dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c97f457d75724fd29a32be088e5f8a4c | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | [H][H].FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)OCC.S(=O)(=O)([O-])[O-].[Mg+2]>>FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 9ead86cf12aa15d642a54ce216bcf061aaad412b712c6fec7fa57e8d47412e01 | a0caba33875db4cbb9ed690a5345ca767b0ef35f758b719cf286d2968627181f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 95 | [{"value": 95.0, "product": "FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3, 4-Trifluoroaniline (2.94 g) and ethyl pyruvate (2.32 g) were dissolved in methanol (30 ml). After adding 5% Pd—C (2.0 g) and anhydrous magnesium sulfate (2.65 g), the mixture was stirred at 50° C. in a hydrogen atmosphere for 16 hours. After filtering off Pd—C and magnesium sulfate, the obtained filtrate was conce... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>[Pd].CO>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4116153d24484c368b5531235418d367 | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | Cl.FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)OC>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | O=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 9ead86cf12aa15d642a54ce216bcf061aaad412b712c6fec7fa57e8d47412e01 | a0caba33875db4cbb9ed690a5345ca767b0ef35f758b719cf286d2968627181f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 81.8 | [{"value": 81.8, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | 2,3,4-Trifluoroaniline (1.01 g) and methyl pyruvate (0.87 g) were dissolved in methanol (8 ml). After adding 5% Pd—C (0.11 g) and conc. hydrochloric acid (0.03 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa (converted from 30 kgf/cm2) for 2 hours. After filtering off Pd—C, the obtained ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | 40 | 2 | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>[Pd].CO>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70f6d86b6a29466c9e871d6a54e57035 | CCOC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | Cl.FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)OCC>>FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].O=[N+:8]([O-])[c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCOC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | C(C)O | Functional Group Interconversion | OtherReaction | afc456d3801dde7d01420f0407f1359d2151a7caf861685c22d21aa320014574 | 7a6ac26784750edae2ec5255c2f631040bbac914a02bb7a5f5351faf04e687c3 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 97.9 | [{"value": 97.9, "product": "FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | 2,3,4-Trifluoronitrobenzene (1.01 g) and ethyl pyruvate (1.15 g) were dissolved in ethanol (8 ml). After adding 5% Pd—C (0.11 g) and conc. hydrochloric acid (0.03 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | 40 | 3 | CCOC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].C(C)O>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0f2a87299a64a6e9bc3a81dbecb66f0 | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | Cl.FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)OC>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | O=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 9ead86cf12aa15d642a54ce216bcf061aaad412b712c6fec7fa57e8d47412e01 | a0caba33875db4cbb9ed690a5345ca767b0ef35f758b719cf286d2968627181f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 95.8 | [{"value": 95.8, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | 2,3,4-Trifluoroaniline (0.83 g) and methyl pyruvate (0.87 g) were dissolved in methanol (8 ml). After adding 5% Pd—C (0.11 g) and conc. hydrochloric acid (0.03 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa for 2 hours. After filtering off Pd—C, the obtained filtrate was concentrated un... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | 40 | 2 | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>[Pd].CO>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-780ebbded9684dac917e308488340b2f | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | Cl.FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)OCC>>FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 9ead86cf12aa15d642a54ce216bcf061aaad412b712c6fec7fa57e8d47412e01 | a0caba33875db4cbb9ed690a5345ca767b0ef35f758b719cf286d2968627181f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 94.6 | [{"value": 94.6, "product": "FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | 2,3,4-Trifluoroaniline (0.83 g) and ethyl pyruvate (1.15 g) were dissolved in ethanol (8 ml). After adding 5% Pd—C (0.11 g) and conc. hydrochloric acid (0.03 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated unde... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | 40 | 3 | CCOC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>[Pd].C(C)O>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2ae1fef10194c6597c1745779551014 | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)O.[H][H]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | O=[C:2]([CH3:1])[C:13](=[O:14])[OH:15].O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | [Pd] | C(C)(C)O | Functional Group Interconversion | OtherReaction | 2a80f1107073927a3cc13d35960c7eb81b5ea7d5c6acd854c0510ae23de22ab7 | bd85798e25b55cb028f2f01bf29e4fa858f9c4a4a772d7dd4b3e45adffc7b449 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 98.1 | [{"value": 98.1, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluoronitrobenzene (5.03 g) and pyruvic acid (2.75 g) were dissolved in isopropanol (IPA; 40 ml). After adding 10% Pd—C (0.21 g), the mixture was stirred at 40° C. under atmospheric pressure in a hydrogen atmosphere for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Secondary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(C)O | null | null | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].C(C)(C)O>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-000aaf21ce6b430c92135e59c6c72ea3 | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)O>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | O=[C:2]([CH3:1])[C:13](=[O:14])[OH:15].O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | [Pd] | CC(C)O | Functional Group Interconversion | OtherReaction | 2a80f1107073927a3cc13d35960c7eb81b5ea7d5c6acd854c0510ae23de22ab7 | bd85798e25b55cb028f2f01bf29e4fa858f9c4a4a772d7dd4b3e45adffc7b449 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 97.8 | [{"value": 97.8, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | HOUR | 2,3,4-Trifluoronitrobenzene (5.03 g) and pyruvic acid (2.75 g) were dissolved in IPA (40 ml). After adding 10% Pd—C (0.21 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Secondary amine | null | null | c1ccccc1 | Other | [Pd].CC(C)O | 40 | 3 | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].CC(C)O>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fb047e8329c4843bff603683d0831d1 | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)O>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | O=[C:2]([CH3:1])[C:13](=[O:14])[OH:15].O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | 2a80f1107073927a3cc13d35960c7eb81b5ea7d5c6acd854c0510ae23de22ab7 | bd85798e25b55cb028f2f01bf29e4fa858f9c4a4a772d7dd4b3e45adffc7b449 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 96 | [{"value": 96.0, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 5 | HOUR | 2,3,4-Trifluoronitrobenzene (1.01 g) and pyruvic acid (0.75 g) were dissolved in methanol (8 ml). After adding 5% Pd—C (0.11 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 4.9 MPa (converted from 50 kgf/cm2) for 5 hours. After filtering off Pd—C, the obtained filtrate was concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | 40 | 5 | CC(=O)C(=O)O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].CO>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fb9e8a6076c244cb9ed9b7dc84a1a78e | CC(=O)C(=O)O.Nc1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)O.[H][H]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | O=[C:2]([CH3:1])[C:13](=[O:14])[OH:15].[NH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | CC(=O)C(=O)O.Nc1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | [Pd] | CC(C)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 91.4 | [{"value": 91.4, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluoroaniline (4.18 g) and pyruvic acid (2.75 g) were dissolved in IPA (40 ml). After adding 10% Pd—C (0.21 g), the mixture was stirred at 40° C. under atmospheric pressure in a hydrogen atmosphere for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the ti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | [Pd].CC(C)O | null | null | CC(=O)C(=O)O.Nc1ccc(F)c(F)c1F>[Pd].CC(C)O>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b10cb0936e1470cb7743fcc2219590f | COC(=O)C(C)Nc1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F.[OH-].[Li+]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([CH:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)C(C)Nc1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 99.7 | [{"value": 99.7, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Methyl 2-(2,3,4-trifluoroanilino)propionate (46.64 g) was dissolved in methanol (130 ml) and an aqueous solution (3 mol/l; 100 ml) of lithium hydroxide was slowly added thereto at 0° C. After stirring at room temperature for 3 hours, the solvent was evaporated. After adding water, the residue was washed with chloroform... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 3 | COC(=O)C(C)Nc1ccc(F)c(F)c1F>CO>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11ea0b2a940b4be2882a47ea40b946fa | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F.[OH-].[Na+]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | CC[O:15][C:13]([CH:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 100 | [{"value": 100.0, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Ethyl 2-(2,3,4-trifluoroanilino)propionate (2.47 g) was dissolved in ethanol (40 ml) and an aqueous solution (3 mol/l; 10 ml) of sodium hydroxide was slowly added thereto at 0° C. After stirring at room temperature for 3 hours, the solvent was evaporated. After adding water, the residue was washed with chloroform. Next... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(C)O | null | 3 | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F>C(C)O>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-986c58db94c34ad9b522d1f578e9a935 | CO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O>>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@H](C(=O)O)C)C=CC(=C1F)F.CO.Cl>>FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F | [CH3:1][OH:2].O[C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | CO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C;D1;H3:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[#7:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | null | null | (2S)-2-(2,3,4-trifluoroanilino)propionic acid (1.1 g; 99% ee) was dissolved in methanol (10 ml) and hydrochloric acid (5 mol/l; 1 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O>>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29f1fec1ccfb4007ab039e491accdbec | CO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O>>COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@@H](C(=O)O)C)C=CC(=C1F)F.CO.Cl>>FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F | [CH3:1][OH:2].O[C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | CO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C;D1;H3:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[#7:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C;D1;H3:6] | null | [] | null | null | null | null | (2R)-2-(2,3,4-trifluoroanilino)propionic acid (1.1 g; 98% ee) was dissolved in methanol (10 ml) and hydrochloric acid (5 mol/l; 1 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O>>COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c010bf21eb44d308a098365cac4795c | CCO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O>>CCOC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@H](C(=O)O)C)C=CC(=C1F)F.C(C)O.Cl>>FC1=C(N[C@H](C(=O)OCC)C)C=CC(=C1F)F | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[C@H:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | CCOC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C;D1;H3:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[#7:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | (2S)-2-(2,3,4-trifluoroanilino)propionic acid (219 mg; 99% ee) was dissolved in ethanol (2 ml) and hydrochloric acid (5 mol/l; 0.2 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O>>CCOC(=O)[C@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cefec37d8b7542628f3b9646541dcee4 | CCO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O>>CCOC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@@H](C(=O)O)C)C=CC(=C1F)F.C(C)O.Cl>>FC1=C(N[C@@H](C(=O)OCC)C)C=CC(=C1F)F | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[C@@H:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O | CCOC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4])-[C;D1;H3:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[#7:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | null | null | (2R)-2-(2,3,4-trifluoroanilino)propionic acid (219 mg; 99% ee) was dissolved in ethanol (2 ml) and hydrochloric acid (5 mol/l; 0.2 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CCO.C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O>>CCOC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4422656219334b068b517b82fbb0d016 | COC(=O)C(C)Nc1ccc(F)c(F)c1F>>C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F.P(=O)([O-])([O-])[O-].Cl>>FC1=C(N[C@H](C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([CH:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][C@H:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)C(C)Nc1ccc(F)c(F)c1F | C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | null | null | C(Cl)Cl | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 30 | CELSIUS | null | null | Methyl 2-(2,3,4-trifluoroanilino)propionate (2.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 400 ml). After adding Protease N (manufactured by Amano Seiyaku, originating in a bacterium belonging to the genus Bacillus; 0.4 g), the mixture was gently stirred. The mixture was further stirred for 14 hour... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(Cl)Cl | 30 | null | COC(=O)C(C)Nc1ccc(F)c(F)c1F>C(Cl)Cl>C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d25e9a67e11f44edbe19e5ee44815d44 | COC(=O)C(C)Nc1ccc(F)c(F)c1F>>C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O | COC(C(C)NC1=C(C(=C(C=C1)F)F)F)=O.P(=O)([O-])([O-])[O-].Cl>>FC1=C(N[C@@H](C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([CH:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][C@@H:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)C(C)Nc1ccc(F)c(F)c1F | C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O | null | null | C(Cl)Cl | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 30 | CELSIUS | null | null | Methyl2-(2,3,4-trifluoroanilino)propionate (1.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 200 ml). After adding α-chymotrypsin (manufactured by Sigma; 0.2 g), the mixture was gently stirred. The mixture was further stirred for 16 hours while maintaining at 30° C. After adding methylene chloride, th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | C(Cl)Cl | 30 | null | COC(=O)C(C)Nc1ccc(F)c(F)c1F>C(Cl)Cl>C[C@@H](Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-636e813181f848728e478a98a7f62007 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F.FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F>>FC1=C(N[C@H](C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([C@@H:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][C@H:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O | null | null | P(=O)([O-])([O-])[O-] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 47.9 | [{"value": 47.9, "product": "FC1=C(N[C@H](C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 48 | HOUR | Microbial cells (IFO-1575; Zygoascus hellenicus) were cultured in an MY medium (pH 6.0; 50 ml) at 30° C. for 48 hours. Methyl 2-(2,3,4-trifluoroanilino)propionate (1.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 90 ml). Then the above-described liquid culture (10 ml) was added thereto and gently stir... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | P(=O)([O-])([O-])[O-] | 30 | 48 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>P(=O)([O-])([O-])[O-]>C[C@H](Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fb84b9cd02047b8b821ce5357076070 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F.N12CCCCCC2=NCCC1.Cl>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 86.8 | [{"value": 86.8, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 16 | HOUR | Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (100 mg, 38% ee) was dissolved in toluene (2 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 71.8 mg) was added thereto at room temperature. Then the liquid reaction mixture was stirred at 110° C. for 16 hours. After adding hydrochloric acid (1 mol/l; 1 ml) to the liqui... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C1(=CC=CC=C1)C | 110 | 16 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>C1(=CC=CC=C1)C>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dcdfa56e5c394108a82fb8e388523d1e | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F.C([O-])([O-])=O.[K+].[K+].O>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 85 | [{"value": 85.0, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 19 | HOUR | Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (50 mg, 57% ee) was dissolved in N,N-dimethylformamide (DMF; 1 ml) and potassium carbonate (63.2 mg) was added thereto at room temperature. Then the liquid reaction mixture was stirred at 110° C. for 19 hours. After adding water to the liquid reaction mixture, the aqueou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | CN(C=O)C | 110 | 19 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>CN(C=O)C>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ededfd14e64e4ad0b58e9594ed60cb25 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F.C([O-])([O-])=O.[K+].[K+].O>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | null | CC(=O)N(C)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 89.5 | [{"value": 89.5, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 19 | HOUR | Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 57% ee) was dissolved in dimethylacetamide (DMAc; 3 ml) and potassium carbonate (474.1 mg) was added thereto at room temperature. Then the liquid reaction mixture was stirred at 95° C. for 19 hours. After adding water to the liquid reaction mixture, the aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | CC(=O)N(C)C | 95 | 19 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>CC(=O)N(C)C>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61b34c6c1be54403acdd2d511f0f11ed | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | Cl.CC(C)([O-])C.[K+].FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F.[OH-].[Na+]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([C@@H:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | null | CC(=O)N(C)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 98.3 | [{"value": 98.3, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Potassium tertiary-butoxide (123.4 mg) was suspended in DMAc (2 ml). Under ice-cooling, a solution of methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) in DMAc (2 ml) was added thereto. The liquid reaction mixture was stirred at the same temperature for 1 hour. Then an aqueous solution of sodium hydroxi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CC(=O)N(C)C | null | 1 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>CC(=O)N(C)C>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d94bae62b134576aecf16ab2364ced8 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>>CC(Nc1ccc(F)c(F)c1F)C(=O)O | Cl.C([O-])([O-])=O.[K+].[K+].FC1=C(N[C@@H](C(=O)OC)C)C=CC(=C1F)F.[OH-].[Na+]>>FC1=C(NC(C(=O)O)C)C=CC(=C1F)F | C[O:15][C:13]([C@@H:2]([CH3:1])[NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])=[O:14]>>[CH3:1][CH:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[F:12])[C:13](=[O:14])[OH:15] | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F | CC(Nc1ccc(F)c(F)c1F)C(=O)O | null | null | CC(=O)N(C)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 94.5 | [{"value": 94.5, "product": "FC1=C(NC(C(=O)O)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 19 | HOUR | Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) was dissolved in DMAc (3 ml) and potassium carbonate (474.1 mg) was added thereto at room temperature. The liquid reaction mixture was stirred at 95° C. for 19 hours. After adding an aqueous solution of sodium hydroxide (3 mol/l), the liquid reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CC(=O)N(C)C | 95 | 19 | COC(=O)[C@@H](C)Nc1ccc(F)c(F)c1F>CC(=O)N(C)C>CC(Nc1ccc(F)c(F)c1F)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d5a9bdc3c81411cb148de996528a9c6 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | C(O)([O-])=O.[Na+].[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.Cl>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | CO.CC(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 84.1 | [{"value": 84.0, "product": "FC1=C(N[C@H](CO)C)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "FC1=C(N[C@H](CO)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | Under ice-cooling, sodium borohydride (1.2 g) was dissolved in IPA (50 ml). After adding methanol (5 ml), a solution of the compound (5.0 g) obtained in Example 1 in IPA was dropped therein to. Then the liquid reaction mixture was heated to 50° C. and stirred for 1 hour. Next, hydrochloric acid (1 mol/l) was added and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | CO.CC(C)O | 50 | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>CO.CC(C)O>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19d731cc636645b29e4fa498f8f1f52e | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 6 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in toluene (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in toluene was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 6 hours. Then water was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C | null | 6 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C1(=CC=CC=C1)C>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b3497d821714899838080df19bf8f51 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | ClC1=CC=CC=C1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 6 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in chlorobenzene (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in chlorobenzene was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 6 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | ClC1=CC=CC=C1 | null | 6 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>ClC1=CC=CC=C1>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a862437db974243b40e28649006b823 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | CCCCCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in hexane (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in hexane was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. Then water was ad... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | CCCCCC | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>CCCCCC>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e1d5fafd74a45d0b8b598bf6622fd89 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C1CCCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 6 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in cyclohexane (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in cyclohexane was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 6 hours. Then w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1CCCCC1 | null | 6 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C1CCCCC1>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-114c8b0cd3ee46b0b31d316ba3f13637 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | [BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 2 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in IPE (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in IPE was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 2 hours. Then water was added t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | O | null | 2 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>O>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df8c448ae5194ed18654920404b87f55 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C(C)(C)(C)OC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in methyl t-butyl ether (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in methyl t-butyl ether was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred f... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(C)(C)(C)OC | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C(C)(C)(C)OC>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-904f8a232335426ca76f1efc5b037012 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in THF (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in THF was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. Then water was added to... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C1CCOC1>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca71e4439f8a46408b5c9887a26e760f | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | COCCOC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in 1,2-dimethoxyethane (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in DME was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. Then wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | COCCOC | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>COCCOC>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d41860e8df61493585a8648d492110f5 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C(Cl)(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 6 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in chloroform (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in chloroform was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 6 hours. Then wat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(Cl)(Cl)Cl | null | 6 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C(Cl)(Cl)Cl>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29ebbd36a0d347fd8065424702aa0c74 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | C(Cl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in methylene chloride (0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in metylene chloride was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>C(Cl)Cl>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3f9312d4e5640bcb0674e938ed1d2ae | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>>C[C@@H](CO)Nc1ccc(F)c(F)c1F | O.[BH4-].[Na+].FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F.CO>>FC1=C(N[C@H](CO)C)C=CC(=C1F)F | CO[C:3]([C@H:2]([CH3:1])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])=[O:4]>>[CH3:1][C@@H:2]([CH2:3][OH:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | C[C@@H](CO)Nc1ccc(F)c(F)c1F | null | null | ClCCCl.C(CCl)Cl | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[#7:4])-[C;D1;H3:5]>>[#7:4]-[C:3](-[C;D1;H3:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 1 | HOUR | At room temperature, sodium borohydride (35.7 mg) was suspended in 1,2-dichloroethane (EDC, 0.2 ml). Then a solution (0.8 ml) of methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (200 mg, 99.8% ee) in EDC was added to the solution. After adding methanol (137.4 mg), the liquid reaction mixture was stirred for 1 hour. The... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | ClCCCl.C(CCl)Cl | null | 1 | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F>ClCCCl.C(CCl)Cl>C[C@@H](CO)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fdce4243602453b99f4511ddffe2546 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | CC(=O)C | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 84 | [{"value": 84.0, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | The compound (300 mg) obtained in Example 51, diethyl ethoxymethylenemalonate (632 mg) and tetrahexylammonium chloride (57 mg) were dissolved in acetone (3 ml). After adding potassium carbonate (445 mg), the mixture was stirred at room temperature for 4.5 hours. After the completion of the reaction, the solvent was eva... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CC(=O)C | null | 4.5 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>[Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CC(=O)C>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05a1c88e83fc4495b20a55fb1c3be8ed | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | ClCCl | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 78.4 | [{"value": 78.0, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | The compound (103 mg) obtained in Example 51, diethyl ethoxymethylenemalonate (108 mg) and tetrahexylammonium chloride (29 mg) were dissolved in dichloromethane (1 ml). After adding potassium carbonate (138 mg), the mixture was stirred at room temperature for 22 hours. After the completion of the reaction, the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.ClCCl | null | 22 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>[Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.ClCCl>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c96adb10928b41d7981fb57fdafcfa77 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | CC(C)([O-])C.[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | null | CN(C)C=O | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 75 | [{"value": 75.0, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Potassium tertiary-butoxide (62 mg) was added to DMF (2 ml) and cooled to 0° C. Then a solution of the compound (100 mg) obtained in Example 51 in DMF (200 μl) was dropped therein to. After stirring for 15 minutes, diethyl ethoxymethylenemalonate was dropped therein to and the resultant mixture was stirred for 8 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | CN(C)C=O | 0 | 0.25 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>CN(C)C=O>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-426f633887724b84bb4638f94290938a | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | null | null | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 78 | [{"value": 78.0, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | To the compound (103 mg) obtained in Example 51 was added diethyl ethoxymethylenemalonate (127 mg). Then the obtained mixture was stirred for 1 hour while heating to 100° C. under atmospheric pressure. Further, it was stirred at the same temperature for 1.5 hour under reduced pressure and then under atmospheric pressur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | null | 100 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed8211677cac405d8fa028af6a5bb94f | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | O.[OH-].[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC(C(C(=O)OCC)=COCC)=O>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | CN(C)C=O | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 90.2 | [{"value": 90.2, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | At room temperature, potassium hydroxide (330 mg) and tetrahexylammonium chloride (190.1 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. After ad... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CN(C)C=O | 0 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>[Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CN(C)C=O>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4daeda6e673429492ae870b3e630a02 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | O.[OH-].[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC(C(C(=O)OCC)=COCC)=O>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 92.9 | [{"value": 92.9, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | At room temperature, potassium hydroxide (330 mg) and tetrabutylammonium hydrogensulfate (82.7 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. Af... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 0 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b70b5d96668a4a3a90823c7b62b9d362 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | O.[OH-].[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC(C(C(=O)OCC)=COCC)=O>>FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:22](=[O:23])[O:24][CH2:25][CH3:26].[NH:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:19])[CH2:20][OH:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]([c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17])[C@@H:18]([CH3:... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Protection | OtherReaction | a404aeb09d7e35f7a303a5a3e9f556c7b7fcbac4f4d9ef85c100807423d27605 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15](-[CH;D2;+0:4]=[C:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2]... | 90.2 | [{"value": 90.2, "product": "FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | At room temperature, potassium hydroxide (330 mg) and tetrabutylammonium hydrogensulfate (82.7 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. Af... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | null | null | c1ccccc1 | HO- | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 0 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03f445e855fe427bb8ab9a84c995bd04 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | CC(C)([O-])C.[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:21](=[O:22])[O:23][CH2:24][CH3:25].F[c:16]1[c:9]([NH:8][C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:2... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | null | CN(C)C=O | Protection | OtherReaction | 8bfc9093150cd321259d05077543032142a370ee46fd61ca9254b3d5012f71fd | c89dded6991b73a47d28d45bea3df6e708ff5714257b335fd58112fb4d400d14 | c1ccc2c(c1)NCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].F-[c;H0;D3;+0:12](:[c:13](-[F;D1;H0:14]):[c:15]):[c:16](-[NH;D2;+0:17]-[C:18](-[C;D1;H3:19])-[C:20]-[OH;D1;+0:21]):[c:22]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C:3](=[CH;D2;+0:4]-[N;H0;D3;+0:17]1-[... | 65.2 | [{"value": 65.0, "product": "FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To DMF (2 ml) was added potassium tertiary-butoxide (226 mg) under ice-cooling. After dropping a solution of the compound (100 mg) obtained in Example 51 and diethyl ethoxymethylenemalonate (293 mg) in DMF (0.5 ml), the resultant mixture was stirred at room temperature for 18 hours. After treating in a conventional man... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ether.Primary alcohol.Secondary amine | Enamine.Ester.Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | CN(C)C=O | null | null | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7714985961f941faaa20baf817e41c9a | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | O.[OH-].[K+].FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | F[c:16]1[c:9]([N:8]([CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:21](=[O:22])[O:23][CH2:24][CH3:25])[C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20])... | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 835cadbd4417bd775c2ccf096918bb34e5431a3b7189c9ad25e3954d6fcab1e1 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)NCCO2 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[#7:6](-[C:7]-[C:8]-[OH;D1;+0:9])-[C:10]=[C:11]):[c:12]>>[C:11]=[C:10]-[#7:6]1-[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5]-1:[c:12] | null | [] | 60 | CELSIUS | 2 | HOUR | Potassium hydroxide (180 mg) and tetrabutylammonium hydrogensulfate (90.4 mg) were dissolved in DMF (15 ml) by heating to 60° C. and a solution of diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate (1g, 99.8% ee) and diethyl ethoxymethylenemalonate (120 mg) in DMF 85 ml) was added thereto. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 60 | 2 | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb07df41301c4fcea44fcee88458c19b | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | O.[OH-].[K+].FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | F[c:16]1[c:9]([N:8]([CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:21](=[O:22])[O:23][CH2:24][CH3:25])[C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20])... | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 835cadbd4417bd775c2ccf096918bb34e5431a3b7189c9ad25e3954d6fcab1e1 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)NCCO2 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[#7:6](-[C:7]-[C:8]-[OH;D1;+0:9])-[C:10]=[C:11]):[c:12]>>[C:11]=[C:10]-[#7:6]1-[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5]-1:[c:12] | null | [] | 70 | CELSIUS | 4 | HOUR | Potassium hydroxide (180 mg) and benzyltrimethylammonium chloride (49.5 mg) were dissolved in DMF (15 ml) by heating to 70° C. and a solution of diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (120 mg) in DMF (5 ml) was added thereto. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CN(C)C=O | 70 | 4 | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>[Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09aad72a49c54100a1770b7ca03a3bcc | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | O.[OH-].[K+].FC1=C(N([C@H](CO)C)C=C(C(=O)OCC)C(=O)OCC)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>C(C)OC(C(C(=O)OCC)=CN1[C@H](COC2=C1C=CC(=C2F)F)C)=O | F[c:16]1[c:9]([N:8]([CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:21](=[O:22])[O:23][CH2:24][CH3:25])[C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20])... | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 835cadbd4417bd775c2ccf096918bb34e5431a3b7189c9ad25e3954d6fcab1e1 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)NCCO2 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[#7:6](-[C:7]-[C:8]-[OH;D1;+0:9])-[C:10]=[C:11]):[c:12]>>[C:11]=[C:10]-[#7:6]1-[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5]-1:[c:12] | null | [] | 60 | CELSIUS | 7 | HOUR | Potassium hydroxide (180 mg) and benzyltrimethylammonium chloride (60.7 mg) were dissolved in DMF (15 ml) by heating to 60° C. and a solution (5 ml) of diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (120 mg) in DMF was added thereto. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CN(C)C=O | 60 | 7 | CCOC(=O)C(=CN(c1ccc(F)c(F)c1F)[C@@H](C)CO)C(=O)OCC>[Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffa02a76540e496189594119513487f8 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | O.[OH-].[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC.[OH-].[K+].C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:21](=[O:22])[O:23][CH2:24][CH3:25].F[c:16]1[c:9]([NH:8][C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:2... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 8a82dc194f7c9690c3cbd3fa800de98e53200b3133d63ee06769afd5f0ed30b5 | 68e68e386c82dc1767144117efd94cadccbdd18dfed1600b96f0291087886e00 | c1ccc2c(c1)NCCO2 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].F-[c;H0;D3;+0:11](:[c:12](-[F;D1;H0:13]):[c:14]):[c:15](-[NH;D2;+0:16]-[C:17](-[C;D1;H3:18])-[C:19]-[OH;D1;+0:20]):[c:21]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2](=[CH;D2;+0:1]-[N;H0;D3;+0:16]1-[C:17](-[C;D1;H3:18])-[C:19]-[O;H... | null | [] | 60 | CELSIUS | 1 | HOUR | At room temperature, KOH (330 mg) and tetrahexylammonium chloride (190.1 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (2.09 g) in DMF, the mixture was stirred for 1 hour. Next, it was heated to 60° C. and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary alcohol.Secondary amine | Enamine.Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CN(C)C=O | 60 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>[Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC.CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61fc9b1ea01943a4846e42c4f31dec93 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | O.[OH-].[K+].FC1=C(N[C@H](CO)C)C=CC(=C1F)F.C(C)OC=C(C(=O)OCC)C(=O)OCC.[OH-].[K+].C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:21](=[O:22])[O:23][CH2:24][CH3:25].F[c:16]1[c:9]([NH:8][C@H:19]([CH2:18][OH:17])[CH3:20])[cH:10][cH:11][c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:2... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 8a82dc194f7c9690c3cbd3fa800de98e53200b3133d63ee06769afd5f0ed30b5 | 68e68e386c82dc1767144117efd94cadccbdd18dfed1600b96f0291087886e00 | c1ccc2c(c1)NCCO2 | C-C-O-[CH;D2;+0:1]=[C:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].F-[c;H0;D3;+0:11](:[c:12](-[F;D1;H0:13]):[c:14]):[c:15](-[NH;D2;+0:16]-[C:17](-[C;D1;H3:18])-[C:19]-[OH;D1;+0:20]):[c:21]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2](=[CH;D2;+0:1]-[N;H0;D3;+0:16]1-[C:17](-[C;D1;H3:18])-[C:19]-[O;H... | null | [] | 60 | CELSIUS | 1 | HOUR | At room temperature, KOH (330 mg) and tetrabutylammonium hydrogensulfate (82.7 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (2.09 g) in DMF, the mixture was stirred for 1 hour. Next, it was heated to 60° ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary alcohol.Secondary amine | Enamine.Ether | c1ccccc1 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HF | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | 60 | 1 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@@H](CO)Nc1ccc(F)c(F)c1F>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db2c78a2be8b4889be10b76ac296dc5d | C[C@@H](CO)Nc1ccc(F)c(F)c1F>>C[C@H]1COc2c(ccc(F)c2F)N1 | FC1=C(N[C@H](CO)C)C=CC(=C1F)F.[H-].[Na+]>>FC1=C(C2=C(N[C@H](CO2)C)C=C1)F | F[c:5]1[c:6]([NH:13][C@@H:2]([CH3:1])[CH2:3][OH:4])[cH:7][cH:8][c:9]([F:10])[c:11]1[F:12]>>[CH3:1][C@H:2]1[CH2:3][O:4][c:5]2[c:6]([cH:7][cH:8][c:9]([F:10])[c:11]2[F:12])[NH:13]1 | C[C@@H](CO)Nc1ccc(F)c(F)c1F | C[C@H]1COc2c(ccc(F)c2F)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b28314405bf4549608208018ade03ca880bddbde6854e23c0e7edbaaba0f2762 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)NCCO2 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[#7:6]-[C:7]-[C:8]-[OH;D1;+0:9]):[c:10]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1]1:[c:5](:[c:10])-[#7:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-1 | 66.5 | [{"value": 66.0, "product": "FC1=C(C2=C(N[C@H](CO2)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "FC1=C(C2=C(N[C@H](CO2)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To DMF (2 ml) was added sodium hydride (39 mg) and the mixture was heated to 60° C. in an oil bath. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped therein to and the obtained mixture was stirred for 1 hour. After treating in a conventional manner, the mixture was subjected to silica... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | HF | CN(C)C=O | 60 | 1 | C[C@@H](CO)Nc1ccc(F)c(F)c1F>CN(C)C=O>C[C@H]1COc2c(ccc(F)c2F)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-660669f44f7a4e25a072a55d2b7faf91 | C[C@@H](CO)Nc1ccc(F)c(F)c1F>>C[C@H]1COc2c(ccc(F)c2F)N1 | FC1=C(N[C@H](CO)C)C=CC(=C1F)F.CC(C)([O-])C.[K+]>>FC1=C(C2=C(N[C@H](CO2)C)C=C1)F | F[c:5]1[c:6]([NH:13][C@@H:2]([CH3:1])[CH2:3][OH:4])[cH:7][cH:8][c:9]([F:10])[c:11]1[F:12]>>[CH3:1][C@H:2]1[CH2:3][O:4][c:5]2[c:6]([cH:7][cH:8][c:9]([F:10])[c:11]2[F:12])[NH:13]1 | C[C@@H](CO)Nc1ccc(F)c(F)c1F | C[C@H]1COc2c(ccc(F)c2F)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b28314405bf4549608208018ade03ca880bddbde6854e23c0e7edbaaba0f2762 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)NCCO2 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[#7:6]-[C:7]-[C:8]-[OH;D1;+0:9]):[c:10]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1]1:[c:5](:[c:10])-[#7:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-1 | 79.8 | [{"value": 79.0, "product": "FC1=C(C2=C(N[C@H](CO2)C)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "FC1=C(C2=C(N[C@H](CO2)C)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To DMF (2 ml) was added potassium tertiary-butoxide (110 mg) under ice-cooling. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped thereinto and the obtained mixture was stirred for 30 minutes. After treating in a conventional manner, the mixture was subjected to silica gel column chrom... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | HF | CN(C)C=O | null | 0.5 | C[C@@H](CO)Nc1ccc(F)c(F)c1F>CN(C)C=O>C[C@H]1COc2c(ccc(F)c2F)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4eb0b563d26541c38317838c6ee3f3f4 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | CC(C)([O-])C.[K+].FC1=C(C2=C(N[C@H](CO2)C)C=C1)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:21](=[O:22])[O:23][CH2:24][CH3:25].[NH:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1 | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | null | CN(C)C=O | Protection | OtherReaction | 4f1ebcbe524e3f62c37b4b08e0b458078cf94da45d68e88468561ca50f6c2c76 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccc2c(c1)NCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C:13]1-[C:14]-[#8:15]-[c:16]:[c:17](:[c:18])-[NH;D2;+0:19]-1>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C:3](=[CH;D2;+0:4]-[N;H0;D3;+0:19]1-[C:13](-[C;D1;H3:12])-[C:14]-[#8:15]-[c:16]:[c:1... | 88 | [{"value": 88.0, "product": "FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To DMF (2.5 ml) was added potassium tertiary-butoxide (75 mg) under ice-cooling. After dropping a solution of the compound (100 mg) obtained in Example 78 and diethyl ethoxymethylenemalonate (233 mg) in DMF (0.5 ml), the resultant mixture was stirred for 2 hours. After treating in a conventional manner, the obtained re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HO- | CN(C)C=O | null | null | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1>CN(C)C=O>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dde17727a88d4679878c9148fa1c04fb | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1>>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | FC1=C(C2=C(N[C@H](CO2)C)C=C1)F.C(C)OC=C(C(=O)OCC)C(=O)OCC>>FC1=C(C2=C(N([C@H](CO2)C)C=C(C(=O)OCC)C(=O)OCC)C=C1)F | CCO[C:4](=[O:5])[C:6](=[CH:7][O:3][CH2:2][CH3:1])[C:21](=[O:22])[O:23][CH2:24][CH3:25].[NH:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][N:8]1[c:9]2[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]2[O:17][CH2:18][C@@H:19]1[CH3:20... | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1 | CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 4f1ebcbe524e3f62c37b4b08e0b458078cf94da45d68e88468561ca50f6c2c76 | f4a5c4557f368ee0ab25d2b690aeff7a3e2423f61650d49f976093b451174b85 | c1ccc2c(c1)NCCO2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[CH;D2;+0:4]-[O;H0;D2;+0:5]-[C:6]-[C;D1;H3:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[C:13]1-[C:14]-[#8:15]-[c:16]:[c:17](:[c:18])-[NH;D2;+0:19]-1>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[C:3](=[CH;D2;+0:4]-[N;H0;D3;+0:19]1-[C:13](-[C;D1;H3:12])-[C:14]-[#8:15]-[c:16]:[c:1... | null | [] | null | null | 30 | MINUTE | 1.20 g (99.8% ee) of (3S)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was dissolved in toluene (0.5 ml). After adding diethyl ethoxymethylenemalonate (1.92 g), the mixture was stirred at 120 for 30 minutes and then at 140° C. under reduced pressure for 30 minutes. The residue was subjected to silica gel colum... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Secondary amine | Enamine.Ester | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HO- | C1(=CC=CC=C1)C | null | 0.5 | CCOC=C(C(=O)OCC)C(=O)OCC.C[C@H]1COc2c(ccc(F)c2F)N1>C1(=CC=CC=C1)C>CCOC(=O)C(=CN1c2ccc(F)c(F)c2OC[C@@H]1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1821794b14ae472f84774307a0bd3dd8 | CC(O)CO.O=C(Cl)c1ccc([N+](=O)[O-])cc1>>CC(O)COC(=O)c1ccc([N+](=O)[O-])cc1 | OC(CO)C.C(C)N(CC)CC.ClCCl.[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1>>[N+](=O)([O-])C1=CC=C(C(=O)OCC(C)O)C=C1 | [CH3:1][CH:2]([OH:3])[CH2:4][OH:5].Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][CH:2]([OH:3])[CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1 | CC(O)CO.O=C(Cl)c1ccc([N+](=O)[O-])cc1 | CC(O)COC(=O)c1ccc([N+](=O)[O-])cc1 | null | null | C1(=CC=CC=C1)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 51 | [{"value": 51.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)OCC(C)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "[N+](=O)([O-])C1=CC=C(C(=O)OCC(C)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Hydroxypropanol (4.57 g) was dissolved in toluene (80 ml) by stirring and triethylamine (6.68 g) was dropped thereinto at 0° C. After stirring at the same temperature for 30 minutes, a solution of p-nitrobenzoyl chloride (11.4 g) dissolved in toluene (12 ml) was slowly added thereto. The resultant mixture was heated ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | null | CC(O)CO.O=C(Cl)c1ccc([N+](=O)[O-])cc1>C1(=CC=CC=C1)C>CC(O)COC(=O)c1ccc([N+](=O)[O-])cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9c2db406ba04ff19a18aae05cb13930 | CN1CCNCC1.C[C@H]1COc2c(F)c(F)cc3c(=O)c(C(=O)O)cn1c23>>C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23 | FC=1C(=C2C=3N([C@H](CO2)C)C=C(C(C3C1)=O)C(=O)O)F.CN1CCNCC1>>FC=1C(=C2C=3N([C@H](CO2)C)C=C(C(C3C1)=O)C(=O)O)N1CCN(CC1)C | [NH:7]1[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]1.F[c:6]1[c:5]2[c:26]3[c:17]([cH:16][c:14]1[F:15])[c:18](=[O:19])[c:20]([C:21](=[O:22])[OH:23])[cH:24][n:25]3[C@@H:2]([CH3:1])[CH2:3][O:4]2>>[CH3:1][C@H:2]1[CH2:3][O:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]3)[c:14]([F:15])[cH:16][c:17]3[c:18... | CN1CCNCC1.C[C@H]1COc2c(F)c(F)cc3c(=O)c(C(=O)O)cn1c23 | C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 5a1e408c17885f63b93776bf2c8aa1754347f534f8d996377326543fd3d30ab3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1ccn2c3c(c(N4CCNCC4)ccc13)OCC2 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6]2:[#7;a:7](:[c:8])-[C:9]-[C:10]-[#8:11]-[c:12]:2:1.