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-62d31b89ec784a0aa8451b3f2a6e1fb5 | COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1>>O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)OC)C=C1.[OH-].[Na+]>>BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][C@@H:6]1[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][C@H:6]1[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1 | COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1 | O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)C1CC1 | 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] | 96 | [{"value": 95.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | DAY | Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate (10.34 g, 36.52 mmol) was dissolved in MeOH (100 mL), and then 15 mL 50% aqueous NaOH solution was added. The reaction mixture was stirred at 40° C. for 3 days. Solvent was removed by rotary evaporation and the residue was dissolved in water. Concentrated HCl was add... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccccc1 | Other | CO | 40 | 72 | COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1>CO>O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a764fe4df3f4c62aea42b76e9d94364 | COC(C)(C)OC.O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1>>COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)O)C=C1.COC(C)(C)OC.Cl>>BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)OC)C=C1 | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1 | COC(C)(C)OC.O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 | COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 83.5 | [{"value": 83.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 8 | HOUR | To a solution of trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.43 g, 32.59 mmol) in MeOH (200 mL) was added 2,2-dimethoxypropane (10.18 g, 97.77 mmol) and HCl (4.0 M in dioxane, 4.0 mL). The resulting solution was stirred at 40° C. overnight, and then evaporated to dryness. The resulting residue was purified b... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CC1.c1ccccc1 | HO- | CO | 40 | 8 | COC(C)(C)OC.O=C(O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1>CO>COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b28c0f30eb30467e9c09a76d8c83cc55 | COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>>COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=C(C(=O)[C@H]2[C@@H](C2)C(=O)OC)C=C1.NC1=CC=C(C=C1)B(O)O.ClCCl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](C1)C(=O)OC | Br[c:13]1[cH:12][cH:11][c:10]([C:8]([C@H:7]2[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]2)=[O:9])[cH:22][cH:21]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([NH2:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([NH2:18])[cH:19][cH:20]2)[cH:21]... | COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1 | COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CCOC(=O)C.CCO.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)cc1)C1CC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 66.3 | [{"value": 66.0, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Methyl trans-2-(4-bromobenzoyl)cyclopropanecarboxylate (1.33 g, 4.70 mmol) and 4-amino-phenyl boronic acid (0.98 g, 5.64 mmol) were combined in a dry flask under argon. Toluene (25 mL), EtOH (10 mL), and 3 M aqueous Na2CO3 (7 mL, 20 mmol) were added, and the resulting solution was degassed for 30 minutes by using a flo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CC1.c1ccccc1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C | 85 | null | COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C>COC(=O)[C@@H]1C[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-faa82ea8037f49a8beba89354950b23d | COC(C)(C)OC.O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1>>COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@H]2[C@@H](CC2)C(=O)O)C=C1.COC(C)(C)OC.Cl>>BrC1=CC=C(C(=O)[C@H]2[C@@H](CC2)C(=O)OC)C=C1 | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1 | COC(C)(C)OC.O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1 | COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CCC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 78 | [{"value": 78.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CC2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CC2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of trans-2-(4-bromobenzoyl)cyclobutanecarboxylic acid (8.2 g, 28.94 mmol) in MeOH (250 mL) was added 2,2-dimethoxypropane (3.65 g, 35.02 mmol) and HCl (4.0 M in dioxane) (2.0 mL). The resulting solution was stirred at rt for 3 days, and then evaporated to dryness. The resulting residue was purified with f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CCC1.c1ccccc1 | HO- | CO | null | 72 | COC(C)(C)OC.O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1>CO>COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bcf2b9ca09445f5b276604eaf8986b6 | COC(C)(C)OC.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1>>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1.COC(C)(C)OC.Cl>>BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1 | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | COC(C)(C)OC.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CCCC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 83.2 | [{"value": 83.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 8 | HOUR | To a solution of trans-2-(4-bromobenzoyl)cyclopentanecarboxylic acid (2.0 g, 6.26 mmol) in MeOH (70 mL) was added 2,2-dimethoxypropane (1.63 g, 15.65 mmol) and HCl (4.0 M in dioxane) (1.0 mL). The resulting solution was stirred at 40° C. overnight and then evaporated to dryness. The resulting residue was purified by fl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CCCC1.c1ccccc1 | HO- | CO | 40 | 8 | COC(C)(C)OC.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1>CO>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ea95650f399478f9361dfa1114d80a8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1.NC1=CC=C(C=C1)B(O)O.ClCCl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC | Br[c:15]1[cH:14][cH:13][c:12]([C:10]([C@H:9]2[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8]2)=[O:11])[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19](... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CCOC(=O)C.CCO.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)cc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 67.4 | [{"value": 67.0, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Methyl trans-2-(4-bromobenzoyl)cyclopentanecarboxylate (1.60 g, 5.14 mmol) and 4-aminophenyl boronic acid (1.07 g, 6.17 mmol) were combined in a dry flask under argon. Toluene (25 mL), EtOH (10 mL), and 3 M aqueous Na2CO3 (8.50 mL, 25 mmol) were added and resulting solution was degassed for 30 minutes by using a flow o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCC1.c1ccccc1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C | 85 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-814ba5bff74441219c973e99d8628a05 | Brc1ccccc1.CCOC(C)=O.CN(C)C=O>>COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=CC=C1.CCOC(=O)C.[Al+3].[Cl-].[Cl-].[Cl-].O=S(Cl)Cl.CN(C)C=O>>COC(=O)[C@H]1[C@H](CCC1)C(C1=CC=C(C=C1)Br)=O | [cH:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1.[O:2]([C:3](=[O:4])[CH3:5])[CH2:6][CH3:7].N([CH3:1])([CH3:8])[CH:10]=[O:11]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | Brc1ccccc1.CCOC(C)=O.CN(C)C=O | COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | de9c0b97abd82b18a96cadfbb90788052155ab520401a70007846281ba505fa8 | eb8050c459e412c26f0cd4e10c85de87aa0f8fdc2ff7ce7483393097c534a212 | O=C(c1ccccc1)C1CCCC1 | [CH3;D1;+0:1]-N(-[CH3;D1;+0:2])-[CH;D2;+0:3]=[O;D1;H0:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[c:11]:[c:12]:[cH;D2;+0:13]:[c:14]:[c:15]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[C:6](=[O;D1;H0:7])-[C@@H;D3;+0:5]1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:2]-[C:16]-1-[C;H0;D3;+0:3](=[O;D1;H0:... | 95 | [{"value": 95.0, "product": "COC(=O)[C@H]1[C@H](CCC1)C(C1=CC=C(C=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of the monomethyl ester (92.0 g, 534.3 mmol), SOCl2 (116.3 mL, 1.60 mol), and DMF (1 mL) in 850 mL CH2Cl2 was stirred at rt overnight under N2. NMR analysis showed little starting material remaining. The solvent was removed by rotary evaporation at <40° C., and the residue was dried in vacuo for 1 h. This dr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Tertiary amide | Ketone.Ester | c1ccccc1 | C1CCCC1.c1ccccc1 | C1CCCC1.c1ccccc1 | null | C(Cl)Cl | null | 4 | Brc1ccccc1.CCOC(C)=O.CN(C)C=O>C(Cl)Cl>COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c22397a0792547ccbaedca4a5b962ebd | COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | [OH-].[Na+].COC(=O)[C@H]1[C@H](CCC1)C(C1=CC=C(C=C1)Br)=O>>BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1 | COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)C1CCCC1 | 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] | 83 | [{"value": 83.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of NaOH (128.2 g, 3.2 mol) in 700 mL water was added to a solution of cis-2-(4-bromo-benzoyl)-cyclopentanecarboxylic acid methyl ester (166.3 g, 534.3 mmol) in MeOH (700 mL). The reaction mixture was stirred at rt overnight. NMR analysis showed that little starting material remained. After ca. 1 L solvent wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1.c1ccccc1 | Other | CO.O | null | 8 | COC(=O)[C@@H]1CCC[C@@H]1C(=O)c1ccc(Br)cc1>CO.O>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5371b54496fc4e8fb22218bcae433455 | Nc1ccc(I)cc1F.O=CO>>O=CNc1ccc(I)cc1F | IC1=CC(=C(N)C=C1)F.C(C)(=O)OC(C)=O.C(=O)O>>FC1=C(C=CC(=C1)I)NC=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][c:10]1[F:11].O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][c:10]1[F:11] | Nc1ccc(I)cc1F.O=CO | O=CNc1ccc(I)cc1F | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.O1CCCC1.Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 97.1 | [{"value": 97.0, "product": "FC1=C(C=CC(=C1)I)NC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "FC1=C(C=CC(=C1)I)NC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a cooled solution (0° C.) of 4-iodo-2 fluoroaniline (3.05 g, 12.9 mmol) in tetrahydrofuran (15 mL) and toluene (15 mL), was slowly added a mixture of acetic anhydride (1.39 mL, 14.7 mmol) and formic acid (0.83 mL, 22.0 mmol). The reaction mixture was stirred at rt overnight, then diluted with ethyl acetate (100 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C.C(C)(=O)OCC.O1CCCC1.Cl | null | 8 | Nc1ccc(I)cc1F.O=CO>C1(=CC=CC=C1)C.C(C)(=O)OCC.O1CCCC1.Cl>O=CNc1ccc(I)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4206c7f805fd4769a8114cbbd699fa8a | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F>>COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | FC1=C(C=CC(=C1)I)NC=O.C(C)(=O)[O-].[K+].BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC | Br[c:15]1[cH:14][cH:13][c:12]([C:10]([C@H:9]2[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8]2)=[O:11])[cH:27][cH:26]1.I[c:16]1[cH:17][cH:18][c:19]([NH:20][CH:21]=[O:22])[c:23]([F:24])[cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C=O)C | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | O=C(c1ccc(-c2ccccc2)cc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 169.4 | [{"value": 65.0, "product": "FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 169.4, "product": "FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of 2-fluoro-4-iodophenylformamide (5.11 g, 19.28 mmol) bis(pinacolato)diboron (4.89 g, 19.28 mmol), potassium acetate (5.67 g, 57.84 mmol), and palladium acetate (129 mg, 0.58 mmol) in N,N-dimethylformamide (125 mL) was bubbled through argon for 30 minutes. The reaction mixture was then heated at 80° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCC1.c1ccccc1.c1ccccc1 | Br-.I- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C | 80 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C>COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d36461a5b9b4aaf9debfc514fc25769 | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1>>COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 | FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC.Cl>>NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC)F | O=C[NH:20][c:19]1[cH:18][cH:17][c:16](-[c:15]2[cH:14][cH:13][c:12]([C:10]([CH:9]3[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8]3)=[O:11])[cH:25][cH:24]2)[cH:23][c:21]1[F:22]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([NH2:... | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C(c1ccc(-c2ccccc2)cc1)C1CCCC1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89.3 | [{"value": 89.0, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of methyl 2-{[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-carbonyl}cyclopentanecarboxylate (4.24 g, 11.48 mmol) in methanol (34 mL) was added conc. HCl (11.4 mL), and the resulting solution was stirred at rt for 2 h. Solvent was then removed, the residual mixture was dissolved in water, and the acidity... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | C1CCCC1.c1ccccc1.c1ccccc1 | Other | CO | null | 2 | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1>CO>COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2cdaf61949d6482f90619953faff2a79 | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | FC1=C(C=CC(=C1)I)NC=O.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+].BrC1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O | Br[c:14]1[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:26][cH:25]1.I[c:15]1[cH:16][cH:17][c:18]([NH:19][CH:20]=[O:21])[c:22]([F:23])[cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH... | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.CN(C=O)C | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 46 | [{"value": 46.0, "product": "FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of 2-fluoro-4-iodophenylformamide (1.94 g, 7.35 mmol, prepared as described above), bis(pinacolato)diboron (1.86 g, 7.35 mmol), potassium acetate (2.16 g, 22.1 mmol), and palladium acetate (49.4 mg, 0.22 mmol) in N,N-dimethylformamide (50 mL) was degassed by bubbling a flow of argon through the mixture for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.I- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.CN(C=O)C | 80 | null | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.CN(C=O)C>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a825343b56b045bc88ebcee19973a6ae | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 | FC=1C=C(C=CC1NC=O)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.Cl>>NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)F | O=C[NH:19][c:18]1[cH:17][cH:16][c:15](-[c:14]2[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:24][cH:23]2)[cH:22][c:20]1[F:21]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[c:20]([F:... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(-c2ccccc2)cc1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89.4 | [{"value": 89.0, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of methyl 4-[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (1.21 g, 3.39 mmol) in methanol (10 mL) was added conc. HCl (3.5 mL), and the resulting solution was stirred at rt for 16 h. The mixture was then concentrated, diluted with water, and the acidity was adjusted to pH ˜7 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 16 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)c(F)c2)cc1>CO>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b89a5422216e445c85367d92f4364d21 | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.COc1cc(Cl)ccc1[N+](=O)[O-]>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1 | BrC1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+].ClC=1C=CC(=C(C1)OC)[N+](=O)[O-].C([O-])([O-])=O.[Cs+].[Cs+]>>COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O | Br[c:14]1[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:27][cH:26]1.Cl[c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]([O:23][CH3:24])[cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17... | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.COc1cc(Cl)ccc1[N+](=O)[O-] | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.CN(C=O)C | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 48.2 | [{"value": 48.0, "product": "COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of methyl 4-(4-bromophenyl)-2,2-dimethyl-4-oxobutanoate (200 mg, 0.67 mmol), bis(pinacolato)diboron (170 mg, 0.67 mmol), potassium acetate (197 mg, 2.01 mmol), and palladium acetate (5 mg, 0.02 mmol) in N,N-dimethylformamide (4.0 mL) was degassed by bubbling a flow of argon for 30 minutes. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.CN(C=O)C | 80 | null | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.COc1cc(Cl)ccc1[N+](=O)[O-]>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.CN(C=O)C>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c4822aa92be40e0b6bc55a8704b5cb2 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(OC)c2)cc1 | COC=1C=C(C=CC1[N+](=O)[O-])C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.Cl>>NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)OC | O=[N+:19]([O-])[c:18]1[cH:17][cH:16][c:15](-[c:14]2[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:25][cH:24]2)[cH:23][c:20]1[O:21][CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:1... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(OC)c2)cc1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67 | [{"value": 67.0, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl 4-(3′-methoxy-4′-nitro-1,1′-biphenyl-4-yl)-2,2-dimethyl -4-oxobutanoate (670 mg, 1.80 mmol) in 85% aqueous ethanol (27 mL) was added iron powder (1.01 g, 18.04 mmol) and 2 N aqueous HCl (0.9 mL, 1.8 mmol), and the resulting suspension was heated at reflux for 2.5 h. The mixture was then cooled t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Fe].C(C)O | null | null | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])c(OC)c2)cc1>[Fe].C(C)O>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)c(OC)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b8faee746e147b69f20751ab4e1c852 | CC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1C.O=[N+]([O-])c1ccc(B(O)O)cc1>>CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | FC(S(=O)(=O)OC1=CC(=C(C=C1)C(C)=O)C)(F)F.