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{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{30}"
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"amount": {
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"value": 0.27000001072883606,
"units": "MILLIMOLE"
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"reaction_role": "REACTANT",
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],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #3, product 4{30,9,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC=C(N12)C1=CC=C(C)C=C1)C1=CSC=C1 |c:13,15,25,31,t:9,11,20,22,28|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{30,9,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8784060473"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 79.9000015258789,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 71
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[3] | Record 4 | REACTANT: Cc1ccnc(C=O)c1 REACTANT: Nc1ccc2OCCc2n1 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1 · YIELD: 70% [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[3]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc2OCCc2n1.Cc1ccnc(C=O)c1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccnc(C=O)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{10}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc2OCCc2n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{31}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #4, product 4{31,10,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC3=C(CCO3)N12)C1=NC=CC(C)=C1 |c:13,26,29,t:9,11,15,24|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{31,10,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8778277510"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 72,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 70
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[4] | Record 5 | REACTANT: FC(F)(F)Cn1ccc(C=O)n1 REACTANT: CP(=O)(C)c1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1 · AMOUNT: — [isolated] CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1 · YIELD: 69% [isolated] CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[4]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CP(=O)(C)c1ccnc(N)c1.FC(F)(F)Cn1ccc(C=O)n1.[C-]#[N+]C1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "FC(F)(F)Cn1ccc(C=O)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{11}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(=O)(C)c1ccnc(N)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{32}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #5, product 4{32,11,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CP(C)(=O)C1=CC2=NC(=C(NC3CCOCC3)N2C=C1)C1=NN(CC(F)(F)F)C=C1 |c:20,31,t:4,6,8,23|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{32,11,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8803896935"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 82.4000015258789,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 69
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[5] | Record 6 | REACTANT: O=Cc1ccsc1 REACTANT: CCCSc1cccc(N)n1 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1 · AMOUNT: — [isolated] CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1 · YIELD: 66% [isolated] CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[5]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CCCSc1cccc(N)n1.O=Cc1ccsc1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccsc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{9}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCSc1cccc(N)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{33}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #6, product 4{33,9,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCCSC1=CC=CC2=NC(=C(NCCCC(=O)OCC)N12)C1=CSC=C1 |c:6,27,t:4,8,10,24|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{33,9,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8797783068"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 72,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 66
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[6] | Record 7 | REACTANT: COc1ccc(C=O)cn1 REACTANT: CP(=O)(C)c1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O · AMOUNT: — [isolated] COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O · YIELD: 66% [isolated] COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[6]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CP(=O)(C)c1ccnc(N)c1.COc1ccc(C=O)cn1.[C-]#[N+]C1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(C=O)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{12}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(=O)(C)c1ccnc(N)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
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}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
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{
"type": "NAME",
"value": "methanol"
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{
"type": "SMILES",
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],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #7, product 4{32,12,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=NC=C(C=C1)C1=C(NC2CCOCC2)N2C=CC(=CC2=N1)P(C)(C)=O |c:4,6,9,20,22,25,t:2|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{32,12,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8798985026"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 70.9000015258789,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 66
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[7] | Record 8 | REACTANT: Cc1[nH]nnc1C=O REACTANT: Cc1nc(n[nH]1)c2ccnc(N)c2 CATALYST: p-toluenesulfonic acid REACTANT: COC(=O)C(Cc1ccccc1)[N+]#[C-] SOLVENT: methanol | Not reported | COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1 · AMOUNT: — [isolated] COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1 · YIELD: 65% [isolated] COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[7]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1nc(n[nH]1)c2ccnc(N)c2.Cc1[nH]nnc1C=O.COC(=O)C(Cc1ccccc1)[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1[nH]nnc1C=O"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{13}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1nc(n[nH]1)c2ccnc(N)c2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{34}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)C(Cc1ccccc1)[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{8}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #8, product 4{34,13,8}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC(=O)C(CC1=CC=CC=C1)NC1=C(N=C2C=C(C=CN12)C1=NNC(C)=N1)C1=C(C)NN=N1 |c:8,10,18,20,29,32,36,t:6,14,16,25|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{34,13,8}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8801681814"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 80.0999984741211,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 65
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[8] | Record 9 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Cc1ccc(N)nc1 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1 · YIELD: 64% [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[8]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1ccc(N)nc1.Cc1ccc(C=O)cc1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{14}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"amine": {
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{
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{
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}
},
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"is_limiting": true
}
],
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},
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{
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{
"type": "NAME",
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},
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}
],
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{
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},
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},
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}
],
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},
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},
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"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
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},
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{
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{
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},
{
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{
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},
{
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{
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],
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},
"is_mined": false
}
} | |||||
| reactions[9] | Record 10 | REACTANT: COc1ccc(C=O)cc1 REACTANT: Nc1ccc(Br)cn1 CATALYST: p-toluenesulfonic acid REACTANT: C[N+]#[C-] SOLVENT: methanol | Not reported | CNC1=C(N=C2C=CC(Br)=CN12)C1=CC=C(OC)C=C1 · AMOUNT: — [isolated] CNC1=C(N=C2C=CC(Br)=CN12)C1=CC=C(OC)C=C1 · YIELD: 64% [isolated] CNC1=C(N=C2C=CC(Br)=CN12)C1=CC=C(OC)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
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{
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}
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{
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{
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{
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{
"identifiers": [
{
"type": "SMILES",
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},
{
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},
{
"type": "CUSTOM",
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},
{
"type": "CUSTOM",
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],
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{
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}
}
],
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},
"is_mined": false
}
} | |||||
| reactions[10] | Record 11 | REACTANT: Cn1ncc(CNC(=O)OC(C)(C)C)c1C=O REACTANT: Cl.Nc1cccc(n1)C(F)F REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOC1 SOLVENT: methanol | Not reported | CN1N=CC(CNC(=O)OC(C)(C)C)=C1C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · AMOUNT: — [isolated] CN1N=CC(CNC(=O)OC(C)(C)C)=C1C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · YIELD: 63% [isolated] CN1N=CC(CNC(=O)OC(C)(C)C)=C1C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[10]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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},
