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-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e8c3752e4d84c4e94e8850476690a70 | Cc1cc(C#N)cc([N+](=O)[O-])c1NC(=O)C(F)(F)F>>Cc1cc(C#N)cc([N+](=O)[O-])c1N | C(#N)C1=CC(=C(C(=C1)[N+](=O)[O-])NC(C(F)(F)F)=O)C.N>>NC1=C(C=C(C#N)C=C1[N+](=O)[O-])C | O=C(C(F)(F)F)[NH:13][c:12]1[c:2]([CH3:1])[cH:3][c:4]([C:5]#[N:6])[cH:7][c:8]1[N+:9](=[O:10])[O-:11]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]1[NH2:13] | Cc1cc(C#N)cc([N+](=O)[O-])c1NC(=O)C(F)(F)F | Cc1cc(C#N)cc([N+](=O)[O-])c1N | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccccc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.9 | [{"value": 99.9, "product": "NC1=C(C=C(C#N)C=C1[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(4-cyano-2-methyl-6-nitro-phenyl)-2,2,2-trifluoro-acetamide (5 g, 18.3 mmol) and 2 M ammonia in methanol (80 mL) was heated to reflux for 14 h and then cooled to room temperature. After concentration in vacuo, the residue was purified by flash chromatography (20% EtOAc/hexane) to yield the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccccc1 | Other | CO | null | null | Cc1cc(C#N)cc([N+](=O)[O-])c1NC(=O)C(F)(F)F>CO>Cc1cc(C#N)cc([N+](=O)[O-])c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76f4bc838b0749879a6e5332ddbcc273 | Cc1cc(C#N)cc([N+](=O)[O-])c1N>>Cc1cc(C#N)cc(N)c1N | NC1=C(C=C(C#N)C=C1[N+](=O)[O-])C.O.O.[Sn](Cl)(Cl)(Cl)Cl>>NC=1C=C(C#N)C=C(C1N)C | O=[N+:9]([O-])[c:8]1[cH:7][c:4]([C:5]#[N:6])[cH:3][c:2]([CH3:1])[c:10]1[NH2:11]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][c:8]([NH2:9])[c:10]1[NH2:11] | Cc1cc(C#N)cc([N+](=O)[O-])c1N | Cc1cc(C#N)cc(N)c1N | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 81 | [{"value": 81.0, "product": "NC=1C=C(C#N)C=C(C1N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "NC=1C=C(C#N)C=C(C1N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-amino-3-methyl-5-nitro-benzonitrile (3.24 g, 18.3 mmol) in ethanol (80 mL) was added tin chloride dihydrate (8.67 g, 49.75 mmol). The reaction mixture was heated to reflux for 14 h, then cooled to room temperature, and concentrated in vacuum. The residue was diluted with ethyl acetate (100 mL) and tr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | Cc1cc(C#N)cc([N+](=O)[O-])c1N>C(C)O>Cc1cc(C#N)cc(N)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7db9bd74a30493389370bacecebb099 | COc1nccc(I)c1C=O.Cc1cc(C#N)cc(N)c1N>>COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1 | NC=1C=C(C#N)C=C(C1N)C.IC1=C(C(=NC=C1)OC)C=O.II>>IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)C#N)C | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([C:17]#[N:18])[cH:19][c:20]1[NH2:21]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([C:17]#[N:18])[cH:19][c:20]2[nH:21]1 | COc1nccc(I)c1C=O.Cc1cc(C#N)cc(N)c1N | COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cncc(-c2nc3ccccc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | 46 | [{"value": 46.0, "product": "IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)C#N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.1, "product": "IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 3,4-diamino-5-methyl-benzonitrile (2.00 g, 13.6 mmol) in MeOH (40 mL) was added 4-iodo-2-methoxy-pyridine-3-carbaldehyde (3.6 g, 13.6 mmol) in MeOH (20 mL) at 0° C. The resulting slurry was stirred at 0° C. for 1 h. Iodine (1.73 g, 8.8 mmol) in MeOH (10 mL) was added dropwise via a dropping funnel to t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1 | HO- | CO | 0 | 1 | COc1nccc(I)c1C=O.Cc1cc(C#N)cc(N)c1N>CO>COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e9b129fd196c4375af69d56e4306eba2 | COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1.Cl>>Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 | IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)C#N)C.O1CCOCC1.Cl>>ClC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C | C[O:18][c:17]1[c:11](-[c:10]2[nH:9][c:8]3[cH:7][c:4]([C:5]#[N:6])[cH:3][c:2]([CH3:1])[c:20]3[n:19]2)[c:12](I)[cH:14][cH:15][n:16]1.[ClH:13]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][c:8]2[nH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][nH:16][c:17]3=[O:18])[n:19][c:20]12 | COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1.Cl | Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 | null | null | null | Acylation | OtherReaction | e951b62dd313cc815c5edb5634072da74631e71e2f87b3bd3a8160fd520a7e58 | e36bd0e1759e0304f05a7d022d4761db897d009399240b55b59d114a1955055a | O=c1[nH]cccc1-c1nc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c;H0;D3;+0:6](-I):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[ClH;D0;+0:11]>>[#7;a:9]:[c:8](-[c:7]1:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:11]):[c:5]:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1]):[#7;a:10] | null | [] | 80 | CELSIUS | null | null | A suspension of 2-(4-iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile (1.8 g, 4.63 mmol) in 4 M HCl dioxane (40 mL) was heated to 80° C. for 6 h and cooled to room temperature. The precipitate was filtered and dried. The crude product (1.08 g, 82%) was used for the next step without purification. L... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Aromatic halide | c1ccncc1 | c1cccnc1 | c1ccc2[nH]cnc2c1.c1cccnc1 | HI | null | 80 | null | COc1nccc(I)c1-c1nc2c(C)cc(C#N)cc2[nH]1.Cl>>Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-272c0a8206af4a4e90ea31603bc4498d | Cc1cc(Br)cc([N+](=O)[O-])c1N>>Cc1cc(Br)cc(N)c1N | BrC1=CC(=C(C(=C1)[N+](=O)[O-])N)C.O.O.