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>>CC=1C=C(C=CC1C(C)=O)C1=CC=C(C=C1)[N+](=O)[O-] | O=S(=O)(O[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:18]([CH3:19])[cH:17]1)C(F)(F)F.OB(O)[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH3:19] | CC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1C.O=[N+]([O-])c1ccc(B(O)O)cc1 | CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | null | null | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids OTf | 3fcd38cd143accaacc097756f175627a8a766b312949d1dc56f9f30bda1e5856 | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1ccc(-c2ccccc2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 99.9 | [{"value": 99.0, "product": "CC=1C=C(C=CC1C(C)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "CC=1C=C(C=CC1C(C)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 8 | HOUR | A mixture of 4-acetyl-3-methylphenyl trifluoromethanesulfonate (6.90 g, 24.0 mmol), 4-nitrophenylboronic acid (3.80 g, 24 mmol), 2 N aqueous sodium carbonate (88.0 mL), dioxane (88.0 mL), and toluene (296 mL) was purged with argon for 30 minutes before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | TfOH.HO-.B | C1(=CC=CC=C1)C | 85 | 8 | CC(=O)c1ccc(OS(=O)(=O)C(F)(F)F)cc1C.O=[N+]([O-])c1ccc(B(O)O)cc1>C1(=CC=CC=C1)C>CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1babce0031024287921edca41706873d | CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C.[Br-]>>Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr | CC=1C=C(C=CC1C(C)=O)C1=CC=C(C=C1)[N+](=O)[O-].[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>BrCC(=O)C1=C(C=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-])C | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17](=[O:18])[CH3:19].[Br-:20]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17](=[O:18])[CH2:19][Br:20] | CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C.[Br-] | Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccc(-c2ccccc2)cc1 | [Br-;H0;D0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 59 | [{"value": 59.0, "product": "BrCC(=O)C1=C(C=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "BrCC(=O)C1=C(C=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 3 | HOUR | A mixture of 1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone (5.66 g, 22 mmol), pyridinium tribromide (10.63 g, 33.0 mmol), and glacial acetic acid (60 mL) was stirred at 110° C. for 3 h. The reaction mixture was cooled to 0–5° C., and the precipitated product was collected by filtration and washed with small amounts ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1.c1ccccc1 | null | C(C)(=O)O | 110 | 3 | CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C.[Br-]>C(C)(=O)O>Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7e1c1360b964ec8b788fbdb3219f1f6 | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr>>CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC | C(C)(=O)OCC.C1(=CC=CC=C1)CCC(C(=O)OCC)C(=O)OCC.[H-].[Na+].BrCC(=O)C1=C(C=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-])C>>CC=1C=C(C=CC1C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:34](=[O:35])[O:36][CH2:37][CH3:38].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29][cH:30]2)[cH:31][c:32]1[CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C... | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC | null | null | O.O1CCCC1 | C-C Coupling | OtherReaction | 4bb1433a83171a818741815ed1611f54dc47d930932c002b83e8524407ba2582 | d7a41d4d502746dc050b2738c9dd1b697535250fee467eca2d3c201fc4e0267b | O=C(CCCCc1ccccc1)c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]-[C:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[C:10]-[C:11])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 85.3 | [{"value": 82.0, "product": "CC=1C=C(C=CC1C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "CC=1C=C(C=CC1C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 45 | MINUTE | To a cold suspension (0–5° C.) of 95% sodium hydride (3.53 g, 13.0 mmol) in dry tetrahydrofuran (30 mL) was slowly added diethyl 2-phenylethylmalonate (3.53 g, 13 mmol). The ice bath was removed and the reaction mixture was stirred at rt for 45 minutes. A solution of 2-bromo-1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)etha... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Ester | Ketone.Ester.Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O.O1CCCC1 | null | 0.75 | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.Cc1cc(-c2ccc([N+](=O)[O-])cc2)ccc1C(=O)CBr>O.O1CCCC1>CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc5c41d608fa4163b1a900774a6d08b6 | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC>>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | CC=1C=C(C=CC1C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-].[OH-].[Na+].C(C)O>>CC=1C=C(C=CC1C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-] | CCOC(=O)[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29][cH:30]2)[cH:31][c:32]1[CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:1... | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | null | null | CC(=O)C | Reduction | OtherReaction | 33f176f6ce02426b2726e71e3c19f64673952a2b50dd48518b89a08efe25965b | b45711df98eaf2a3f54e3027da3f1b57580ab2f6d54e9ac2a56731961e64969a | O=C(CCCCc1ccccc1)c1ccc(-c2ccccc2)cc1 | C-C-O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])(-[C:6]-[C:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])-[C:6]-[C:7] | 99 | [{"value": 99.0, "product": "CC=1C=C(C=CC1C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "CC=1C=C(C=CC1C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | A mixture of diethyl 2-[2-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]-2-(2-phenylethyl)malonate (4.87 g, 9.41 mmol), 1 N aqueous sodium hydroxide (10.4 mL, 10.40 mmol), ethanol (10 mL), and acetone (10 mL) was stirred at 50° C. overnight. The mixture was concentrated and the residue was dissolved in dimethoxyeth... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CC(=O)C | 50 | 8 | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C)C(=O)OCC>CC(=O)C>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8a77732f5954ca9bac9acf99965f4a4 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C>>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1C | CC=1C=C(C=CC1C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O)C1=CC=C(C=C1)[N+](=O)[O-].Cl>>NC1=CC=C(C=C1)C1=CC(=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O)C | O=[N+:26]([O-])[c:25]1[cH:24][cH:23][c:22](-[c:21]2[cH:20][cH:19][c:18]([C:16]([CH2:15][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)=[O:17])[c:30]([CH3:31])[cH:29]2)[cH:28][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13... | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1C | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(CCCCc1ccccc1)c1ccc(-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of ethyl 4-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (3.40 g, 7.60 mmol), iron powder (4.20 g, 76.00 mmol), 2 N aqueous hydrochloric acid (3.80 mL, 7.60 mmol), and 85/15 ethanol/water (100 mL) was stirred at reflux for 2.5 h. The reaction mixture was filtered through a pad of Cel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Fe].C(C)O.O | null | null | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1C>[Fe].C(C)O.O>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91d88768cce04ee0ad43e92984f286b8 | COC(C)(C)OC.O=C(O)[C@H]1CCC[C@H](C(=O)c2ccc(Br)cc2)C1>>COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1 | BrC1=CC=C(C(=O)[C@@H]2C[C@H](CCC2)C(=O)O)C=C1.COC(C)(C)OC>>COC(=O)C1CC(CCC1)C(C1=CC=C(C=C1)Br)=O | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]2)[CH2:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]2)[CH2:19]1 | COC(C)(C)OC.O=C(O)[C@H]1CCC[C@H](C(=O)c2ccc(Br)cc2)C1 | COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1 | null | Cl | CO.O1CCOCC1 | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CCCCC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 95.7 | [{"value": 95.7, "product": "COC(=O)C1CC(CCC1)C(C1=CC=C(C=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "COC(=O)C1CC(CCC1)C(C1=CC=C(C=C1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of trans-3-(4-bromobenzoyl)cyclohexane-1-carboxylic acid (500 mg, 1.61 mmol, obtained from Rieke Metals Inc., Lincoln, Nebr., USA) and 2,2-dimethoxypropane (669 mg, 6.43 mmol) in methanol (20 mL), 5 drops of 4 M HCl in dioxane was added, and this reaction mixture was heated at 50° C. overnight. The solven... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CCCCC1.c1ccccc1 | HO- | Cl.CO.O1CCOCC1 | 50 | null | COC(C)(C)OC.O=C(O)[C@H]1CCC[C@H](C(=O)c2ccc(Br)cc2)C1>Cl.CO.O1CCOCC1>COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-518dedb9e440475fa6ec69241f8a3706 | COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1.Nc1ccc(B(O)O)cc1>>COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1 | COC(=O)C1CC(CCC1)C(C1=CC=C(C=C1)Br)=O.NC1=CC=C(C=C1)B(O)O>>COC(=O)C1CC(CCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)N | Br[c:15]1[cH:14][cH:13][c:12]([C:10]([CH:9]2[CH2:8][CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:25]2)=[O:11])[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([NH2:20])[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][CH2:8][CH:9]([C:10](=[O:11])[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][c:1... | COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1.Nc1ccc(B(O)O)cc1 | COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1 | null | null | C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)cc1)C1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 38.5 | [{"value": 38.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester (500 mg, 1.54 mmol) and 4-aminophenyl boronic acid (252 mg, 1.85 mmol) in toluene (40 mL) and dioxane (10 mL), 2 N aqueous Na2CO3 (10 mL) was added, and the mixture was degassed by bubbling with a flow of argon for 45 minutes. (1,1-Bis(dipheny... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr.B | C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.C1(=CC=CC=C1)C | 80 | null | COC(=O)C1CCCC(C(=O)c2ccc(Br)cc2)C1.Nc1ccc(B(O)O)cc1>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.C1(=CC=CC=C1)C>COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c44a57cc9a1c464bb06670086ed74e6d | Cl.Nc1nc2ccc(C(F)(F)F)cc2s1>>FC(F)(F)c1ccc2nc(Cl)sc2c1 | N(=O)OC(C)(C)C.NC=1SC2=C(N1)C=CC(=C2)C(F)(F)F.Cl>>ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F | [ClH:11].N[c:10]1[n:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14][c:13]2[s:12]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([Cl:11])[s:12][c:13]2[cH:14]1 | Cl.Nc1nc2ccc(C(F)(F)F)cc2s1 | FC(F)(F)c1ccc2nc(Cl)sc2c1 | null | [Cu] | C(C)#N | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 92 | [{"value": 92.0, "product": "ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | In a three-necked flask fitted with a condenser, a suspension of copper II chloride (370 mg, 2.75 mmol) in acetonitrile (5 mL) was treated with tert-butyl nitrite (0.41 mL, 3.44 mmol) and stirred at rt for 10 minutes. A solution of 2-amino-6-trifluoromethylbenzthiazole (500 mg, 2.29 mmol) in acetonitrile (1 mL) was the... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu].C(C)#N | null | 0.166667 | Cl.Nc1nc2ccc(C(F)(F)F)cc2s1>[Cu].C(C)#N>FC(F)(F)c1ccc2nc(Cl)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8bad3c990f7478fabae4a1573965eda | Cc1cccc2sc(N)nc12.Cl>>Cc1cccc2sc(Cl)nc12 | Cl.N(=O)OCCC(C)C.NC=1SC2=C(N1)C(=CC=C2)C>>ClC=1SC2=C(N1)C(=CC=C2)C | N[c:8]1[s:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:11]2[n:10]1.[ClH:9]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[s:7][c:8]([Cl:9])[n:10][c:11]12 | Cc1cccc2sc(N)nc12.Cl | Cc1cccc2sc(Cl)nc12 | null | [Cu](Cl)Cl | C(C)#N | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 71 | [{"value": 71.0, "product": "ClC=1SC2=C(N1)C(=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution containing copper chloride (II) (1.96 g, 14.61 mmol) and tri(ethylene glycol) dimethyl ether (6 mL) in acetonitrile (100 mL) was added isoamyl nitrite (2.14 g, 18.27 mmol), and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 2-amino-4-methylbenzot... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu](Cl)Cl.C(C)#N | null | 0.5 | Cc1cccc2sc(N)nc12.Cl>[Cu](Cl)Cl.C(C)#N>Cc1cccc2sc(Cl)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1d3138809e7413ab40947cf032e2724 | Cl.Nc1nc2c(F)cc(F)cc2s1>>Fc1cc(F)c2nc(Cl)sc2c1 | Cl.N(=O)OCCC(C)C.FC1=CC(=CC2=C1N=C(S2)N)F>>ClC=1SC2=C(N1)C(=CC(=C2)F)F | [ClH:9].N[c:8]1[n:7][c:6]2[c:4]([F:5])[cH:3][c:2]([F:1])[cH:12][c:11]2[s:10]1>>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]2[n:7][c:8]([Cl:9])[s:10][c:11]2[cH:12]1 | Cl.Nc1nc2c(F)cc(F)cc2s1 | Fc1cc(F)c2nc(Cl)sc2c1 | null | [Cu](Cl)Cl | C(C)#N | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 99 | [{"value": 99.0, "product": "ClC=1SC2=C(N1)C(=CC(=C2)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution containing copper chloride (II) (0.87 g, 6.45 mmol) and tri(ethylene glycol) dimethyl ether (3 mL) in acetonitrile (50 mL) was added isoamyl nitrite (0.94 g, 8.06 mmol), and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 4,6-difluoro-1,3-benzothi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu](Cl)Cl.C(C)#N | null | 0.5 | Cl.Nc1nc2c(F)cc(F)cc2s1>[Cu](Cl)Cl.C(C)#N>Fc1cc(F)c2nc(Cl)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-405e37b0937d460898462bc7780bccea | Cl.Nc1nc2ccc(OC(F)(F)F)cc2s1>>FC(F)(F)Oc1ccc2nc(Cl)sc2c1 | Cl.N(=O)OCCC(C)C.FC(OC1=CC2=C(N=C(S2)N)C=C1)(F)F>>ClC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F | [ClH:12].N[c:11]1[n:10][c:9]2[cH:8][cH:7][c:6]([O:5][C:2]([F:1])([F:3])[F:4])[cH:15][c:14]2[s:13]1>>[F:1][C:2]([F:3])([F:4])[O:5][c:6]1[cH:7][cH:8][c:9]2[n:10][c:11]([Cl:12])[s:13][c:14]2[cH:15]1 | Cl.Nc1nc2ccc(OC(F)(F)F)cc2s1 | FC(F)(F)Oc1ccc2nc(Cl)sc2c1 | null | [Cu](Cl)Cl | C(C)#N | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | null | [] | null | null | 30 | MINUTE | To a solution containing dry copper (II) chloride (3.44 g, 25.62 mmol) and tri(ethylene glycol) dimethyl ether (10 g) in acetonitrile (150 mL) was added isoamyl nitrite (4.5 mL, 32.02 mmol). The reaction mixture was stirred at rt under argon for 30 minutes. To this suspension was added dropwise, a solution containing 6... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu](Cl)Cl.C(C)#N | null | 0.5 | Cl.Nc1nc2ccc(OC(F)(F)F)cc2s1>[Cu](Cl)Cl.C(C)#N>FC(F)(F)Oc1ccc2nc(Cl)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c0dac246ef34adebe28927fa5547233 | N#C[S-].Nc1cc(F)cc(F)c1>>NC(=S)Nc1cc(F)cc(F)c1 | [OH-].[NH4+].[OH-].[Na+].C(C1=CC=CC=C1)(=O)Cl.[S-]C#N.[NH4+].FC=1C=C(N)C=C(C1)F.Cl>>FC=1C=C(C=C(C1)F)NC(=S)N | [N:1]#[C:2][S-:3].[NH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1>>[NH2:1][C:2](=[S:3])[NH:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1 | N#C[S-].Nc1cc(F)cc(F)c1 | NC(=S)Nc1cc(F)cc(F)c1 | null | null | CC(=O)C.O | Heteroatom Alkylation and Arylation | OtherReaction | 42eba0434e01c5077fe474f99d70dfa303f7fb16e20dbd38eacfbefa3576aa9e | 5d425eb1cdcb05eaa7642d1bd0c9c22fd483e30b54ceb4617e277bc1fc89be52 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[S;H0;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 48.3 | [{"value": 48.0, "product": "FC=1C=C(C=C(C1)F)NC(=S)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "FC=1C=C(C=C(C1)F)NC(=S)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | Benzoyl chloride (5.44 g, 38.73 mmol) was added to a stirred solution of ammonium thiocyanate (3.83 g, 50.35 mmol) in acetone (80 mL) at 30° C. The mixture was stirred at reflux for 30 minutes, then cooled to 50° C., and a solution of 3,5-difluoroaniline (5.00 g, 38.73 mmol) in acetone (10 mL) was added in one portion.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Thiourea | null | null | c1ccccc1 | null | CC(=O)C.O | 50 | 0.5 | N#C[S-].Nc1cc(F)cc(F)c1>CC(=O)C.O>NC(=S)Nc1cc(F)cc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f7aa1f4483046469aab193d0211f406 | NC(=S)Nc1cc(F)cc(F)c1>>Nc1nc2cc(F)cc(F)c2s1 | FC=1C=C(C=C(C1)F)NC(=S)N.BrBr>>FC=1C=C(C2=C(N=C(S2)N)C1)F | [NH2:1][C:2]([NH:3][c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([F:10])[cH:11]1)=[S:12]>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[cH:8][c:9]([F:10])[c:11]2[s:12]1 | NC(=S)Nc1cc(F)cc(F)c1 | Nc1nc2cc(F)cc(F)c2s1 | null | null | ClCCCl | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc2scnc2c1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](-[N;D1;H2:8])=[S;H0;D1;+0:9]):[c:10]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[s;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[n;H0;D2;+0:6]:[c:5]:1:[c:10] | 90.7 | [{"value": 90.0, "product": "FC=1C=C(C2=C(N=C(S2)N)C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "FC=1C=C(C2=C(N=C(S2)N)C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | To a suspension of N-(3,5-difluorophenyl) thiourea (3.40 g, 18.07 mmol) in DCE (95 mL) was added a solution of bromine in DCE (5 mL) below 30° C. The mixture was heated at reflux for 2.5 h, then cooled to 10° C., and the precipitate formed was collected by filtration and washed with DCE. The solid was stirred with wate... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | ClCCCl | 10 | null | NC(=S)Nc1cc(F)cc(F)c1>ClCCCl>Nc1nc2cc(F)cc(F)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8939b22e09be4a668a6ecc714a698e12 | Cl.Nc1nc2cc(F)cc(F)c2s1>>Fc1cc(F)c2sc(Cl)nc2c1 | Cl.FC=1C=C(C2=C(N=C(S2)N)C1)F.N(=O)OCCC(C)C>>ClC=1SC2=C(N1)C=C(C=C2F)F | [ClH:9].N[c:8]1[s:7][c:6]2[c:4]([F:5])[cH:3][c:2]([F:1])[cH:12][c:11]2[n:10]1>>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6]2[s:7][c:8]([Cl:9])[n:10][c:11]2[cH:12]1 | Cl.Nc1nc2cc(F)cc(F)c2s1 | Fc1cc(F)c2sc(Cl)nc2c1 | null | [Cu](Cl)Cl | C(C)#N | Miscellaneous | OtherReaction | 71794c41e9e34c59e54f72d2d4e2a5da760ee16a1c6392802d18a408ac4e63ad | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 48 | [{"value": 48.0, "product": "ClC=1SC2=C(N1)C=C(C=C2F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution containing copper chloride (H) (0.89 g, 6.64 mmol) and tri(ethylene glycol) dimethyl ether (6 mL) in acetonitrile (60 mL) was added isoamyl nitrite (0.97 g, 8.30 mmol) and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 5,7-difluoro-1,3-benzothiaz... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [Cu](Cl)Cl.C(C)#N | null | 0.5 | Cl.Nc1nc2cc(F)cc(F)c2s1>[Cu](Cl)Cl.C(C)#N>Fc1cc(F)c2sc(Cl)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03a8e4e583c2422abcd7983a9ed2f29e | Nc1nc2cc(F)cc(F)c2s1>>Nc1nc2ccccc2s1 | FC=1C=C(C=C(C1)F)NC(=S)N.FC=1C=C(C2=C(N=C(S2)N)C1)F.NC(=S)N>>NC=1SC2=C(N1)C=CC=C2 | F[c:6]1[cH:5][c:4]2[n:3][c:2]([NH2:1])[s:10][c:9]2[c:8](F)[cH:7]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[s:10]1 | Nc1nc2cc(F)cc(F)c2s1 | Nc1nc2ccccc2s1 | null | null | null | Reduction | OtherReaction | ef64b1186023cc3974a5c78dbf6ab70e4b9c57f439da272be52f8dc17b4c9184 | 0ecff68b4ffbd9fa417ba42b220387f06d93399a1e61c4d05eaeeacbdad5d93b | c1ccc2scnc2c1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:2:[c;H0;D3;+0:8](-F):[c:9]:1>>[#16;a:6]1:[c:5]:[#7;a:4]:[c:3]2:[c:2]:[cH;D2;+0:1]:[c:9]:[cH;D2;+0:8]:[c:7]:1:2 | null | [] | null | null | null | null | In certain cases the requisite 2-amino-1,3-benzothiazole was prepared from the corresponding thiourea as described above for the preparation of N-(3,5-difluorophenyl) thiourea and 5,7-difluoro-1,3-benzothiazol-2-amine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | null | null | null | Nc1nc2cc(F)cc(F)c2s1>>Nc1nc2ccccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af7ba1a7ab60417d86d4e7b9a1184323 | Fc1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl>>Fc1ccc2sc(Cl)nc2c1 | S(=O)(=O)(Cl)Cl.FC=1C=CC2=C(N=C(S2)S)C1>>ClC=1SC2=C(N1)C=C(C=C2)F | S[c:7]1[s:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:11][c:10]2[n:9]1.O=S(=O)(Cl)[Cl:8]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[s:6][c:7]([Cl:8])[n:9][c:10]2[cH:11]1 | Fc1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl | Fc1ccc2sc(Cl)nc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 0f784028f62f2a4cbed8e8484f90ae40cb6168d4f6f83851cc78fd3025ba6979 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | c1ccc2scnc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | null | [] | null | null | 1 | HOUR | Sulfuryl chloride (50 μL, 0.65 mmol) was added neat to 5-fluoro-1,3-benzothiazole-2-thiol (100 mg, 0.54 mmol). The mixture was stirred at ambient temperature for 1 h, then heated at 60° C. for 30 minutes. The resulting solution was cooled to rt, and poured onto ice. The title compound was collected by filtration, washe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HCl | null | null | 1 | Fc1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl>>Fc1ccc2sc(Cl)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-661e57de66044a9898eced4c290b9652 | Nc1cc(C(F)(F)F)ccc1Cl.S=C=S>>FC(F)(F)c1ccc2sc(S)nc2c1 | C(=S)=S.[H-].[Na+].C(C)OCCOCCO.ClC1=C(N)C=C(C=C1)C(F)(F)F>>SC=1SC2=C(N1)C=C(C=C2)C(F)(F)F | Cl[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14][c:13]1[NH2:12].[S:9]=[C:10]=[S:11]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[s:9][c:10]([SH:11])[n:12][c:13]2[cH:14]1 | Nc1cc(C(F)(F)F)ccc1Cl.S=C=S | FC(F)(F)c1ccc2sc(S)nc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | bd44fd812a6572ea6453f445ab298c6be743caada0c8ebfb512312963ab9977a | c8d671ee4b4adb8a19087b23be30f3f861fd854b43cb961da1b0b468b78f9092 | c1ccc2scnc2c1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].[S;H0;D1;+0:7]=[C;H0;D2;+0:8]=[S;H0;D1;+0:9]>>[SH;D1;+0:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:5]:[c:4](:[c:6]):[c;H0;D3;+0:1](:[c:2]:[c:3]):[s;H0;D2;+0:9]:1 | 44.1 | [{"value": 44.0, "product": "SC=1SC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.1, "product": "SC=1SC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of sodium hydride (0.98 g, 40.91 mmol) and diethylene glycol monoethyl ether (25 mL) was added 2-chloro-5-(trifluoromethyl)aniline (5.00 g, 25.57 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at rt for 30 minutes, and then carbon disulfide (3.89 g, 51.13 mmol) was added. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Aromatic thiol | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HCl | null | null | 0.5 | Nc1cc(C(F)(F)F)ccc1Cl.S=C=S>>FC(F)(F)c1ccc2sc(S)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d12c540085124d09aa48e1da1b1b4a13 | FC(F)(F)c1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl>>FC(F)(F)c1ccc2sc(Cl)nc2c1 | S(=O)(=O)(Cl)Cl.S(=O)(=O)(Cl)Cl.SC=1SC2=C(N1)C=C(C=C2)C(F)(F)F>>ClC=1SC2=C(N1)C=C(C=C2)C(F)(F)F | S[c:10]1[s:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14][c:13]2[n:12]1.O=S(=O)(Cl)[Cl:11]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[s:9][c:10]([Cl:11])[n:12][c:13]2[cH:14]1 | FC(F)(F)c1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl | FC(F)(F)c1ccc2sc(Cl)nc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 0f784028f62f2a4cbed8e8484f90ae40cb6168d4f6f83851cc78fd3025ba6979 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | c1ccc2scnc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 94 | [{"value": 94.0, "product": "ClC=1SC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "ClC=1SC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sulfuryl chloride (9.09 g, 67.33 mmol) was added with stirring to 2-mercapto-5-(trifluoromethyl)benzothiazole (2.64 g, 11.22 mmol) over a period of 5 minutes. The reaction mixture was then allowed to stand for approximately 1 h. Ice water was added to the reaction mixture with stirring to decompose the excess of sulfur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HCl | null | null | 1 | FC(F)(F)c1ccc2sc(S)nc2c1.O=S(=O)(Cl)Cl>>FC(F)(F)c1ccc2sc(Cl)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6e11d08e1fd40d8a5547054fc45b562 | Cl.Nc1ccc(C(F)(F)F)cc1Cl>>FC(F)(F)c1ccc2nc(Cl)sc2c1 | ClC1=C(N)C=CC(=C1)C(F)(F)F.C([S-])(OCC)=S.[K+].Cl>>ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F | [ClH:11].Cl[c:13]1[c:8]([NH2:9])[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([Cl:11])[s:12][c:13]2[cH:14]1 | Cl.Nc1ccc(C(F)(F)F)cc1Cl | FC(F)(F)c1ccc2nc(Cl)sc2c1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 91a37b0c501e1c443a9faa052f72667e05e3017eac877e2d9f24f3883ed72526 | de7ca61bb3b1fd47318d35fc573fe1764e21216e485e156cc616d366a0d01a95 | c1ccc2scnc2c1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6].[ClH;D0;+0:7]>>[Cl;H0;D1;+0:7]-[c:8]1:[#16;a:9]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:6]):[n;H0;D2;+0:5]:1 | 99 | [{"value": 99.0, "product": "ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-chloro-4-trifluoromethylaniline (15.0 g, 76.7 mmol) and potassium O-ethyl dithiocarbonate (29.5 g, 184.1 mmol) in 75 mL anhydrous.DMF was heated at 130° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, and then 1 N HCl solution (200 mL) was added with stirring to induce pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Aromatic halide | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HCl | CN(C)C=O | null | null | Cl.Nc1ccc(C(F)(F)F)cc1Cl>CN(C)C=O>FC(F)(F)c1ccc2nc(Cl)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dff72be06ffa49d882790277e1d786cf | FC(F)(F)c1ccc2nc(S)sc2c1.O=S(=O)(Cl)Cl>>FC(F)(F)c1ccc2nc(Cl)sc2c1 | SC=1SC2=C(N1)C=CC(=C2)C(F)(F)F.S(=O)(=O)(Cl)Cl>>ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F | S[c:10]1[n:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:14][c:13]2[s:12]1.O=S(=O)(Cl)[Cl:11]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([Cl:11])[s:12][c:13]2[cH:14]1 | FC(F)(F)c1ccc2nc(S)sc2c1.O=S(=O)(Cl)Cl | FC(F)(F)c1ccc2nc(Cl)sc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 0f784028f62f2a4cbed8e8484f90ae40cb6168d4f6f83851cc78fd3025ba6979 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | c1ccc2scnc2c1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#16;a:3]:[c:4]:[c:5]:[#7;a:6]:1 | 91 | [{"value": 91.0, "product": "ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sulfuryl chloride (40 mL) was added with stirring to 2-mercapto-6-(trifluoromethyl)-benzothiazole (18.0 g, 76.7 mmol) at <20° C. under a nitrogen atmosphere, and the suspension was then stirred at rt for 2 h. The reaction mixture was poured into ice water with stirring. Precipitation was formed, and stirring was contin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | HCl | null | null | 2 | FC(F)(F)c1ccc2nc(S)sc2c1.O=S(=O)(Cl)Cl>>FC(F)(F)c1ccc2nc(Cl)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86a9af2fbb5c41128ab0a4dfdac636cf | Cc1ccc(N)c(O)c1>>Cc1ccc2[nH]c(=S)oc2c1 | NC=1C=CC(=CC1O)C.O(C(=S)[S-])CC.[K+].Cl>>CC1=CC2=C(NC(O2)=S)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:10]([OH:9])[cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7](=[S:8])[o:9][c:10]2[cH:11]1 | Cc1ccc(N)c(O)c1 | Cc1ccc2[nH]c(=S)oc2c1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | e5eb030f5407e8a4a781d3d8e4b3d7d02ddf3ccf3adb7fe59ca08f15017de34b | 94f29894f73fa405cebace4e3be9b5e7b09e8f95c1bb353d798627950215e50f | S=c1[nH]c2ccccc2o1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6]>>[S;D1;H0:7]=[c:8]1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:6]):[o;H0;D2;+0:5]:1 | 92.3 | [{"value": 92.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 6-amino-m-cresol (593.7 mg, 4.82 mmol) and potassium O-ethyl xanthate (850 mg, 5.30 mmol) in pyridine (10 mL) was stirred and heated to reflux for 2 h. It was cooled to rt, poured into a mixture of ice-water (40 mL), and concentrated HCl (4 mL). The solid was collected, washed with water, and dried in the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Thiocarbonyl | c1ccccc1 | c1ccc2ncoc2c1 | c1ccc2ncoc2c1 | Other | N1=CC=CC=C1 | null | 3 | Cc1ccc(N)c(O)c1>N1=CC=CC=C1>Cc1ccc2[nH]c(=S)oc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3262dfcd76f846518796ae0f5231d23d | CI.Cc1ccc2[nH]c(=S)oc2c1>>CSc1nc2ccc(C)cc2o1 | CC1=CC2=C(NC(O2)=S)C=C1.IC.C([O-])([O-])=O.[K+].[K+]>>CC1=CC2=C(N=C(O2)SC)C=C1 | I[CH3:1].[S:2]=[c:3]1[nH:4][c:5]2[cH:6][cH:7][c:8]([CH3:9])[cH:10][c:11]2[o:12]1>>[CH3:1][S:2][c:3]1[n:4][c:5]2[cH:6][cH:7][c:8]([CH3:9])[cH:10][c:11]2[o:12]1 | CI.Cc1ccc2[nH]c(=S)oc2c1 | CSc1nc2ccc(C)cc2o1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | ad842350682ac43dfec546bd4c5b7cfc4bf8f9879e6b8070822e398b74cd895f | e73b6e23c9de2770653dfe1c031448ae08eae1a1e8b31e289bfc4b4719e52064 | c1ccc2ocnc2c1 | I-[CH3;D1;+0:1].[S;H0;D1;+0:2]=[c;H0;D3;+0:3]1:[#8;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:9]:1>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c;H0;D3;+0:3]1:[#8;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[n;H0;D2;+0:9]:1 | 35.6 | [{"value": 35.6, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 6-Methyl-1,3-benzoxazole-2(3H)-thione (375 mg, 2.27 mmol) was dissolved in THF (2.0 mL), and iodomethane (1610.8 mg, 11.35 mmol) and potassium carbonate (627.36 mg, 4.54 mmol) were added. This reaction mixture was stirred vigorously at rt overnight. The reaction mixture was filtered and the solid was rinsed with additi... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Monosulfide | c1ccc2ncoc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HI | C1CCOC1 | null | 8 | CI.Cc1ccc2[nH]c(=S)oc2c1>C1CCOC1>CSc1nc2ccc(C)cc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6c3407adb094fd186601245d5ddcf08 | N#CBr.Nc1cc(F)c(F)cc1N>>Nc1nc2cc(F)c(F)cc2[nH]1 | NC1=C(C=C(C(=C1)F)F)N.N#CBr.C([O-])(O)=O.[Na+]>>FC1=CC2=C(NC(=N2)N)C=C1F | Br[C:2]#[N:1].[NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[NH2:12]>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]2[nH:12]1 | N#CBr.Nc1cc(F)c(F)cc1N | Nc1nc2cc(F)c(F)cc2[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 162b5b518f3855d928d61cbc5142349190cf6480b5393ad29cbbeeb4810591c1 | e635cd5faf85aa8fd14b255a023602051ac390a16c997130c14be3163304717a | c1ccc2[nH]cnc2c1 | Br-[C;H0;D2;+0:1]#[N;H0;D1;+0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[NH2;D1;+0:7]):[c:8]>>[NH2;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c:6](:[c:8]):[c:4](:[c:5]):[nH;D2;+0:3]:1 | 98.8 | [{"value": 59.0, "product": "FC1=CC2=C(NC(=N2)N)C=C1F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "FC1=CC2=C(NC(=N2)N)C=C1F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The procedure used was similar to that reported in J. Med. Chem. 40:811–818, 1997. A solution of 1,2-diamino-4,5-difluorobenzene (500 mg, 3.47 mmol) in water (5 mL) was cooled to 0° C. and then treated with a solution of cyanogen bromide (0.83 mL, 4.16 mmol, 5 M in acetonitrile) and solid sodium bicarbonate (583 mg, 6.... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine.Primary amine | Primary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HBr | O | null | 8 | N#CBr.Nc1cc(F)c(F)cc1N>O>Nc1nc2cc(F)c(F)cc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0467d96bb5b948119f036634bf79f67c | Cl.Nc1nc2cc(F)c(F)cc2[nH]1>>Fc1cc2nc(Cl)[nH]c2cc1F | Cl.N(=O)OC(C)(C)C.FC1=CC2=C(NC(=N2)N)C=C1F.N(=O)OC(C)(C)C>>ClC1=NC2=C(N1)C=C(C(=C2)F)F | [ClH:7].N[c:6]1[n:5][c:4]2[cH:3][c:2]([F:1])[c:11]([F:12])[cH:10][c:9]2[nH:8]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][c:6]([Cl:7])[nH:8][c:9]2[cH:10][c:11]1[F:12] | Cl.Nc1nc2cc(F)c(F)cc2[nH]1 | Fc1cc2nc(Cl)[nH]c2cc1F | null | [Cu](Cl)Cl | CC(=O)C | Miscellaneous | OtherReaction | 857c8f1e64ccd27863105cbe22e92e556631542f0a4a501417bddd8e9b7bc616 | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2[nH]cnc2c1 | N-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[ClH;D0;+0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 73 | [{"value": 73.0, "product": "ClC1=NC2=C(N1)C=C(C(=C2)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | The procedure used was similar to that reported in J. Med. Chem. 40:811–818, 1997. To a mixture of copper(II) chloride (795 mg, 5.91 mmol) in acetone (20 mL) was added tert-butyl nitrite (0.53 mL, 4.43 mmol). The reaction mixture was stirred at rt for 20 minutes, 5,6-difluoro-1H-benzimidazol-2-amine (500 mg, 2.96 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | Other | [Cu](Cl)Cl.CC(=O)C | null | 0.333333 | Cl.Nc1nc2cc(F)c(F)cc2[nH]1>[Cu](Cl)Cl.CC(=O)C>Fc1cc2nc(Cl)[nH]c2cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbac10e252ac4979bdfd19db99c5bac4 | Nc1ccc(C(F)(F)F)cc1N.S=C=Nc1ccc(Br)cc1>>FC(F)(F)c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 | C1(CCCCC1)N=C=NC1CCCCC1.NC1=C(C=CC(=C1)C(F)(F)F)N.BrC1=CC=C(C=C1)N=C=S>>BrC1=CC=C(C=C1)NC1=NC2=C(N1)C=C(C=C2)C(F)(F)F | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:20]([NH2:19])[cH:21]1.S=[C:10]=[N:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]3)[nH:19][c:20]2[cH:21]1 | Nc1ccc(C(F)(F)F)cc1N.S=C=Nc1ccc(Br)cc1 | FC(F)(F)c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | b379a633a6d6a7ef71a4ec729ac27ffb0470b0a7feb5a79c5b4b49860868cf5b | 85c21648c239f13e3de224b3880be5fbcc059dde8446f4822bf814f376b11c25 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[nH;D2;+0:6]:1):[c:5] | 30 | [{"value": 30.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 15 | MINUTE | 1,2-Diamino-5-trifluoromethylbenzene (0.25 g, 1.42 mmol) was diluted in toluene (5 mL) and treated with 4-bromophenylisothiocyanate (0.30 g, 1.42 mmol). The dark solution was stirred at 100° C. for 15 minutes, then treated with 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol). The reaction was maintained at 100° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | C1(=CC=CC=C1)C | 100 | 0.25 | Nc1ccc(C(F)(F)F)cc1N.S=C=Nc1ccc(Br)cc1>C1(=CC=CC=C1)C>FC(F)(F)c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66414de28ead4eef90b6009cd06980d8 | Fc1cc(Br)ccc1N=C=S.Nc1ccc(C(F)(F)F)cc1N>>Fc1cc(Br)ccc1Nc1nc2cc(C(F)(F)F)ccc2[nH]1 | NC1=C(C=CC(=C1)C(F)(F)F)N.BrC1=CC(=C(C=C1)N=C=S)F.C1(CCCCC1)N=C=NC1CCCCC1>>BrC1=CC(=C(C=C1)NC1=NC2=C(N1)C=CC(=C2)C(F)(F)F)F | S=[C:10]=[N:9][c:8]1[c:2]([F:1])[cH:3][c:4]([Br:5])[cH:6][cH:7]1.[NH2:11][c:12]1[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]1[NH2:22]>>[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[NH:9][c:10]1[n:11][c:12]2[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20][c:21]2[nH:22]1 | Fc1cc(Br)ccc1N=C=S.Nc1ccc(C(F)(F)F)cc1N | Fc1cc(Br)ccc1Nc1nc2cc(C(F)(F)F)ccc2[nH]1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | b379a633a6d6a7ef71a4ec729ac27ffb0470b0a7feb5a79c5b4b49860868cf5b | 85c21648c239f13e3de224b3880be5fbcc059dde8446f4822bf814f376b11c25 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[c:8]:[c:7]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]):[nH;D2;+0:10]:[c:9]:1:[c:11] | null | [] | 45 | CELSIUS | 15 | MINUTE | 1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | ClCCl | 45 | 0.25 | Fc1cc(Br)ccc1N=C=S.Nc1ccc(C(F)(F)F)cc1N>ClCCl>Fc1cc(Br)ccc1Nc1nc2cc(C(F)(F)F)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cad3517ed4d644248f7d8749337b1526 | Cc1ccc(NC(=S)Nc2ccc(I)cc2)cc1>>Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1 | [OH-].