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},
"notes": {
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],
"outcomes": [
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{
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{
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},
{
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},
{
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],
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},
"is_mined": false
}
} | |||||
| reactions[11] | Record 12 | REACTANT: CCOc1cnc(C=O)nc1 REACTANT: Nc1cc(C#N)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: C[N+]#[C-] SOLVENT: methanol | Not reported | CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N · AMOUNT: — [isolated] CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N · YIELD: 63% [isolated] CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[11]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1cc(C#N)ccn1.CCOc1cnc(C=O)nc1.C[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOc1cnc(C=O)nc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{17}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1cc(C#N)ccn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{38}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{9}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #12, product 4{38,17,9}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC1=CN=C(N=C1)C1=C(NC)N2C=CC(=CC2=N1)C#N |c:5,7,10,15,17,20,t:3|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{38,17,9}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810902991"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 50,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 63
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[12] | Record 13 | REACTANT: Cc1ccnc(C=O)c1 REACTANT: Nc1ncc(Br)c2CCCc21 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1 · YIELD: 61% [isolated] CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[12]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ncc(Br)c2CCCc21.Cc1ccnc(C=O)c1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccnc(C=O)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{10}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ncc(Br)c2CCCc21"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{39}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #13, product 4{39,10,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2N1C=C(Br)C1=C2CCC1)C1=NC=CC(C)=C1 |c:11,18,27,30,t:9,15,25|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{39,10,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8784060925"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 75.9000015258789,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 61
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[13] | Record 14 | REACTANT: OCCn1cc(C=O)cn1 REACTANT: Cc1cc(cc(N)n1)C(F)(F)F CATALYST: p-toluenesulfonic acid REACTANT: Cn1nnc(C[N+]#[C-])n1 SOLVENT: methanol | Not reported | CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1 · AMOUNT: — [isolated] CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1 · YIELD: 61% [isolated] CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[13]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1cc(cc(N)n1)C(F)(F)F.OCCn1cc(C=O)cn1.Cn1nnc(C[N+]#[C-])n1>Cc1ccc(cc1)S(=O)(=O)O.CO>CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OCCn1cc(C=O)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{18}"
}
],
"amount": {
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}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
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},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{40}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
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}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1nnc(C[N+]#[C-])n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{4}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #14, product 4{40,18,4}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CN1N=NC(CNC2=C(N=C3C=C(C=C(C)N23)C(F)(F)F)C2=CN(CCO)N=C2)=N1 |c:2,11,29,31,t:7,9,13,23|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{40,18,4}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8781341796"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 69.69999694824219,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 61
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[14] | Record 15 | REACTANT: COc1cnn(C)c1C=O REACTANT: Cc1cnc(N)cn1 CATALYST: p-toluenesulfonic acid REACTANT: Brc1cccc(C[N+]#[C-])c1 SOLVENT: methanol | Not reported | COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1 · AMOUNT: — [isolated] COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1 · YIELD: 61% [isolated] COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[14]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1cnc(N)cn1.COc1cnn(C)c1C=O.Brc1cccc(C[N+]#[C-])c1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cnn(C)c1C=O"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{19}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1cnc(N)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{41}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cccc(C[N+]#[C-])c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{11}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #15, product 4{41,19,11}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=C(N(C)N=C1)C1=C(NCC2=CC(Br)=CC=C2)N2C=C(C)N=CC2=N1 |c:6,9,16,18,25,28,t:2,13,22|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{41,19,11}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8781341780"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 70.30000305175781,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 61
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[15] | Record 16 | REACTANT: CCn1cc(C=O)nn1 REACTANT: CSc1ccc(N)nc1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1 · AMOUNT: — [isolated] CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1 · YIELD: 59% [isolated] CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[15]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CSc1ccc(N)nc1.CCn1cc(C=O)nn1.[C-]#[N+]C1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCn1cc(C=O)nn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{20}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CSc1ccc(N)nc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{42}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #16, product 4{42,20,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCN1C=C(N=N1)C1=C(NC2CCOCC2)N2C=C(SC)C=CC2=N1 |c:3,5,8,23,26,t:19|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{42,20,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810902980"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 57.5,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 59
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[16] | Record 17 | REACTANT: O=Cc1ccn2ncnc2c1 REACTANT: CC(C)(C)OC(=O)N1Cc2ccc(N)nc2C1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOC1 SOLVENT: methanol | Not reported | CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1 · AMOUNT: — [isolated] CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1 · YIELD: 58% [isolated] CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[16]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CC(C)(C)OC(=O)N1Cc2ccc(N)nc2C1.O=Cc1ccn2ncnc2c1.[C-]#[N+]CC1CCOC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccn2ncnc2c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{21}"
}
],
"amount": {
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}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)OC(=O)N1Cc2ccc(N)nc2C1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
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{
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}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOC1"
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{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #17, product 4{43,21,12}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC(C)(C)OC(=O)N1CC2=C(C1)N1C(NCC3CCOC3)=C(N=C1C=C2)C1=CC2=NC=NN2C=C1 |c:9,22,24,27,34,38,t:30,32|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{43,21,12}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8798985027"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 74.5999984741211,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 58
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[17] | Record 18 | REACTANT: O=Cc1ccccc1 REACTANT: CCc1cnc(N)cn1 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1 · YIELD: 58% [isolated] CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[17]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CCc1cnc(N)cn1.O=Cc1ccccc1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccccc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{22}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCc1cnc(N)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{44}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #18, product 4{44,22,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2C=NC(CC)=CN12)C1=CC=CC=C1 |c:13,17,24,26,t:9,11,22|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{44,22,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8741907003"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 54.900001525878906,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 58