[Sn](Cl)(Cl)(Cl)Cl>>BrC1=CC(=C(C(=C1)N)N)C | O=[N+:8]([O-])[c:7]1[cH:6][c:4]([Br:5])[cH:3][c:2]([CH3:1])[c:9]1[NH2:10]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([NH2:8])[c:9]1[NH2:10] | Cc1cc(Br)cc([N+](=O)[O-])c1N | Cc1cc(Br)cc(N)c1N | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 59.3 | [{"value": 59.0, "product": "BrC1=CC(=C(C(=C1)N)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "BrC1=CC(=C(C(=C1)N)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-bromo-2-methyl-6-nitro-phenylamine (20 g, 0.086 mol) in ethanol (200 mL) was added tin chloride dihydrate (49.2 g, 0.258 mol). The reaction mixture was heated to reflux for 14 h, cooled to room temperature, and concentrated in vacuo. The residue was diluted with ethyl acetate (150 mL) and treated w... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | Cc1cc(Br)cc([N+](=O)[O-])c1N>C(C)O>Cc1cc(Br)cc(N)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b00853eeb464eee89cdc6d5482df125 | COc1nccc(I)c1C=O.Cc1cc(Br)cc(N)c1N>>COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1 | BrC=1C=C(C(=C(C1)N)N)C.IC1=C(C(=NC=C1)OC)C=O.II>>BrC=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([Br:17])[cH:18][c:19]1[NH2:20]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([Br:17])[cH:18][c:19]2[nH:20]1 | COc1nccc(I)c1C=O.Cc1cc(Br)cc(N)c1N | COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cncc(-c2nc3ccccc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | 46 | [{"value": 46.0, "product": "BrC=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.8, "product": "BrC=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-bromo-3-methyl-1,2-phenylenediamine (4 g, 19.9 mmol) in methanol (80 mL) was added 4-iodo-2-methoxy-pyridine-3-carbaldehyde (5.23 g, 19.9 mmol) in methanol (20 mL) dropwise at 0° C. The resulting slurry was stirred for 30 min at room temperature. Then iodine (2.53 g, 9.95 mmol) in methanol (20 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1 | HO- | CO | null | 0.5 | COc1nccc(I)c1C=O.Cc1cc(Br)cc(N)c1N>CO>COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e55b6a1c8dc4ba9bdb4fb040e6f8307 | COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1.Cl>>Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 | BrC=1C=C(C2=C(NC(=N2)C=2C(=NC=CC2I)OC)C1)C.Cl>>BrC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C | C[O:17][c:16]1[c:10](-[c:9]2[nH:8][c:7]3[cH:6][c:4]([Br:5])[cH:3][c:2]([CH3:1])[c:19]3[n:18]2)[c:11](I)[cH:13][cH:14][n:15]1.[ClH:12]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]2[nH:8][c:9](-[c:10]3[c:11]([Cl:12])[cH:13][cH:14][nH:15][c:16]3=[O:17])[n:18][c:19]12 | COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1.Cl | Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 | null | null | O1CCOCC1 | Acylation | OtherReaction | e951b62dd313cc815c5edb5634072da74631e71e2f87b3bd3a8160fd520a7e58 | e36bd0e1759e0304f05a7d022d4761db897d009399240b55b59d114a1955055a | O=c1[nH]cccc1-c1nc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c;H0;D3;+0:6](-I):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[ClH;D0;+0:11]>>[#7;a:9]:[c:8](-[c:7]1:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:11]):[c:5]:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1]):[#7;a:10] | 100 | [{"value": 100.0, "product": "BrC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | The suspension of 6-bromo-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole (4 g, 9.03 mmol) and 60 mL of 4 M HCl in dioxane was heated to 80° C. for 6 h and cooled to room temperature. The precipitate was filtered and dried to yield the title compound (3.0 g, 100%) as a brown powder. The crude product was us... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Aromatic halide | c1ccncc1 | c1cccnc1 | c1ccc2[nH]cnc2c1.c1cccnc1 | HI | O1CCOCC1 | 80 | null | COc1nccc(I)c1-c1nc2c(C)cc(Br)cc2[nH]1.Cl>O1CCOCC1>Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd1da47032174001bd7f6f2b2c98d939 | Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1>>Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | BrC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C.N[C@H](CO)CC1=CC=CC=C1.CN1CCOCC1>>C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br | Cl[c:11]1[c:10](-[c:9]2[nH:8][c:7]3[cH:6][c:4]([Br:5])[cH:3][c:2]([CH3:1])[c:29]3[n:28]2)[c:26](=[O:27])[nH:25][cH:24][cH:23]1.[NH2:12][C@H:13]([CH2:14][OH:15])[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]2[nH:8][c:9](-[c:10]3[c:11]([NH:12][C@H:13]([CH2:14][OH:15])[CH2... | Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1 | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e72e852090cf7435e97b85905772f4450e91af32c902e1e774d793ceb6479b9b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[C:11]-[C:12](-[C:13])-[NH2;D1;+0:14]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](=[O;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:14]-[C:12](-[C:11])-[C:13]):[#7;a:10] | 74 | [{"value": 74.0, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 3-(6-bromo-4-methyl-1H-benzimidazol-2-yl)-4-chloro-1H-pyridin-2-one (1.42 g, 3.78 mmol) in DMF (15 mL) were added (S)-(−)-2-amino-3-phenyl-1-propanol (1.43 g, 9.45 mmol) and N-methyl morpholine (1.5 mL). The reaction mixture was heated to 80° C. for 6 h and cooled to room temperature. The solvent was r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cccnc1 | c1cccnc1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HCl | CN(C)C=O | 80 | null | Cc1cc(Br)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1>CN(C)C=O>Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d27feae59ba64f999664ce3ebcec9fe0 | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12 | C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl.C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br.C(=O)([O-])[O-].