[NH4+].IC1=CC=C(C=C1)NC(=S)NC1=CC=C(C=C1)C.BrBr.S(O)(O)=O>>IC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]2)=[S:16])[cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([I:13])[cH:14][cH:15]3)[s:16][c:17]2[cH:18]1 | Cc1ccc(NC(=S)Nc2ccc(I)cc2)cc1 | Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc(Nc2nc3ccccc3s2)cc1 | [S;H0;D1;+0:1]=[C;H0;D3;+0:2](-[#7:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:8]1:[s;H0;D2;+0:1]:[c;H0;D3;+0:2](-[#7:3]-[c:4]):[n;H0;D2;+0:5]:[c:6]:1:[c:7] | 97 | [{"value": 97.0, "product": "IC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": "IC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A suspension of N-(4-iodophenyl)-N′-(4-methylphenyl) thiourea (0.62 g, 4.68 mmol) in chloroform (23 mL) was treated with a solution of bromine (2.65 g, 16.59 mmol) in chloroform (1 mL). The reaction mixture was stirred at rt for 5 minutes and then heated at 50° C. for 5 minutes. Then the reaction mixture was allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | null | C(Cl)(Cl)Cl | null | 0.083333 | Cc1ccc(NC(=S)Nc2ccc(I)cc2)cc1>C(Cl)(Cl)Cl>Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3859a45296554bedb58e00427182e1ee | Cc1cccc2sc(Cl)nc12.Nc1ccc(Br)cc1F>>Cc1cccc2sc(Nc3ccc(Br)cc3F)nc12 | ClC=1SC2=C(N1)C(=CC=C2)C.BrC1=CC(=C(N)C=C1)F.Cl>>BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C(=CC=C2)C)F | Cl[c:8]1[s:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:19]2[n:18]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1[F:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[s:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]3[F:17])[n:18][c:19]12 | Cc1cccc2sc(Cl)nc12.Nc1ccc(Br)cc1F | Cc1cccc2sc(Nc3ccc(Br)cc3F)nc12 | null | null | CCCCO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 32798d554dc80c085869b4a43a5b4fb6dfd5a087e49c559b1d6e1572d282c401 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3ccccc3s2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9] | 89.4 | [{"value": 89.0, "product": "BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C(=CC=C2)C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C(=CC=C2)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 2-chloro-4-methyl-1,3-benzothiazole (0.25 g, 1.36 mmol) in n-BuOH (8 mL) was added 4-bromo-2-fluoroaniline (0.52 g, 2.72 mmol) and HCl (4.0 M in dioxane, 0.5 mL). The reaction was heated at 90° C. overnight. Solvent was removed by rotary evaporation and 1 N aqueous HCl was added. The aqueous layer was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | HCl | CCCCO | 90 | null | Cc1cccc2sc(Cl)nc12.Nc1ccc(Br)cc1F>CCCCO>Cc1cccc2sc(Nc3ccc(Br)cc3F)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ef69b9d21794e6c8556094586f591f4 | Fc1ccc2nc(Cl)sc2c1.Nc1ccc(Br)cc1F>>Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1 | FC1=C(N)C=CC(=C1)Br.BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C(=CC=C2)C)F.BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)F.ClC=1SC2=C(N1)C=CC(=C2)F>>BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)F)F | Cl[c:7]1[n:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:19][c:18]2[s:17]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]1[F:16]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]3[F:16])[s:17][c:18]2[cH:19]1 | Fc1ccc2nc(Cl)sc2c1.Nc1ccc(Br)cc1F | Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 32798d554dc80c085869b4a43a5b4fb6dfd5a087e49c559b1d6e1572d282c401 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3ccccc3s2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9] | 78 | [{"value": 78.0, "product": "BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner to that described above for the preparation of N-(4-bromo-2-fluorophenyl)-4-methyl-1,3-benzothiazol-2-amine and N-(4-bromo-2-fluorophenyl)-N-(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amine, using 2-chloro-6-fluoro-1,3-benzothiazole and 2-fluoro-4-bromoaniline, was prepared the desired product as a w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | HCl | null | null | null | Fc1ccc2nc(Cl)sc2c1.Nc1ccc(Br)cc1F>>Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d138c95ab1b4327808ade8f930cea49 | Clc1ccc2nc(Cl)sc2c1.Nc1ccc(I)cc1F>>Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1 | ClC=1SC2=C(N1)C=CC(=C2)Cl.ClC=1SC2=C(N1)C=CC(=C2)Cl.FC1=C(N)C=CC(=C1)I.Cl>>IC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)Cl)F | Cl[c:10]1[n:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[s:19]1.[F:1][c:2]1[cH:3][c:4]([I:5])[cH:6][cH:7][c:8]1[NH2:9]>>[F:1][c:2]1[cH:3][c:4]([I:5])[cH:6][cH:7][c:8]1[NH:9][c:10]1[n:11][c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]2[s:19]1 | Clc1ccc2nc(Cl)sc2c1.Nc1ccc(I)cc1F | Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 32798d554dc80c085869b4a43a5b4fb6dfd5a087e49c559b1d6e1572d282c401 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3ccccc3s2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9] | 38 | [{"value": 38.0, "product": "IC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)Cl)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.8, "product": "IC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 2,6-dichlorobenzothiazole (1.0 g, 4.9 mmol) and 2-fluoro-4-iodoaniline (2.32 g, 9.8 mmol) in 20 mL BuOH was stirred at 90° C., and then HCl (4 M in dioxane, 1.0 mL) was added. The reaction mixture was stirred with heating at 90° C. overnight, under argon. NMR analysis then showed little 2,6-dichlorobenzoth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1 | HCl | C(CCC)O | 90 | null | Clc1ccc2nc(Cl)sc2c1.Nc1ccc(I)cc1F>C(CCC)O>Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b422eaaf261343ee8c69e17472724450 | Cc1ccc(O)c(N)c1.S=C=Nc1ccc(Br)cc1>>Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | Cl.CN(CCCN=C=NCC)C.BrC1=CC=C(C=C1)N=C=S.NC1=C(C=CC(=C1)C)O.BrC1=CC=C(C=C1)NC(=S)NC1=C(C=CC(=C1)C)O>>BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:17]([NH2:16])[cH:18]1.S=[C:7]=[N:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]3)[n:16][c:17]2[cH:18]1 | Cc1ccc(O)c(N)c1.S=C=Nc1ccc(Br)cc1 | Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | null | null | CCOCC.C(C)O | Aromatic Heterocycle Formation | OtherReaction | fefd803169996589e15aee921d18474fd75a051b372d09083062969fafd8d12d | 00dbbf821799ce8a249e25702f112b17b0b8c6f22030ac97b31a241810059498 | c1ccc(Nc2nc3ccccc3o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1):[c:5] | 60 | [{"value": 60.0, "product": "BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | In a 250-mL round-bottom flask, 1-bromo-4-isothiocyanatobenzene (4.28 g, 20 mmol) and 2-amino-4-methyl-phenol (2.46 g, 20 mmol) were stirred in 120 mL ethanol at rt overnight. The formation of N-(4-bromophenyl)-N′-(2-hydroxy-5-methylphenyl)thiourea was confirmed by LC-MS. To the mixture, 1.5 eq. 1-(3-dimethylaminopropy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccccc1 | Other | CCOCC.C(C)O | null | 2 | Cc1ccc(O)c(N)c1.S=C=Nc1ccc(Br)cc1>CCOCC.C(C)O>Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7d2367f51754c8a9d86866ac0fbbed9 | Nc1cc(C(F)(F)F)ccc1O.S=C=Nc1ccc(Br)cc1>>FC(F)(F)c1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | NC1=C(C=CC(=C1)C(F)(F)F)O.BrC1=CC=C(C=C1)N=C=S>>BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C(F)(F)F | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:20]([NH2:19])[cH:21]1.S=[C:10]=[N:11][c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[o:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]3)[n:19][c:20]2[cH:21]1 | Nc1cc(C(F)(F)F)ccc1O.S=C=Nc1ccc(Br)cc1 | FC(F)(F)c1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fefd803169996589e15aee921d18474fd75a051b372d09083062969fafd8d12d | 00dbbf821799ce8a249e25702f112b17b0b8c6f22030ac97b31a241810059498 | c1ccc(Nc2nc3ccccc3o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[OH;D1;+0:10]):[c:11]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:11]):[o;H0;D2;+0:10]:1):[c:5] | 62.6 | [{"value": 62.0, "product": "BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Amino-4-(trifluoromethyl)phenol (250 mg, 1.41 mmol) and 1-bromo-4-isothio-cyanatobenzene (302 mg, 1.41 mmol) were stirred in ethyl alcohol at ambient temperature for 18 h. The flask was charged with 1-[3-(dimethylamino)propyl]-3-ethylcarhodiimide hydrochloride (EDCI) (405 mg, 2.12 mmol), and the mixture was stirred f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccccc1 | Other | C(C)O | null | 2 | Nc1cc(C(F)(F)F)ccc1O.S=C=Nc1ccc(Br)cc1>C(C)O>FC(F)(F)c1ccc2oc(Nc3ccc(Br)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a03d33c741245218a6391c02310a4c2 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O | [OH-].[Na+].NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.ClC=1SC2=C(N1)C=CC=C2.Cl.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)OC)(C)C)=O>>S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O | C[O:31][C:29]([C:2]([CH3:1])([CH3:3])[CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:25][cH:26]2)[cH:27][cH:28]1)=[O:30].Cl[c:16]1[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[s:24]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1 | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 45 | [{"value": 45.0, "product": "S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | In a 8-mL screw-cap vial, a mixture of methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (60 mg, 0.19 mmol) and 2chloro-1,3-benzothiazole (40 mg, 0.23 mmol) in 3 mL n-butanol were heated at 90° C. overnight. The formation of methyl 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | C(CCC)O | 90 | 8 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1>C(CCC)O>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c562ef6bea554331af07322689ed1205 | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O.Clc1nc2ccccc2[nH]1>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4[nH]3)cc2)cc1)C(=O)O | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.ClC1=NC2=C(N1)C=CC=C2.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O>>N1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O | s1[c:16]([NH:15][c:14]2[cH:13][cH:12][c:11](-[c:10]3[cH:9][cH:8][c:7]([C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[C:29](=[O:30])[OH:31])=[O:6])[cH:28][cH:27]3)[cH:26][cH:25]2)[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12.Clc1nc2ccccc2[nH:24]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:... | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O.Clc1nc2ccccc2[nH]1 | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4[nH]3)cc2)cc1)C(=O)O | null | null | null | Miscellaneous | OtherReaction | 13f7f96cab26f8214fab22b0df75f7e695d5b5d236430120c7e1e4ff30654ef4 | f004e58a958e83ed69c0f163c54d2c11d46ff03ec9dbfbb5a519e7e4cb2f94a4 | c1ccc(-c2ccc(Nc3nc4ccccc4[nH]3)cc2)cc1 | Cl-c1:[nH;D2;+0:1]:c2:c:c:c:c:c:2:n:1.[c:2]-[#7:3]-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10]):s:1>>[c:2]-[#7:3]-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10]):[nH;D2;+0:1]:1 | 48 | [{"value": 48.0, "product": "N1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.9, "product": "N1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (64 mg, 0.21 mmol) and 2-chloro-1H-benzimidazole (37.6 mg, 0.25 mmol) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providing 40.7 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | HCl | null | null | null | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O.Clc1nc2ccccc2[nH]1>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4[nH]3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de96e5cf34ce47fb82cf53831d4106dd | Brc1nccs1.CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nccs3)cc2)cc1)C(=O)O | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.BrC=1SC=CN1.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O>>CC(C(=O)O)(CC(C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1SC=CN1)=O)C | Br[c:16]1[n:17][cH:18][cH:19][s:20]1.c1ccc2sc([NH:15][c:14]3[cH:13][cH:12][c:11](-[c:10]4[cH:9][cH:8][c:7]([C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[C:25](=[O:26])[OH:27])=[O:6])[cH:24][cH:23]4)[cH:22][cH:21]3)nc2c1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH:15][c:16... | Brc1nccs1.CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nccs3)cc2)cc1)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 389173be250e83b81b7b928d74cf66ebc6dc077e4176832a6eafe86177a7cb8b | 4e90f991a320650127e80d8b2ceeaa7777833b188cfdb14e4fe7fb141cf7e5e9 | c1ccc(-c2ccc(Nc3nccs3)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[c:6]:[c:7](-[NH;D2;+0:8]-c1:n:c2:c:c:c:c:c:2:s:1):[c:9]>>[c:6]:[c:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9] | 24 | [{"value": 24.0, "product": "CC(C(=O)O)(CC(C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1SC=CN1)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (64 mg, 0.21 mmol) and 2-bromothiazole (41 mg, 0.25 mmol) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providing 18.6 mg (24%) of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Secondary amine | c1cscn1.c1ccc2scnc2c1 | c1cscn1 | c1ccccc1.c1ccccc1.c1cscn1 | HBr | null | null | null | Brc1nccs1.CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nccs3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-130e09a555fe4f7c91c6f21fe694c841 | COC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)CCC1=CC=CC=C1)=O.ClC=1SC2=C(N1)C=CC(=C2)Cl.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O)C=C1 | C[O:15][C:13]([CH:4]([CH2:3][C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]([NH2:24])[cH:35][cH:36]2)[cH:37][cH:38]1)[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].Cl[c:25]1[n:26][c:27]2[cH:28][cH:29][c:30]([Cl:31])[cH:32][c:33]2[s:34]1>>[O:1]=[C:2]([CH2:3][CH:4]([CH2:5][CH2:6][c:7... | COC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1 | O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(CCCCc1ccccc1)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 25 | [{"value": 25.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.7, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (78 mg, 0.20 mmol), 2,6-dichloro-1,3-benzothiazole (61.6 mg, 0.30 mmol) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | null | null | null | COC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6d87980c92542e9aff42fd72cfa5451 | CCCC(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)OC.Clc1ccc2nc(Cl)sc2c1>>CCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)CCC)=O.ClC=1SC2=C(N1)C=CC(=C2)Cl.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC)=O)C=C1 | C[O:33][C:31]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([NH2:16])[cH:27][cH:28]2)[cH:29][cH:30]1)=[O:32].Cl[c:17]1[n:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]2[s:26]1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:1... | CCCC(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)OC.Clc1ccc2nc(Cl)sc2c1 | CCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 18 | [{"value": 18.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from methyl 2-[2-(4′-amino-1,1′-biphenyl-4-yl)-2-oxoethyl]-pentanoate (68 mg, 0.20 mmol) and 2,6-dichloro-1,3-benzothiazole (61.3 mg, 0.30 mmol) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic acid, providing 17... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | null | null | null | CCCC(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)OC.Clc1ccc2nc(Cl)sc2c1>>CCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-171e3503a70341fda8474b8f5df5840b | CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1>>COCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O | [OH-].[Na+].Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCOC)=O.ClC=1SC2=C(N1)C=CC=C2>>S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCOC)=O | CC[O:33][C:31]([CH:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:27][cH:28]2)[cH:29][cH:30]1)=[O:32].Cl[c:18]1[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[s:26]1>>[CH3:1][O:2][CH2:3][CH2:4][CH:5]([CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12](... | CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1 | COCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O | null | null | CO.C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 31 | [{"value": 31.0, "product": "S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.0, "product": "S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | To a solution of ethyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2-(2-methoxyethyl)-4-oxobutanoate (75 mg, 0.21 mmol) in butanol (4 mL), 2-chloro-benzothiazole (43 mg, 0.25 mmol) was added and the reaction mixture was heated at 90° C. overnight. The solvent was removed by rotary evaporation, the residue was redissolved in DMF (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | CO.C(CCC)O | 90 | 8 | CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2s1>CO.C(CCC)O>COCCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c19388199054a7cbfef998edf07e7ca | COC(=O)C(CCN(C)C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>CN(C)CCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O | FC(C(=O)[O-])(F)F.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)CCN(C)C)=O.ClC=1SC2=C(N1)C=CC(=C2)Cl.S1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)(C)C)=O>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCN(C)C)=O)C=C1 | C[O:35][C:33]([CH:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([NH2:18])[cH:29][cH:30]2)[cH:31][cH:32]1)=[O:34].Cl[c:19]1[n:20][c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]2[s:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH:6]([CH2:7][C:8](=[O:9])[... | COC(=O)C(CCN(C)C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1 | CN(C)CCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 16.3 | [{"value": 13.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCN(C)C)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.3, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCN(C)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2-[2-(dimethyl-amino)ethyl]-4-oxobutanoate (60 mg, 0.17 mmol) and 2,6-dichloro-1,3-benzothiazole (51.8 mg, 0.25 mmol)) in a similar manner to the method described for 4-[4′-(1,3-benzothiazol-2-ylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoic ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | null | null | null | COC(=O)C(CCN(C)C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>CN(C)CCC(CC(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91db071b1f494ddaa49f96c7422a9c42 | CCCCO.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.COc1ccc2nc(S(C)(=O)=O)sc2c1>>CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1 | COC1=CC2=C(N=C(S2)S(=O)(=O)C)C=C1.COC1=CC2=C(N=C(S2)S(=O)(=O)C)C=C1.Cl.NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC)F.C(CCC)O>>FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][OH:5].CO[C:6](=[O:7])[C@@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([NH2:23])[c:35]([F:36])[cH:37]2)[cH:38][cH:39]1.CS(=O)(=O)[c:24]1[n:25][c:26]2[cH:27][cH:28][c:29]([O:30][CH3:31])[cH:32][c:33]2[s:34]1>>[CH3:1][CH2:2][CH2:3... | CCCCO.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.COc1ccc2nc(S(C)(=O)=O)sc2c1 | CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1 | null | null | null | Acylation | OtherReaction | 0f9119b0bd7bb262749509680e72c9ce4d60072c01426fdb1185277a2f082d75 | 001870bbed3e63e26a0c61c6adb985aac11f4817a8dba3c60cc05bf03fd24907 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11].C-S(=O)(=O)-[c;H0;D3;+0:12]1:[#16;a:13]:[c:14]:[c:15]:[#7;a:16]:1.[C:17]-[C:18]-[OH;D1;+0:19]>>[C:17]-[C:18]-[O;H0;D2;+0:19]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[O;D1;H0:7].[c:10]:[c:9](-[NH;D2;... | 65 | [{"value": 65.0, "product": "FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OCCCC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | Methyl (1R,2R)-2-[(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)carbonyl]cyclo-pentanecarboxylate (462 mg, 1.35 mmol) was dissolved in n-butanol (15 mL), and 6-methoxy-2-(methylsulfonyl)-1,3-benzothiazole (162 mg, 0.8 mmol) and 4 M aqueous HCl (1.5 mL) were added. The mixture was heated at 90° C. for 5 h. An additional portio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol.Primary amine.Sulfone | Ester.