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[18] | Record 19 | REACTANT: FC(F)(F)c1nc(C=O)c2CCCCn12 REACTANT: Cl.Nc1cc(F)ccn1 REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOC1 SOLVENT: methanol | Not reported | FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F · AMOUNT: — [isolated] FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F · YIELD: 57% [isolated] FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[18]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cl.Nc1cc(F)ccn1.FC(F)(F)c1nc(C=O)c2CCCCn12.[C-]#[N+]C1CCOC1>Cc1ccc(cc1)S(=O)(=O)O.CO>FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "FC(F)(F)c1nc(C=O)c2CCCCn12"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cl.Nc1cc(F)ccn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{45}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{10}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) and iPr2NEt (1.0 equiv, 0.270 mmol; amine used as the salt) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #19, product 4{45,23,10}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "FC1=CC2=NC(=C(NC3CCOC3)N2C=C1)C1=C2CCCCN2C(=N1)C(F)(F)F |c:16,19,27,t:1,3,5|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{45,23,10}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8803896946"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 62.900001525878906,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[19] | Record 20 | REACTANT: OCCn1cc(C=O)cn1 REACTANT: Nc1ccccn1 CATALYST: p-toluenesulfonic acid REACTANT: COc1ccc(C[N+]#[C-])cc1 SOLVENT: methanol | Not reported | COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1 · AMOUNT: — [isolated] COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1 · YIELD: 57% [isolated] COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[19]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccccn1.OCCn1cc(C=O)cn1.COc1ccc(C[N+]#[C-])cc1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OCCn1cc(C=O)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{18}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccccn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{46}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(C[N+]#[C-])cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{13}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #20, product 4{46,18,13}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=CC=C(CNC2=C(N=C3C=CC=CN23)C2=CN(CCO)N=C2)C=C1 |c:12,14,25,28,t:2,4,8,10,19|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{46,18,13}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810903006"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 55.79999923706055,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[20] | Record 21 | REACTANT: CN(C)c1cccc(C=O)c1 REACTANT: Cl.Nc1cc(ccn1)S(=O)(=O)N REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: COCC[N+]#[C-] SOLVENT: methanol | Not reported | COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C · AMOUNT: — [isolated] COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C · YIELD: 57% [isolated] COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[20]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cl.Nc1cc(ccn1)S(=O)(=O)N.CN(C)c1cccc(C=O)c1.COCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1cccc(C=O)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{24}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cl.Nc1cc(ccn1)S(=O)(=O)N"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{47}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{14}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) and iPr2NEt (1.0 equiv, 0.270 mmol; amine used as the salt) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #21, product 4{47,24,14}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COCCNC1=C(N=C2C=C(C=CN12)S(N)(=O)=O)C1=CC(=CC=C1)N(C)C |c:9,11,22,24,t:5,7,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{47,24,14}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8798985048"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 59.599998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[21] | Record 22 | REACTANT: O=Cc1cnc(nc1)C2CCOCC2 REACTANT: CS(=O)(=O)c1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: CC[N+]#[C-] SOLVENT: methanol | Not reported | CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1 · AMOUNT: — [isolated] CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1 · YIELD: 57% [isolated] CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[21]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CS(=O)(=O)c1ccnc(N)c1.O=Cc1cnc(nc1)C2CCOCC2.CC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1cnc(nc1)C2CCOCC2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{25}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)c1ccnc(N)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{48}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{15}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #22, product 4{48,25,15}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCNC1=C(N=C2C=C(C=CN12)S(C)(=O)=O)C1=CN=C(N=C1)C1CCOCC1 |c:7,9,20,22,t:3,5,18|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{48,25,15}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8781341798"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 61.400001525878906,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[22] | Record 23 | REACTANT: O=CCCc1ccccc1 REACTANT: Nc1cccc(CO)n1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · AMOUNT: — [isolated] OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · YIELD: 57% [isolated] OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[22]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1cccc(CO)n1.O=CCCc1ccccc1.[C-]#[N+]C1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=CCCc1ccccc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{26}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1cccc(CO)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{49}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #23, product 4{49,26,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "OCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 |c:4,13,15,t:2,6,11,17|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{49,26,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8741906954"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 53.79999923706055,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[23] | Record 24 | REACTANT: Cc1nc(C=O)nn1C REACTANT: CP(=O)(C)c1cccc(N)n1 CATALYST: p-toluenesulfonic acid REACTANT: Cc1cccc(C)c1[N+]#[C-] SOLVENT: methanol | Not reported | CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1 · AMOUNT: — [isolated] CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1 · YIELD: 57% [isolated] CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[23]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CP(=O)(C)c1cccc(N)n1.Cc1nc(C=O)nn1C.Cc1cccc(C)c1[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1nc(C=O)nn1C"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{27}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(=O)(C)c1cccc(N)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{50}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1cccc(C)c1[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{16}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #24, product 4{50,27,16}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CN1N=C(N=C1C)C1=C(NC2=C(C)C=CC=C2C)N2C(C=CC=C2P(C)(C)=O)=N1 |c:2,4,8,11,14,16,22,24,30|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{50,27,16}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8781341789"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 62.5,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[24] | Record 25 | REACTANT: O=Cc1ccccc1 REACTANT: Cc1nc(N)ccc1Cl CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1 · AMOUNT: — [isolated] CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1 · YIELD: 57% [isolated] CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[24]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1nc(N)ccc1Cl.O=Cc1ccccc1.[C-]#[N+]CC1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccccc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{22}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1nc(N)ccc1Cl"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{51}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{17}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #25, product 4{51,22,17}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC1=C(Cl)C=CC2=NC(=C(NCC3CCOCC3)N12)C1=CC=CC=C1 |c:1,4,24,26,t:6,8,22|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{51,22,17}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8741907089"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 54.400001525878906,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[25] | Record 26 | REACTANT: O=Cc1cnn(c1)C2CCS(=O)(=O)C2 REACTANT: Nc1ccc(cn1)C2(CC2)C(F)(F)F CATALYST: p-toluenesulfonic acid REACTANT: CC(C)(C)[N+]#[C-] SOLVENT: methanol | Not reported | CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1 · AMOUNT: — [isolated] CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1 · YIELD: 57% [isolated] CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[25]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc(cn1)C2(CC2)C(F)(F)F.O=Cc1cnn(c1)C2CCS(=O)(=O)C2.CC(C)(C)[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1cnn(c1)C2CCS(=O)(=O)C2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{28}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(cn1)C2(CC2)C(F)(F)F"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{52}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{18}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #26, product 4{52,28,18}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC(C)(C)NC1=C(N=C2C=CC(=CN12)C1(CC1)C(F)(F)F)C1=CN(N=C1)C1CCS(=O)(=O)C1 |c:9,11,27,t:5,7,24|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{52,28,18}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8801681827"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 73.5999984741211,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[26] | Record 27 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Nc1ccc(CO)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1 · AMOUNT: — [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1 · YIELD: 57% [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[26]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc(CO)cn1.Cc1ccc(C=O)cc1.[C-]#[N+]CC1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{14}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(CO)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{53}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{17}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #27, product 4{53,14,17}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CO)C=CC2=N1 |c:3,5,8,24,27,t:1,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{53,14,17}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690320"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 53.70000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[27] | Record 28 | REACTANT: O=Cc1ccccc1 REACTANT: Nc1ccc(Br)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1 · AMOUNT: — [isolated] BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1 · YIELD: 57% [isolated] BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[27]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc(Br)cn1.O=Cc1ccccc1.[C-]#[N+]CC1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccccc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{22}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(Br)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{36}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{17}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #28, product 4{36,22,17}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "BrC1=CN2C(C=C1)=NC(=C2NCC1CCOCC1)C1=CC=CC=C1 |c:5,7,9,23,25,t:1,21|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{36,22,17}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8700285600"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 59,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 57