[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[F;D1;H0:3]-[c:2]1:[c:4]:[c:5]:[c:6]2:[#7;a:7](:[c:8])-[C:9]-[C:10]-[#8:11]-[c:12]:2:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13]-[C:18]-[C:17]-1 | 51.9 | [{"value": 51.9, "product": "FC=1C(=C2C=3N([C@H](CO2)C)C=C(C(C3C1)=O)C(=O)O)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | 1 | HOUR | (S)-(−)-9,10-Difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid (21 mg) and N-methylpiperazine (30 mg) were dissolved in anhydrous dimethyl sulfoxide (3 ml) and stirred at 130 to 140° C. for 1 hour. After evaporating the solvent, ethanol (2 ml) was added to the residue. The solid ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cc2c3c(cccn3CCO2)c1 | C1C[NH]CC[NH]1.c1cc2c3c(cccn3CCO2)c1 | C1C[NH]CC[NH]1.c1cc2c3c(cccn3CCO2)c1 | HF | CS(=O)C | 135 | 1 | CN1CCNCC1.C[C@H]1COc2c(F)c(F)cc3c(=O)c(C(=O)O)cn1c23>CS(=O)C>C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-355d452942e54325bec58b0626c5dd9e | CCOC(=O)c1ccc(F)cc1.Cc1cccc(Cl)n1>>O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | ClC1=CC=CC(=N1)C.FC1=CC=C(C(=O)OCC)C=C1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)F | CCO[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1.[CH3:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[n:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([Cl:9])[n:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | CCOC(=O)c1ccc(F)cc1.Cc1cccc(Cl)n1 | O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccccn1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 66 | [{"value": 66.0, "product": "ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.8, "product": "ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | To a cold (0° C.) solution of 6-chloro-2-picoline (21.4 mL, 196.0 mmol) and ethyl 4-fluorobenzoate (57.5 mL, 391.2 mmol) in tetrahydrofuran (311 mL) was added lithium bis(trimethylsilyl)amide (391 mL, 1.0 M in tetrahydrofuran, 391.0 mmol) dropwise via a pressure equalizing funnel over 1 hour. Upon complete addition, th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1 | HO- | O1CCCC1 | 45 | null | CCOC(=O)c1ccc(F)cc1.Cc1cccc(Cl)n1>O1CCCC1>O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1cba992df354c92a199a0657d882fcd | NO.O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1>>ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | [OH-].[Na+].ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)F.Cl.NO>>ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)F | [OH:1][NH2:2].O=[C:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[n:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[OH:1][N:2]=[C:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[n:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | NO.O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(Cc1ccccn1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[#7;a:4]:[c:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[O;D1;H1:9])-[c:5](:[c:6]):[c:7] | 86 | [{"value": 86.0, "product": "ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (74.9 g, 299.8 mmol) in methanol (900 mL) was added hydroxylamine hydrochloride (104 g, 1.49 mol) followed by sodium hydroxide (600 mL, 10% aqueous, 1.5. mol). The resultant suspension was heated to reflux for 2 hours and then cooled to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccncc1.c1ccccc1 | HO- | CO | null | null | NO.O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1>CO>ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f81762d9fc7e453d9a6e196d69290dfb | ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1>>Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | C(C)N(CC)CC.ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)F.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)F | O[N:15]=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1)[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([Cl:13])[n:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]3[cH:9][cH:10][cH:11][c:12]([Cl:13])[n:14]3[n:15]2)[cH:16][cH:17]1 | ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1 | Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | null | [Fe](Cl)Cl | COCCOC | Aromatic Heterocycle Formation | OtherReaction | eb06b64c3f1e34c5ece58a586a196c3e564df3ceec641c6b6ac1954bda6f0891 | e4c614fd5a14fb8b7819c9887a8a3123bc2600c241ecd15d2c3f8ffc5fe30baf | c1ccc(-c2cc3ccccn3n2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[c:4](:[c:5]):[n;H0;D2;+0:6]:[c:7](-[Cl;D1;H0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[Cl;D1;H0:8]-[c:7](:[c:9]):[n;H0;D3;+0:6]1:[n;H0;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[cH;D2;+0:3]:[c:4]:1:[c:5] | 68.3 | [{"value": 68.0, "product": "ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 1.5 | HOUR | To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (109.2 g, 414 mmol) in 1,2-dimethoxyethane (500 mL) at 0° C. was added trifluoroacetic anhydride (59 mL, 414 mmol), keeping the temperature below 10° C. After the addition was complete, the reaction was warmed to 15° C. The solution was then coo... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | c1ccncc1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HO- | [Fe](Cl)Cl.COCCOC | 15 | 1.5 | ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1>[Fe](Cl)Cl.COCCOC>Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab5572eafb6c4af3850eb536ff39cf7c | CC(=O)OC(C)=O.Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1>>CC(=O)c1c(-c2ccc(F)cc2)nn2c(Cl)cccc12 | B(F)(F)F.ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)F.C(C)(=O)OC(C)=O>>ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)F | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[n:13][n:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]12>>[CH3:1][C:2](=[O:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[n:13][n:14]2[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]12 | CC(=O)OC(C)=O.Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | CC(=O)c1c(-c2ccc(F)cc2)nn2c(Cl)cccc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Friedel-Crafts acylation | 202ee4eacbf5a64e631dc5b199026ef8a0e6891baed537bbc108bdabe4842b8e | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccc(-c2cc3ccccn3n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[#7;a:5]1:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:[c:10]:1:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:9]1:[c:10](:[c:11]):[#7;a:5](:[c:4]):[#7;a:6]:[c:7]:1-[c:8] | 77 | [{"value": 77.0, "product": "ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (10.0 g, 40.5 mmol) in toluene (225 mL) at room temperature was added acetic anhydride (4.6 mL, 48.6 mmol). Boron trifluoride diethyletherate (5.6 mL, 44.6 mmol) was then added dropwise and the resultant solution was heated to reflux for 3.5 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)OC(C)=O.Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1>C1(=CC=CC=C1)C>CC(=O)c1c(-c2ccc(F)cc2)nn2c(Cl)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26ae1657dff14b76b8058061e5b513d1 | CC(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.COC(OC)N(C)C>>CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12 | C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)F.COC(N(C)C)OC.C(C)OC(C)=O.O>>C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(\C=C\N(C)C)=O)C2=CC=C(C=C2)F | [CH3:5][C:6](=[O:7])[c:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[n:17][n:18]2[c:19]([NH:20][CH:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27][cH:28][c:29]12.CO[CH:4](OC)[N:2]([CH3:1])[CH3:3]>>[CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[c:8]1[c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:1... | CC(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.COC(OC)N(C)C | CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12 | null | null | null | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | c1ccc(-c2cc3cccc(NC4CCCC4)n3n2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])/[CH;D2;+0:1]=[CH;D2;+0:5]/[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | 99 | [{"value": 99.0, "product": "C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(\\C=C\\N(C)C)=O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (3.1 g, 9.2 mmol) in N,N-dimethylformamide dimethyl acetal (25 mL) was heated to reflux for 6 days. The mixture was cooled to room temperature, ethylacetate was added followed by water. The organic layer was washed with brine. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.C1CCCC1.c1ccn2nccc2c1 | HO- | null | null | null | CC(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.COC(OC)N(C)C>>CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45f4fc4214974f4db51dc25706acaead | N#CN.Nc1ccccc1.O=[N+]([O-])O>>NC(=[NH2+])Nc1ccccc1.O=[N+]([O-])[O-] | [N+](=O)(O)[O-].NC1=CC=CC=C1.N#CN>>[N+](=O)([O-])[O-].C1(=CC=CC=C1)NC(=[NH2+])N | [N:1]#[C:2][NH2:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:11]=[N+:12]([O-:13])[OH:14]>>[NH2:1][C:2](=[NH2+:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:11]=[N+:12]([O-:13])[O-:14] | N#CN.Nc1ccccc1.O=[N+]([O-])O | NC(=[NH2+])Nc1ccccc1.O=[N+]([O-])[O-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 8980c9c7a2a3cf9244c0b60eeb227f7897b33b43c7eb750f87d7d7c6862c414d | 50b51df4262f52466dc83399cfe46c19be73dee0760243d32794686add22bdcb | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7].[O;-;D1;H0:8]-[#7;+:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[NH2+;D1:3]=[C;H0;D3;+0:2](-[NH2;D1;+0:1])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O-;H0;D1:11]-[#7;+:9](-[O;-;D1;H0:8])=[O;D1;H0:10] | 32 | [{"value": 32.0, "product": "[N+](=O)([O-])[O-].C1(=CC=CC=C1)NC(=[NH2+])N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a room temperature solution of aniline (10.0 g, 107 mmol) in ethanol (100 mL) was added cyanamide (9.6 mL, 50 wt% in water, 123 mmol) followed by the dropwise addition of concentrated nitric acid (7.56 mL). The mixture was heated at reflux for 3.5 hours and allowed to cool to room temperature. The mixture was concen... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Amidinium.Amidinium | null | null | c1ccccc1 | null | C(C)O | null | null | N#CN.Nc1ccccc1.O=[N+]([O-])O>C(C)O>NC(=[NH2+])Nc1ccccc1.O=[N+]([O-])[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e5a1f4b49b9413593cc333fd48c3a24 | CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.NC(=[NH2+])Nc1ccccc1>>Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | CCOCC.C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(\C=C\N(C)C)=O)C2=CC=C(C=C2)F.[N+](=O)([O-])[O-].C1(=CC=CC=C1)NC(=[NH2+])N.C([O-])([O-])=O.[K+].[K+]>>N(C1=CC=CC=C1)C1=NC=CC(=N1)C=1C(=NN2C1C=CC=C2NC2CCCC2)C2=CC=C(C=C2)F | CN(C)/[CH:23]=[CH:22]/[C:21](=O)[c:20]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:35][cH:34]2)[n:7][n:8]2[c:9]([NH:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][cH:18][c:19]21.[NH2+:24]=[C:25]([NH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[NH2:33]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([... | CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.NC(=[NH2+])Nc1ccccc1 | Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | null | null | O.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | d01a6847655e91b862704dc76d3ecccca3a1e733fd3d888dd06b3fce7d19c019 | c9f54e5566ec08d66d7bacb54aaffeaf7f3bfcc00abe64cc2f2bda00f14e87e0 | c1ccc(Nc2nccc(-c3c(-c4ccccc4)nn4c(NC5CCCC5)cccc34)n2)cc1 | C-N(-C)/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5](:[c:6]):[#7;a:7](:[c:8]):[#7;a:9]:[c:10]:1-[c:11].[NH2+;D1:12]=[C;H0;D3;+0:13](-[NH2;D1;+0:14])-[#7:15]-[c:16]>>[c:6]:[c:5]1:[#7;a:7](:[c:8]):[#7;a:9]:[c:10](-[c:11]):[c;H0;D3;+0:4]:1-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:12]:[c;... | null | [] | 140 | CELSIUS | null | null | To a solution of (2E)-1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (100 mg, 0.25 mmol) in N,N-dimethylformamide (5 mL) was added N-phenylguanidinium nitrate (252 mg, 1.27 mmol) and potassium carbonate (175 mg, 1.27 mmol). The suspension was heated at 140 ° C. (... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Amidinium.Amidinium.Ketone | null | null | c1cncnc1 | c1ccccc1.C1CCCC1.c1ccn2nccc2c1.c1cncnc1.c1ccccc1 | HO- | O.CN(C=O)C | 140 | null | CN(C)/C=C/C(=O)c1c(-c2ccc(F)cc2)nn2c(NC3CCCC3)cccc12.NC(=[NH2+])Nc1ccccc1>O.CN(C=O)C>Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39d0af338eaa465986e9bf3aba631903 | COc1cc(N)cc(OC)c1OC.N#CN.O=[N+]([O-])O>>COc1cc(NC(N)=[NH2+])cc(OC)c1OC.O=[N+]([O-])[O-] | [N+](=O)(O)[O-].COC=1C=C(N)C=C(C1OC)OC.N#CN>>[N+](=O)([O-])[O-].COC=1C=C(C=C(C1OC)OC)NC(=[NH2+])N | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:10][c:11]([O:12][CH3:13])[c:14]1[O:15][CH3:16].[C:7](#[N:8])[NH2:9].[O:17]=[N+:18]([OH:19])[O-:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7]([NH2:8])=[NH2+:9])[cH:10][c:11]([O:12][CH3:13])[c:14]1[O:15][CH3:16].[O:17]=[N+:18]([O-:19])[O-:20] | COc1cc(N)cc(OC)c1OC.N#CN.O=[N+]([O-])O | COc1cc(NC(N)=[NH2+])cc(OC)c1OC.O=[N+]([O-])[O-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 8980c9c7a2a3cf9244c0b60eeb227f7897b33b43c7eb750f87d7d7c6862c414d | 50b51df4262f52466dc83399cfe46c19be73dee0760243d32794686add22bdcb | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7].[O;-;D1;H0:8]-[#7;+:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[NH2+;D1:3]=[C;H0;D3;+0:2](-[NH2;D1;+0:1])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O-;H0;D1:11]-[#7;+:9](-[O;-;D1;H0:8])=[O;D1;H0:10] | 46 | [{"value": 46.0, "product": "[N+](=O)([O-])[O-].COC=1C=C(C=C(C1OC)OC)NC(=[NH2+])N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a room temperature solution of 3,4,5-trimethoxyaniline (3.46 g,18.9 mmol) in ethanol (20 mL) was added cyanamide (1.68 mL, 50 wt % in water, 21.7 mmol) followed by the dropwise addition of concentrated nitric acid (1.33 mL). The mixture was heated at reflux for 13 hours and allowed to cool to room temperature. The m... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Amidinium.Amidinium | null | null | c1ccccc1 | null | C(C)O | null | null | COc1cc(N)cc(OC)c1OC.N#CN.O=[N+]([O-])O>C(C)O>COc1cc(NC(N)=[NH2+])cc(OC)c1OC.O=[N+]([O-])[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a0a39a08fc94f9eb7edeb3803282105 | COc1ccc(N)cc1.N#CN.O=[N+]([O-])O>>COc1ccc(NC(N)=[NH2+])cc1.O=[N+]([O-])[O-] | [N+](=O)(O)[O-].COC1=CC=C(N)C=C1.N#CN>>[N+](=O)([O-])[O-].COC1=CC=C(C=C1)NC(=[NH2+])N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:11][cH:12]1.[C:8](#[N:9])[NH2:10].[O:13]=[N+:14]([O-:15])[OH:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([NH2:9])=[NH2+:10])[cH:11][cH:12]1.[O:13]=[N+:14]([O-:15])[O-:16] | COc1ccc(N)cc1.N#CN.O=[N+]([O-])O | COc1ccc(NC(N)=[NH2+])cc1.O=[N+]([O-])[O-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 8980c9c7a2a3cf9244c0b60eeb227f7897b33b43c7eb750f87d7d7c6862c414d | 50b51df4262f52466dc83399cfe46c19be73dee0760243d32794686add22bdcb | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7].[O;-;D1;H0:8]-[#7;+:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[NH2+;D1:3]=[C;H0;D3;+0:2](-[NH2;D1;+0:1])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O-;H0;D1:11]-[#7;+:9](-[O;-;D1;H0:8])=[O;D1;H0:10] | 38 | [{"value": 38.0, "product": "[N+](=O)([O-])[O-].COC1=CC=C(C=C1)NC(=[NH2+])N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a room temperature solution of 4-methoxyaniline (10.0 g, 81.19 mmol) in ethanol (100 mL) was added cyanamide (7.24 mL, 50 wt % in water, 93.37 mmol) followed by the dropwise addition of concentrated nitric acid (5.71 mL). The mixture was heated at reflux for 3 hours and allowed to cool to room temperature. The resul... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Amidinium.Amidinium | null | null | c1ccccc1 | null | C(C)O | null | null | COc1ccc(N)cc1.N#CN.O=[N+]([O-])O>C(C)O>COc1ccc(NC(N)=[NH2+])cc1.O=[N+]([O-])[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6656788808ec4627bf81fed1d8c98130 | CCOC(=O)c1ccc(OC)cc1.Cc1cccc(Cl)n1>>COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1 | ClC1=CC=CC(=N1)C.COC1=CC=C(C(=O)OCC)C=C1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)OC | CCO[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1)=[O:8].[CH3:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Cl:15])[n:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]([Cl:15])[n:16]2)[cH:17][cH:18]1 | CCOC(=O)c1ccc(OC)cc1.Cc1cccc(Cl)n1 | COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccccn1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 86 | [{"value": 86.0, "product": "ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | To a cold (0° C.) solution of 6-chloro-2-picoline (18.3 mL 166.5 mmol) and ethyl 4-methoxybenzoate (30.0 g, 166.5 mmol) in tetrahydrofuran (300 mL) was added lithium bis(trimethylsilyl)amide (333 mL, 1.0 M in tetrahydrofuran, 332.7 mmol) dropwise via a pressure equalizing funnel over 1 hour. Upon complete addition, the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccccc1.c1ccncc1 | HO- | O1CCCC1 | 45 | null | CCOC(=O)c1ccc(OC)cc1.Cc1cccc(Cl)n1>O1CCCC1>COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c17249c5c72c44bfba8adb802f0e1183 | COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1.NO>>COc1ccc(C(Cc2cccc(Cl)n2)=NO)cc1 | [OH-].