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HO- | null | 90 | 8 | CCCCO.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.COc1ccc2nc(S(C)(=O)=O)sc2c1>>CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9127b4d7ff9c4ca1a75f65c8ee03a551 | CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1>>COc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)sc2c1 | FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OCCCC.[OH-].[Na+]>>FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O | CCCC[O:27][C:25]([C@H:24]1[C@H:20]([C:18]([c:17]2[cH:16][cH:15][c:14](-[c:13]3[cH:12][cH:11][c:10]([NH:9][c:8]4[n:7][c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:35][c:34]5[s:33]4)[c:31]([F:32])[cH:30]3)[cH:29][cH:28]2)=[O:19])[CH2:21][CH2:22][CH2:23]1)=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([NH:9][c:10]3[cH... | CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1 | COc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)sc2c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-C-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] | 30 | [{"value": 30.0, "product": "FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | To a solution of butyl (1R,2R)-2-({3′-fluoro-4′-[(6-methoxy-1,3-benzothiazol-2-yl)-amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentanecarboxylate in methanol (8 mL) was added 1 N aqueous sodium hydroxide (6.15 mL), and the mixture was stirred at 50° C. overnight. The solvent was then removed by rotary evaporation. Water (5... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2scnc2c1.c1ccccc1.c1ccccc1.C1CCCC1 | Other | CO | 50 | 8 | CCCCOC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC)cc4s3)c(F)c2)cc1>CO>COc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a18740d4bfe14cca8aefbb9921da9aa9 | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.O=[N+]([O-])c1cnc(Br)s1>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3ncc([N+](=O)[O-])s3)cc2)cc1)C(=O)O | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O.BrC=1SC(=CN1)[N+](=O)[O-]>>CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1SC(=CN1)[N+](=O)[O-])C | [CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:24][cH:25]2)[cH:26][cH:27]1)[C:28](=[O:29])[OH:30].Br[c:16]1[n:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[s:23]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([N... | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.O=[N+]([O-])c1cnc(Br)s1 | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3ncc([N+](=O)[O-])s3)cc2)cc1)C(=O)O | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 8de8ca2517a540af5504af5f928939db3734aebd9b72e44df71c2713b5eb2f08 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc(Nc3nccs3)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9] | 10.5 | [{"value": 10.0, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1SC(=CN1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1SC(=CN1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | In a 8-mL screw-cap vial, a mixture of 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid (60 mg, 0.20 mmol) and 2-bromo-5-nitro-1,3-thiazole (63.3 mg, 0.30 mmol) in 4 mL n-butanol was heated at 90° C. overnight. The solvent was removed under reduced pressure. The mixture was dissolved in 5 mL 1:4 MeOH/DMF... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cscn1 | c1cscn1 | c1ccccc1.c1ccccc1.c1cscn1 | HBr | C(CCC)O | 90 | null | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.O=[N+]([O-])c1cnc(Br)s1>C(CCC)O>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3ncc([N+](=O)[O-])s3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d5afee1f93d4fd7bcaa34e9dc73811f | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.N#CSCC(=O)c1ccc(Cl)cc1>>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc(-c4ccc(Cl)cc4)cs3)cc2)cc1)C(=O)O | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O.ClC1=CC=C(C=C1)C(CSC#N)=O>>ClC1=CC=C(C=C1)C=1N=C(SC1)NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:28][cH:29]2)[cH:30][cH:31]1)[C:32](=[O:33])[OH:34].O=[C:18]([c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1)[CH2:26][S:27][C:16]#[N:17]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c... | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.N#CSCC(=O)c1ccc(Cl)cc1 | CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc(-c4ccc(Cl)cc4)cs3)cc2)cc1)C(=O)O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | e20632cb7d0ceb8da1b3e30ae2dd48fc9c1a15072b6dd5615686c1bf36001ff7 | d33af41f40c1b40b5d0ab1995e712cbb42a1c67e1c310ece3c879597bd7aeccd | c1ccc(-c2ccc(Nc3nc(-c4ccccc4)cs3)cc2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[S;H0;D2;+0:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[cH;D2;+0:2]:[s;H0;D2;+0:3]:1):[c:14] | 7 | [{"value": 7.0, "product": "ClC1=CC=C(C=C1)C=1N=C(SC1)NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.9, "product": "ClC1=CC=C(C=C1)C=1N=C(SC1)NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | In a 8-mL screw-cap vial, a mixture of 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid (60 mg, 0.20 mmol) and 2-(4-chlorophenyl)-2-oxoethyl thiocyanate (64 mg, 0.30 mmol) in 4 mL n-butanol was heated at 90° C. overnight. The solvent was removed under reduced pressure. The mixture was dissolved in 5 mL 1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine.Monosulfide | Secondary amine | null | c1cscn1 | c1ccccc1.c1ccccc1.c1cscn1.c1ccccc1 | HO- | C(CCC)O | 90 | null | CC(C)(CC(=O)c1ccc(-c2ccc(N)cc2)cc1)C(=O)O.N#CSCC(=O)c1ccc(Cl)cc1>C(CCC)O>CC(C)(CC(=O)c1ccc(-c2ccc(Nc3nc(-c4ccc(Cl)cc4)cs3)cc2)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-76471614d22c4503b487026d147d7e22 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2o1>>O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 | NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O.ClC=1OC2=C(N1)C=CC=C2.[OH-].[Na+]>>O1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O | CC[O:15][C:13]([CH:4]([CH2:3][C:2](=[O:1])[c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23]([NH2:24])[cH:34][cH:35]2)[cH:36][cH:37]1)[CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)=[O:14].Cl[c:25]1[n:26][c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[o:33]1>>[O:1]=[C:2]([CH2:3][CH:4]([CH2:5][CH2:6][c:7]1[cH:8... | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2o1 | O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e40b0d3e68fee98781e60ff179737b04f1ec5089aa99c59ec0fca6672696f406 | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(CCCCc1ccccc1)c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:1):[c:8] | 33 | [{"value": 33.0, "product": "O1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.6, "product": "O1C(=NC2=C1C=CC=C2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(CC(C(=O)O)CCC2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of ethyl 4-(4′-amino-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (100 mg, 0.25 mmol) and 2-chlorobenzoxazole (38.3 mg, 0.25 mmol) in toluene (1.0 mL) was heated at reflux for 16 h. Solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane. The solution was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ocnc2c1 | HCl | C1(=CC=CC=C1)C | null | 16 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1nc2ccccc2o1>C1(=CC=CC=C1)C>O=C(CC(CCc1ccccc1)C(=O)O)c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-358c6c3fc4bc4a5197223625f6445648 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1>>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)oc2c1 | [OH-].[Na+].Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.CC1=CC2=C(N=C(O2)S(=O)(=O)C)C=C1>>CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=CC(=C2)C)C | C[O:25][C:23]([C:20]([CH2:19][C:17]([c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([NH2:8])[cH:29][cH:28]2)[cH:27][cH:26]1)=[O:18])([CH3:21])[CH3:22])=[O:24].CS(=O)(=O)[c:7]1[n:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][c:31]2[o:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12](-[... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1 | Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)oc2c1 | null | null | CO.ClC(C)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 24413f4436d27050855541887d93d14a27a6eca1e25e2eecde1af97e352660a6 | d1dd3246cc33a0da853a7a6c3b7d972abe26a6e6b3a0c7c81ab0ee2fdf51bfc7 | c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:13] | 32.1 | [{"value": 32.1, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=CC(=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=CC(=C2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (74 mg, 0.24 mmol) in dichloroethane (3 mL), 6-methyl-2-(methylsulfonyl)-1,3-benzoxazole (50 mg, 0.24 mmol) was added, and the mixture was heated at 85° C. overnight. The solvent was removed by rotary evaporation, and the residue was re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Sulfone | Carboxylic acid.Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1 | HO- | CO.ClC(C)Cl | 85 | null | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1>CO.ClC(C)Cl>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)oc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf64bfd674a7432d9aea04c6531e87b0 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1cccc2oc(S(C)(=O)=O)nc12>>Cc1cccc2oc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)nc12 | [OH-].[Na+].Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.CC1=CC=CC2=C1N=C(O2)S(=O)(=O)C>>CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C(=CC=C2)C)C | C[O:26][C:24]([C:21]([CH2:20][C:18]([c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([NH2:9])[cH:30][cH:29]2)[cH:28][cH:27]1)=[O:19])([CH3:22])[CH3:23])=[O:25].CS(=O)(=O)[c:8]1[o:7][c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:32]2[n:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[o:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1cccc2oc(S(C)(=O)=O)nc12 | Cc1cccc2oc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)nc12 | null | null | CO.ClC(C)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 24413f4436d27050855541887d93d14a27a6eca1e25e2eecde1af97e352660a6 | d1dd3246cc33a0da853a7a6c3b7d972abe26a6e6b3a0c7c81ab0ee2fdf51bfc7 | c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:13] | 32.1 | [{"value": 32.1, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C(=CC=C2)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "CC(C(=O)O)(CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C(=CC=C2)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (74 mg, 0.24 mmol) in dichloroethane (3 mL), 4-methyl-2-(methylsulfonyl)-1,3-benzoxazole (50 mg, 0.24 mmol) was added, and the mixture was heated at 85° C. overnight. The solvent was removed by rotary evaporation and the residue was red... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Sulfone | Carboxylic acid.Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1 | HO- | CO.ClC(C)Cl | 85 | null | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1.Cc1cccc2oc(S(C)(=O)=O)nc12>CO.ClC(C)Cl>Cc1cccc2oc(Nc3ccc(-c4ccc(C(=O)CC(C)(C)C(=O)O)cc4)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-413351cac0774ed5921977575cb1bfa8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.CS(=O)(=O)c1nc2cc(F)ccc2o1>>O=C(O)C1CCCC1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4o3)cc2)cc1 | [OH-].[Na+].Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC.FC=1C=CC2=C(N=C(O2)S(=O)(=O)C)C1>>FC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)C2C(CCC2)C(=O)O)C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:30][cH:31]2)[cH:32][cH:33]1.CS(=O)(=O)[c:20]1[n:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]2[o:29]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]1[C:9](=[O:10])[c... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.CS(=O)(=O)c1nc2cc(F)ccc2o1 | O=C(O)C1CCCC1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4o3)cc2)cc1 | null | null | CO.ClC(C)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 24413f4436d27050855541887d93d14a27a6eca1e25e2eecde1af97e352660a6 | d1dd3246cc33a0da853a7a6c3b7d972abe26a6e6b3a0c7c81ab0ee2fdf51bfc7 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCC1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:13] | 31.7 | [{"value": 31.4, "product": "FC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)C2C(CCC2)C(=O)O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "FC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)C2C(CCC2)C(=O)O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclopentane carboxylate (100 mg, 0.31 mmol) in dichloroethane (3 mL), 5-fluoro-2-(methylsulfonyl)-1,3-benzoxazole (80 mg, 0.37 mmol) was added and the mixture was heated at 85° C. overnight. The solvent was removed by rotary evaporation, and the re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Sulfone | Carboxylic acid.Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2ocnc2c1 | HO- | CO.ClC(C)Cl | 85 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.CS(=O)(=O)c1nc2cc(F)ccc2o1>CO.ClC(C)Cl>O=C(O)C1CCCC1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4o3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-201f9aee2a71433e8ce551470722f6b8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1>>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1 | NC1=C(C=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC)F.CC1=CC2=C(N=C(O2)S(=O)(=O)C)C=C1>>FC=1C=C(C=CC1NC=1OC2=C(N1)C=CC(=C2)C)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([NH2:20])[c:31]([F:32])[cH:33]2)[cH:34][cH:35]1.CS(=O)(=O)[c:21]1[n:22][c:23]2[cH:24][cH:25][c:26]([CH3:27])[cH:28][c:29]2[o:30]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1 | null | null | ClC(C)Cl | Heteroatom Alkylation and Arylation | OtherReaction | bc24464683de0142b9214b41efe4688928ae65ec962befb092899f60b7bbcea3 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCC1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:9] | 42.7 | [{"value": 42.7, "product": "FC=1C=C(C=CC1NC=1OC2=C(N1)C=CC(=C2)C)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of methyl (1R,2R)-2-[(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)carbonyl]-cyclopentanecarboxylate (800 mg, 2.34 mmol, 78% ee) in dichloroethane (15 mL), 6-methyl-2-(methylsulfonyl)-1,3-benzoxazole (891 mg, 4.22 mmol) was added, and the mixture was heated at 85° C. overnight. The solvent was removed by rotary ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2ocnc2c1 | HO- | ClC(C)Cl | 85 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)c(F)c2)cc1.Cc1ccc2nc(S(C)(=O)=O)oc2c1>ClC(C)Cl>COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7b3e4962de241219997253920a4eda7 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1>>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)oc2c1 | FC=1C=C(C=CC1NC=1OC2=C(N1)C=CC(=C2)C)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC.[OH-].[Na+]>>FC=1C=C(C=CC1NC=1OC2=C(N1)C=CC(=C2)C)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O | C[O:26][C:24]([C@H:23]1[C@H:19]([C:17]([c:16]2[cH:15][cH:14][c:13](-[c:12]3[cH:11][cH:10][c:9]([NH:8][c:7]4[n:6][c:5]5[cH:4][cH:3][c:2]([CH3:1])[cH:34][c:33]5[o:32]4)[c:30]([F:31])[cH:29]3)[cH:28][cH:27]2)=[O:18])[CH2:20][CH2:21][CH2:22]1)=[O:25]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:1... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1 | Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)oc2c1 | null | null | O1CCOCC1.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCC1 | 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] | 15 | [{"value": 15.0, "product": "FC=1C=C(C=CC1NC=1OC2=C(N1)C=CC(=C2)C)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of methyl (1R,2R)-2-[(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)carbonyl]-cyclopentanecarboxylate (800 mg, 2.34 mmol, 78% ee) in dichloroethane (15 mL), 6-methyl-2-(methylsulfonyl)-1,3-benzoxazole (891 mg, 4.22 mmol) was added, and the mixture was heated at 85° C. overnight. The solvent was removed by rotary ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1.C1CCCC1 | Other | O1CCOCC1.C1CCOC1 | 50 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C)cc4o3)c(F)c2)cc1>O1CCOCC1.C1CCOC1>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3F)oc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39c1247472484a9181d8206e24581e9a | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1ccc2sc(Cl)nc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 | ClC=1SC2=C(N1)C=C(C=C2)F.Cl.O1CCOCC1.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC>>FC=1C=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:30][cH:31]2)[cH:32][cH:33]1.Cl[c:20]1[n:21][c:22]2[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]2[s:29]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1ccc2sc(Cl)nc2c1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 77 | [{"value": 77.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | 2-Chloro-5-fluoro-1,3-benzothiazole (29 mg, 0.16 mmol) and methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclopentanecarboxylate (50 mg, 0.16 mmol) were combined in 1-butanol. The solution was treated with 4 M HCl in dioxane (4 μL, 0.016 mmol) and heated at 90° C. for 18 h. The reaction mixture was concentrated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | C(CCC)O | 90 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1ccc2sc(Cl)nc2c1>C(CCC)O>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89e1b566444047c999b485ad57944331 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 | [OH-].[Na+].FC=1C=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C1.CO>>FC=1C=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH:19][c:20]3[n:21][c:22]4[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]4[s:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | 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] | 84 | [{"value": 84.0, "product": "FC=1C=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "FC=1C=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 60 | CELSIUS | null | null | A solution of 1 N aqueous sodium hydroxide solution (1 mL) was added to trans-methyl 2-({4′-[(5-fluoro-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentane-carboxylate (55 mg, 0.12 mmol) in THF (2 mL). Methanol was added until the mixture became homogeneous, and the resulting solution was heated at 60°... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | Other | C1CCOC1 | 60 | null | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1>C1CCOC1>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)ccc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f1a1d3329434fdb97cf67b0883184dc | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.FC(F)(F)c1ccc2nc(Cl)sc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C(F)(F)F)cc4s3)cc2)cc1 | Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CCC1)C(=O)OC.ClC=1SC2=C(N1)C=CC(=C2)C(F)(F)F>>FC(C1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1)(F)F | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:33][cH:34]2)[cH:35][cH:36]1.Cl[c:20]1[n:21][c:22]2[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]2[s:32]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.FC(F)(F)c1ccc2nc(Cl)sc2c1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C(F)(F)F)cc4s3)cc2)cc1 | null | null | C(C)OCC.C(CCC)O.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 13 | [{"value": 13.0, "product": "FC(C1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.7, "product": "FC(C1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "... | 90 | CELSIUS | 8 | HOUR | A mixture of methyl (1R,2R)-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclopentane-carboxylate (150 mg, 0.464 mmol) and 2-chloro-6-(trifluoromethyl)-1,3-benzothiazole(132 mg, 0.557 mmol) was diluted with n-butanol (3 mL) and treated with a catalytic amount of 4 M HCl in dioxane. The suspension was heated at 90° C. overn... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | C(C)OCC.C(CCC)O.O1CCOCC1 | 90 | 8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.FC(F)(F)c1ccc2nc(Cl)sc2c1>C(C)OCC.C(CCC)O.O1CCOCC1>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(C(F)(F)F)cc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-947301e8b5bd42b680eea3d2d619713c | Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)c(F)c2)cc1 | BrC1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1.C(=O)([O-])[O-].[Cs+].[Cs+].IC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)Cl)F.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.CC(=O)[O-].[K+]>>ClC1=CC2=C(N=C(S2)NC2=C(C=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)F)C=C1 | I[c:15]1[cH:16][cH:17][c:18]([NH:19][c:20]2[n:21][c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]3[s:29]2)[c:30]([F:31])[cH:32]1.Br[c:14]1[cH:13][cH:12][c:11]([C:9]([C@H:8]2[C@H:4]([C:2](=[O:1])[OH:3])[CH2:5][CH2:6][CH2:7]2)=[O:10])[cH:34][cH:33]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10]... | Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)c(F)c2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O.CN(C)C=O | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 60 | [{"value": 60.0, "product": "ClC1=CC2=C(N=C(S2)NC2=C(C=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.5, "product": "ClC1=CC2=C(N=C(S2)NC2=C(C=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_des... | 85 | CELSIUS | null | null | A suspension of N-(4-iodo-2-fluorophenyl)-6-chloro-1,3-benzothiazol-2-amine (200 mg, 0.49 mmol), bis(pinacolato)diboron (130 mg, 0.52 mmol), KOAc (150 mg, 1.48 mmol), and PdCl2(dppf) (30 mg, 0.04 mmol) in DMF (5.0 mL) was degassed by bubbling a flow of nitrogen for 30 minutes. The reaction mixture was heated under nitr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | Br-.I- | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O | 85 | null | Fc1cc(I)ccc1Nc1nc2ccc(Cl)cc2s1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(Br)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7d13e8b265d44deab7c9b18657558b9 | COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | [OH-].[Na+].NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CC1)C(=O)OC.ClC=1SC2=C(N1)C=CC(=C2)Cl>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CC2)C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][C@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([NH2:18])[cH:29][cH:30]2)[cH:31][cH:32]1.Cl[c:19]1[n:20][c:21]2[cH:22][cH:23][c:24]([Cl:25])[cH:26][c:27]2[s:28]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][C@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][... | COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1 | O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 10.8 | [{"value": 10.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.8, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 90 | CELSIUS | 8 | HOUR | To a solution of methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl) carbonyl]cyclobutane-carboxylate (100 mg, 0.32 mmol) in n-butanol (15 mL) was added 2,6-dichloro-1,3-benzothiazole (396 mg, 1.94 mmol), and the resulting reaction mixture was heated at 90° C. overnight. The mixture was evaporated to dryness and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | C(CCC)O | 90 | 8 | COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>C(CCC)O>O=C(O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b327ff9ad34646b780476c79d35c08ae | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1>>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)sc2c1 | [OH-].[Na+].C(=O)(O)[O-].[Na+].IC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)C.CC1(OB(OC1(C)C)C1=CC=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC)C=C1)C.ClCCl>>CC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1 | CC1(C)OB([c:13]2[cH:14][cH:15][c:16]([C:17](=[O:18])[C@@H:19]3[CH2:20][CH2:21][CH2:22][C@H:23]3[C:24](=[O:25])[O:26]C)[cH:27][cH:28]2)OC1(C)C.I[c:12]1[cH:11][cH:10][c:9]([NH:8][c:7]2[n:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:33][c:32]3[s:31]2)[cH:30][cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH:8][c:9]3[cH:10][... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1 | Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)sc2c1 | null | null | CCO.CCOC(=O)C.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8f1c516cec4aae5ed8cf0f752a7a880f2fe87c5a169b2a3c81e8ab5ad99d487a | 19e12f96077001742aefca80d4454ef69c504b5600649c2dc62814171c24514f | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-O-C-1(-C)-C.C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].I-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:13]:[c:14] | 74 | [{"value": 19.0, "product": "CC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "CC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 85 | CELSIUS | 8 | HOUR | N-(4-iodophenyl)-6-methyl-1,3-benzothiazol-2-amine (0.28 g, 0.78 mmol) and methyl trans-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]cyclopentanecarboxylate (0.25 g, 0.71 mmol) were combined in a dry flask under argon. Toluene (15 mL), EtOH (6 mL), and saturated aqueous NaHCO3 (2 mL) were then added, and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic ester | Carboxylic acid | B1OCCO1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1.c1ccccc1.C1CCCC1 | HI.B | CCO.CCOC(=O)C.C1(=CC=CC=C1)C | 85 | 8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1.Cc1ccc2nc(Nc3ccc(I)cc3)sc2c1>CCO.CCOC(=O)C.C1(=CC=CC=C1)C>Cc1ccc2nc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-110a2526de0c455a8953e7fc8c2033c8 | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2nc(Cl)sc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4c(F)cc(F)cc4s3)cc2)cc1 | [OH-].[Na+].NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CC1)C(=O)OC.ClC=1SC2=C(N1)C(=CC(=C2)F)F.C(CCC)O>>FC1=CC(=CC2=C1N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)F | OCCC[CH3:7].C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:31][cH:32]2)[cH:33][cH:34]1.Cl[c:20]1[n:21][c:22]2[c:23]([F:24])[cH:25][c:26]([F:27])[cH:28][c:29]2[s:30]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O... | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2nc(Cl)sc2c1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4c(F)cc(F)cc4s3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2c045bcd2c6100e0e5346bd7e50410759982d61214713c30937eb6c2557b1a33 | 0f501feb6f7f3b8bf26e68897118744371cb7a838746ae3abea3f18a241ad82f | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[CH2;D2;+0:6]-[C@H;D3;+0:7]-1-[C:8](=[O;D1;H0:9])-[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14].Cl-[c;H0;D3;+0:15]1:[#16;a:16]:[c:17]:[c:18]:[#7;a:19]:1.O-C-C-C-[CH3;D1;+0:20]>>[O;D1;H0:9]=[C:8](-[c:10])-[C@@H;D3;+0:7]1-[CH2;D2;+0:20]-[CH2;D2;+0:6]-[C:5]-[C:4]-1-[C:2](=[... | 43 | [{"value": 43.0, "product": "FC1=CC(=CC2=C1N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)F", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | To a solution of racemic methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclobutane-carboxylate (250 mg, 0.77 mmol) in n-butanol (15 mL) was added 2-chloro-4,6-difluoro-1,3-benzothiazole (318 mg, 1.55 mmol), and the resulting solution was heated at 90° C. overnight. The mixture was then evaporated to dryness und... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester.Primary alcohol.Primary amine | Carboxylic acid.Ketone.Secondary amine | C1CCC1.c1ccc2scnc2c1 | C1CCCC1.c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | null | 90 | 8 | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2nc(Cl)sc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4c(F)cc(F)cc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6bc3d9a67d954c3aa8168070a865da7d | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1 | FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC>>FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH:19][c:20]3[n:21][c:22]4[cH:23][cH:24][c:25]([O:26][C:27]([F:28])([F:29])[F:30])[cH:31][c:32]4[s:33]3)[c:34]([F:35])[cH:36]2)[cH:37][cH:38]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:... | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1 | null | null | C1CCOC1.O1CCOCC1.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | 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] | 80 | [{"value": 80.0, "product": "FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O", "details": "CALCULATEDPERCENTYIELD... | null | null | 8 | HOUR | In 250-mL round-bottom flask, methyl (1R,2R)-2-[(3′-fluoro-4′-{[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]amino}-1,1′-biphenyl-4-yl)carbonyl]cyclopentanecarboxylate (2.53 g, 4.53 mmol) was dissolved in 100 mL of 1:1 THF/dioxane containing 5.0 molar equivalents of 1 N aqueous NaOH. The mixture was stirred at rt overnig... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | Other | C1CCOC1.O1CCOCC1.[OH-].[Na+] | null | 8 | COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1>C1CCOC1.O1CCOCC1.[OH-].[Na+]>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4706427144144d9c940b3c0fc5769e48 | CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccccc1Br.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1.Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1>>CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c2)cc1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c2)cc1 | FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC.BrC1=C(C(=O)[C@H]2[C@@H](CCC2)C(=O)OC(C)(C)C)C=CC=C1.BrC1=CC(=C(C=C1)NC=1SC2=C(N1)C=CC(=C2)F)F>>FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)OC(C)(C)C.FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)F)C2=CC=C(C=... | Br[c:38]1[c:15]([C:13]([C@H:12]2[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]2)=[O:14])[cH:16][cH:17][cH:18][cH:37]1.C[O:41][C:40](=[O:39])[C@@H:42]1[CH2:43][CH2:44][CH2:45][C@H:46]1[C:47](=[O:48])[c:49]1[cH:50][cH:51][c:52](-[c:53]2[cH:54][cH:55][c:56]([NH:57][c:58]3[n:59][c:60]4[cH:... | CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccccc1Br.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1.Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1 | CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c2)cc1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c2)cc1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | C-C Coupling | OtherReaction | 61b11d9b971308da0325cf7c7a87a92ee13bd33eafe557b9aedc01d22ca98513 | 22c9200aa7e90b52fa31cf87d9616d984f4a8526a6b18670f752329a653d41b9 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1.O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6]1:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:[c:11]:1-[C:12](-[C:13])=[O;D1;H0:14].C-[O;H0;D2;+0:15]-[C:16](-[C:17])=[O;D1;H0:18].F-C(-F)(-[F;H0;D1;+0:19])-O-[c;H0;D3;+0:20]1:[c:21]:[c:22]:[c:23]2:[#7;a:24]:[c:25]:[#16;a:26]:[c:27]:2:[c:28]:1>>[C:17]-[C:16](=[O;D1;H0:18... | 77 | [{"value": 77.0, "product": "FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl (1R,2R)-2-({3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-1,1′-biphenyl-4-yl}carbonyl)cyclopentanecarboxylate was prepared from tert-butyl (1R,2R)-2-(bromobenzoyl)-cyclopentanecarboxylate and N-(4-bromo-2-fluorophenyl)-N-(6-fluoro-1,3-benzothiazol-2-yl)amine in a similar manner to that described above... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Ester.Ether | Aromatic halide.Carboxylic acid | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1.C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HF.Br- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | null | CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccccc1Br.COC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1.Fc1ccc2nc(Nc3ccc(Br)cc3F)sc2c1>C(=O)(C(F)(F)F)O.C(Cl)Cl>CC(C)(C)OC(=O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c2)cc1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(F)cc4s3)c(F)c... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b17c21f2f46f4fe0a90d984846a7e30c | Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1>>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)nc2c1 | BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C.FC=1C=C(C=CC1NC=1SC2=C(N1)C=CC(=C2)OC(F)(F)F)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O>>CC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1 | Br[c:12]1[cH:11][cH:10][c:9]([NH:8][c:7]2[o:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:33][c:32]3[n:31]2)[cH:30][cH:29]1.Fc1cc(-[c:13]2[cH:14][cH:15][c:16]([C:17](=[O:18])[C@@H:19]3[CH2:20][CH2:21][CH2:22][C@H:23]3[C:24](=[O:25])[OH:26])[cH:27][cH:28]2)ccc1Nc1nc2ccc(OC(F)(F)F)cc2s1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]... | Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1 | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)nc2c1 | null | null | null | C-C Coupling | OtherReaction | 7e030365ea763a8b20725bdf7cc4e4b81d7cae69f702f2ba7bcf0abc9aaae53d | 31aec7e79c6cfceac6a53ebd119e0224e1c781e24c2b8226575d46b34c1e30ac | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].F-c1:c:c(-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):c:c:c:1-N-c1:n:c2:c:c:c(-O-C(-F)(-F)-F):c:c:2:s:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 17 | [{"value": 17.0, "product": "CC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared from N-(4-bromophenyl)-N-(5-methyl-1,3-benzoxazol-2-yl)amine (0.50 g, 1.65 mmol), methyl (1R,2R)-2-(4-bromobenzoyl) cyclopentanecarboxylate (0.57 g, 1.83 mmol, 94.5% ee) in a similar manner to the method described for (1R,2R)-2-({3′-fluoro-4′-[(6-trifluoromethoxy-1,3-benzothiazol-2-yl)amino]-... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Ether.Secondary amine | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | c1ccccc1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1.C1CCCC1 | HF.Br- | null | null | null | Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1.O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(OC(F)(F)F)cc4s3)c(F)c2)cc1>>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCC[C@H]5C(=O)O)cc4)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-513ad0f6b80f44bd92d4d8d324b682f5 | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2sc(Cl)nc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)cc(F)c4s3)cc2)cc1 | [OH-].[Na+].NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@H]1[C@@H](CC1)C(=O)OC.ClC=1SC2=C(N1)C=C(C=C2F)F.Cl.C(CCC)O>>FC=1C=C(C2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1)F | OCCC[CH3:7].C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][C@H:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:31][cH:32]2)[cH:33][cH:34]1.Cl[c:20]1[n:21][c:22]2[cH:23][c:24]([F:25])[cH:26][c:27]([F:28])[c:29]2[s:30]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O... | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2sc(Cl)nc2c1 | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)cc(F)c4s3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2c045bcd2c6100e0e5346bd7e50410759982d61214713c30937eb6c2557b1a33 | 0f501feb6f7f3b8bf26e68897118744371cb7a838746ae3abea3f18a241ad82f | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[CH2;D2;+0:6]-[C@H;D3;+0:7]-1-[C:8](=[O;D1;H0:9])-[c:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14].Cl-[c;H0;D3;+0:15]1:[#16;a:16]:[c:17]:[c:18]:[#7;a:19]:1.O-C-C-C-[CH3;D1;+0:20]>>[O;D1;H0:9]=[C:8](-[c:10])-[C@@H;D3;+0:7]1-[CH2;D2;+0:20]-[CH2;D2;+0:6]-[C:5]-[C:4]-1-[C:2](=[... | 58 | [{"value": 58.0, "product": "FC=1C=C(C2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C1)F", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | To a solution of methyl trans-2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclobutanecarboxylate (80 mg, 0.25 mmol) in n-butanol (8 mL) was added 2-chloro-5,7-difluoro-1,3-benzothiazole (102 mg, 0.49 mmol) and HCl (4.0 M in dioxane, 0.2 mL). The resulting reaction mixture was heated at 90° C. overnight. The mixture was ev... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester.Primary alcohol.Primary amine | Carboxylic acid.Ketone.Secondary amine | C1CCC1.c1ccc2scnc2c1 | C1CCCC1.c1ccc2scnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | null | 90 | 8 | CCCCO.COC(=O)[C@@H]1CC[C@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc(F)c2sc(Cl)nc2c1>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)cc(F)c4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00bd96e732804164bae07121e61b8ef7 | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>>O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | [OH-].