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[28] | Record 29 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Cl.CN(C)C(=O)c1ccc(N)nc1 REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1 · YIELD: 56% [isolated] CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[28]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cl.CN(C)C(=O)c1ccc(N)nc1.Cc1ccc(C=O)cc1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{14}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cl.CN(C)C(=O)c1ccc(N)nc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{54}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) and iPr2NEt (1.0 equiv, 0.270 mmol; amine used as the salt) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #29, product 4{54,14,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2C=CC(=CN12)C(=O)N(C)C)C1=CC=C(C)C=C1 |c:13,15,30,t:9,11,25,27|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{54,14,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690341"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 62.29999923706055,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 56
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[29] | Record 30 | REACTANT: CCn1ccc(C=O)n1 REACTANT: CSc1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: CCOC(=O)CCC[N+]#[C-] SOLVENT: methanol | Not reported | CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1 · AMOUNT: — [isolated] CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1 · YIELD: 56% [isolated] CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[29]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CSc1ccnc(N)c1.CCn1ccc(C=O)n1.CCOC(=O)CCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCn1ccc(C=O)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{29}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CSc1ccnc(N)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{55}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{6}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #30, product 4{55,29,6}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCOC(=O)CCCNC1=C(N=C2C=C(SC)C=CN12)C1=NN(CC)C=C1 |c:17,27,t:9,11,13,22|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{55,29,6}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8797781157"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 58.70000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 56
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[30] | Record 31 | REACTANT: O=Cc1ccsc1 REACTANT: Cn1ccc(n1)c2ccc(N)nc2 CATALYST: p-toluenesulfonic acid REACTANT: COCC[N+]#[C-] SOLVENT: methanol | Not reported | COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1 · AMOUNT: — [isolated] COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1 · YIELD: 56% [isolated] COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[30]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cn1ccc(n1)c2ccc(N)nc2.O=Cc1ccsc1.COCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccsc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{9}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1ccc(n1)c2ccc(N)nc2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{56}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{14}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #31, product 4{56,9,14}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COCCNC1=C(N=C2C=CC(=CN12)C1=NN(C)C=C1)C1=CSC=C1 |c:9,11,20,26,t:5,7,16,23|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{56,9,14}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8780122427"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 53.20000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 56
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[31] | Record 32 | REACTANT: CC(=O)N1CCC(CC1)C=O REACTANT: CC(C)Oc1cnc(N)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]Cc1cccs1 SOLVENT: methanol | Not reported | CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1 · AMOUNT: — [isolated] CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1 · YIELD: 56% [isolated] CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[31]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CC(C)Oc1cnc(N)cn1.CC(=O)N1CCC(CC1)C=O.[C-]#[N+]Cc1cccs1>Cc1ccc(cc1)S(=O)(=O)O.CO>CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)N1CCC(CC1)C=O"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{30}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cnc(N)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{57}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]Cc1cccs1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{19}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #32, product 4{57,30,19}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC(C)OC1=CN2C(C=N1)=NC(C1CCN(CC1)C(C)=O)=C2NCC1=CC=CS1 |c:8,10,22,29,t:4,27|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{57,30,19}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8786958905"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 62.20000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 56
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[32] | Record 33 | REACTANT: O=CCCc1ccccc1 REACTANT: Nc1cc(OC2COC2)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1 · AMOUNT: — [isolated] C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1 · YIELD: 56% [isolated] C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[32]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1cc(OC2COC2)ccn1.O=CCCc1ccccc1.[C-]#[N+]C1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=CCCc1ccccc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{26}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1cc(OC2COC2)ccn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
"moles": {
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"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #33, product 4{58,26,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "C(CC1=CC=CC=C1)C1=C(NC2CCOCC2)N2C=CC(OC3COC3)=CC2=N1 |c:4,6,9,20,28,31,t:2|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{58,26,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690336"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 59.099998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 56
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[33] | Record 34 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Nc1ccc(CN2CCOCC2)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1 · AMOUNT: — [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1 · YIELD: 55% [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[33]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc(CN2CCOCC2)cn1.Cc1ccc(C=O)cc1.[C-]#[N+]CC1CCOCC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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],
"amount": {
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"units": "MILLIMOLE"
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],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(CN2CCOCC2)cn1"
},
{
"type": "CUSTOM",
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}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
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},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
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}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOCC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{17}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #34, product 4{59,14,17}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(CN3CCOCC3)C=CC2=N1 |c:3,5,8,30,33,t:1,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{59,14,17}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690335"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 62.79999923706055,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[34] | Record 35 | REACTANT: CCn1ccc(C=O)n1 REACTANT: COc1cnc(N)c(F)c1 CATALYST: p-toluenesulfonic acid REACTANT: COCC[N+]#[C-] SOLVENT: methanol | Not reported | CCN1C=CC(=N1)C1=C(NCCOC)N2C=C(OC)C=C(F)C2=N1 · AMOUNT: — [isolated] CCN1C=CC(=N1)C1=C(NCCOC)N2C=C(OC)C=C(F)C2=N1 · YIELD: 55% [isolated] CCN1C=CC(=N1)C1=C(NCCOC)N2C=C(OC)C=C(F)C2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[34]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
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{
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],
"inputs": {
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"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCn1ccc(C=O)n1"
},
{
"type": "CUSTOM",
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],
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},
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],
"addition_order": 1
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{
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{
"type": "SMILES",
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],
"amount": {
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},
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],
"addition_order": 1
},
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{
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{
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"amount": {
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}
],
"addition_order": 1
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{
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{
"type": "SMILES",
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{
"type": "CUSTOM",
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"amount": {
"moles": {
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"addition_order": 1
},
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{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
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{
"type": "SMILES",
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"volume": {
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"units": "MILLILITER"
},
"volume_includes_solutes": false
},
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}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #35, product 4{60,29,14}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