[Na+].ClC1=CC=CC(=N1)CC(=O)C1=CC=C(C=C1)OC.Cl.NO>>ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)OC | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][cH:18]1)[CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[n:15]1.[NH2:16][OH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([Cl:14])[n:15]2)=[N:16][OH:17])[cH:18][cH:19]1 | COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1.NO | COc1ccc(C(Cc2cccc(Cl)n2)=NO)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(Cc1ccccn1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[#7;a:4]:[c:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[O;D1;H1:9])-[c:5](:[c:6]):[c:7] | 97.9 | [{"value": 97.0, "product": "ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "ClC1=CC=CC(=N1)CC(=NO)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-methoxyphenyl)ethanone (37.4 g, 142.9 mmol) in methanol (500 mL) was added hydroxylamine hydrochloride (49.7 g, 714.5 mmol) followed by the addition of a sodium hydroxide solution (28.6 g, 714.5 mmol in 50 mL of water). The resulting suspension was heated at reflux for 2 h... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccncc1 | HO- | CO | null | null | COc1ccc(C(=O)Cc2cccc(Cl)n2)cc1.NO>CO>COc1ccc(C(Cc2cccc(Cl)n2)=NO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ac1125695fe41e882e014c7fc9b3c1c | COc1ccccc1C(Cc1cccc(Cl)n1)=NO>>COc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | O.C(C)N(CC)CC.ClC1=CC=CC(=N1)CC(=NO)C1=C(C=CC=C1)OC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)OC | O[N:16]=[C:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[n:15]1)[c:18]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[cH:10][cH:11][cH:12][c:13]([Cl:14])[n:15]3[n:16]2)[cH:17][cH:18]1 | COc1ccccc1C(Cc1cccc(Cl)n1)=NO | COc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | null | [Fe](Cl)Cl | COCCOC | Aromatic Heterocycle Formation | OtherReaction | 411bd0649f627d1f8ca686435bab674c584515e6f88887945a68f7487ba63ad1 | e4c614fd5a14fb8b7819c9887a8a3123bc2600c241ecd15d2c3f8ffc5fe30baf | c1ccc(-c2cc3ccccn3n2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[c:4](:[c:5]):[n;H0;D2;+0:6]:[c:7](-[Cl;D1;H0:8]):[c:9])-[c;H0;D3;+0:10]1:[c:11]:[cH;D2;+0:12]:[c:13]:[c:14]:[c:15]:1-[#8:16]>>[#8:16]-[c:15]1:[c:14]:[c:13]:[c;H0;D3;+0:12](-[c;H0;D3;+0:2]2:[cH;D2;+0:3]:[c:4](:[c:5]):[n;H0;D3;+0:6](:[n;H0;D2;+0:1]:2):[c:7](-[Cl;D1;H0:8]):[... | 52 | [{"value": 52.0, "product": "ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 1.5 | HOUR | To a solution of 2-(6-chloro-2-pyridinyl)-1-(methoxyphenyl)ethanone oxime (38.7 g, 140 mmol) in 1,2-dimethoxyethane (156 mL) at 0° C. was added trifluoroacetic anhydride (20 mL, 140 mmol), keeping the temperature below 10° C. during the addition. After the addition was complete, the reaction was warmed to 15° C. The so... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HO- | [Fe](Cl)Cl.COCCOC | 15 | 1.5 | COc1ccccc1C(Cc1cccc(Cl)n1)=NO>[Fe](Cl)Cl.COCCOC>COc1ccc(-c2cc3cccc(Cl)n3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f179c5c0362475e8db73d9a8dcae6a5 | CC(=O)OC(C)=O.COc1ccc(-c2cc3cccc(Cl)n3n2)cc1>>COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1 | B(F)(F)F.ClC1=CC=CC=2N1N=C(C2)C2=CC=C(C=C2)OC.C(C)(=O)OC(C)=O>>ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC | CC(=O)O[C:17]([CH3:18])=[O:19].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[cH:16]2)[cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[c:16]2[C:17]([CH3:18])=[O:19])[cH:20][cH:21]1 | CC(=O)OC(C)=O.COc1ccc(-c2cc3cccc(Cl)n3n2)cc1 | COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Friedel-Crafts acylation | 202ee4eacbf5a64e631dc5b199026ef8a0e6891baed537bbc108bdabe4842b8e | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | c1ccc(-c2cc3ccccn3n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[#7;a:5]1:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:[c:10]:1:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:9]1:[c:10](:[c:11]):[#7;a:5](:[c:4]):[#7;a:6]:[c:7]:1-[c:8] | 65.2 | [{"value": 65.0, "product": "ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridine (18.7 g, 72.4 mmol) in toluene (300 mL) at room temperature was added acetic anhydride (8.2 mL, 86.9 mmol). Boron trifluoride diethyletherate (10.1 mL, 79.6 mmol) was then added dropwise and the resulting solution was heated at reflux for 4 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)OC(C)=O.COc1ccc(-c2cc3cccc(Cl)n3n2)cc1>C1(=CC=CC=C1)C>COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03a1e91ef1d84052b96a96a7599d04fc | COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1.NC1CCCC1>>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(C)=O)cc1 | C(C)OCC.ClC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC.C([O-])([O-])=O.[Cs+].[Cs+].C1(CCCC1)N>>C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC | Cl[c:10]1[n:9]2[n:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][cH:25]3)[c:21]([C:22]([CH3:23])=[O:24])[c:20]2[cH:19][cH:18][cH:17]1.[NH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([NH:11][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)[cH:17][cH:18][cH:... | COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1.NC1CCCC1 | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(C)=O)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | O.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e8c82b4f8a5597e31832115c04c533f9cd7e300ef5e2958a4a89b323d40969a6 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cc3cccc(NC4CCCC4)n3n2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[NH;D2;+0:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7])-[C:11] | 97.6 | [{"value": 97.0, "product": "C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(C)=O)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 4 | HOUR | To a solution of 1-[7-(chloro)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (5.0 g, 16.6 mmol) in toluene (100 mL) was added successively racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (620 mg, 1.0 mmol), cesium carbonate (8.12 g, 24.9 mmol), cyclopentylamine (8.2 mL, 83.1 mmol), and palladium (II) acet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.C1CCCC1.c1ccn2nccc2c1 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.O.C1(=CC=CC=C1)C | 95 | 4 | COc1ccc(-c2nn3c(Cl)cccc3c2C(C)=O)cc1.NC1CCCC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.O.C1(=CC=CC=C1)C>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87029d2911b1461884aaf8aea8da9ffd | N#CN.Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])O>>NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])[O-] | CCOCC.NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1.N#CN.N#CN.[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>[N+](=O)([O-])[O-].C(C1=CC=CC=C1)(=O)C=1C=C(C=CC1)NC(=[NH2+])N | [N:1]#[C:2][NH2:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1.[O:19]=[N+:20]([O-:21])[OH:22]>>[NH2:1][C:2](=[NH2+:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1.[O:19]=[N+:20]([O-:21])[O-:22] | N#CN.Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])O | NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])[O-] | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 8980c9c7a2a3cf9244c0b60eeb227f7897b33b43c7eb750f87d7d7c6862c414d | 50b51df4262f52466dc83399cfe46c19be73dee0760243d32794686add22bdcb | O=C(c1ccccc1)c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7].[O;-;D1;H0:8]-[#7;+:9](=[O;D1;H0:10])-[OH;D1;+0:11]>>[NH2+;D1:3]=[C;H0;D3;+0:2](-[NH2;D1;+0:1])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O-;H0;D1:11]-[#7;+:9](-[O;-;D1;H0:8])=[O;D1;H0:10] | 41 | [{"value": 41.0, "product": "[N+](=O)([O-])[O-].C(C1=CC=CC=C1)(=O)C=1C=C(C=CC1)NC(=[NH2+])N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a room temperature solution of 3-aminobenzophenone (4.0 g, 20.2 mmol) in ethanol (50 mL) was added cyanamide (1.8 mL 50 wt % in water, 23.3 mmol) followed by the dropwise addition of concentrated nitric acid (1.42 mL). The mixture was heated at reflux for 2 hours and then additional cyanamide (1.8 mL, 50 wt % in wat... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Amidinium.Amidinium | null | null | c1ccccc1.c1ccccc1 | null | C(C)O | null | null | N#CN.Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])O>C(C)O>NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1.O=[N+]([O-])[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe066957bc43427db7620231eae9e5aa | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(=O)/C=C/N(C)C)cc1.NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1>>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3-c3cccc(C=O)c3)n2)cc1 | CCOCC.C1(CCCC1)NC1=CC=CC=2N1N=C(C2C(\C=C\N(C)C)=O)C2=CC=C(C=C2)OC.[N+](=O)([O-])[O-].C(C1=CC=CC=C1)(=O)C=1C=C(C=CC1)NC(=[NH2+])N.C([O-])([O-])=O.[K+].[K+]>>C1(CCCC1)NC1=CC=CC=2N1N=C(C2C2=NC(=NC=C2)NC2=C(C=CC=C2)C=2C=C(C=CC2)C=O)C2=CC=C(C=C2)OC | CN(C)/[CH:24]=[CH:23]/[C:22](=O)[c:21]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][cH:43]2)[n:8][n:9]2[c:10]([NH:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18][cH:19][c:20]21.[NH2+:25]=[C:26]([NH:27][c:34]1[cH:35][cH:36][cH:37][c:38]([C:39]([c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)=[O:40])[cH:41... | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(=O)/C=C/N(C)C)cc1.NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1 | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3-c3cccc(C=O)c3)n2)cc1 | null | null | O.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | b767f686aa91ca7ec809e0afc9dca4d1b9d89a308104529c633e055e33e60db6 | 24b4c7102e569bd1344bc37a71bf3e1e97998af2abd685404330d20b433d317e | c1ccc(-c2ccccc2Nc2nccc(-c3c(-c4ccccc4)nn4c(NC5CCCC5)cccc34)n2)cc1 | C-N(-C)/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5](:[c:6]):[#7;a:7](:[c:8]):[#7;a:9]:[c:10]:1-[c:11].[NH2+;D1:12]=[C;H0;D3;+0:13](-[NH2;D1;+0:14])-[NH;D2;+0:15]-[c;H0;D3;+0:16]1:[c:17]:[c:18]:[c:19]:[c:20](-[C;H0;D3;+0:21](=[O;D1;H0:22])-[c;H0;D3;+0:23]2:[c:24]:[c:25]:[c:26]:[c:27]:[cH;D2;+0:28]... | 76 | [{"value": 76.0, "product": "C1(CCCC1)NC1=CC=CC=2N1N=C(C2C2=NC(=NC=C2)NC2=C(C=CC=C2)C=2C=C(C=CC2)C=O)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "C1(CCCC1)NC1=CC=CC=2N1N=C(C2C2=NC(=NC=C2)NC2=C(C=CC=C2)C=2C=C(C=CC2)C=O)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD... | 140 | CELSIUS | null | null | To a solution of (2E)-1-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (100 mg, 0.25 mmol) in N,N-dimethylformamide (5 mL) was added N-(3-benzoylphenyl)guanidinium nitrate (223 mg, 0.74 mmol) and potassium carbonate (102 mg, 0.74 mmol). The suspension was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Amidinium.Amidinium.Ketone.Ketone | Aldehyde.Secondary amine | c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1ccccc1.C1CCCC1.c1ccn2nccc2c1.c1cncnc1.c1ccccc1.c1ccccc1 | HO- | O.CN(C=O)C | 140 | null | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2C(=O)/C=C/N(C)C)cc1.NC(=[NH2+])Nc1cccc(C(=O)c2ccccc2)c1>O.CN(C=O)C>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3ccccc3-c3cccc(C=O)c3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94f2a48dfffc4dbe8606f31631f44660 | CCOC(=O)c1ccc(F)cc1.Cc1cc(Cl)ccn1>>O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | ClC1=CC(=NC=C1)C.FC1=CC=C(C(=O)OCC)C=C1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>ClC1=CC(=NC=C1)CC(=O)C1=CC=C(C=C1)F | CCO[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1.[CH3:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][n:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][n:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1 | CCOC(=O)c1ccc(F)cc1.Cc1cc(Cl)ccn1 | O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccccn1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 99 | [{"value": 99.0, "product": "ClC1=CC(=NC=C1)CC(=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "ClC1=CC(=NC=C1)CC(=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a cold (0 ° C.) solution of 4-chloro-2-picoline (5.0 g,39 mmol) and ethyl 4-fluorobenzoate (6.6 g, 39 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (80 mL, 1.0 M in tetrahydrofuran, 80 mmol) dropwise via a pressure equalizing funnel over 30 minutes. Upon complete addition, the cold bat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccncc1.c1ccccc1 | HO- | O1CCCC1 | null | 15 | CCOC(=O)c1ccc(F)cc1.Cc1cc(Cl)ccn1>O1CCCC1>O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3cdb861796ec4284a88970d317d8ad26 | NO.O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1>>ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | [OH-].[Na+].ClC1=CC(=NC=C1)CC(=O)C1=CC=C(C=C1)F.Cl.NO>>ClC1=CC(=NC=C1)CC(=NO)C1=CC=C(C=C1)F | [OH:1][NH2:2].O=[C:3]([CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][n:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[OH:1][N:2]=[C:3]([CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][n:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | NO.O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(Cc1ccccn1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[O;D1;H1:9]>>[#7;a:4]:[c:3]-[C:2]-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[O;D1;H1:9])-[c:5](:[c:6]):[c:7] | 84 | [{"value": 84.0, "product": "ClC1=CC(=NC=C1)CC(=NO)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "ClC1=CC(=NC=C1)CC(=NO)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 38 mmol) in methanol (200 mL) was added hydroxylamine hydrochloride (13.5 g, 190 mmol) followed by the addition of a sodium hydroxide solution (7.8 g, 190 mmol in 50 mL of water). The resulting suspension was heated at reflux for 2 hours and t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccncc1.c1ccccc1 | HO- | CO | null | null | NO.O=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1>CO>ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0dd7b29960b94ef1aaca212f5b05d9dd | ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1>>Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1 | O.C(C)N(CC)CC.ClC1=CC(=NC=C1)CC(=NO)C1=CC=C(C=C1)F.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>ClC1=CC=2N(C=C1)N=C(C2)C2=CC=C(C=C2)F | O[N:15]=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1)[CH2:7][c:8]1[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]3[cH:9][c:10]([Cl:11])[cH:12][cH:13][n:14]3[n:15]2)[cH:16][cH:17]1 | ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1 | Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1 | null | [Fe](Cl)Cl | COCCOC | Aromatic Heterocycle Formation | OtherReaction | eb06b64c3f1e34c5ece58a586a196c3e564df3ceec641c6b6ac1954bda6f0891 | e4c614fd5a14fb8b7819c9887a8a3123bc2600c241ecd15d2c3f8ffc5fe30baf | c1ccc(-c2cc3ccccn3n2)cc1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[CH2;D2;+0:3]-[c:4](:[c:5]):[n;H0;D2;+0:6]:[c:7]:[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:8]:[c:7]:[n;H0;D3;+0:6]1:[n;H0;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[cH;D2;+0:3]:[c:4]:1:[c:5] | 57 | [{"value": 57.0, "product": "ClC1=CC=2N(C=C1)N=C(C2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "ClC1=CC=2N(C=C1)N=C(C2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (8.0 g, 30 mmol) in 1,2-dimethoxyethane (50 mL) at 0° C. was added trifluoroacetic anhydride (6.3 g, 30 mmol), keeping the temperature below 10° C. during the addition. After the addition was complete, the reaction was warmed to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | c1ccncc1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HO- | [Fe](Cl)Cl.COCCOC | null | 1.5 | ON=C(Cc1cc(Cl)ccn1)c1ccc(F)cc1>[Fe](Cl)Cl.COCCOC>Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9dd927b9d0ef4882bfcfbe35c38a9c3d | CN(C)C=O.Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1>>O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 | ClC1=CC=2N(C=C1)N=C(C2)C2=CC=C(C=C2)F.P(=O)(Cl)(Cl)Cl.CN(C=O)C.[OH-].[NH4+]>>ClC1=CC=2N(C=C1)N=C(C2C=O)C2=CC=C(C=C2)F | CN(C)[CH:2]=[O:1].[cH:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][n:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12>>[O:1]=[CH:2][c:3]1[c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][n:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]12 | CN(C)C=O.Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1 | O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 | null | null | null | C-C Coupling | OtherReaction | fbbc693464897575eb3638bafa13ea5e2af946f3a547fe2a232e64ac2b2403ad | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc(-c2cc3ccccn3n2)cc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[c:3]:[#7;a:4]1:[#7;a:5]:[c:6](-[c:7]):[cH;D2;+0:8]:[c:9]:1:[c:10]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:8]1:[c:9](:[c:10]):[#7;a:4](:[c:3]):[#7;a:5]:[c:6]:1-[c:7] | null | [] | null | null | 10 | MINUTE | Phosphorous oxychloride (0.6 mL, 6.4 mmol) was added to N,N-dimethylformamide (10 mL) and the resulting mixture stirred at room temperature for 10 minutes. 