[Cs+].[Cs+]>>C(C1=CC=CC=C1)[C@@H](COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br | [CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]2[nH:8][c:9](-[c:10]3[c:11]([NH:12][C@H:13]([CH2:14][OH:15])[CH2:35][c:36]4[cH:37][cH:38][cH:39][cH:40][cH:41]4)[cH:42][cH:43][nH:44][c:45]3=[O:46])[n:47][c:48]12.Cl[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)([c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)[c:29]1[cH:30][c... | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | O=c1[nH]ccc(N[C@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)Cc2ccccc2)c1-c1nc2ccccc2[nH]1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 73 | [{"value": 73.0, "product": "C(C1=CC=CC=C1)[C@@H](COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "C(C1=CC=CC=C1)[C@@H](COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br", "d... | null | null | null | null | To a solution of (S)-4-(1-benzyl-2-hydroxy-ethylamino)-3-(6-bromo-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one (0.9 g, 1.98 mmol) in THF (30 mL), was added Cs2CO3 (1.29 g, 3.96 mmol) followed by triphenylmethyl chloride (1.10 g, 3.96 mmol). The reaction mixture was heated to reflux for 14 h under nitrogen and then c... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cccnc1 | HCl | C1CCOC1 | null | null | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a84bd83a5a4b41d2a9adea572eb3afa2 | CC(=O)N1CCNCC1.Cc1cc(Br)cc([N+](=O)[O-])c1N>>CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1 | BrC1=CC(=C(C(=C1)[N+](=O)[O-])N)C.C(C)(=O)N1CCNCC1.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[Na+]>>NC1=C(C=C(C=C1[N+](=O)[O-])N1CCN(CC1)C(C)=O)C | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:19][CH2:20]1.Br[c:8]1[cH:9][c:10]([CH3:11])[c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]([CH3:11])[c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[CH2:19][CH2:20]1 | CC(=O)N1CCNCC1.Cc1cc(Br)cc([N+](=O)[O-])c1N | CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:2]:[c:3] | 70 | [{"value": 70.0, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])N1CCN(CC1)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "NC1=C(C=C(C=C1[N+](=O)[O-])N1CCN(CC1)C(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 4-bromo-2-methyl-6-nitro-phenylamine (5 g, 21.64 mmol), 1-acetylpiperazine (4.2 g, 32.46 mmol), palladium acetate (244 mg, 1.08 mmol), tri-tert-butylphosphine (440 mg, 2.16 mmol) and sodium tert-butoxide (4.2 g, 43.29 mmol) in toluene (70 mL) was heated to 100° C. for 14 h under nitrogen. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C.CCOC(=O)C | 100 | null | CC(=O)N1CCNCC1.Cc1cc(Br)cc([N+](=O)[O-])c1N>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C.CCOC(=O)C>CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bed9fbed16c64e1a92b66c057757d180 | CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1>>CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1 | NC1=C(C=C(C=C1[N+](=O)[O-])N1CCN(CC1)C(C)=O)C.CO.[H][H]>>NC=1C=C(C=C(C1N)C)N1CCN(CC1)C(C)=O | O=[N+:15]([O-])[c:14]1[c:12]([NH2:13])[c:10]([CH3:11])[cH:9][c:8]([N:7]2[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:18][CH2:17]2)[cH:16]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]([CH3:11])[c:12]([NH2:13])[c:14]([NH2:15])[cH:16]2)[CH2:17][CH2:18]1 | CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1 | CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1 | null | [Pd] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "NC=1C=C(C=C(C1N)C)N1CCN(CC1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.4, "product": "NC=1C=C(C=C(C1N)C)N1CCN(CC1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 1-[4-(4-amino-3-methyl-5-nitro-phenyl)-piperazin-1-yl]-ethanone (4.5 g, 16.2 mmol) and 10% palladium on carbon (400 mg) were added methanol (50 mL) and acetic acid (5 mL) under nitrogen. The reaction mixture was stirred under hydrogen atmosphere (hydrogen balloon) for 14 h. The dark solution was filtered through a p... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Pd].C(C)(=O)O | null | null | CC(=O)N1CCN(c2cc(C)c(N)c([N+](=O)[O-])c2)CC1>[Pd].C(C)(=O)O>CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-345fd5f6485d4d448ab744a28d2fce9f | CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1.COc1nccc(I)c1C=O>>COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1 | NC=1C=C(C=C(C1N)C)N1CCN(CC1)C(C)=O.IC1=C(C(=NC=C1)OC)C=O>>IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)N2CCN(CC2)C(C)=O)C | [NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([N:17]2[CH2:18][CH2:19][N:20]([C:21]([CH3:22])=[O:23])[CH2:24][CH2:25]2)[cH:26][c:27]1[NH2:28].O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([N:17]3[CH2:... | CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1.COc1nccc(I)c1C=O | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cncc(-c2nc3ccc(N4CCNCC4)cc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | 66 | [{"value": 66.0, "product": "IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)N2CCN(CC2)C(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)N2CCN(CC2)C(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 1-[4-(3,4-diamino-5-methyl-phenyl)-piperazin-1-yl]-ethanone (4.00 g, 16.18 mmol) in methanol (100 mL) was added 4-iodo-2-methoxy-pyridine-3-carbaldehyde (4.25 g, 16.18 mmol). The reaction mixture was stirred at room temperature for 14 h. After concentration, the residue was purified by flash column chr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.C1C[NH]CC[NH]1 | HO- | CO | null | 14 | CC(=O)N1CCN(c2cc(C)c(N)c(N)c2)CC1.COc1nccc(I)c1C=O>CO>COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93c4cc724c774189a107cfeb372b15b6 | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1.Cl>>CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1 | IC1=C(C(=NC=C1)OC)C=1NC2=C(N1)C(=CC(=C2)N2CCN(CC2)C(C)=O)C.O.Cl>>C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C | C[O:22][c:21]1[c:15](-[c:14]2[n:13][c:12]3[c:10]([CH3:11])[cH:9][c:8]([N:7]4[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:27][CH2:26]4)[cH:25][c:24]3[nH:23]2)[c:16](I)[cH:18][cH:19][n:20]1.