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],
"amount": {
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"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
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{
"identifiers": [
{
"type": "SMILES",
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},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCN1C=CC(=N1)C1=C(NCCOC)N2C=C(OC)C=C(F)C2=N1 |c:3,5,8,24,t:16,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{60,29,14}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8780122035"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 49.70000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
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"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[35] | Record 36 | REACTANT: COc1ccc(C=O)cc1 REACTANT: Nc1cc(C#N)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: COCC[N+]#[C-] SOLVENT: methanol | Not reported | COCCNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(OC)C=C1 · AMOUNT: — [isolated] COCCNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(OC)C=C1 · YIELD: 55% [isolated] COCCNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(OC)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[35]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_SMILES",
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},
{
"type": "REACTION_TYPE",
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],
"inputs": {
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{
"identifiers": [
{
"type": "SMILES",
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{
"type": "CUSTOM",
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],
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"amine": {
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{
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{
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{
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],
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},
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],
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},
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{
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{
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{
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],
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],
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{
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{
"type": "SMILES",
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{
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],
"addition_order": 1
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"solvent": {
"components": [
{
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{
"type": "NAME",
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{
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],
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"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #36, product 4{38,15,14}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
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{
"type": "NAME",
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{
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],
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}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(OC)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COCCNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(OC)C=C1 |c:9,11,24,t:5,7,18,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{38,15,14}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8711876682"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
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"amount": {
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}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
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],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
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"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
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"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[36] | Record 37 | REACTANT: O=CCCc1ccccc1 REACTANT: CCc1cccc(N)n1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOCC1 SOLVENT: methanol | Not reported | CCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · AMOUNT: — [isolated] CCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · YIELD: 55% [isolated] CCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
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"inputs": {
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{
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{
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{
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"isonitrile": {
"components": [
{
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{
"type": "SMILES",
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{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{7}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #37, product 4{61,26,7}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCC1=CC=CC2=NC(CCC3=CC=CC=C3)=C(NC3CCOCC3)N12 |c:4,13,15,t:2,6,11,17|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{61,26,7}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690325"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 52.099998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[37] | Record 38 | REACTANT: O=Cc1cnc[nH]1 REACTANT: Nc1cc(CO)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: COc1ccc([N+]#[C-])c(C)c1 SOLVENT: methanol | Not reported | COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1 · AMOUNT: — [isolated] COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1 · YIELD: 55% [isolated] COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[37]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1cc(CO)ccn1.O=Cc1cnc[nH]1.COc1ccc([N+]#[C-])c(C)c1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1cnc[nH]1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{31}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1cc(CO)ccn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{62}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc([N+]#[C-])c(C)c1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{20}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #38, product 4{62,31,20}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=CC(C)=C(NC2=C(N=C3C=C(CO)C=CN23)C2=CN=CN2)C=C1 |c:16,23,27,t:2,5,8,10,12,21|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{62,31,20}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810902966"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 52.099998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[38] | Record 39 | REACTANT: Cn1nccc1[C@@H]2C[C@H]2C=O REACTANT: COc1c(C)ccnc1N CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOC1 SOLVENT: methanol | Not reported | COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C · AMOUNT: — [isolated] COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C · YIELD: 55% [isolated] COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[38]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "COc1c(C)ccnc1N.Cn1nccc1[C@@H]2C[C@H]2C=O.[C-]#[N+]C1CCOC1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cn1nccc1[C@@H]2C[C@H]2C=O"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "Cn1nccc1[C@@H]2C[C@H]2C=O |&1:6,8,r|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{32}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1c(C)ccnc1N"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{63}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1CCOC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{10}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #39, product 4{63,32,10}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=C(C)C=CN2C(NC3CCOC3)=C(N=C12)[C@@H]1C[C@H]1C1=CC=NN1C |&1:18,20,r,c:2,5,15,27,t:17,25|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{63,32,10}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810903003"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 54.599998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[39] | Record 40 | REACTANT: COc1ccc(C=O)cc1 REACTANT: Nc1cc(CO)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: COc1ccc(C[N+]#[C-])cc1 SOLVENT: methanol | Not reported | COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1 · AMOUNT: — [isolated] COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1 · YIELD: 55% [isolated] COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[39]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1cc(CO)ccn1.COc1ccc(C=O)cc1.COc1ccc(C[N+]#[C-])cc1>Cc1ccc(cc1)S(=O)(=O)O.CO>COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{15}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
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}
],
"addition_order": 1
},
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{
"identifiers": [
{
"type": "SMILES",
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{
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"amount": {
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}
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}
],
"addition_order": 1
},
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{
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{
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{
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],
"amount": {
"moles": {
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}
},
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}
],
"addition_order": 1
},
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{
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"type": "SMILES",
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{
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],
"amount": {
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},
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}
],
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},
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{
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{
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{
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],
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"units": "MILLILITER"
},
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},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #40, product 4{62,15,13}."