5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridine (1.0 g, 4.1 mmol) was added and the reaction mixture was stirred at room temperature for 12 hours. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | Other | null | null | 0.166667 | CN(C)C=O.Fc1ccc(-c2cc3cc(Cl)ccn3n2)cc1>>O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ef00c729de647079938140ebda98e31 | O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12>>CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 | O.ClC1=CC=2N(C=C1)N=C(C2C=O)C2=CC=C(C=C2)F.C(#C)[Mg]Br.O1CCCC1>>ClC1=CC=2N(C=C1)N=C(C2C(C#CC)=O)C2=CC=C(C=C2)F | [CH:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15][n:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]12>>[CH3:1][C:2]#[C:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[n:15][n:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]12 | O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 | CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 | null | null | null | Miscellaneous | OtherReaction | 85be4f94be922eda0329bac5658391a7e57e408668cc303f8316f8ca7b2631ab | c4b17b2501c93982efc0dacb8c14f90df9c0c54b8e1283d853ac6af36f5a3067 | c1ccc(-c2cc3ccccn3n2)cc1 | [O;D1;H0:1]=[CH;D2;+0:2]-[c:3]1:[c:4](:[c:5]):[#7;a:6](:[c:7]):[#7;a:8]:[c:9]:1-[c:10]>>[C:11]#[C:12]-[C;H0;D3;+0:2](=[O;D1;H0:1])-[c:3]1:[c:4](:[c:5]):[#7;a:6](:[c:7]):[#7;a:8]:[c:9]:1-[c:10] | 62 | [{"value": 62.0, "product": "ClC1=CC=2N(C=C1)N=C(C2C(C#CC)=O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-chloro-2-(4fluorophenyl)pyrazolo[1,5-α]pyridine-3-carbaldehyde (0.93 g, 3.4 mmol) in tetrahydrofuran (20 mL) at −78° C. was added ethynylmagnesium bromide (16 mL, 0.5 M in tetrahydrofuran, 8.0 mmol). The mixture was allowed to warm to room temperature and stirred for 1 hour. Water was added to the re... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ketone.Alkyne | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | null | null | 1 | O=Cc1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12>>CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4312566ec3fb4e8680562808fdee4830 | CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12.N=C(N)Nc1ccccc1>>Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | ClC1=CC=2N(C=C1)N=C(C2C(C#CC)=O)C2=CC=C(C=C2)F.[N+](=O)(O)[O-].C1(=CC=CC=C1)NC(=N)N.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC=2N(C=C1)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F | C[C:18]#[C:17][C:16](=O)[c:15]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:30][cH:29]2)[n:7][n:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]21.[NH:19]=[C:20]([NH:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[NH2:28]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[c:15]2-[c:16]2[... | CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12.N=C(N)Nc1ccccc1 | Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | null | null | CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | 0cbda98ef34aa5b5272c5c025bd2e8c90d5a73e98d709bf1c424c7b4e7908589 | 90e5427edd48b74dbad700e9f8787e3d6b03d177513f387c03b425fd38cb283b | c1ccc(Nc2nccc(-c3c(-c4ccccc4)nn4ccccc34)n2)cc1 | C-[C;H0;D2;+0:1]#[C;H0;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[c:5](:[c:6]):[#7;a:7](:[c:8]):[#7;a:9]:[c:10]:1-[c:11].[NH2;D1;+0:12]-[C;H0;D3;+0:13](=[NH;D1;+0:14])-[#7:15]-[c:16]>>[c:6]:[c:5]1:[#7;a:7](:[c:8]):[#7;a:9]:[c:10](-[c:11]):[c;H0;D3;+0:4]:1-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:14]:[c;H... | 36 | [{"value": 36.0, "product": "ClC1=CC=2N(C=C1)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.8, "product": "ClC1=CC=2N(C=C1)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | To a solution of 1-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-butyn-1-one (1.0 g, 3.36 mmol) in 1-methyl-2-pyrrolidinone (4 mL) was added N-phenylguanidine nitrate (1.0 g, 5.0 mmol) and anhydrous potassium carbonate (0.7 g, 5.0 mmol). The resulting mixture was heated at 150° C. for 12 hours and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Alkyne | null | null | c1cncnc1 | c1ccccc1.c1ccn2nccc2c1.c1cncnc1.c1ccccc1 | HO- | CN1C(CCC1)=O | 150 | null | CC#CC(=O)c1c(-c2ccc(F)cc2)nn2ccc(Cl)cc12.N=C(N)Nc1ccccc1>CN1C(CCC1)=O>Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87058de6158440a7af624a3373595eef | Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1.NC1CCCC1>>Fc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC.ClC1=CC=2N(C=C1)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F.C1(=CC=CC=C1)P(C1=C(C2=CC=CC=C2C=C1)C1=C(C=CC2=CC=CC=C12)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+].C1(CCCC1)N>>N(C1=CC=CC=C1)C... | Cl[c:11]1[cH:10][cH:9][n:8]2[n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:35][cH:34]3)[c:20](-[c:21]3[cH:22][cH:23][n:24][c:25]([NH:26][c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[n:33]3)[c:19]2[cH:18]1.[NH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]... | Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1.NC1CCCC1 | Fc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e8c82b4f8a5597e31832115c04c533f9cd7e300ef5e2958a4a89b323d40969a6 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3c(-c4ccccc4)nn4ccc(NC5CCCC5)cc34)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]2:[#7;a:5]:[c:6]:[c:7]:[c:8]:2:[c:9]:1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]2:[#7;a:5]:[c:6]:[c:7]:[c:8]:2:[c:9]:1)-[C:13] | 36 | [{"value": 36.0, "product": "N(C1=CC=CC=C1)C1=NC=CC(=N1)C=1C(=NN2C1C=C(C=C2)NC2CCCC2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 24 | HOUR | To a solution of 4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-phenyl-2-pyrimidinamine (100 mg, 0.24 mmol) in cyclopentylamine (5 mL) was added successively racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (72 mg), cesium carbonate (200 mg), and palladium (II) acetate (16 mg). The resulting mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1.C1CCCC1.c1cncnc1.c1ccccc1 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O | 100 | 24 | Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1.NC1CCCC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O>Fc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56267b581f904460a878984962e92f00 | CCSSCC.Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1>>CCSc1cc(Cl)cc2c(-c3ccnc(Nc4ccccc4)n3)c(-c3ccc(F)cc3)nn12 | C(C)SSCC.O.ClC1=CC=2N(C=C1)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F.C(CCC)[Li]>>ClC1=CC=2N(C(=C1)SCC)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F | CCS[S:3][CH2:2][CH3:1].[cH:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]([NH:16][c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[n:23]3)[c:24](-[c:25]3[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]3)[n:32][n:33]12>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10](-[c:11]3[cH:12][cH:1... | CCSSCC.Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1 | CCSc1cc(Cl)cc2c(-c3ccnc(Nc4ccccc4)n3)c(-c3ccc(F)cc3)nn12 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8f2f499f6e852de60c34bcbcfa10e3c41339cca309fdc0032a6d8a6eb432464c | 19099c5abc7af7f1b3d32ffaaaa6b84236f3e8c2bf9cb204008fe61bb9aa47e2 | c1ccc(Nc2nccc(-c3c(-c4ccccc4)nn4ccccc34)n2)cc1 | C-C-S-[S;H0;D2;+0:1]-[C:2]-[C;D1;H3:3].[c:4]:[#7;a:5]:[#7;a:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:3]-[C:2]-[S;H0;D2;+0:1]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[#7;a:6](:[c:7]):[#7;a:5]:[c:4] | 22.1 | [{"value": 22.0, "product": "ClC1=CC=2N(C(=C1)SCC)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.1, "product": "ClC1=CC=2N(C(=C1)SCC)N=C(C2C2=NC(=NC=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine (80 mg, 0.19 mmol) in tetrahydrofuran (5 mL) was added n-butyllithium (0.43 mL of 1.6M solution in hexane, 0.67 mmol) at −78° C. The resulting dark solution was stirred for 10 minutes, then quenched by the addition of ... | 10.6084/m9.figshare.5104873.v1 | null | Disulfide | Monosulfide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccn2nccc2c1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 0.166667 | CCSSCC.Fc1ccc(-c2nn3ccc(Cl)cc3c2-c2ccnc(Nc3ccccc3)n2)cc1>C(C)(=O)OCC.O1CCCC1>CCSc1cc(Cl)cc2c(-c3ccnc(Nc4ccccc4)n3)c(-c3ccc(F)cc3)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70663752c89d42869644e5dfac14c2ed | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N)c3)n2)cc1>>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N=[N+]=[N-])c3)n2)cc1 | N(=O)[O-].[Na+].N(=O)[O-].[Na+].[N-]=[N+]=[N-].[Na+].[N-]=[N+]=[N-].[Na+].C([O-])(O)=O.[Na+].C1(CCCC1)NC1=CC=CC=2N1N=C(C2C2=NC(=NC=C2)NC=2C=C(C=CC2)N)C2=CC=C(C=C2)OC>>N(=[N+]=[N-])C=1C=C(NC2=NC=CC(=N2)C=2C(=NN3C2C=CC=C3NC3CCCC3)C3=CC=C(C=C3)OC)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([NH:11][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)[cH:17][cH:18][cH:19][c:20]3[c:21]2-[c:22]2[cH:23][cH:24][n:25][c:26]([NH:27][c:28]3[cH:29][cH:30][cH:31][c:32]([NH2:33])[cH:36]3)[n:37]2)[cH:38][cH:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[... | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N)c3)n2)cc1 | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N=[N+]=[N-])c3)n2)cc1 | null | null | O.C(C)(=O)O.O.CCOCC | Miscellaneous | Amine to azide | 874c0cf1984ab0c3156493e6524e4a76434860bf4d8c4f6115608f4b54932f2a | 0dcf06f7cec37f2f50b2497bf88be0f43ce4890a2df8b6f4eb18df3f7b6a2a7d | c1ccc(Nc2nccc(-c3c(-c4ccccc4)nn4c(NC5CCCC5)cccc34)n2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;-;D1;H0:5]=[#7;+:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 23 | [{"value": 23.0, "product": "N(=[N+]=[N-])C=1C=C(NC2=NC=CC(=N2)C=2C(=NN3C2C=CC=C3NC3CCCC3)C3=CC=C(C=C3)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | The following transformation was performed in the dark. To a cold (0° C.) solution of N′-{4-[7-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinyl}-1,3-benzenediamine (16.5 mg, 0.03 mmol) in acetic acid/water (80/20, 1 mL) was added aqueous sodium nitrite (0.32 mL of a stock solution prepar... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Azide | null | null | c1ccccc1.C1CCCC1.c1ccn2nccc2c1.c1cncnc1.c1ccccc1 | Other | O.C(C)(=O)O.O.CCOCC | 0 | 0.25 | COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N)c3)n2)cc1>O.C(C)(=O)O.O.CCOCC>COc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(Nc3cccc(N=[N+]=[N-])c3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bb4283dc5764564964b1c088089be4f | Brc1cccc2c1ccc1ccccc12>>[Li][c]1cccc2c1ccc1ccccc12 | BrC1=CC=CC=2C3=CC=CC=C3C=CC12.C(CCC)[Li]>>[Li]C1=CC=CC=2C3=CC=CC=C3C=CC12 | Br[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21>>[Li:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21 | Brc1cccc2c1ccc1ccccc12 | [Li][c]1cccc2c1ccc1ccccc12 | null | null | CCCCCCC | Miscellaneous | Preparation of organolithium compounds | b8b5a684c0bbe5bc0b441246971c59d0a716f3b9c69dea25505b38f3ea8c97bc | b74e09b9a6bbb0311fc1db764a25c5a719efefaac386e11fdf0023b3ff360a3e | c1ccc2c(c1)ccc1ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6]>>[Li;D1;H0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 2.1 Grams (8.3 mmols) of a 1-bromophenanthrene was dissolved in 43 ml of heptane, 5.3 ml (1.6 mols/l, 8.5 mmols) of butyl lithium was added thereto at room temperature to obtain a 1-lithiophenanthrene, which was cooled down to −5° C., followed by the addition of 2.2 g (5.2 mmols) of the above DBBF. The mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aryl lithium | c1ccc2c(c1)ccc1ccccc12 | c1ccc2c(c1)ccc1ccccc12 | c1ccc2c(c1)ccc1ccccc12 | null | CCCCCCC | null | null | Brc1cccc2c1ccc1ccccc12>CCCCCCC>[Li][c]1cccc2c1ccc1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b71e3bfdd4e143178595b21c8d1514f9 | Brc1cccc2c1ccc1ccccc12>>[Li][c]1cccc2c1ccc1ccccc12 | BrC1=CC=CC=2C3=CC=CC=C3C=CC12.C(CCC)[Li]>>[Li]C1=CC=CC=2C3=CC=CC=C3C=CC12 | Br[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21>>[Li:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]21 | Brc1cccc2c1ccc1ccccc12 | [Li][c]1cccc2c1ccc1ccccc12 | null | null | CCCCCCC | Miscellaneous | Preparation of organolithium compounds | b8b5a684c0bbe5bc0b441246971c59d0a716f3b9c69dea25505b38f3ea8c97bc | b74e09b9a6bbb0311fc1db764a25c5a719efefaac386e11fdf0023b3ff360a3e | c1ccc2c(c1)ccc1ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6]>>[Li;D1;H0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 2.1 Grams (8.3 mmols) of a 1-bromophenanthrene was dissolved in 43 ml of heptane, and to which was added 5.3 ml (1.6 mols/l, 8.5 mmols) of butyllithium to obtain a 1-lithiophenanthrene, which was, then, cooled down to −5° C. 1.6 Grams (5.2 mmols) of the 3.9-dimethoxy-5-hydroxybenzo[c]fluorene-7-one was added thereto, a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aryl lithium | c1ccc2c(c1)ccc1ccccc12 | c1ccc2c(c1)ccc1ccccc12 | c1ccc2c(c1)ccc1ccccc12 | null | CCCCCCC | null | null | Brc1cccc2c1ccc1ccccc12>CCCCCCC>[Li][c]1cccc2c1ccc1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b2708b9760e412ba365ccc68af26b1b | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO>>O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1 | C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O.OO>>C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@H]5[C@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O | [O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][c:6]2[c:7]([OH:8])[cH:9][c:10]([OH:11])[cH:12][c:13]2[O:14][C@@H:15]1[c:16]1[cH:17][c:18]([OH:19])[c:20]([OH:21])[c:33]([OH:34])[cH:32]1)[c:44]1[cH:45][c:46]([OH:47])[c:48]([OH:49])[c:50]([OH:51])[cH:52]1.[OH:24][OH:26]>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][c:6]2[c:7]([OH:8])[cH:9][c:10]([... | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO | O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 0da77ac34170a9b3425085971931d5b7c39e272a9fdfd81918a6b9bdbc4b9e51 | 86917598d21a420ba5375a127bd51cc17291cd724ec8a7a6b75734ad4bfb91d0 | O=C(O[C@H]1Cc2ccccc2O[C@H]1c1cccc2cc(=O)cc([C@@H]3CCc4ccccc4O3)cc12)c1ccccc1 | [C:1]-[C:2](-[c;H0;D3;+0:3]1:[c:4]:[c:5](-[O;D1;H1:6]):[c;H0;D3;+0:7](-[O;D1;H1:8]):[c;H0;D3;+0:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1)-[#8:12]-[c:13].[OH;D1;+0:14]-[OH;D1;+0:15]>>[#8:16]-[c:17]1:[c:18]:[c:19]:[c:20]:[c;H0;D3;+0:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1.[C:1]-[C:2](-[c;H0;D3;+0:3]1:[c:4]:[c:5](-[O;D1;H1:6]):[c;H0;D... | 28.1 | [{"value": 28.1, "product": "C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@H]5[C@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | EC (1 g) and EGCG (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentra... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Peroxide | Phenol.Ether.Secondary alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2 | c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | Other | CC(=O)C | null | null | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO>CC(=O)C>O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85fb8685fe69496fa138220055177233 | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO>>O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3OC(=O)c3cc(O)c(O)c(O)c3)c2c1)c1cc(O)c(O)c(O)c1 | C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O.OO>>C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@@H]5[C@@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O | [O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][c:6]2[c:7]([OH:8])[cH:9][c:10]([OH:11])[cH:12][c:13]2[O:14][C@@H:15]1[c:16]1[cH:17][c:18]([OH:19])[c:48]([OH:49])[c:46]([OH:47])[cH:45]1)[c:55]1[cH:56][c:57]([OH:58])[c:59]([OH:60])[c:61]([OH:62])[cH:63]1.[OH:21][OH:34]>>[O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][c:6]2[c:7]([OH:8])[cH:9][c:10](... | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3OC(=O)c3cc(O)c(O)c(O)c3)c2c1)c1cc(O)c(O)c(O)c1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | fef2d5597bf75af07a76cfaf99a68765ff4ab5c45e281c8fd0dcccfe9294804f | 920a181d7f77b0c00f835e1de3066911717502822d7c661bfce52dea0090bc6e | O=C(O[C@@H]1Cc2ccccc2O[C@@H]1c1cc(=O)cc2cccc([C@H]3Oc4ccccc4C[C@H]3OC(=O)c3ccccc3)c2c1)c1ccccc1 | [C:1]-[C:2](-[c;H0;D3;+0:3]1:[c:4]:[c;H0;D3;+0:5](-[OH;D1;+0:6]):[c;H0;D3;+0:7](-[O;D1;H1:8]):[c:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1)-[#8:12]-[c:13].[OH;D1;+0:14]-[OH;D1;+0:15]>>[C:1]-[C:2](-[c;H0;D3;+0:3]1:[c:4]:[c;H0;D3;+0:5](=[O;H0;D1;+0:6]):[c:16](-[OH;D1;+0:14]):[c:17]:[c:18]:[c:19]:1)-[#8:12]-[c:13].[C:20]-[c:21]1:... | 10.6 | [{"value": 10.6, "product": "C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@@H]5[C@@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | ECG (1 g) and EGCG (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Peroxide | Phenol.Ester.Ether.