[ClH:17]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][c:10]([CH3:11])[c:12]3[n:13][c:14](-[c:15]4[c:16]([Cl:17])[cH:... | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1.Cl | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1 | null | null | O1CCOCC1 | Acylation | OtherReaction | e951b62dd313cc815c5edb5634072da74631e71e2f87b3bd3a8160fd520a7e58 | e36bd0e1759e0304f05a7d022d4761db897d009399240b55b59d114a1955055a | O=c1[nH]cccc1-c1nc2ccc(N3CCNCC3)cc2[nH]1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c;H0;D3;+0:6](-I):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[ClH;D0;+0:11]>>[#7;a:9]:[c:8](-[c:7]1:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:11]):[c:5]:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1]):[#7;a:10] | 100 | [{"value": 100.0, "product": "C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 1-{4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzimidazol-5-yl]-piperazin-1-yl}-ethanone (5.2 g, 10.6 mmol) in 4 M HCl in dioxane (60 mL) was added water (5 mL). The reaction mixture was stirred at room temperature for 14 h. Concentration of the reaction mixture gave the title compound (4.02 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Aromatic halide | c1ccncc1 | c1cccnc1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1.c1cccnc1 | HI | O1CCOCC1 | null | 14 | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(C)=O)CC3)cc2[nH]1.Cl>O1CCOCC1>CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da0b643c52044c48bbae7a61052bcc6d | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1.N[C@H](CO)Cc1ccccc1>>CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1 | C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2Cl)=O)C1)C.N[C@H](CO)CC1=CC=CC=C1.CN1CCOCC1>>C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2N[C@@H](CC2=CC=CC=C2)CO)=O)C1)C | Cl[c:16]1[c:15](-[c:14]2[n:13][c:12]3[c:10]([CH3:11])[cH:9][c:8]([N:7]4[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:37][CH2:36]4)[cH:35][c:34]3[nH:33]2)[c:31](=[O:32])[nH:30][cH:29][cH:28]1.[NH2:17][C@H:18]([CH2:19][OH:20])[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:... | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1.N[C@H](CO)Cc1ccccc1 | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e72e852090cf7435e97b85905772f4450e91af32c902e1e774d793ceb6479b9b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(N3CCNCC3)cc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[C:11]-[C:12](-[C:13])-[NH2;D1;+0:14]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](=[O;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:14]-[C:12](-[C:11])-[C:13]):[#7;a:10] | 69.1 | [{"value": 69.0, "product": "C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2N[C@@H](CC2=CC=CC=C2)CO)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.1, "product": "C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2N[C@@H](CC2=CC=CC=C2)CO)=O)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | 80 | CELSIUS | null | null | To a solution of 3-[6-(4-acetyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-chloro-1 H-pyridin-2-one (1 g, 2.6 mmol) in DMF (10 mL) was added (S)-(−)-2-amino-3-phenyl-propanol (0.78 mg, 5.2 mmol) and N-methyl morpholine (2 mL). The reaction mixture was heated to 80° C. for 12 h, cooled to room temperature and conc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cccnc1 | c1cccnc1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HCl | CN(C)C=O | 80 | null | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(Cl)cc[nH]c4=O)[nH]c3c2)CC1.N[C@H](CO)Cc1ccccc1>CN(C)C=O>CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2f19c51f51d48769083a354c2fbc81b | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1>>Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | C(C)(=O)N1CCN(CC1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2N[C@@H](CC2=CC=CC=C2)CO)=O)C1)C.O>>OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2 | CC(=O)[N:8]1[CH2:7][CH2:6][N:5]([c:4]2[cH:3][c:2]([CH3:1])[c:34]3[c:12]([cH:11]2)[nH:13][c:14](-[c:15]2[c:16]([NH:17][C@H:18]([CH2:19][OH:20])[CH2:21][c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28][cH:29][nH:30][c:31]2=[O:32])[n:33]3)[CH2:10][CH2:9]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:1... | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1 | Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | null | Cl.O1CCOCC1 | Reduction | Hydrogenolysis of tertiary amines | 75fd52c1630f43905d9d003b1db222148a2e7ad2503b4cc3182af52baaf356d3 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(N3CCNCC3)cc2[nH]1 | C-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | 100 | [{"value": 100.0, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.1, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of (S)-3-[6-(4-acetyl-piperazin-1-yl)-4-methyl-1H-benzimidazol-2-yl]-4-(1-hydroxymethyl-2-phenyl-ethylamino)-1H-pyridin-2-one (900 mg, 18 mmol) in 4 M HCl in dioxane (10 mL) was added water (1 mL). The reaction mixture was heated to 80° C. for 14 h and cooled to room temperature. Concentration with high v... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HO- | Cl.O1CCOCC1 | 80 | null | CC(=O)N1CCN(c2cc(C)c3nc(-c4c(N[C@H](CO)Cc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1>Cl.O1CCOCC1>Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fb724584d8e4136acef0b1feedd5538 | Cc1cc(-n2ccnc2)cc(N)c1N.O=Cc1c(Cl)ncnc1Cl>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12 | N1(C=NC=C1)C1=CC(=C(C(=C1)N)N)C.ClC1=NC=NC(=C1C=O)Cl>>ClC1=NC=NC(=C1C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2)Cl | [CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]([NH2:12])[c:23]1[NH2:22].O=[CH:13][c:14]1[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]1[Cl:21]>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:12][c:13](-[c:14]3[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]3[Cl:21])[n:22][c:23]12 | Cc1cc(-n2ccnc2)cc(N)c1N.O=Cc1c(Cl)ncnc1Cl | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cn(-c2ccc3nc(-c4cncnc4)[nH]c3c2)cn1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[Cl;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13](:[c:15]):[c:11](:[c:12]):[nH;D2;+0:10]:... | 55 | [{"value": 55.0, "product": "ClC1=NC=NC(=C1C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.3, "product": "ClC1=NC=NC(=C1C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 5-imidazol-1-yl-3-methyl-benzene-1,2-diamine (180 mg, 0.96 mmol) in methanol (4 mL) was added a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (183 mg, 0.96 mmol) in methanol (1 mL). The reaction mixture was stirred at room temperature for 14 h. After concentration, the residue was purified by flas... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1cncnc1 | HO- | CO | null | 14 | Cc1cc(-n2ccnc2)cc(N)c1N.O=Cc1c(Cl)ncnc1Cl>CO>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ac54f15ce3d4d5b9b9fb46aa1c6e147 | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.O=[N+]([O-])c1c(F)cc(F)cc1F>>CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-] | FC1=C(C(=CC(=C1)F)F)[N+](=O)[O-].[H-].[Na+].C(CC(=O)OC(C)(C)C)(=O)OC(C)(C)C>>C(C)(C)(C)OC(C(C(=O)OC(C)(C)C)C1=C(C(=CC(=C1)F)F)[N+](=O)[O-])=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15].F[c:16]1[cH:17][c:18]([F:19])[cH:20][c:21]([F:22])[c:23]1[N+:24](=[O:25])[O-:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[cH:17][c:1... | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.O=[N+]([O-])c1c(F)cc(F)cc1F | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-] | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[CH2;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D3;+0:14](-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[... | null | [] | null | null | 30 | MINUTE | To a suspension of NaH (54.6 g, 60%, 1.365 mol) in 600 mL of DMF was added di-t-Butyl malonate (118 g, 0.546 mol) at 0° C. and stirred for 30 min. 2,4,6 trifluoronitrobenzene was added as a solution in 400 mL of DMF (75 g, 0.42 mol) over 3 hours and the solution stirred at ambient temperature for 12 hours. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C)C=O | null | 0.5 | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.O=[N+]([O-])c1c(F)cc(F)cc1F>CN(C)C=O>CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c906666b77984af38ebc24c91eac38d1 | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-].N>>CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-] | C(C)(C)(C)OC(C(C(=O)OC(C)(C)C)C1=C(C(=CC(=C1)F)F)[N+](=O)[O-])=O.N>>C(C)(C)(C)OC(C(C(=O)OC(C)(C)C)C1=C(C(=CC(=C1)F)N)[N+](=O)[O-])=O | F[c:21]1[cH:20][c:18]([F:19])[cH:17][c:16]([CH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:23]1[N+:24](=[O:25])[O-:26].[NH3:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[cH:17][... | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-].N | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-] | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5cea7b75c7f95cc50fd74029efa1cddce51f01200160afa4aaecfa45e52a1621 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH3;D0;+0:7]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH2;D1;+0:7]):[c:2]:[c:3] | null | [] | 85 | CELSIUS | null | null | To the crude 2-(3,5-Difluoro-2-nitro-phenyl)-malonic acid di-tert-butyl ester (62 g, 0.42 mol) was added 700 mL of 2M ammonia in methanol in a pressure bottle. The vessel was sealed and heated to 85° C. for 18 hours. The reaction mixture was cooled and the vessel opened carefully and the methanol solution concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CO | 85 | null | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(F)c1[N+](=O)[O-].N>CO>CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae98883c29bc486cb8fa1214b299bb7a | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-]>>Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-] | C(C)(C)(C)OC(C(C(=O)OC(C)(C)C)C1=C(C(=CC(=C1)F)N)[N+](=O)[O-])=O.O>>NC=1C(=C(C=C(C1)F)CC(=O)O)[N+](=O)[O-] | CC(C)(C)OC(=O)[CH:8]([c:7]1[cH:6][c:4]([F:5])[cH:3][c:2]([NH2:1])[c:12]1[N+:13](=[O:14])[O-:15])[C:9](=[O:10])[O:11]C(C)(C)C>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[c:12]1[N+:13](=[O:14])[O-:15] | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-] | Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-] | null | null | Cl.O1CCOCC1 | Reduction | OtherReaction | 73d165f371e7be9e7ac8a17da558f54492bf9b0746a90d7cc3220d78efbe0c09 | 60f3a79f391ea73b07965c28fa39ab5eb6558d5e98c32a693ba93254730088b7 | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C(-C)(-C)-C)-[c:5](:[c:6]):[c:7]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | 40 | CELSIUS | null | null | To the 2-(3-Amino-5-fluoro-2-nitro-phenyl)-malonic acid di-tert-butyl ester (140 g) in 500 mL of 4N HCl in dioxane was added 50 mL of water and heated to 40° C. for 2 days. The solution was extracted with ethyl acetate (3×'s) and the ethyl acetate washed with water (3×'s) and brine. The organic fraction was dried over ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Boc.Boc | Carboxylic acid | null | null | c1ccccc1 | HO- | Cl.O1CCOCC1 | 40 | null | CC(C)(C)OC(=O)C(C(=O)OC(C)(C)C)c1cc(F)cc(N)c1[N+](=O)[O-]>Cl.O1CCOCC1>Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e1d92b6b2bb4884b6c3f6b0a7867493 | Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-]>>Cc1cc(F)cc(N)c1[N+](=O)[O-] | NC=1C(=C(C=C(C1)F)CC(=O)O)[N+](=O)[O-].CO>>NC1=C(C(=CC(=C1)F)C)[N+](=O)[O-] | O=C(O)[CH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([NH2:8])[c:9]1[N+:10](=[O:11])[O-:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][c:7]([NH2:8])[c:9]1[N+:10](=[O:11])[O-:12] | Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-] | Cc1cc(F)cc(N)c1[N+](=O)[O-] | null | null | C(C)#N | Reduction | OtherReaction | 1dcdb0afd061fc08423f0103da81d9d30c22c6dc8004c40ee82cae1f931e4d18 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | c1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 103.2 | [{"value": 103.2, "product": "NC1=C(C(=CC(=C1)F)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To the crude 3-Amino-5-fluoro-2-nitro phenyl acetic acid (3.6 g, 16.8 mmol) was added Cu2O (10.1 g, 70.6 mmol) in 120 mL of acetonitrile along with 50 uL of methanol and the suspension was refluxed for 12 hours. The reaction mixture was filtered through Celite and the Celite pad washed with water and ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1 | Other | C(C)#N | null | null | Nc1cc(F)cc(CC(=O)O)c1[N+](=O)[O-]>C(C)#N>Cc1cc(F)cc(N)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9a2fc936f9594840b92354ee9937ee3d | C1COCCN1.Cc1cc(Br)cc([N+](=O)[O-])c1N>>Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N | BrC1=CC(=C(N)C(=C1)[N+](=O)[O-])C.N1CCOCC1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+]>>CC1=C(C(=CC(=C1)N1CCOCC1)[N+](=O)[O-])N | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:16]([NH2:17])[c:12]([N+:13](=[O:14])[O-:15])[cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[NH2:17] | C1COCCN1.Cc1cc(Br)cc([N+](=O)[O-])c1N | Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1):[c:4]:[c:5] | null | [] | 85 | CELSIUS | 3 | DAY | To a 800 ml pressure flask was added Tris(dibenzylideneacetone)dipalladium (2.64 g, 2.88 mmol), 2-(Di-t-butylphosphino)biphenyl (1.42 g, 4.75 mmol) and sodium tert-butoxide (17.5 g, 182 mmol). Then dry THF (500 mL), 4-bromo-2-methyl-6-nitroaniline (30.0 g, 130 mmol) and morpholine (34 ml, 390 mmol) were added. Argon wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1 | 85 | 72 | C1COCCN1.Cc1cc(Br)cc([N+](=O)[O-])c1N>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1CCOC1>Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8941fe6b357b4ce0a624b54fdaa3df7f | COc1nccc(I)c1C=O.Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N>>COc1nccc(I)c1-c1nc2c(C)cc(N3CCOCC3)cc2[nH]1 | IC1=C(C(=NC=C1)OC)C=O.CC1=C(C(=CC(=C1)N1CCOCC1)[N+](=O)[O-])N.[H][H]>>IC1=C(C(=NC=C1)OC)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2 | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].O=[N+:25]([O-])[c:24]1[c:12]([NH2:11])[c:13]([CH3:14])[cH:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[cH:23]1>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([N:17]3[CH2:18][CH2:19][O:20... | COc1nccc(I)c1C=O.Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N | COc1nccc(I)c1-c1nc2c(C)cc(N3CCOCC3)cc2[nH]1 | null | [Pd] | CO | Aromatic Heterocycle Formation | OtherReaction | 6161308e092fb05dde676728d8c9bfcf96275c4c41363553beada2b38c1d58af | 46498ab5071aa0a2ab021e592d13610349d3200939c6e7581494a316286b7467 | c1cncc(-c2nc3ccc(N4CCOCC4)cc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].O=[N+;H0;D3:10](-[O-])-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c:13](:[c:15]):[c:11](:[c:12]):[nH;D2;+0:10]:1 | 51 | [{"value": 51.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 2-Methyl-4-morpholin-4-yl-6-nitro-phenylamine (15.2 g, 64 mmol) was suspended in methanol (200 ml) in a PARR flask. Palladium on carbon (1.0 g, 10% Pd) was added and the suspension shaken under 60 psi of hydrogen overnight. The mixture was filtered through a pad of celite (under argon) into a 3-neck flask, the celite r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.C1COCC[NH]1 | HO- | [Pd].CO | 0 | null | COc1nccc(I)c1C=O.Cc1cc(N2CCOCC2)cc([N+](=O)[O-])c1N>[Pd].CO>COc1nccc(I)c1-c1nc2c(C)cc(N3CCOCC3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-288035b9ce3f40df81acfcf242399ce5 | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | FC=1C=C(C(=C(C1)N)[N+](=O)[O-])C.C(=O)(OC(C)(C)C)N1CCNCC1.CN1CCOCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N | [NH:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]1.F[c:4]1[cH:3][c:2]([CH3:1])[c:21]([N+:22](=[O:23])[O-:24])[c:19]([NH2:20])[cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[cH:18][c:19... | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-] | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | null | null | C(C)(=O)OCC.CN1CCCC1=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 83 | [{"value": 83.