},
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{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
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"components": [
{
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{
"type": "NAME",
"value": "DMSO"
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{
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"amount": {
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"value": 1,
"precision": 0.5,
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},
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}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
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},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
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{
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{
"type": "SMILES",
"value": "COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC1=CC=C(CNC2=C(N=C3C=C(CO)C=CN23)C2=CC=C(OC)C=C2)C=C1 |c:16,27,30,t:2,4,8,10,12,21,23|"
},
{
"type": "CUSTOM",
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{
"type": "CUSTOM",
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"value": "Z8776690332"
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],
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{
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},
{
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"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
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"type": "WEIGHT",
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}
}
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"provenance": {
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},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[40] | Record 41 | REACTANT: CC(=O)N1CCCC(C1)C=O REACTANT: Cl.Nc1cccc(n1)C(F)F REAGENT: N,N-diisopropylethylamine CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1CCOC1 SOLVENT: methanol | Not reported | CC(=O)N1CCCC(C1)C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · AMOUNT: — [isolated] CC(=O)N1CCCC(C1)C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · YIELD: 55% [isolated] CC(=O)N1CCCC(C1)C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
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],
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{
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},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) and iPr2NEt (1.0 equiv, 0.270 mmol; amine used as the salt) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #41, product 4{37,33,10}."
},
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{
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"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
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"components": [
{
"identifiers": [
{
"type": "NAME",
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{
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],
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"volume": {
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},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
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"units": "HOUR"
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{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)N1CCCC(C1)C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC(=O)N1CCCC(C1)C1=C(NC2CCOC2)N2C(C=CC=C2C(F)F)=N1 |c:10,21,23,28|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{37,33,10}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810903046"
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],
"is_desired_product": true,
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}
}
},
{
"analysis_key": "isolated",
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"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
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],
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],
"analyses": {
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"type": "LCMS",
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"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
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"doi": "10.3762/bjoc.20.143",
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},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[41] | Record 42 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Nc1ccc(cn1)N2CCCS2(=O)=O CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(C=CC2=N1)N1CCCS1(=O)=O · AMOUNT: — [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(C=CC2=N1)N1CCCS1(=O)=O · YIELD: 55% [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(C=CC2=N1)N1CCCS1(=O)=O · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
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},
{
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}
],
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{
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],
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{
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],
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],
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{
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],
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},
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},
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},
"notes": {
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}
},
{
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},
{
"type": "OTHER_CHROMATOGRAPHY",
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}
],
"outcomes": [
{
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{
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{
"type": "SMILES",
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},
{
"type": "CXSMILES",
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},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{64,14,17}"
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{
"type": "CUSTOM",
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"value": "Z8776690346"
}
],
"is_desired_product": true,
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"type": "AMOUNT",
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}
},
{
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"percentage": {
"value": 55
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},
{
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],
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}
],
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"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
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}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[42] | Record 43 | REACTANT: CP(=O)(C)c1ccc(C=O)cc1 REACTANT: Nc1ccc(CO)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CC1 SOLVENT: methanol | Not reported | CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1 · AMOUNT: — [isolated] CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1 · YIELD: 55% [isolated] CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[42]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Nc1ccc(CO)cn1.CP(=O)(C)c1ccc(C=O)cc1.[C-]#[N+]CC1CC1>Cc1ccc(cc1)S(=O)(=O)O.CO>CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(=O)(C)c1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{34}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1ccc(CO)cn1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{53}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
}
],
"amount": {
"moles": {
"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CC1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{21}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #43, product 4{53,34,21}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CP(C)(=O)C1=CC=C(C=C1)C1=C(NCC2CC2)N2C=C(CO)C=CC2=N1 |c:6,8,11,24,27,t:4,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{53,34,21}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810902970"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 54.70000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[43] | Record 44 | REACTANT: Cc1c(Cl)c(C=O)nn1C REACTANT: CCc1cncc(N)n1 CATALYST: p-toluenesulfonic acid REACTANT: COCCC[N+]#[C-] SOLVENT: methanol | Not reported | CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl · AMOUNT: — [isolated] CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl · YIELD: 55% [isolated] CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[43]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CCc1cncc(N)n1.Cc1c(Cl)c(C=O)nn1C.COCCC[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1c(Cl)c(C=O)nn1C"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{35}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCc1cncc(N)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{65}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
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}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "p-toluenesulfonic acid"
},
{
"type": "SMILES",
"value": "Cc1ccc(cc1)S(=O)(=O)O"
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],
"amount": {
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},
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}
],
"addition_order": 1
},
"isonitrile": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "COCCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{5}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
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"reaction_role": "REACTANT",
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],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