[Na+].NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@@H]1[C@@H](CCCC1)C(=O)OC.ClC=1SC2=C(N1)C=CC(=C2)Cl>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([NH2:20])[cH:31][cH:32]2)[cH:33][cH:34]1.Cl[c:21]1[n:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]2[s:30]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]1[C:1... | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1 | O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 15.5 | [{"value": 15.0, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.5, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired... | 90 | CELSIUS | 8 | HOUR | To a solution of cis-methyl 2-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]cyclohexanecarboxylate (200 mg, 0.59 mmol) in n-butanol (8 mL) was added 2,6-dichloro-1,3-benzothiazole (241 mg, 1.19 mmol), and the resulting reaction mixture was heated at 90° C. overnight. The mixture was evaporated to dryness and the residue was c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | C(CCC)O | 90 | 8 | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Clc1ccc2nc(Cl)sc2c1>C(CCC)O>O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4ccc(Cl)cc4s3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62b28e7d87c145e390d6d486f41ed3c7 | C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1.Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1 | C(=O)(O)[O-].[Na+].BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C.C[Si](CCOC(=O)[C@H]1[C@@H](CCCC1)C(C1=CC=C(C=C1)Br)=O)(C)C.ClCCl>>C[Si](CCOC(=O)[C@H]1[C@@H](CCCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C)(C)C | Br[c:13]1[cH:14][cH:15][c:16]([C:17](=[O:18])[C@@H:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C@H:24]2[C:25](=[O:26])[O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35]1.Br[c:12]1[cH:11][cH:10][c:9]([NH:8][c:7]2[o:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:40][c:39]3[n:38]2)[cH:37][cH:36]1>>[CH3:1][c:2]1[cH:3... | C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1.Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CCOC(=O)C.CCO.C1(=CC=CC=C1)C | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 50.2 | [{"value": 50.0, "product": "C[Si](CCOC(=O)[C@H]1[C@@H](CCCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "C[Si](CCOC(=O)[C@H]1[C@@H](CCCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C)(C)C", "details": "CALCULATEDPE... | 90 | CELSIUS | null | null | N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine (76.70 mg, 0.25 mmol) and trans-2-(trimethylsilyl)ethyl-2-(4-bromobenzoyl)cyclohexanecarboxylate (105.45 mg, 0.23 mmol) were combined in a clean dry flask under argon. Toluene (25 mL), EtOH (8 mL), and saturated aqueous NaHCO3 (5 mL) were added, and the resulting soluti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | Br- | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C | 90 | null | C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1.Cc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8712231646084d08be809f790c04ef32 | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1>>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)O)cc4)cc3)nc2c1 | [NH4+].[Cl-].C[Si](CCOC(=O)[C@H]1[C@@H](CCCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)C)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C1 | C[Si](C)(C)CC[O:27][C:25]([C@H:24]1[C@H:19]([C:17]([c:16]2[cH:15][cH:14][c:13](-[c:12]3[cH:11][cH:10][c:9]([NH:8][c:7]4[o:6][c:5]5[cH:4][cH:3][c:2]([CH3:1])[cH:34][c:33]5[n:32]4)[cH:31][cH:30]3)[cH:29][cH:28]2)=[O:18])[CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:26]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]([NH:8][c:9]3[cH:1... | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1 | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)O)cc4)cc3)nc2c1 | null | null | C1CCOC1.CCOC(=O)C.O | Deprotection | Ester saponification (alkyl deprotection) | a3c1e490feb6b7fce3c6323047260c78ad5d894f96ffb52fbe21f86a88668678 | 5b01c4b72bcb1d31e02ab060e26bc1888b853fee0b286003b9b19e22cf024145 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4o3)cc2)cc1)C1CCCCC1 | C-[Si](-C)(-C)-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] | 84 | [{"value": 84.0, "product": "CC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "CC=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 16 | HOUR | To a solution of trans-2-(trimethylsilyl)ethyl-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)-amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylate (64 mg, 0.12mmol) in THF (2 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 0.70 mL), and then the reaction mixture was stirred at rt for 16 h. Saturated aqueous NH4Cl was a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Silyl protective group | Carboxylic acid | null | null | c1ccc2ocnc2c1.c1ccccc1.c1ccccc1.C1CCCCC1 | Other | C1CCOC1.CCOC(=O)C.O | null | 16 | Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)OCC[Si](C)(C)C)cc4)cc3)nc2c1>C1CCOC1.CCOC(=O)C.O>Cc1ccc2oc(Nc3ccc(-c4ccc(C(=O)[C@@H]5CCCC[C@H]5C(=O)O)cc4)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fbc8056ffd84fbdb675268123ce07fe | COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1.Clc1ccc2nc(Cl)sc2c1>>O=C(O)[C@H]1CCC[C@@H](C(=O)c2ccc(-c3ccc(Nc4nc5ccc(Cl)cc5s4)cc3)cc2)C1 | [OH-].[Na+].COC(=O)C1CC(CCC1)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)N.ClC=1SC2=C(N1)C=CC(=C2)Cl.ClC=1SC2=C(N1)C=CC(=C2)Cl.Cl>>ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2C[C@H](CCC2)C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:30][cH:31]3)[cH:32][cH:33]2)[CH2:34]1.Cl[c:20]1[n:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]2[s:29]1>>[O:1]=[C:2]([OH:3])[C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]([C:9](=[O:10]... | COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1.Clc1ccc2nc(Cl)sc2c1 | O=C(O)[C@H]1CCC[C@@H](C(=O)c2ccc(-c3ccc(Nc4nc5ccc(Cl)cc5s4)cc3)cc2)C1 | null | Cl.Cl | CO.C(CCC)O.O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | f9986fd127a6da7b0ddf48b96a5b2ec782e9d78dd6773ebb8f986b1aa4d9d75f | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4s3)cc2)cc1)C1CCCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 23.4 | [{"value": 23.4, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2C[C@H](CCC2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.6, "product": "ClC1=CC2=C(N=C(S2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2C[C@H](CCC2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": ... | 90 | CELSIUS | null | null | To a solution of 3-(4′-amino-biphenyl-4-carbonyl)-cyclohexanecarboxylic acid methyl ester (100 mg, 0.3 mmol) in butanol (5 mL), 2,6-dichloro-benzothiazole (60 mg, 0.3 mmol) and 5 drops of 4 M HCl in dioxane were added, and the reaction mixture was heated at 90° C. for 5 h. An additional sample of 2,6-dichlorobenzothiaz... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccc2scnc2c1 | HCl | Cl.Cl.CO.C(CCC)O.O1CCOCC1 | 90 | null | COC(=O)C1CCCC(C(=O)c2ccc(-c3ccc(N)cc3)cc2)C1.Clc1ccc2nc(Cl)sc2c1>Cl.Cl.CO.C(CCC)O.O1CCOCC1>O=C(O)[C@H]1CCC[C@@H](C(=O)c2ccc(-c3ccc(Nc4nc5ccc(Cl)cc5s4)cc3)cc2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2221d47fa7cf42b4b8a49b4187fa1ea1 | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc2nc(Cl)[nH]c2cc1F>>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)c(F)cc4[nH]3)cc2)cc1 | ClC1=NC2=C(N1)C=C(C(=C2)F)F.Cl.NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)C1C(CCC1)C(=O)OC.[OH-].[Na+]>>FC1=CC2=C(NC(=N2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1F | C[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]1[C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:31][cH:32]2)[cH:33][cH:34]1.Cl[c:20]1[n:21][c:22]2[cH:23][c:24]([F:25])[c:26]([F:27])[cH:28][c:29]2[nH:30]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[c... | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc2nc(Cl)[nH]c2cc1F | O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)c(F)cc4[nH]3)cc2)cc1 | null | null | C(CCC)O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 65a04004c81793963f7068ea64a1102a59e6e0f4ff093cf5443495fee7e7ce04 | de5a4a1c21f0a9f757d533080e1d67a6200de123fe2d9421ccc3db04c6765633 | O=C(c1ccc(-c2ccc(Nc3nc4ccccc4[nH]3)cc2)cc1)C1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[c:7]:[c:6](-[NH;D2;+0:5]-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[c:8] | 98.6 | [{"value": 3.0, "product": "FC1=CC2=C(NC(=N2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "FC1=CC2=C(NC(=N2)NC2=CC=C(C=C2)C2=CC=C(C=C2)C(=O)[C@H]2[C@@H](CCC2)C(=O)O)C=C1F", "details": "CALCULATEDPERCENTYIELD", "is_desired": ... | 90 | CELSIUS | 16 | HOUR | Methyl 2-[(4′-aminobiphenyl-4-yl)carbonyl]cyclopentanecarboxylate (264 mg, 0.02 mmol) was dissolved in n-butanol (8 mL), 2-chloro-5,6-difluoro-1H-benzimidazole (185 mg, 0.98 mmol) and 4 N HCl (0.2 mL) were then added, and the resulting mixture was heated at 90° C. for 5 h. The mixture was then cooled to rt, and solvent... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Carboxylic acid.Secondary amine | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | C1CCCC1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | HCl | C(CCC)O.O1CCCC1 | 90 | 16 | COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(N)cc2)cc1.Fc1cc2nc(Cl)[nH]c2cc1F>C(CCC)O.O1CCCC1>O=C(O)[C@@H]1CCC[C@H]1C(=O)c1ccc(-c2ccc(Nc3nc4cc(F)c(F)cc4[nH]3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d696bea668f4b758ccefed342a68beb | CCOC(=O)CBr.Oc1ccccc1C(F)(F)F>>CCOC(=O)COc1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)O)(F)F.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC>>C(C)OC(COC1=C(C=CC=C1)C(F)(F)F)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17] | CCOC(=O)CBr.Oc1ccccc1C(F)(F)F | CCOC(=O)COc1ccccc1C(F)(F)F | null | null | O.C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 2 | HOUR | A mixture of 2-trifluoromethylphenol (1.62 g) in anhydrous acetonitrile was treated with cesium carbonate (3.25 g) and ethyl bromoacetate (1.75 g) and the reaction mixture stirred at room temperature for 2 hours. The reaction mixture was diluted with water and ethyl acetate and the organic layer washed with water and d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | O.C(C)(=O)OCC.C(C)#N | null | 2 | CCOC(=O)CBr.Oc1ccccc1C(F)(F)F>O.C(C)(=O)OCC.C(C)#N>CCOC(=O)COc1ccccc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d337718b4324e0dae33ac3f4b6f3bab | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)CBr>>CCOC(=O)COc1ccc(C(C)=O)cc1C | OC1=C(C=C(C=C1)C(C)=O)C.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(=O)OCC>>C(C)OC(COC1=C(C=C(C=C1)C(C)=O)C)=O | [OH:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][c:16]1[CH3:17].Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])=[O:14])[cH:15][c:16]1[CH3:17] | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)CBr | CCOC(=O)COc1ccc(C(C)=O)cc1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | 40 | CELSIUS | null | null | 1-(4-Hydroxy-3-methylphenyl)ethanone (90 g) and cesium carbonate (216 g) were stirred in acetonitrile (900 ml) at room temperature under nitrogen for 10 minutes. Ethyl bromoacetate (73 ml) was added and the mixture heated to 40° C. for 3 hours. Further ethyl bromoacetate (2.5 ml) and cesium carbonate (1 g) were added a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)#N | 40 | null | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)CBr>C(C)#N>CCOC(=O)COc1ccc(C(C)=O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55f2e447a6be46f59025fb20b44ca092 | CCOC(=O)COc1ccc(OC(C)=O)cc1C>>CCOC(=O)COc1ccc(O)cc1C | Cl.C(C)OC(COC1=C(C=C(C=C1)OC(C)=O)C)=O.C(C)OC(COC1=C(C=C(C=C1)OC(C)=O)C)=O.[O-]CC.[Na+]>>C(C)OC(COC1=C(C=C(C=C1)O)C)=O | CC(=O)[O:12][c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:14]([CH3:15])[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]1[CH3:15] | CCOC(=O)COc1ccc(OC(C)=O)cc1C | CCOC(=O)COc1ccc(O)cc1C | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 45 | CELSIUS | null | null | A solution of ethyl[4-(acetyloxy)-2-methylphenoxy]acetate (intermediate 6, 148 g) in ethanol (1300 ml) was treated with sodium ethoxide (41.3 g) and the mixture heated to 45° C. for 2.5 hours. The mixture as cooled to 22° C. and concentrated hydrochloric acid added to give a neutral (pH 7) solution. The resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccccc1 | HO- | C(C)O | 45 | null | CCOC(=O)COc1ccc(OC(C)=O)cc1C>C(C)O>CCOC(=O)COc1ccc(O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9e3abe3037745ca9722783f856fcc9a | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)C(C)(C)Br>>CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C | BrC(C(=O)OCC)(C)C.OC1=C(C=C(C=C1)C(C)=O)C.C([O-])([O-])=O.[Cs+].[Cs+].BrC(C(=O)OCC)(C)C>>C(C)(=O)C1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C | [OH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])=[O:16])[cH:17][c:18]1[CH3:19].Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([C:14]([CH3:15])=[O:16])[cH:17][c:18]1[CH3:19] | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)C(C)(C)Br | CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 657b1e065fabda84e4d6cc80f4d94ce754af0792c9117981e41887a4384f6981 | 2495a256265ef36132d409a6a3e2bd04c3acda5f236d910f184b0a36a846defe | c1ccccc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | 2 | MINUTE | A suspension of 1-(4-hydroxy-3-methylphenyl)ethanone (20.1 g) in acetonitrile (200 ml) was added to a suspension of cesium carbonate (86.6 g) in acetonitrile (400 ml) and the mixture stirred under nitrogen at room temperature for 2 minutes. ethyl 2-bromo-2-methylpropanoate (33 g) was added and the mixture stirred for 2... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)(=O)OCC.C(C)#N | null | 0.033333 | CC(=O)c1ccc(O)c(C)c1.CCOC(=O)C(C)(C)Br>C(C)(=O)OCC.C(C)#N>CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac4f6997785540cfabd1e40607d0df66 | CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.O=C(OO)c1cccc(Cl)c1>>CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C | ClC1=CC(=CC=C1)C(=O)OO.[I-].[K+].C(C)(=O)C1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C.C(C)(=O)C1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(=O)OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C | CC(=O)[c:13]1[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[c:19]([CH3:20])[cH:18]1.CCOC(=O)C(C)(C)Oc1ccc([C:15]([CH3:16])=[O:17])cc1C.O=C(O[OH:14])c1cccc(Cl)c1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][C:15]([CH3:16])=[O:17])[cH:... | CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.O=C(OO)c1cccc(Cl)c1 | CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C | null | null | ClCCl | Acylation | OtherReaction | 35b28e989881322933498674f2c4dccb0eab4c77e02b5ec25db4066a2b748ac7 | c45996d99826cc61baa8e9116eecb8f713996b49f3bcf39e83d67817593d72b7 | c1ccccc1 | C-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-O-C(=O)-C(-C)(-C)-O-c1:c:c:c(-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;D1;H0:8]):c:c:1-C.Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:9]):c:1>>[C;D1;H3:7]-[C;H0;D3;+0:6](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 40 | CELSIUS | 19 | HOUR | A solution of ethyl 2-(4-acetyl-2-methylphenoxy)-2-methylpropanoate (intermediate 8, 37.33 g) in dichloromethane (650 ml) was treated with 4-toluenesulphonic acid (2.75 g) followed by m-chloroperbenzoic acid (60.5 g) and the mixture warmed to 40° C. and stirred under nitrogen for 19 hours. The cooled mixture was treate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ketone.Ester.Ether.Peroxide | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | ClCCl | 40 | 19 | CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.CCOC(=O)C(C)(C)Oc1ccc(C(C)=O)cc1C.O=C(OO)c1cccc(Cl)c1>ClCCl>CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cde935c22f454ba4aabd0f9182db7aa1 | CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C>>CCOC(=O)C(C)(C)Oc1ccc(O)cc1C | Cl.C(C)(=O)OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C.C(C)(=O)OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C.[O-]CC.[Na+]>>OC1=CC(=C(OC(C(=O)OCC)(C)C)C=C1)C | CC(=O)[O:14][c:13]1[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[c:16]([CH3:17])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]1[CH3:17] | CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 50 | CELSIUS | null | null | A solution of ethyl 2-[4-(acetyloxy)-2-methylphenoxy]-2-methylpropanoate (intermediate 9, 40.8 g) in ethanol (280 ml) was treated with sodium ethoxide (12.9 g) at room temperature under nitrogen. The resulting solution was heated to 50° C. for 1 hour. 2M hydrochloric acid (95 ml) was added to the cooled reaction and th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccccc1 | HO- | C(C)O | 50 | null | CCOC(=O)C(C)(C)Oc1ccc(OC(C)=O)cc1C>C(C)O>CCOC(=O)C(C)(C)Oc1ccc(O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d306e3fc497442fa8890ead9fcc7c78 | CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1C>>CCOC(=O)CCc1ccc(O)cc1C | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)C.C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C=CC(=O)OCC)C>>OC1=CC(=C(C=C1)CCC(=O)OCC)C | c1ccc(C[O:12][c:11]2[cH:10][cH:9][c:8]([CH:7]=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:14]([CH3:15])[cH:13]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]1[CH3:15] | CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1C | CCOC(=O)CCc1ccc(O)cc1C | null | [OH-].[OH-].[Pd+2] | C(C)O | Deprotection | OtherReaction | c76694668c0e332530904a141ee2b96aceffe3198e38d575690f4dae4070da9d | e00f9a9e80835d92a5562f8e4d77c15ee40726b40cd6dcf858e9b9fabcbd50cd | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-C-c2:c:c:c:c:c:2):[c:12]:[c:13]:1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:[c:13]:1 | null | [] | null | null | 3 | HOUR | A solution of ethyl 3-[4-(benzyloxy)-2-methylphenyl]prop-2-enoate (intermediate 11, 1.054 g) in ethanol (50 ml) was added to a suspension of palladium hydroxide on carbon (0.15 g) in ethanol (5 ml) under nitrogen gas. The resulting suspension was then stirred under a hydrogen atmosphere for 3 hours. The mixture was fil... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [OH-].[OH-].[Pd+2].C(C)O | null | 3 | CCOC(=O)C=Cc1ccc(OCc2ccccc2)cc1C>[OH-].[OH-].[Pd+2].C(C)O>CCOC(=O)CCc1ccc(O)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42f38fc69f714700a45eeb1a3594703c | CCOC(=O)CBr.Cc1cc(CO)cc(C)c1O>>CCOC(=O)COc1c(C)cc(CO)cc1C | OCC1=CC(=C(C(=C1)C)O)C.BrCC(=O)OCC.