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2.c1ccccc1 | c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2.c1ccccc1.c1ccccc1 | Other | CC(=O)C | null | null | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.OO>CC(=O)C>O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3OC(=O)c3cc(O)c(O)c(O)c3)c2c1)c1cc(O)c(O)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aaaa2f5ab5bb40d1ae85edc2fc0aab4a | OO.Oc1cc(O)c2c(c1)OC(c1ccc(O)c(O)c1)C(O)C2>>O=c1cc([C@H]2Oc3cc(O)cc(O)c3C[C@H]2O)cc2c([C@H]3Oc4cc(O)cc(O)c4C[C@@H]3O)cc(O)c(O)c2c1O | C1=CC(=C(C=C1C2C(CC=3C(=CC(=CC3O2)O)O)O)O)O.OO>>C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@@H]5[C@H](CC6=C(C=C(C=C6O5)O)O)O)O)O | [OH:1][OH:36].[c:2]1([OH:13])[cH:3][cH:34][c:20]([CH:21]2[O:22][c:23]3[cH:24][c:25]([OH:26])[cH:27][c:28]([OH:29])[c:30]3[CH2:31][CH:32]2[OH:33])[cH:8][c:9]1[OH:10]>>[O:1]=[c:2]1[cH:3][c:4]([C@H:5]2[O:6][c:7]3[cH:8][c:9]([OH:10])[cH:11][c:12]([OH:13])[c:14]3[CH2:15][C@H:16]2[OH:17])[cH:18][c:19]2[c:20]([C@H:21]3[O:22][... | OO.Oc1cc(O)c2c(c1)OC(c1ccc(O)c(O)c1)C(O)C2 | O=c1cc([C@H]2Oc3cc(O)cc(O)c3C[C@H]2O)cc2c([C@H]3Oc4cc(O)cc(O)c4C[C@@H]3O)cc(O)c(O)c2c1O | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 912c2e2fca486e4a3b74beecd6681efea46a5701b551347a7af5e214f3dcf9f3 | 81b29c74812cd78f847e5e7780f568572abb597675022a7be9e683598b7c805a | O=c1cc([C@@H]2CCc3ccccc3O2)cc2c([C@@H]3CCc4ccccc4O3)cccc2c1 | [O;D1;H1:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[CH;D3;+0:5]2-[#8:6]-[c:7]:[c:8]-[C:9]-[CH;D3;+0:10]-2-[O;D1;H1:11]):[cH;D2;+0:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14]:1-[OH;D1;+0:15].[OH;D1;+0:16]-[OH;D1;+0:17]>>[O;D1;H1:1]-[c;H0;D3;+0:2]1:[c:18]:[c:19](-[OH;D1;+0:15]):[c:20]:[c:21](:[cH;D2;+0:3]:1)-[#8:22]-[C:23]-[... | null | [] | null | null | null | null | C (catechin) (0.8 g) and EGC (0.8 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). Af... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Peroxide | Phenol.Ether.Secondary alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1 | c1ccc2c(c1)CCCO2.c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1 | Other | CC(=O)C | null | null | OO.Oc1cc(O)c2c(c1)OC(c1ccc(O)c(O)c1)C(O)C2>CC(=O)C>O=c1cc([C@H]2Oc3cc(O)cc(O)c3C[C@H]2O)cc2c([C@H]3Oc4cc(O)cc(O)c4C[C@@H]3O)cc(O)c(O)c2c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-113213f2c3bc44289c47214ea6d78761 | O=C(O)c1cc(O)c(O)c(O)c1.Oc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@@H](O)C2>>O=C(O)c1ccc2cc(O)c(O)c(O)c2c(=O)c1O | C1=CC(=C(C=C1[C@H]2[C@H](CC=3C(=CC(=CC3O2)O)O)O)O)O.C(C1=CC(O)=C(O)C(O)=C1)(=O)O.OO>>C1=CC(=C(C(=O)C2=C(C(=C(C=C21)O)O)O)O)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:13]([OH:14])[c:15]([OH:12])[c:16]([OH:17])[cH:18]1.Oc1ccc([C@@H]2Oc3c[c:7](O)[cH:8][c:9]([OH:10])[c:11]3[CH2:6][C@@H]2O)cc1[OH:19]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([OH:14])[c:15]2[c:16](=[O:17])[c:18]1[OH:19] | O=C(O)c1cc(O)c(O)c(O)c1.Oc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@@H](O)C2 | O=C(O)c1ccc2cc(O)c(O)c(O)c2c(=O)c1O | null | null | CC(=O)C | Acylation | OtherReaction | 3df8aba215007aeb6465bd331b95957cf062ad5734963f674c34572fb90af4af | 9e9de26d49181ee12fd7c4aebfbf922c70cdbf0f5b0d278f2db8861f9df173ae | O=c1ccccc2ccccc12 | O-[C@H]1-[CH2;D2;+0:1]-[c;H0;D3;+0:2]2:[c:3](-[O;D1;H1:4]):[c:5]:[c;H0;D3;+0:6](-O):c:c:2-O-[C@H]-1-c1:c:c:c(-O):c(-[OH;D1;+0:7]):c:1.[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[c:11]1:[cH;D2;+0:12]:[c;H0;D3;+0:13](-[OH;D1;+0:14]):[c;H0;D3;+0:15](-[OH;D1;+0:16]):[c;H0;D3;+0:17](-[O;D1;H1:18]):[cH;D2;+0:19]:1>>[O;D1;H0:8]=[C:9](-... | null | [] | null | null | null | null | Epicatechin (EC) (0.5 g) and gallic acid (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1: 10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (5... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Phenol.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCO2 | c1cccc2ccccc2c1 | c1cccc2ccccc2c1 | HO- | CC(=O)C | null | null | O=C(O)c1cc(O)c(O)c(O)c1.Oc1cc(O)c2c(c1)O[C@@H](c1ccc(O)c(O)c1)[C@@H](O)C2>CC(=O)C>O=C(O)c1ccc2cc(O)c(O)c(O)c2c(=O)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58d9642ade4b467aadb2af0aa39f7ca2 | OO.Oc1cccc(O)c1O.Oc1ccccc1O>>O=c1c(O)cccc2cc(O)c(O)c(O)c12 | C1(O)=C(O)C(O)=CC=C1.C=1(O)C(O)=CC=CC1.OO>>C=1C2=C(C(=C(C1O)O)O)C(=O)C(=CC=C2)O | O[OH:1].O[c:16]1[c:8]([OH:4])[cH:7][cH:6][cH:5][c:14]1[OH:15].c1[cH:3][cH:2][c:12]([OH:13])[c:10]([OH:11])[cH:9]1>>[O:1]=[c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:8]2[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([OH:15])[c:16]12 | OO.Oc1cccc(O)c1O.Oc1ccccc1O | O=c1c(O)cccc2cc(O)c(O)c(O)c12 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 572358fac4732262a49d7f7c8f35b8bd0d883b0a16c687445949f1191e04f91c | 227288829d52a0aa0ba0ba6034d44c2a9ef68ca3b18a402fa5e1c3842d43083f | O=c1ccccc2ccccc12 | O-[OH;D1;+0:1].O-[c;H0;D3;+0:2]1:[c;H0;D3;+0:3](-[O;D1;H1:4]):[cH;D2;+0:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[OH;D1;+0:9].[O;D1;H1:10]-[c:11]1:[cH;D2;+0:12]:c:[cH;D2;+0:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]:1-[O;D1;H1:16]>>[O;D1;H1:10]-[c:11]1:[cH;D2;+0:12]:[c;H0;D3;+0:8]2:[c:7]:[c:6]:[cH;D2;+0:5]:[c;H0;D3;+0:13](-[OH;D1;+0:9])... | 17.2 | [{"value": 17.2, "product": "C=1C2=C(C(=C(C1O)O)O)C(=O)C(=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Pyrogallol (1 g) and catechol (1.5 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). A... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Peroxide | Phenol.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccc2cccccc2c1 | c1ccc2cccccc2c1 | HO- | CC(=O)C | null | null | OO.Oc1cccc(O)c1O.Oc1ccccc1O>CC(=O)C>O=c1c(O)cccc2cc(O)c(O)c(O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4a5e269e226475482ae8126d27a45fe | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1>>O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@@H]... | C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O.C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C(=CC(=C4O)O)[C@H]5[C@H](CC6=C(C=C(C=C6O5)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O)O)O.C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O>>C1[C@@H]([C@@H](OC2=CC(=... | O[c:22]1[c:23]([OH:24])c[c:68]([C@@H:67]2[C@H:56]([O:55][C:54](=[O:53])[c:107]3[cH:108][c:109]([OH:110])[c:111]([OH:112])[c:113]([OH:114])[cH:115]3)[CH2:57][c:58]3[c:59]([OH:60])[cH:61][c:62]([OH:63])[cH:64][c:65]3[O:66]2)[cH:69][c:25]1[OH:26].O[c:42]1[c:20]([OH:21])[c:18]([OH:19])[cH:17][c:16]([C@@H:15]2[C@H:4]([O:3][... | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1 | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@@H]3Oc4cc(O)cc(O)c4C[C@@H]3O)c2c1)c1cc(O)c(O)c(O)c1.O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3OC(=O)c3cc(O)c(O)c(O)c3)c2c1)c1cc(O)c(O)c(O)c1 | null | null | null | Acylation | OtherReaction | 12deb89e1c81e801ddfdad11e40581a8c8d0e659cb09efce7d4267a23529dac8 | 421f1e8c96be9b9948bf8f286a6929ee71171c1abb8b96f065117c9e9707f00d | O=C(O[C@@H]1Cc2ccccc2O[C@@H]1c1cc(=O)cc2cccc([C@H]3CCc4ccccc4O3)c2c1)c1ccccc1.O=C(O[C@@H]1Cc2ccccc2O[C@@H]1c1cc(=O)cc2cccc([C@H]3Oc4ccccc4C[C@H]3OC(=O)c3ccccc3)c2c1)c1ccccc1 | O-[c;H0;D3;+0:1]1:[c;H0;D3;+0:2](-[O;D1;H1:3]):c:[c;H0;D3;+0:4](-[C:5](-[C:6])-[#8:7]-[c:8]):[cH;D2;+0:9]:[c;H0;D3;+0:10]:1-[O;D1;H1:11].O-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16](-[OH;D1;+0:17]):[c;H0;D3;+0:18]:1-[O;D1;H1:19].[C:20]-[C:21](-[O;H0;D2;+0:22]-[C;H0;D3;+0:23](=[O;D1;H0:24])-[c:25](:[c:26]):[c... | null | [] | null | null | null | null | EC (1 g, 3.5 mmol) and EGC (1 g, 3.3 mmol) were dissolved into the 200 mL of phosphate-citrate buffer (50 mM, pH 5.0) along with 2 g of crude PPO enzyme. The enzymatic oxidation was carried out at room temperature for 6 hour with stirring. The reaction solution was then subjected to fractionation with the same volume o... | 10.6084/m9.figshare.5104873.v1 | null | Phenol.Ester.Secondary alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Phenol.Phenol.Ester.Secondary alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccccc1.c1cc2ccccc2ccc1 | c1cc2ccccc2ccc1.c1cc2ccccc2ccc1 | c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2.c1ccccc1.c1ccc2c(c1)CCCO2.c1cc2ccccc2ccc1.c1ccc2c(c1)CCCO2.c1ccccc1.c1ccccc1 | HO- | null | null | null | O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(O)c(O)c(O)c1)c1cc(O)c(O)c(O)c1.O=C(O[C@H]1Cc2c(O)cc(O)cc2O[C@H]1c1cc(O)c(O)c2c(O)c(=O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3O)cc12)c1cc(O)c(O)c(O)c1>>O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@@H]... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce27fe380dda453696f70618851eb0ac | CC(=O)OC(C)=O.NC[C@H](O)CCl>>CC(=O)NC[C@@H](CCl)OC(C)=O | C([O-])([O-])=O.[K+].[K+].Cl.NC[C@@H](CCl)O.C(C)(=O)OC(C)=O.N1=CC=CC=C1>>C(C)(=O)O[C@@H](CNC(C)=O)CCl | O([C:2]([CH3:1])=[O:3])[C:10]([CH3:11])=[O:12].[NH2:4][CH2:5][C@@H:6]([CH2:7][Cl:8])[OH:9]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@@H:6]([CH2:7][Cl:8])[O:9][C:10]([CH3:11])=[O:12] | CC(=O)OC(C)=O.NC[C@H](O)CCl | CC(=O)NC[C@@H](CCl)OC(C)=O | null | null | O.C(Cl)Cl | Acylation | OtherReaction | 0f5940c5f5fba7ee13a03b24e44ee685674e5d1e6cfcaafe0442de5688d270b5 | 4d06cc1366db26ff20a4cf1cedce57766c1055cc948627755b0ce59590aa85c9 | null | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-O-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[NH2;D1;+0:11]>>[C:7]-[C:8](-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:4](-[C;D1;H3:5])=[O;D1;H0:6])-[O;H0;D2;+0:9]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;D1;H0:3] | null | [] | 42 | CELSIUS | 22 | HOUR | To a slurry of (S)-1-amino-3-chloro-2-propanol hydrochloride (500 g, 3.43 mol) in methylene chloride (1.54 kg) and acetic anhydride (803 g, 7.87 mol) is added pyridine (340 g, 4.3 mol) over 1 h while maintaining 38 to 46° C. The mixture is then stirred at 21 to 46° C. for 22 h. Water (600 ml) is added at 22 to 24° C. t... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol.Primary amine | Ester.Secondary amide | null | null | null | HO- | O.C(Cl)Cl | 42 | 22 | CC(=O)OC(C)=O.NC[C@H](O)CCl>O.C(Cl)Cl>CC(=O)NC[C@@H](CCl)OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f285b67dc294e238ffc1f95e39f39b1 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1ccc(C2=CCSCC2)c(F)c1>>CC(=O)NC[C@H]1CN(c2ccc(C3=CCSCC3)c(F)c2)C(=O)O1 | C(C)(=O)O.CC(C)([O-])C.[Li+].CC(COC(NC1=CC(=C(C=C1)C=1CCSCC1)F)=O)C.C(C)(=O)O[C@@H](CNC(C)=O)CCl>>S1CCC(=CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F | C[C:22](=[O:23])[O:24][C@H:6]([CH2:5]Cl)[CH2:7][NH:4][C:2]([CH3:1])=[O:3].CC(C)COC(=O)[NH:8][c:9]1[cH:10][cH:11][c:12]([C:13]2=[CH:14][CH2:15][S:16][CH2:17][CH2:18]2)[c:19]([F:20])[cH:21]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([C:13]3=[CH:14][CH2:15][S:16][CH2:17][CH2:18]3)[c... | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1ccc(C2=CCSCC2)c(F)c1 | CC(=O)NC[C@H]1CN(c2ccc(C3=CCSCC3)c(F)c2)C(=O)O1 | null | C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O | CO.CN(C=O)C.C1(=CC=CC=C1)C | Protection | OtherReaction | 973707246e5fc5a30d32be10455927a8889a34915e22bd954f8848b2e504302e | 88bede48978b8019d71fea373b51945d9f33e927291c4240a249bb71db22aa3b | O=C1OCCN1c1ccc(C2=CCSCC2)cc1 | C-C(-C)-C-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[CH2;D2;+0:9]-Cl)-[CH2;D2;+0:10]-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]>>[C;D1;H3:13]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:11]-[CH2;D2;+0:9]-[C:8]1-[#8:7]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]... | 78.5 | [{"value": 78.5, "product": "S1CCC(=CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "S1CCC(=CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 17 | HOUR | To a mixture of [4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]carbamic acid 2-methylpropyl ester (17.89 g, 57.83 mmol), (S)—N-[2-(acetyloxy)-3-chloropropyl]acetamide (22.35 g, 115.42 mmol, 2.00 eq), methanol (3.66 g, 114 mmol, 1.97 eq), 2,6-di-tert-butyl-4-methylphenol (0.1365 g, 0.6194 mmol, 0.0107 eq), toluene (5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ester.Ether.Secondary amide | Carbamic ester.Ether.Secondary amide | null | C1COC[NH]1 | C1COC[NH]1.c1ccccc1.C1=CCSCC1 | HCl | C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O.CO.CN(C=O)C.C1(=CC=CC=C1)C | 15 | 17 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1ccc(C2=CCSCC2)c(F)c1>C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O.CO.CN(C=O)C.C1(=CC=CC=C1)C>CC(=O)NC[C@H]1CN(c2ccc(C3=CCSCC3)c(F)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f67a0952f0d348859053f3c20b62f4a3 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cccc(F)c1>>CC(=O)NC[C@H]1CN(c2cccc(F)c2)C(=O)O1 | CC(COC(NC1=CC(=CC=C1)F)=O)C.C(C)(=O)O[C@@H](CNC(C)=O)CCl.CO.[Cl-].[NH4+]>>FC=1C=C(C=CC1)N1C(O[C@H](C1)CNC(C)=O)=O | CC(=O)[O:18][C@H:6]([CH2:5]Cl)[CH2:7][NH:4][C:2]([CH3:1])=[O:3].CC(C)CO[C:16]([NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]1)=[O:17]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[C:16](=[O:17])[O:18]1 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cccc(F)c1 | CC(=O)NC[C@H]1CN(c2cccc(F)c2)C(=O)O1 | null | null | CCCCCCC.O.CN(C=O)C.C1(=CC=CC=C1)C | Protection | OtherReaction | 973707246e5fc5a30d32be10455927a8889a34915e22bd954f8848b2e504302e | 88bede48978b8019d71fea373b51945d9f33e927291c4240a249bb71db22aa3b | O=C1OCCN1c1ccccc1 | C-C(-C)-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6].C-C(=O)-[O;H0;D2;+0:7]-[C:8](-[CH2;D2;+0:9]-Cl)-[CH2;D2;+0:10]-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]>>[C;D1;H3:13]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:11]-[CH2;D2;+0:9]-[C:8]1-[CH2;D2;+0:10]-[N;H0;D3;+0:3](-[c:4](:[c:5]):[c:6])-[C;H0;D3;+0... | 63 | [{"value": 63.0, "product": "FC=1C=C(C=CC1)N1C(O[C@H](C1)CNC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "FC=1C=C(C=CC1)N1C(O[C@H](C1)CNC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 1.5 | CELSIUS | 21 | HOUR | To a mixture of 3-fluorophenylcarbamic acid 2-methylpropyl ester (300.0 g, 1.42 mol), (S)—N-[2-(acetyloxy)-3-chloropropyl]acetamide (556.1 g, 2.87 mol, 2.02 eq), methanol (90.03 g, 2.81 mol, 1.98 eq) and N,N-dimethylformamide (500 ml) is added a slurry of lithium t-amylate (401.3 g, 4.27 mol, 3.00 eq) in heptane (1 lit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ester.Ether.Secondary amide | Carbamic ester.Ether.Secondary amide | null | C1COC[NH]1 | C1COC[NH]1.c1ccccc1 | HCl | CCCCCCC.O.CN(C=O)C.C1(=CC=CC=C1)C | 1.5 | 21 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cccc(F)c1>CCCCCCC.O.CN(C=O)C.C1(=CC=CC=C1)C>CC(=O)NC[C@H]1CN(c2cccc(F)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb00d1f4e3a84224bd69bdd32b33eb42 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cc(F)c(N2CCS(=O)(=O)CC2)c(F)c1>>CC(=O)NC[C@H]1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 | C(C)(=O)O[C@@H](CNC(C)=O)CCl.O=S1(CCN(CC1)C1=C(C=C(C=C1F)NC(OCC(C)C)=O)F)=O.CC(C)([O-])C.[Li+].CO.C(C)(=O)O>>CC(C)([O-])C.[Li+].O=S1(CCN(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC(C)=O)=O)F)=O | C[C:25](=[O:26])[O:27][C@H:6]([CH2:5]Cl)[CH2:7][NH:4][C:2]([CH3:1])=[O:3].CC(C)COC(=O)[NH:8][c:9]1[cH:10][c:11]([F:12])[c:13]([N:14]2[CH2:15][CH2:16][S:17](=[O:18])(=[O:19])[CH2:20][CH2:21]2)[c:22]([F:23])[cH:24]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([N:14]3[CH2:15][C... | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cc(F)c(N2CCS(=O)(=O)CC2)c(F)c1 | CC(=O)NC[C@H]1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 | null | null | C1CCOC1.O | Protection | OtherReaction | 973707246e5fc5a30d32be10455927a8889a34915e22bd954f8848b2e504302e | 88bede48978b8019d71fea373b51945d9f33e927291c4240a249bb71db22aa3b | O=C1OCCN1c1ccc(N2CCS(=O)(=O)CC2)cc1 | C-C(-C)-C-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[CH2;D2;+0:9]-Cl)-[CH2;D2;+0:10]-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])=[O;D1;H0:14]>>[C;D1;H3:13]-[C:12](=[O;D1;H0:14])-[NH;D2;+0:11]-[CH2;D2;+0:9]-[C:8]1-[#8:7]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]... | 73 | [{"value": 73.0, "product": "O=S1(CCN(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC(C)=O)=O)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | 7.5 | CELSIUS | 15 | MINUTE | A slurry of lithium t-butoxide (18.0 g, 223.5 mmol, 3.00 eq) in THF (100 ml) is prepared. Isobutyl 4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluorophenylcarbamate (27.0 g, 74.5 mmol) is dissolved in THF (180 ml) then added to the lithium t-butoxide slurry while maintaining less than 20° C. The mixture is stirred for 15 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ester.Ether.Secondary amide | Carbamic ester.Ether.Secondary amide | null | C1COC[NH]1 | C1COC[NH]1.c1ccccc1.C1CSCC[NH]1 | HCl | C1CCOC1.O | 7.5 | 0.25 | CC(=O)NC[C@@H](CCl)OC(C)=O.CC(C)COC(=O)Nc1cc(F)c(N2CCS(=O)(=O)CC2)c(F)c1>C1CCOC1.O>CC(=O)NC[C@H]1CN(c2cc(F)c(N3CCS(=O)(=O)CC3)c(F)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6db860dab31434dab410e8efec808ed | C=C[CH2][Mg][Cl].COc1ccncc1.O=C(Cl)OCc1ccccc1>>C=CCC1=CC(=O)CCN1C(=O)OCc1ccccc1 | Cl.C(C=C)[Mg]Cl.COC1=CC=NC=C1.ClC(=O)OCC1=CC=CC=C1>>C(=O)(OCC1=CC=CC=C1)N1CCC(C=C1CC=C)=O | [Cl][Mg][CH2:3][CH:2]=[CH2:1].C[O:7][c:6]1[cH:5][cH:4][n:10][cH:9][cH:8]1.Cl[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH2:1]=[CH:2][CH2:3][C:4]1=[CH:5][C:6](=[O:7])[CH2:8][CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C=C[CH2][Mg][Cl].COc1ccncc1.O=C(Cl)OCc1ccccc1 | C=CCC1=CC(=O)CCN1C(=O)OCc1ccccc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 404492016d9765f512e2df52ccd92d607f11c55df40490eda9a6383d93ba7531 | 9299a9ad1817d564b37def55ac4db98bb5707688a3c561b09dd1299aab462f21 | O=C1C=CN(C(=O)OCc2ccccc2)CC1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:1.Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H2:12]=[C:13]-[CH2;D2;+0:14]-[Mg]-[Cl]>>[C:11]-[#8:10]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[N;H0;D3;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[CH;D... | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 4-methoxypyridine (50 mL, 0.492 mol) in toluene (1 L) is added benzyl chloroformate (70.3 mL, 0.492 mol) at 0° C. The resulting mixture is stirred at 0° C. for 30 minutes then cooled to −75° C. and allyl magnesium chloride (295.5 mL, 0.591 mol) is added. The solution is held at −75° C. for 4 hours and ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Magnesium halide.Ether.Ether.Allyl | Enamine.Carbamic ester.Ketone.Ether.Allyl | c1ccncc1 | C1=C[NH]CCC1 | C1=C[NH]CCC1.c1ccccc1 | HCl.Mg | C1(=CC=CC=C1)C | 0 | 0.5 | C=C[CH2][Mg][Cl].COc1ccncc1.O=C(Cl)OCc1ccccc1>C1(=CC=CC=C1)C>C=CCC1=CC(=O)CCN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8bd411e3c3ab4b63b8ed399336f16009 | CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.N#CCCC1CN(CCc2ccc3ccccc3c2)C(=O)CN1C(=O)C(N)Cc1ccc(F)cc1>>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCC#N | NC(C(=O)N1C(CN(C(C1)=O)CCC1=CC2=CC=CC=C2C=C1)CCC#N)CC1=CC=C(C=C1)F.C(C)(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.CN(CCCN=C=NCC)C>>C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(C(C1)=O)CCC1=CC2=CC=CC=C2C=C1)CCC#N)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O | O[C:14]([C@@H:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1)=[O:15].[NH2:16][CH:17]([CH2:18][c:19]1[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]1)[C:26](=[O:27])[N:28]1[CH2:29][C:30](=[O:31])[N:32]([CH2:33][CH2:34][c:35]2[cH:36][cH:37][c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]3[cH:44... | CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.N#CCCC1CN(CCc2ccc3ccccc3c2)C(=O)CN1C(=O)C(N)Cc1ccc(F)cc1 | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCC#N | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)NC(Cc1ccccc1)C(=O)N1CCN(CCc2ccc3ccccc3c2)C(=O)C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:3](-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7])-[C:8]-[c:9].[#7:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17](-[C:18])-[NH2;D1;+0:19])-[C:20]>>[#7:10]-[C:11](=[O;D1;H0:12])-[C:13]-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17](-[C:18])-[NH;D2;+0:19]-[C;H0;D3;+0:1](... | null | [] | 0 | CELSIUS | 2 | HOUR | To a solution of 3-[1-[2-amino-3-(4-fluorophenyl)proponyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-2-yl]propionitrile, 33, (47.2 g, 100 mmol), N-acetyl-L-tyrosine (22.3 g, 120 mmol), 1-hydroxybenzotriazole (16.2 g, 120 mmol), and N-methylmorpholine (132 mL, 120 mmol) in DMF (150 mL) is cooled to 0° C. and 1-(3-dimet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ccccc2c1 | HO- | O.CN(C)C=O | 0 | 2 | CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O.N#CCCC1CN(CCc2ccc3ccccc3c2)C(=O)CN1C(=O)C(N)Cc1ccc(F)cc1>O.CN(C)C=O>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3071ba7b71a49d8b139e5505012e8dc | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C>>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=N)N | C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(C(C1)=O)CCC1=CC2=CC=CC=C2C=C1)CCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O.FC(C(=O)O)(F)F>>C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(C(C1)=O)CCC1=CC2=CC=CC=C2C=C1)CCCNC(=N)N)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O | CC(C)(C)OC(=O)[N:52]=[C:51]([NH:50][CH2:49][CH2:48][CH2:47][CH:46]1[N:28]([C:26]([CH:17]([NH:16][C:14]([CH:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)=[O:15])[CH2:18][c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)=[O:27])[CH2:29][C:30](=[O:31])[N:32]([CH2:33][CH2:34][c:35]... | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=N)N | null | null | ClCCl | Reduction | Boc amine deprotection of guanidine | 9766f6229fee762ffca87ed66a89907c51d08c86b25c0988ddb4d7c2e968882c | 8451d9ce44c8e1c8be0145c0e21ac06b9d8969460bd0e7e8568f82462587cbce | O=C(CCc1ccccc1)NC(Cc1ccccc1)C(=O)N1CCN(CCc2ccc3ccccc3c2)C(=O)C1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D2;+0:1]=[C:2](-[#7:3])-[NH;D2;+0:4]-C(=O)-O-C(-C)(-C)-C>>[#7:3]-[C:2](-[NH2;D1;+0:4])=[NH;D1;+0:1] | 86 | [{"value": 86.0, "product": "C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(C(C1)=O)CCC1=CC2=CC=CC=C2C=C1)CCCNC(=N)N)CC1=CC=C(C=C1)F)CC1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-acetylamino-N-[2-[2-[3-(N′,N″-di-Boc-guanidino)propyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide, 36, (35 mg, 38 mmol), trifluoroacetic acid (1 mL) and dichloromethane (2 mL) is stirred at room temperature for 5 hours. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ccccc2c1 | HO- | ClCCl | null | null | CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=NC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C>ClCCl>CC(=O)NC(Cc1ccc(O)cc1)C(=O)NC(Cc1ccc(F)cc1)C(=O)N1CC(=O)N(CCc2ccc3ccccc3c2)CC1CCCNC(=N)N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be983771db2641cba6b6dd0a8290a239 | CC(Br)Br.COC(=O)C(Cc1ccc2ccccc2c1)NC(=O)C(CCCNC(=O)OCc1ccccc1)NS(=O)(=O)c1ccccc1[N+](=O)[O-]>>COC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCCNC(=O)OCc2ccccc2)C1=O | OS(=O)(=O)[O-].[K+].COC(C(CC1=CC2=CC=CC=C2C=C1)NC(C(CCCNC(=O)OCC1=CC=CC=C1)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])=O)=O.BrC(C)Br.C([O-])([O-])=O.[K+].[K+]>>COC(C(CC1=CC2=CC=CC=C2C=C1)N1C(C(N(CC1)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])CCCNC(=O)OCC1=CC=CC=C1)=O)=O | Br[CH:19](Br)[CH3:18].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[NH:17][C:48]([CH:33]([NH:20][S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[N+:30](=[O:31])[O-:32])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:39])[O:40][CH2:41][c:42]1[cH:... | CC(Br)Br.COC(=O)C(Cc1ccc2ccccc2c1)NC(=O)C(CCCNC(=O)OCc1ccccc1)NS(=O)(=O)c1ccccc1[N+](=O)[O-] | COC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCCNC(=O)OCc2ccccc2)C1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f4f7dbcac6ff3bfe4e689789cd219afc5273ec2bf66e8265aba0b07fb903874f | c5f3aa8ae68955a07ec724ef1c762f563a90e33f82943b2772a998fd83fb58e9 | O=C(NCCCC1C(=O)N(CCc2ccc3ccccc3c2)CCN1S(=O)(=O)c1ccccc1)OCc1ccccc1 | Br-[CH;D3;+0:1](-Br)-[CH3;D1;+0:2].[C:3]-[C:4](-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9])-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[C:13](-[C:14])-[C:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18]>>[C:3]-[C:4]1-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:12](-[C:13](-[C:14])-[C:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18])-[CH2;D2;... | null | [] | 55 | CELSIUS | 18 | HOUR | A mixture of 2-[5-benzyloxycarbonylamino-2-(2-nitro-benzenesulfonylamino)-pentanoylamino]-3-naphthalen-2-yl-propionic acid methyl ester, 40, (2.4 g, 3.63 mmol), dibromoethane (3.8 mL, 4.36 mmol), potassium carbonate (5.0 g, 36.3 mmol) in DMF (50 mL) is stirred at 55° C. for 18 hours. The reaction mixture is cooled to r... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Secondary halide.Secondary halide.Secondary amide | Tertiary amide.Tertiary amine | null | C1C[NH]CC[NH]1 | c1ccc2ccccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 55 | 18 | CC(Br)Br.COC(=O)C(Cc1ccc2ccccc2c1)NC(=O)C(CCCNC(=O)OCc1ccccc1)NS(=O)(=O)c1ccccc1[N+](=O)[O-]>CN(C)C=O>COC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCCNC(=O)OCc2ccccc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-65bf027c2ce34a99952537c84cd0ebc0 | CC(C)(C)[Si](C)(C)Cl.N[C@@H](CCO)C(=O)O>>CC(C)(C)[Si](C)(C)OCCC(N)C(=O)O | O.N1C=NC=C1.N[C@@H](CCO)C(=O)O.[Si](C)(C)(C(C)(C)C)Cl>>NC(C(=O)O)CCO[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][C@H:11]([NH2:12])[C:13](=[O:14])[OH:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][CH:11]([NH2:12])[C:13](=[O:14])[OH:15] | CC(C)(C)[Si](C)(C)Cl.N[C@@H](CCO)C(=O)O | CC(C)(C)[Si](C)(C)OCCC(N)C(=O)O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | 15 | MINUTE | Imidazole (20.4 g, 300 mmol) is added to a solution of homoserine (11.9 g, 100 mmol) in DMF (100 mL) and the solution is stirred 15 minutes then cooled to 0° C. tert-Butyldimethylsilyl chloride (13.7 g, 91 mmol) added and the mixture is stirred for ten minutes at 0° C. the for 4 hours at room temperature. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | CN(C)C=O | null | 0.25 | CC(C)(C)[Si](C)(C)Cl.N[C@@H](CCO)C(=O)O>CN(C)C=O>CC(C)(C)[Si](C)(C)OCCC(N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c0fb83b039044d3acf999e92efa2059 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCO[Si](C)(C)C(C)(C)C)C1=O>>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCNC(CCO[Si](C)(C)C(C)(C)C)C1=O | [Si](C)(C)(C(C)(C)C)OCCC1C(N(CCN1S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])C(C(=O)NC)CC1=CC2=CC=CC=C2C=C1)=O.FC(C(=O)O)(F)F>>[Si](C)(C)(C(C)(C)C)OCCC1C(N(CCN1)C(C(=O)NC)CC1=CC2=CC=CC=C2C=C1)=O | O=[N+]([O-])c1ccccc1S(=O)(=O)[N:20]1[CH2:19][CH2:18][N:17]([CH:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[cH:16]2)[C:32](=[O:33])[CH:21]1[CH2:22][CH2:23][O:24][Si:25]([CH3:26])([CH3:27])[C:28]([CH3:29])([CH3:30])[CH3:31]>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c:... | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCO[Si](C)(C)C(C)(C)C)C1=O | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCNC(CCO[Si](C)(C)C(C)(C)C)C1=O | null | null | ClCCl | Reduction | Hydrogenolysis of tertiary amines | 1e3235beca6e2a1fbdc609e1f183772e766dab74480823c01cee74e805595e6d | 1e653e20ac001d92972e72ca6294e607303822683eea0adc1fa0a988ff7782b7 | O=C1CNCCN1CCc1ccc2ccccc2c1 | O=[N+](-[O-])-c1:c:c:c:c:c:1-S(=O)(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[C:5]-[C:6](-[#7:7])=[O;D1;H0:8])-[C:9](=[O;D1;H0:10])-[C:11]-1-[C:12]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]-[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:11](-[C:12])-[C:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | 2-[3-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(2-nitrobenzene-sulfonyl)-2-oxo-piperazin-1-yl]-N-methyl-3-naphthalen-2-yl propionamide, 57, (6.5 g, 10 mmol), trifluoroacetic acid (5 mL), and dichloromethane (50 mL) is stirred at room temperature for 2 hours and then concentrated in vacuo. The crude product is dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Secondary amine | c1ccccc1.C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2ccccc2c1.C1C[NH]CCN1 | HO- | ClCCl | null | null | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C(CCO[Si](C)(C)C(C)(C)C)C1=O>ClCCl>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCNC(CCO[Si](C)(C)C(C)(C)C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3580e42ca6e440a485fcbdcf185d8f6d | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO[Si](C)(C)C(C)(C)C)C1>>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1 | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCO[Si](C)(C)C(C)(C)C>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCO | CC(C)(C)[Si](C)(C)[O:31][CH2:30][CH2:29][CH:28]1[N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:19][CH2:18][N:17]([CH:5]([C:3]([NH:2][CH3:1])=[O:4])[CH2:6][c:7]2[cH:8][cH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[cH:16]2)[CH2:32]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2... | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO[Si](C)(C)C(C)(C)C)C1 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1 | null | null | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | c1ccc2cc(CCN3CCNCC3)ccc2c1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of 2-[2-(tert-butyldimethylsilanyloxy)ethyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)-piperazine-1-carboxylic acid tert-butyl ester, 59, (15.9 g, 23.5 mmol) and 1 M tetrabutylammonium fluoride (40 mL) is stirred for 24 hours. The reaction solution is filtered through a pad of silica gel, the filtrate is ... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccc2ccccc2c1.C1C[NH]CC[NH]1 | Other | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | null | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO[Si](C)(C)C(C)(C)C)C1>[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-321e07f4dd94470a9535ec64016b3388 | CC(=O)OC(C)=O.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1>>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCOC(C)=O)C1 | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCO.C(C)(=O)OC(C)=O.N1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCOC(C)=O | CC(=O)O[C:32]([CH3:33])=[O:34].[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[N:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:28]([CH2:29][CH2:30][OH:31])[CH2:35]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8... | CC(=O)OC(C)=O.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCOC(C)=O)C1 | null | null | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccc2cc(CCN3CCNCC3)ccc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | null | null | A solution of 2-(2-hydroxyethyl)-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazine-1-carboxylic acid tert-butyl ester, 60, (4.4 g, 10 mmol), acetic anhydride (13 mL), pyridine (1 mL) and N,N-dimethylaminopyridine (0.25 g) in dichloromethane (50 mL) is stirred for 1.5 hours. The solution is then extracted with wate... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccc2ccccc2c1.C1C[NH]CC[NH]1 | HO- | ClCCl | null | null | CC(=O)OC(C)=O.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCO)C1>ClCCl>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)OC(C)(C)C)C(CCOC(C)=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd4587f83f314674afb5cfab26dbd8f9 | CCN=C=NCCCN(C)C.CN1CCOCC1.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(N)Cc2ccc(F)cc2)C(CCOC(C)=O)C1.O.Oc1cccc2[nH]nnc12>>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1 | CN(CCCN=C=NCC)C.NC(C(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCOC(C)=O)CC1=CC=C(C=C1)F.OC1=CC=CC=2NN=NC21.CN1CCOCC1.O>>C(C)(=O)NC(C(=O)NC(C(=O)N1C(CN(CC1)C(CC1=CC2=CC=CC=C2C=C1)C(NC)=O)CCOC(C)=O)CC1=CC=C(C=C1)F)CC1=C(C=CC=C1)O | CN(C)CCCN=[C:33]=[N:44][CH2:45][CH3:46].CN1CC[O:47][CH2:35][CH2:36]1.[CH3:1][NH:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[cH:16]1)[N:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[CH:23]([CH2:24][c:25]2[cH:26][cH:27][c:28]([F:29])[cH:30][cH:31]2)[NH2:32])[CH:48]([CH2:49][CH2:... | CCN=C=NCCCN(C)C.CN1CCOCC1.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(N)Cc2ccc(F)cc2)C(CCOC(C)=O)C1.O.Oc1cccc2[nH]nnc12 | CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 8b8bebf613656b633e868416881bd73eacda1991c0391e482c1d98208d9d9c55 | 2c35bacb356f541d5d9739d5d8c4ecb892f33937e74373babf94f71f4f2ee424 | O=C(CCc1ccccc1)NC(Cc1ccccc1)C(=O)N1CCN(CCc2ccc3ccccc3c2)CC1 | C-N(-C)-C-C-C-N=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[CH2;D2;+0:3]-[C;D1;H3:4].C-N1-C-C-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1.[C:8]-[#7:9](-[C:10](=[O;D1;H0:11])-[C:12](-[C:13])-[NH2;D1;+0:14])-[C:15].[O;D1;H1:16]-[c:17]1:[c:18]:[c:19]:[c:20]:[c;H0;D3;+0:21]2:[nH]:n:n:[c;H0;D3;+0:22]:1:2.[OH2;D0;+0:23]>>[C:8]-[#7:9](-[... | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of acetic acid 2-{1-[2-amino-3-(4-fluorophenyl)propionyl]-4-(1-methylcarbamoyl-2-naphthalen-2-ylethyl)piperazin-2-yl}-ethyl ester, 64, (54.9 g, 100 mmol), hydroxybenzotriazole (16.2 g, 120 mmol), and N-methylmorpholine (132 mL, 120 mmol) in DMF (150 mL) is cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethy... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Tertiary amine.Tertiary amine | Secondary amide.Secondary amide | C1COCCN1.c1ccc2[nH]nnc2c1 | c1ccccc1 | c1ccc2ccccc2c1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | Other | CN(C)C=O | 0 | 2 | CCN=C=NCCCN(C)C.CN1CCOCC1.CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(N)Cc2ccc(F)cc2)C(CCOC(C)=O)C1.O.Oc1cccc2[nH]nnc12>CN(C)C=O>CNC(=O)C(Cc1ccc2ccccc2c1)N1CCN(C(=O)C(Cc2ccc(F)cc2)NC(=O)C(Cc2ccccc2O)NC(C)=O)C(CCOC(C)=O)C1 |
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