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{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
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},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #44, product 4{65,35,5}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CCC1=CN=CC2=NC(=C(NCCCOC)N12)C1=NN(C)C(C)=C1Cl |c:4,24,t:2,6,8,19|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{65,35,5}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8801681825"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 53.70000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[44] | Record 45 | REACTANT: Cc1nc(C=O)ccc1OC(F)F REACTANT: COCCc1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]C1COC1 SOLVENT: methanol | Not reported | COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1 · AMOUNT: — [isolated] COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1 · YIELD: 55% [isolated] COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[44]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "COCCc1ccnc(N)c1.Cc1nc(C=O)ccc1OC(F)F.[C-]#[N+]C1COC1>Cc1ccc(cc1)S(=O)(=O)O.CO>COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
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}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1nc(C=O)ccc1OC(F)F"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{36}"
}
],
"amount": {
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},
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}
],
"addition_order": 1
},
"amine": {
"components": [
{
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{
"type": "SMILES",
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},
{
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}
],
"amount": {
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},
"reaction_role": "REACTANT",
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],
"addition_order": 1
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"catalyst": {
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{
"identifiers": [
{
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{
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],
"amount": {
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"value": 0.027000000700354576,
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},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]C1COC1"
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{
"type": "CUSTOM",
"details": "compound number in the paper",
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],
"amount": {
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"value": 0.27000001072883606,
"units": "MILLIMOLE"
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},
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],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
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{
"type": "SMILES",
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}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #45, product 4{66,36,22}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
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}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COCCC1=CC2=NC(=C(NC3COC3)N2C=C1)C1=NC(C)=C(OC(F)F)C=C1 |c:18,30,t:4,6,8,21,24|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{66,36,22}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810902992"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 59.79999923706055,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[45] | Record 46 | REACTANT: COc1ccc(C=O)cc1 REACTANT: Cc1cccc(N)n1 CATALYST: p-toluenesulfonic acid REACTANT: C[N+]#[C-] SOLVENT: methanol | Not reported | CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1 · AMOUNT: — [isolated] CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1 · YIELD: 55% [isolated] CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[45]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "Cc1cccc(N)n1.COc1ccc(C=O)cc1.C[N+]#[C-]>Cc1ccc(cc1)S(=O)(=O)O.CO>CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{15}"
}
],
"amount": {
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"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
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},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{67}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
"components": [
{
"identifiers": [
{
"type": "NAME",
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{
"type": "SMILES",
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}
],
"amount": {
"moles": {
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"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C[N+]#[C-]"
},
{
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"value": "3{9}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #46, product 4{67,15,9}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CNC1=C(N=C2C=CC=C(C)N12)C1=CC=C(OC)C=C1 |c:6,20,t:2,4,8,14,16|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{67,15,9}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690314"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 39.5,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 55
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[46] | Record 47 | REACTANT: O=Cc1ccc2CCCc2n1 REACTANT: Nc1cc(C#C)ccn1 CATALYST: p-toluenesulfonic acid REACTANT: COC(=O)CCC([N+]#[C-])C(=O)OC SOLVENT: methanol | Not reported | COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC · AMOUNT: — [isolated] COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC · YIELD: 54% [isolated] COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[46]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_SMILES",
"value": "Nc1cc(C#C)ccn1.O=Cc1ccc2CCCc2n1.COC(=O)CCC([N+]#[C-])C(=O)OC>Cc1ccc(cc1)S(=O)(=O)O.CO>COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC",
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},
{
"type": "REACTION_TYPE",
"value": "Groebke-Blackburn-Bienayme three-component reaction"
}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1ccc2CCCc2n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{37}"
}
],
"amount": {
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}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
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},
{
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"value": "1{68}"
}
],
"amount": {
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}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"catalyst": {
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{
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{
"type": "NAME",
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{
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],
"amount": {
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}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)CCC([N+]#[C-])C(=O)OC"
},
{
"type": "CUSTOM",
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"value": "3{23}"
}
],
"amount": {
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},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
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}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #47, product 4{68,37,23}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
"value": "CS(C)=O"
}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "COC(=O)CCC(NC1=C(N=C2C=C(C=CN12)C#C)C1=NC2=C(CCC2)C=C1)C(=O)OC |c:12,14,29,t:8,10,21,23|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{68,37,23}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8803896955"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 63.599998474121094,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 54
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[47] | Record 48 | REACTANT: CC(=O)N1CCCC(C1)C=O REACTANT: CNC(=O)c1ccnc(N)c1 CATALYST: p-toluenesulfonic acid REACTANT: COc1cccc(C[N+]#[C-])c1 SOLVENT: methanol | Not reported | CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1 · AMOUNT: — [isolated] CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1 · YIELD: 54% [isolated] CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[47]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_SMILES",
"value": "CNC(=O)c1ccnc(N)c1.CC(=O)N1CCCC(C1)C=O.COc1cccc(C[N+]#[C-])c1>Cc1ccc(cc1)S(=O)(=O)O.CO>CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1",
"is_mapped": false
},
{
"type": "REACTION_TYPE",
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}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
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],
"addition_order": 1
},
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{
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{
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],
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},
"reaction_role": "REACTANT",
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],
"addition_order": 1
},
"catalyst": {
"components": [
{
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{
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}
],
"amount": {
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"value": 0.027000000700354576,
"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(C[N+]#[C-])c1"
},
{
"type": "CUSTOM",
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],
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},
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],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
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},
{
"type": "SMILES",
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}
],
"amount": {
"volume": {