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(COC1=C(C=C(C=C1C)CO)C)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[c:9]([CH3:10])[cH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[c:9]([CH3:10])[cH:11][c:12]([CH2:13][OH:14])[cH:15][c:16]1[CH3:17] | CCOC(=O)CBr.Cc1cc(CO)cc(C)c1O | CCOC(=O)COc1c(C)cc(CO)cc1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | A solution of 4-(hydroxymethyl)-2,6-dimethylphenol (P. Claus et al., Monatsh. Chem. 1972, 103(4), 1178–1193) (1.9 g) in acetonitrile (50 ml) was treated with ethyl bromoacetate (2.17 g) and caesium carbonate (4.24 g) and the mixture stirred at room temperature overnight. The solution was concentrated and the residue pa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | C(C)#N | null | 8 | CCOC(=O)CBr.Cc1cc(CO)cc(C)c1O>C(C)#N>CCOC(=O)COc1c(C)cc(CO)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daad5c5a6a204b0ea960dce434566389 | COC(=O)c1ccc(Br)c(C)c1>>Cc1cc(CO)ccc1Br | COC(C1=CC(=C(C=C1)Br)C)=O.[H-].C(C(C)C)[Al+]CC(C)C>>BrC1=C(C=C(C=C1)CO)C | CO[C:5]([c:4]1[cH:3][c:2]([CH3:1])[c:9]([Br:10])[cH:8][cH:7]1)=[O:6]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][OH:6])[cH:7][cH:8][c:9]1[Br:10] | COC(=O)c1ccc(Br)c(C)c1 | Cc1cc(CO)ccc1Br | null | null | O1CCCC1.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](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 2.5 | HOUR | A solution of methyl-4-bromo-3-methylbenzoate (4.31 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to 0° C. under nitrogen gas. A solution of 1.5M diisobutylaluminium hydride in toluene (44 ml) was added slowly and the reaction stirred for 2.5 hours, then quenched with methanol and allowed to warm to 21° C. S... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1.C1(=CC=CC=C1)C | 0 | 2.5 | COC(=O)c1ccc(Br)c(C)c1>O1CCCC1.C1(=CC=CC=C1)C>Cc1cc(CO)ccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1c31f05a7504c58b2c582a15b337fab | BrC(Br)(Br)Br.CCOC(=O)/C=C/c1ccc(CO)cc1C>>CCOC(=O)/C=C/c1ccc(CBr)cc1C | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCC1=CC(=C(C=C1)/C=C/C(=O)OCC)C.OCC1=CC(=C(C=C1)/C=C/C(=O)OCC)C.ClCCl.O.C(Br)(Br)(Br)Br>>BrCC1=CC(=C(C=C1)/C=C/C(=O)OCC)C | BrC(Br)(Br)[Br:13].O[CH2:12][c:11]1[cH:10][cH:9][c:8](/[CH:7]=[CH:6]/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:15]([CH3:16])[cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([CH2:12][Br:13])[cH:14][c:15]1[CH3:16] | BrC(Br)(Br)Br.CCOC(=O)/C=C/c1ccc(CO)cc1C | CCOC(=O)/C=C/c1ccc(CBr)cc1C | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccccc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | A solution of ethyl(2E)-3-[4-(hydroxymethyl)-2-methylphenyl]prop-2-enoate (intermediate 19, 1.389 g) in dry dichloromethane (40 ml) was cooled to 0° C. and treated with carbon tetrabromide (2.3 g) followed by, in small portions, triphenylphosphine (1.82 g). The resulting solution was stirred thus overnight, then poured... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | ClCCl | null | 8 | BrC(Br)(Br)Br.CCOC(=O)/C=C/c1ccc(CO)cc1C>ClCCl>CCOC(=O)/C=C/c1ccc(CBr)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32763027959a429c81902ee9b65452a4 | CCOC(=O)/C=C/c1ccc(CBr)cc1C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)/C=C/c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1C.[Br-] | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrCC1=CC(=C(C=C1)/C=C/C(=O)OCC)C.BrCC1=CC(=C(C=C1)/C=C/C(=O)OCC)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].C(C)OC(/C=C/C1=C(C=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([CH2:12][Br:35])[cH:32][c:33]1[CH3:34].[P:13]([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][... | CCOC(=O)/C=C/c1ccc(CBr)cc1C.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)/C=C/c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1C.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:4]:[c:3](-[CH2;D2;+0:2]-[P+;H0;D4:8](-[c:7](:[c:6]):[c:15])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:5] | null | [] | null | null | null | null | A solution of ethyl(2E)-3-[4-(bromomethyl)-2-methylphenyl]prop-2-enoate (intermediate 20, 1.494 g) in toluene (30 ml) was stirred and treated with triphenylphosphine (1.52 g) and then heated at reflux for 2 hours then at 21° C. overnight. More triphenylphosphine (0.5 g) was then added and the reaction heated at reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | CCOC(=O)/C=C/c1ccc(CBr)cc1C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>CCOC(=O)/C=C/c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1C.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f33b834f86d64fcebdaf4b4e0d91a9c5 | BrBr.COC(=O)c1ccoc1C>>COC(=O)c1cc(Br)oc1C | BrBr.CC=1OC=CC1C(=O)OC.S(=S)(=O)([O-])[O-].[Na+].[Na+]>>BrC1=CC(=C(O1)C)C(=O)OC | Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][o:9][c:10]1[CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[o:9][c:10]1[CH3:11] | BrBr.COC(=O)c1ccoc1C | COC(=O)c1cc(Br)oc1C | null | null | O1CCOCC1 | Functional Group Interconversion | Bromination | 8fe241260e59a5ea657f7922db353078f8cfd5499cbf65d657d1df558a3b8b11 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccoc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#8;a:7]:[cH;D2;+0:8]:[c:9]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#8;a:7]:[c;H0;D3;+0:8](-[Br;H0;D1;+0:1]):[c:9]:1 | null | [] | 0 | CELSIUS | 2 | HOUR | Bromine (2.0 ml) was added drop-wise to a mixture of methyl 2-methyl-3-furancarboxylate (5.0 g) in 1,4-dioxane (35 ml) stirred at 0° C. Stirring was continued at 0° C. for 2 hours and then at ambient temperature for 18 hours. Saturated aqueous sodium thiosulfate was added to the reaction mixture which was then extracte... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccoc1 | c1ccoc1 | c1ccoc1 | HBr | O1CCOCC1 | 0 | 2 | BrBr.COC(=O)c1ccoc1C>O1CCOCC1>COC(=O)c1cc(Br)oc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55af0c1fec17466ca50bb1b0a293d948 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C>>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | CC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.CC=1OC(=CC1C(=O)OC)C1=CC=C(C=C1)C(F)(F)F.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>>CC=1OC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CO[C:17]([c:16]1[c:2]([CH3:1])[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[cH:15]1)=[O:18]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[cH:15][c:16]1[CH2:17][OH:18] | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C | Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | O.O1CCCC1.CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccco2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[C;D1;H3:8]>>[C;D1;H3:8]-[c:7]1:[#8;a:6]:[c:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 4 | HOUR | A solution of methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 23, 0.27 g) in tetrahydrofuran (10 ml) stirred at 0° C. under a nitrogen atmosphere was treated with 1M lithium aluminium hydride in ether (1.0 ml). The reaction mixture was stirred at this temperature for 4 hours and then water (2 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccoc1.c1ccccc1 | Other | O.O1CCCC1.CCOCC | null | 4 | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)oc1C>O.O1CCCC1.CCOCC>Cc1oc(-c2ccc(C(F)(F)F)cc2)cc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81de7a46f06246799d69db5e5b4d91bf | O=C(O)c1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F>>OCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | CO.B.ClC1=CC=C(C=C1)C1=CC(=C(O1)C(F)(F)F)C(=O)O>>ClC1=CC=C(C=C1)C1=CC(=C(O1)C(F)(F)F)CO | O=[C:2]([OH:1])[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[o:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[OH:1][CH2:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]2)[o:13][c:14]1[C:15]([F:16])([F:17])[F:18] | O=C(O)c1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | OCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2ccco2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#8;a:6]:[c:7]:1-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]>>[F;D1;H0:9]-[C:8](-[F;D1;H0:10])(-[F;D1;H0:11])-[c:7]1:[#8;a:6]:[c:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[O;D1;H1:2] | null | [] | 0 | CELSIUS | null | null | A mixture of 5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carboxylic acid (0.30 g) in tetrahydrofuran (10 ml) stirred under a nitrogen atmosphere at 0° C. was treated with a 1M solution of borane in tetrahydrofuran (10.33 ml) and the reaction stirred at room temperature for 2 hours. The reaction was cooled to 0° C.; t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccoc1.c1ccccc1 | Other | O1CCCC1 | 0 | null | O=C(O)c1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F>O1CCCC1>OCc1cc(-c2ccc(Cl)cc2)oc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ea84c7acf084517a9e9625c59ac88bf | CC(=O)c1ccc(C(F)(F)F)cc1.COC(C)(OC)N(C)C>>CC(=CC(=O)c1ccc(C(F)(F)F)cc1)N(C)C | FC(C1=CC=C(C=C1)C(C)=O)(F)F.COC(C)(OC)N(C)C>>CN(C(=CC(=O)C1=CC=C(C=C1)C(F)(F)F)C)C | [CH3:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1.CO[C:2](OC)([CH3:1])[N:16]([CH3:17])[CH3:18]>>[CH3:1][C:2](=[CH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1)[N:16]([CH3:17])[CH3:18] | CC(=O)c1ccc(C(F)(F)F)cc1.COC(C)(OC)N(C)C | CC(=CC(=O)c1ccc(C(F)(F)F)cc1)N(C)C | null | null | C(C)OCC | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | c1ccccc1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C)-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[CH3;D1;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | 112 | CELSIUS | null | null | A mixture of 4′-(trifluoromethyl)acetophenone (9.8 g) and N-(1,1-dimethoxyethyl)-N,N-dimethylamine (8.2 g) was heated at 112° C. overnight, under nitrogen. The reaction mixture was cooled and concentrated giving an orange solid. Trituration with diethyl ether gave the title compound as a yellow solid
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1 | HO- | C(C)OCC | 112 | null | CC(=O)c1ccc(C(F)(F)F)cc1.COC(C)(OC)N(C)C>C(C)OCC>CC(=CC(=O)c1ccc(C(F)(F)F)cc1)N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ea3ca517d7342f6ac2c54fa506a38d2 | CC(C=C(Cl)c1ccc(C(F)(F)F)cc1)=[N+](C)C.CCOC(=O)CS>>CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | C(CS)(=O)OCC.[H-].[Na+].F[P-](F)(F)(F)(F)F.ClC(=CC(C)=[N+](C)C)C1=CC=C(C=C1)C(F)(F)F.F[P-](F)(F)(F)(F)F.ClC(=CC(C)=[N+](C)C)C1=CC=C(C=C1)C(F)(F)F>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC | C[N+](C)=[C:20]([CH:19]=[C:8](Cl)[c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1)[CH3:21].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][SH:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19][c:20]1[CH3:21] | CC(C=C(Cl)c1ccc(C(F)(F)F)cc1)=[N+](C)C.CCOC(=O)CS | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 7d082098d55bd5ee765dcd06cb6a7120294adce6cf5de89d9b57cfbc9694a739 | a4fa40bf2830c6270ea0073d0b0201db1b88d20eb50f5eeccac5ea722f6deffc | c1ccc(-c2cccs2)cc1 | C-[N+](-C)=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-Cl)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[SH;D1;+0:15]>>[C:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:14]1:[s;H0;D2;+0:15]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[cH;D2;+0:3... | null | [] | 110 | CELSIUS | null | null | Sodium hydride (60% dispersion in mineral oil, 0.528 g) was added to dry ethanol (20 ml), N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate (intermediate 34, 2.8 g) was added followed by ethyl thioglycolate (0.79 g) and the mixture heated at 110° C. for 2 hour... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ester.Aliphatic thiol | Ester | null | c1ccsc1 | c1ccsc1.c1ccccc1 | HCl | C(C)O | 110 | null | CC(C=C(Cl)c1ccc(C(F)(F)F)cc1)=[N+](C)C.CCOC(=O)CS>C(C)O>CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffa3f6e62ec945dc861cc1427e46b8f0 | O=Cc1sccc1Br.OB(O)c1cccc(C(F)(F)F)c1>>O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1 | BrC1=C(SC=C1)C=O.FC(C=1C=C(C=CC1)B(O)O)(F)F.C([O-])([O-])=O.[Na+].[Na+].O>>FC(C1=CC=C(C=C1)C=1C=C(SC1)C=O)(F)F | Br[c:4]1[c:3]([CH:2]=[O:1])[s:17][cH:16][cH:5]1.OB(O)[c:6]1[cH:7][cH:8][cH:14][c:9]([C:10]([F:11])([F:12])[F:13])[cH:15]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][s:17]1 | O=Cc1sccc1Br.OB(O)c1cccc(C(F)(F)F)c1 | O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | COCCOC | C-C Coupling | OtherReaction | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccsc2)cc1 | Br-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6]=[O;D1;H0:7].O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[C:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[F;D1;H0:16]):[cH;D2;+0:17]:1>>[F;D1;H0:14]-[C:13](-[F;D1;H0:15])(-[F;D1;H0:16])-[c;H0;D3;+0:12]1:[cH;D2;+0:11]:[cH;D2;+0:17]:[c;H0;D3... | null | [] | 90 | CELSIUS | 18 | HOUR | To a solution of 3-bromothiophene-2-carboxaldehyde (2.0 g) and 3-trifluoromethylbenzene boronic acid (2.19 g) in ethylene glycol dimethyl ether (100 ml) was added sodium carbonate (2.9 g), tetrakis(triphenylphosphine) palladium (0) (0.12 g) and water (50 ml). The mixture was heated to 90° C. under nitrogen. After 18 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | c1ccsc1.c1ccccc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC | 90 | 18 | O=Cc1sccc1Br.OB(O)c1cccc(C(F)(F)F)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC>O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f39bd3263d74268b672227e11e8ee23 | O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1.O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1>>O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1 | Cl(=O)[O-].[Na+].FC(C1=CC=C(C=C1)C=1C=C(SC1)C=O)(F)F.FC(C1=CC=C(C=C1)C=1C=C(SC1)C=O)(F)F.CC(C)=CC.P(=O)(O)(O)[O-].[Na+]>>FC(C1=CC=C(C=C1)C=1C=C(SC1)C(=O)O)(F)F | [O:1]=[CH:2][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][s:18]1.FC(F)(F)c1ccc(-c2csc(C=[O:3])c2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][s:18]1 | O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1.O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1 | O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1 | null | null | O.C(C)(C)(C)O | Acylation | OtherReaction | 08f58e565c9f3b9857eb4669f858310f577661a2fba3f22f628755057f3cbb7e | 4a17d5f833ba6930fa7a2855b06e9a6d496dc0e82391748867e5eb7a6502eb9b | c1ccc(-c2ccsc2)cc1 | F-C(-F)(-F)-c1:c:c:c(-c2:c:s:c(-C=[O;H0;D1;+0:1]):c:2):c:c:1.[O;D1;H0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[#16;a:6]:[c:7]>>[O;D1;H0:2]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | 4 | HOUR | A solution of 4-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (intermediate 37, 1.23 g), t-butanol (20 ml) and 2-methyl-2-butene (10 ml) was cooled to 0° C. To this was added drop-wise, a solution of sodium chlorite (3.8 g) and sodium dihydrogen phosphate (4.03 g) in water (15 ml). After the addition was complete... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aldehyde.Aldehyde | Carboxylic acid | c1ccccc1.c1ccsc1 | null | c1ccsc1.c1ccccc1 | HF | O.C(C)(C)(C)O | null | 4 | O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1.O=Cc1cc(-c2ccc(C(F)(F)F)cc2)cs1>O.C(C)(C)(C)O>O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-92cfef5e59a94c4ba5258e0e370a3505 | Cc1c(-c2ccc(C(F)(F)F)cc2)csc1C(=O)N(C)C(C)(C)C>>Cc1c(-c2ccc(C(F)(F)F)cc2)csc1CO | [BH4-].[Na+].C(C)(C)(C)N(C(=O)C=1SC=C(C1C)C1=CC=C(C=C1)C(F)(F)F)C.C(C)(C)(C)N(C(=O)C=1SC=C(C1C)C1=CC=C(C=C1)C(F)(F)F)C.C(CCC)[Li].[H-].C(C(C)C)[Al+]CC(C)C>>CC1=C(SC=C1C1=CC=C(C=C1)C(F)(F)F)CO | CN(C(C)(C)C)[C:17]([c:16]1[c:2]([CH3:1])[c:3](-[c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[cH:14][s:15]1)=[O:18]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[cH:14][s:15][c:16]1[CH2:17][OH:18] | Cc1c(-c2ccc(C(F)(F)F)cc2)csc1C(=O)N(C)C(C)(C)C | Cc1c(-c2ccc(C(F)(F)F)cc2)csc1CO | null | null | C1CCCCC1.O1CCCC1.C(C)O | Miscellaneous | OtherReaction | 0c75196bc326a5f4df5281c5aa6ae5cdc4819d93f21e68fb7ca3f026ca65886c | cfd0fcbb4b1cf020b5a9adf1c1aee54d845237b6f4e1af15a68ce24628b71452 | c1ccc(-c2ccsc2)cc1 | C-N(-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6])-C(-C)(-C)-C>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 30 | MINUTE | n-Butyllithium (1.6M in hexanes, 1.1 ml) was added dropwise to a mixture of 1M diisobutylaluminium hydride in cyclohexane (1.77 ml) and tetrahydrofuran at 0° C. under nitrogen. This mixture was allowed to stir for 30 minutes then was added to a cooled (0° C.) solution of N-(tert-butyl)-N,3-dimethyl-4-[4-(trifluoromethy... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | C1CCCCC1.O1CCCC1.C(C)O | null | 0.5 | Cc1c(-c2ccc(C(F)(F)F)cc2)csc1C(=O)N(C)C(C)(C)C>C1CCCCC1.O1CCCC1.C(C)O>Cc1c(-c2ccc(C(F)(F)F)cc2)csc1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-01fd9acbd4244adfb8428d8144a29522 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C>>Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1CO | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.Br(=O)(=O)[O-].[Na+].S([O-])(O)=O.[Na+]>>CC=1SC(=CC1CO)C1=CC=C(C=C1)C(F)(F)F | CCOC([c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[cH:15][c:16]1[CH3:17])=[O:18].CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1[CH3:1]>>[CH3:1][c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[cH:15][c:16]1[CH2:17][OH:18] | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1CO | null | null | C1CCCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 32f6d81929b27c463dc3a5d263f4126f89ba1200d37a01f7b71c09e4b88f1ef5 | 8a2b54df8e2ec1489a8908426d4c447ce61780b733cb28160d6006a3d70839f7 | c1ccc(-c2cccs2)cc1 | C-C-O-C(=O)-c1:s:c(-c2:c:c:c(-C(-F)(-F)-F):c:c:2):c:c:1-[CH3;D1;+0:1].C-C-O-C(=[O;H0;D1;+0:2])-[c;H0;D3;+0:3]1:[#16;a:4]:[c:5]:[c:6]:[c:7]:1-[CH3;D1;+0:8]>>[CH3;D1;+0:1]-[c;H0;D3;+0:3]1:[#16;a:4]:[c:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[OH;D1;+0:2] | null | [] | null | null | 2 | HOUR | Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 35, 0.100 g) and sodium bromate (0.144 g) were suspended in a mixture of cyclohexane and water (1:1 v/v, 4 ml). To this was added a solution sodium bisulfite (0.99 g) in water (1 ml). The mixture was stirred for 2 hours, quenched with 1M ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ester.Ester | Primary alcohol | c1ccsc1.c1ccsc1.c1ccccc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | HF | C1CCCCC1.O | null | 2 | CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.CCOC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C>C1CCCCC1.O>Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1CO |
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