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"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #48, product 4{69,33,24}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
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{
"type": "SMILES",
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}
],
"amount": {
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}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CNC(=O)C1=CC2=NC(C3CCCN(C3)C(C)=O)=C(NCC3=CC(OC)=CC=C3)N2C=C1 |c:26,28,33,t:4,6,18,22|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{69,33,24}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8810903000"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 64,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 54
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[48] | Record 49 | REACTANT: O=Cc1cccc(C#C)n1 REACTANT: Nc1nccnc1C2CC2 CATALYST: p-toluenesulfonic acid REACTANT: FCCC[N+]#[C-] SOLVENT: methanol | Not reported | FCCCNC1=C(N=C2N1C=CN=C2C1CC1)C1=NC(=CC=C1)C#C · AMOUNT: — [isolated] FCCCNC1=C(N=C2N1C=CN=C2C1CC1)C1=NC(=CC=C1)C#C · YIELD: 54% [isolated] FCCCNC1=C(N=C2N1C=CN=C2C1CC1)C1=NC(=CC=C1)C#C · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[48]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_SMILES",
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"is_mapped": false
},
{
"type": "REACTION_TYPE",
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}
],
"inputs": {
"aldehyde": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=Cc1cccc(C#C)n1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
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}
],
"amount": {
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"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"amine": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "Nc1nccnc1C2CC2"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "1{70}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
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}
],
"addition_order": 1
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"catalyst": {
"components": [
{
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{
"type": "NAME",
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],
"amount": {
"moles": {
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"units": "MILLIMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 1
},
"isonitrile": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "FCCC[N+]#[C-]"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "3{25}"
}
],
"amount": {
"moles": {
"value": 0.27000001072883606,
"units": "MILLIMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 1
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "methanol"
},
{
"type": "SMILES",
"value": "CO"
}
],
"amount": {
"volume": {
"value": 0.5,
"units": "MILLILITER"
},
"volume_includes_solutes": false
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 1
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #49, product 4{70,38,25}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
},
{
"type": "SMILES",
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}
],
"amount": {
"volume": {
"value": 1,
"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "FCCCNC1=C(N=C2N1C=CN=C2C1CC1)C1=NC(=CC=C1)C#C"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "FCCCNC1=C(N=C2N1C=CN=C2C1CC1)C1=NC(=CC=C1)C#C |c:7,11,13,22,24,t:5,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{70,38,25}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8781341774"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
"uses_internal_standard": false,
"amount": {
"mass": {
"value": 49.20000076293945,
"units": "MILLIGRAM"
}
}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 54
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
"experimenter": {
"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
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"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||
| reactions[49] | Record 50 | REACTANT: Cc1ccc(C=O)cc1 REACTANT: Nc1cnc(I)cn1 CATALYST: p-toluenesulfonic acid REACTANT: [C-]#[N+]CC1CCOCC1 SOLVENT: methanol | Not reported | CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(I)N=CC2=N1 · AMOUNT: — [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(I)N=CC2=N1 · YIELD: 54% [isolated] CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(I)N=CC2=N1 · IDENTITY: — [LCMS] | 10.3762/bjoc.20.143 |
Decoded fields · reactions[49]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_SMILES",
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"is_mapped": false
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{
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],
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{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc(C=O)cc1"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "2{14}"
}
],
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],
"addition_order": 1
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{
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{
"type": "SMILES",
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{
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],
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},
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{
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{
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],
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],
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{
"identifiers": [
{
"type": "SMILES",
"value": "[C-]#[N+]CC1CCOCC1"
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{
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"details": "compound number in the paper",
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],
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{
"identifiers": [
{
"type": "NAME",
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},
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}
],
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}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT",
"details": "room temperature"
}
},
"stirring": {
"type": "CUSTOM",
"details": "stirred in a parallel reactor block (SI File 3, Figure S4)"
}
},
"notes": {
"procedure_details": "Amine 1 (1.0 equiv, 0.270 mmol), aldehyde 2 (1.0 equiv, 0.270 mmol), isonitrile 3 (1.0 equiv, 0.270 mmol), TsOH (0.1 equiv, 0.027 mmol) were mixed in 0.5 mL of MeOH and stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure in a centrifuge, the residue was dissolved in DMSO (approx. 1 mL), filtered, analyzed by LCMS and purified by preparative HPLC (General procedure for the synthesis of library members 4, SI File 3). Source: SI File 2, section 'preliminary screen, TsOH catalyst', entry #50, product 4{71,14,17}."
},
"workups": [
{
"type": "CONCENTRATION",
"details": "solvent evaporated under reduced pressure in a centrifuge"
},
{
"type": "DISSOLUTION",
"details": "residue dissolved in DMSO (approx. 1 mL)",
"input": {
"components": [
{
"identifiers": [
{
"type": "NAME",
"value": "DMSO"
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{
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],
"amount": {
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"precision": 0.5,
"units": "MILLILITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "FILTRATION",
"details": "solution filtered, then analyzed by LCMS",
"keep_phase": "filtrate"
},
{
"type": "OTHER_CHROMATOGRAPHY",
"details": "preparative reversed-phase HPLC (Agilent 1260 Infinity, DAD + MS detection; Waters SunFire C18 OBD Prep, 100 A, 5 um, 19 x 100 mm, with SunFire C18 guard cartridge); gradient deionized water - HPLC-grade MeCN or MeOH; in some cases ammonia or TFA (1%) additive, giving free bases or trifluoroacetate salts of the products, respectively"
}
],
"outcomes": [
{
"reaction_time": {
"value": 16,
"units": "HOUR"
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"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(I)N=CC2=N1"
},
{
"type": "CXSMILES",
"details": "as printed in SI File 2 (ChemAxon CXSMILES; &1 = relative configuration)",
"value": "CC1=CC=C(C=C1)C1=C(NCC2CCOCC2)N2C=C(I)N=CC2=N1 |c:3,5,8,23,26,t:1,20|"
},
{
"type": "CUSTOM",
"details": "compound number in the paper",
"value": "4{71,14,17}"
},
{
"type": "CUSTOM",
"details": "Enamine compound ID (SI File 2 'Internal ID')",
"value": "Z8776690316"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "isolated",
"type": "AMOUNT",
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"value": 65.4000015258789,
"units": "MILLIGRAM"
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}
},
{
"analysis_key": "isolated",
"type": "YIELD",
"details": "isolated yield as reported in SI File 2",
"uses_internal_standard": false,
"percentage": {
"value": 54
}
},
{
"analysis_key": "LCMS",
"type": "IDENTITY"
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "LCMS of the crude solution and HPLC-MS-guided purification"
},
"isolated": {
"type": "WEIGHT",
"details": "mass of product isolated after preparative HPLC"
}
}
}
],
"provenance": {
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"organization": "Enamine Ltd."
},
"city": "Kyiv, Ukraine",
"doi": "10.3762/bjoc.20.143",
"publication_url": "https://doi.org/10.3762/bjoc.20.143",
"record_created": {
"time": {
"value": "2026-10-14"
},
"person": {
"name": "Claude (AI agent via Tokens for Progress, account @jordan)",
"email": "noreply@anthropic.com"
},
"details": "Curated from SI Files 2 and 3 of doi:10.3762/bjoc.20.143 (CC-BY 4.0) by a Tokens for Progress agent (Claude); table parsed by PDF cell geometry and checked with RDKit against a GBB reaction template."
},
"is_mined": false
}
} | |||||