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 3-fluoro-5-amino-6-nitrotoluene (10 g, 58.79 mmol) in anhydrous NMP (160 mL) under nitrogen was added BOC-piperazine (39 g, 209.4 mmol) and 4-methylmorpholine (25.9 mL). The resulting dark solution was heated to reflux for 72 h, cooled to room temperature and diluted with ethyl acetate (4000 mL... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | HF | C(C)(=O)OCC.CN1CCCC1=O | null | 8 | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>C(C)(=O)OCC.CN1CCCC1=O>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f0509400de4444ab9a8454d2b905f7f | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-]>>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)N)N | O=[N+:22]([O-])[c:21]1[c:2]([CH3:1])[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[cH:18][c:19]1[NH2:20]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:16][CH2:17]2)[cH:18][c:19]([NH2:20])[c... | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N | null | [OH-].[OH-].[Pd+2] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a stirred solution of 4-(3-Amino-5-methyl-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (15 g, 44.6 mmol) in methanol (2200 mL) was added 20% Pd(OH)2/C (1.6 g) and the suspension flushed well with nitrogen, followed by hydrogen. The resulting suspension was stirred overnight at room temperature under... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1 | Other | [OH-].[OH-].[Pd+2].CO | null | 8 | Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-]>[OH-].[OH-].[Pd+2].CO>Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94d85650d7304a0aa776d5e084ec41e8 | COc1nccc(I)c1C=O.Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N>>COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC(=C(C(=C1)C)N)N.IC1=C(C(=NC=C1)OC)C=O>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC2=C(N=C(N2)C=2C(=NC=CC2I)OC)C(=C1)C | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([N:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:30][c:31]1[NH2:32]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c:12]2[c:13]([CH... | COc1nccc(I)c1C=O.Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1 | null | null | CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1cncc(-c2nc3ccc(N4CCNCC4)cc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | null | [] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 4-(3,4-Diamino-5-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (44.6 mmol—assuming 100% conversion in previous step) in methanol (ca 2700 mL) at 0° C under a nitrogen atmosphere was slowly added (2 h) via addition funnel, a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (15... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.C1C[NH]CC[NH]1 | HO- | CO | 0 | 0.5 | COc1nccc(I)c1C=O.Cc1cc(N2CCN(C(=O)OC(C)(C)C)CC2)cc(N)c1N>CO>COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff01f46f643c444d89ba3edcdaef3be8 | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1>>Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 | C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC2=C(N=C(N2)C=2C(=NC=CC2I)OC)C(=C1)C.Cl>>IC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2 | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([c:4]2[cH:3][c:2]([CH3:1])[c:24]3[c:12]([cH:11]2)[nH:13][c:14](-[c:15]2[c:16]([I:17])[cH:18][cH:19][n:20][c:21]2[O:22]C)[n:23]3)[CH2:10][CH2:9]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[cH:11][c:12]2[nH:13][c:14](-[c:15]3[c:16]([I:17])[cH:18][cH:19][n... | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1 | Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 | null | null | O1CCOCC1 | Functional Group Interconversion | OtherReaction | 438071654f502827dd43c25cca1177deb9ce031069f2d425f7eae572276ce1b7 | 9b5a00614c71e118fcd337401ca701336e66758b207ecdcc06f62c72fe79cd65 | O=c1[nH]cccc1-c1nc2ccc(N3CCNCC3)cc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.C-[O;H0;D2;+0:7]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[c:10]:[c:11]:[c:12]:[c:13]:1-[c:14](:[#7;a:15]):[#7;a:16]>>[#7;a:15]:[c:14](-[c:13]1:[c:12]:[c:11]:[c:10]:[nH;D2;+0:9]:[c;H0;D3;+0:8]:1=[O;H0;D1;+0:7]):[#7;a:16].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:1]-[C:2]-[... | 93.1 | [{"value": 93.0, "product": "IC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "IC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | To a stirred solution of 4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester (24 g, 43.7 mmol) was added 1,4-dioxane (750 mL) and 6 N aqueous HCl (30 mL) and the mixture was heated to 75° C. overnight. The solution was cooled to room temperature, the supern... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CCN1.c1cccnc1 | C1C[NH]CCN1.c1ccc2[nH]cnc2c1.c1cccnc1 | HO- | O1CCOCC1 | 75 | null | COc1nccc(I)c1-c1nc2c(C)cc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2[nH]1>O1CCOCC1>Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe2414a2165344779d576d356e6081a9 | CC(C)(C)OC(=O)NC1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>>Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | FC=1C=C(C(=C(C1)N)[N+](=O)[O-])C.CC(C)(C)OC(=O)NC1CCNCC1.C(=O)(O)[O-].[Na+]>>C(C)(C)(C)OC(NC1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N)=O | [NH:5]1[CH2:6][CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18]1.F[c:4]1[cH:3][c:2]([CH3:1])[c:22]([N+:23](=[O:24])[O-:25])[c:20]([NH2:21])[cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][CH:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:1... | CC(C)(C)OC(=O)NC1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-] | Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | null | [] | 85 | CELSIUS | 3 | HOUR | 5-Fluoro-3-methyl-2-nitro-phenylamine (0.97 g, 5.7 mmol), 4-N-BOC-aminopiperidine (1.60 g, 8.0 mmol), diusopropylethylamine (2.5 ml, 14 mmol) and DMSO (10 ml) are combined and stirred at 85° C. for 3 hours. The reaction mixture was poured on saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HF | CS(=O)C | 85 | 3 | CC(C)(C)OC(=O)NC1CCNCC1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>CS(=O)C>Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c00c9a603aee440dbcf4d3a14095b221 | COc1nccc(I)c1C=O.Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-]>>COc1nccc(I)c1-c1nc2c(C)cc(N3CCC(NC(=O)OC(C)(C)C)CC3)cc2[nH]1 | C(C)(C)(C)OC(NC1CCN(CC1)C1=CC(=C(C(=C1)C)[N+](=O)[O-])N)=O.[H][H].IC1=C(C(=NC=C1)OC)C=O>>C(C)(C)(C)OC(NC1CCN(CC1)C1=CC2=C(N=C(N2)C=2C(=NC=CC2I)OC)C(=C1)C)=O | O=[CH:10][c:9]1[c:3]([O:2][CH3:1])[n:4][cH:5][cH:6][c:7]1[I:8].O=[N+:11]([O-])[c:12]1[c:13]([CH3:14])[cH:15][c:16]([N:17]2[CH2:18][CH2:19][CH:20]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]2)[cH:31][c:32]1[NH2:33]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([I:8])[c:9]1-[c:10]1[n:11][c... | COc1nccc(I)c1C=O.Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-] | COc1nccc(I)c1-c1nc2c(C)cc(N3CCC(NC(=O)OC(C)(C)C)CC3)cc2[nH]1 | null | [Pd] | CO | Aromatic Heterocycle Formation | OtherReaction | 6161308e092fb05dde676728d8c9bfcf96275c4c41363553beada2b38c1d58af | 46498ab5071aa0a2ab021e592d13610349d3200939c6e7581494a316286b7467 | c1cncc(-c2nc3ccc(N4CCCCC4)cc3[nH]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3](-[#8:4]):[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[I;D1;H0:9].O=[N+;H0;D3:10](-[O-])-[c:11](:[c:12]):[c:13](-[NH2;D1;+0:14]):[c:15]>>[#8:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[I;D1;H0:9]):[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c:13](:[c:15]):[nH;D2;+0:14]:1 | null | [] | 0 | CELSIUS | 8 | HOUR | [1-(3-Amino-5-methyl-4-nitro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (1.54 g, 4.4 mmol) was dissolved in methanol (100 ml). Palladium on carbon (0.3 g, 10% Pd) was added and the suspension stirred vigorously under a balloon pressure of hydrogen overnight. The mixture was filtered through a pad of celite ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.C1CC[NH]CC1 | HO- | [Pd].CO | 0 | 8 | COc1nccc(I)c1C=O.Cc1cc(N2CCC(NC(=O)OC(C)(C)C)CC2)cc(N)c1[N+](=O)[O-]>[Pd].CO>COc1nccc(I)c1-c1nc2c(C)cc(N3CCC(NC(=O)OC(C)(C)C)CC3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8899647ae100409b9ed8d63a864996ee | N#Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1.O>>O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1 | O.CCOC(=O)C.BrC1=CC(=CC2=C1N=C(N2)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)C#N.CC(C)C[AlH]CC(C)C>>BrC1=CC(=CC2=C1N=C(N2)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)C=O | N#[C:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[n:8][c:9](-[c:10]3[c:11]([NH:12][CH2:13][C@@H:14]([OH:15])[c:16]4[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]4)[cH:23][cH:24][nH:25][c:26]3=[O:27])[nH:28][c:29]2[cH:30]1.[OH2:1]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[n:8][c:9](-[c:10]3[c:11]([NH:12][CH2:13][C@@H:14]([OH:15])[... | N#Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1.O | O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[OH2;D0;+0:7]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH;D2;+0:1]=[O;H0;D1;+0:7]):[c:3] | 43 | [{"value": 43.0, "product": "BrC1=CC(=CC2=C1N=C(N2)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)C=O", "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 10 | HOUR | To a solution of (S)-7-Bromo-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzimidazole-5-carbonitrile (150 mg, 0.31 mmol) in THF (50 mL) was added DIBAL-H (1 M toluene solution, 1.55 mL, 1.55 mmol) at −78° C. The reaction mixture was stirred at −40° C. for 10 h and cooled to −78° ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | C1CCOC1 | -40 | 10 | N#Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1.O>C1CCOC1>O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d952351fe42b4cd2974808a923bc8333 | C1=NCCCN1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>>Cc1cc(N2C=NCCC2)cc(N)c1[N+](=O)[O-] | FC=1C=C(C(=C(N)C1)[N+](=O)[O-])C.N1C=NCCC1.C([O-])([O-])=O.[K+].[K+]>>N1(C=NCCC1)C=1C=C(C(=C(N)C1)[N+](=O)[O-])C | [NH:5]1[CH:6]=[N:7][CH2:8][CH2:9][CH2:10]1.F[c:4]1[cH:3][c:2]([CH3:1])[c:14]([N+:15](=[O:16])[O-:17])[c:12]([NH2:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH:6]=[N:7][CH2:8][CH2:9][CH2:10]2)[cH:11][c:12]([NH2:13])[c:14]1[N+:15](=[O:16])[O-:17] | C1=NCCCN1.Cc1cc(F)cc(N)c1[N+](=O)[O-] | Cc1cc(N2C=NCCC2)cc(N)c1[N+](=O)[O-] | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 8058200d0361ca02ecc2569507c9154b237ced21167142f7233da50f542344bf | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | C1=NCCCN1c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1=[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:11]-[#7:6]=[C:7]-1):[c:4]:[c:5] | 67.2 | [{"value": 67.0, "product": "N1(C=NCCC1)C=1C=C(C(=C(N)C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.2, "product": "N1(C=NCCC1)C=1C=C(C(=C(N)C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a stirred solution of 2.0 g (11.76 mmol) of the 5-Flouro-3-methyl-2-nitro aniline in 10 mL of DMSO was added 1.2 g (14.11 mmol) of 1,4,5,6-Tetrahydropyrimidine, and 2.43 g (17.64 mmol) of potassium carbonate, and the mixture was heated at 100° C. for 10 hrs, cooled, diluted with water, and extracted with Ethylacetat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1=NCCCN1.c1ccccc1 | c1ccccc1.C1=NCCC[NH]1 | c1ccccc1.C1=NCCC[NH]1 | HF | O.CS(=O)C | 100 | null | C1=NCCCN1.Cc1cc(F)cc(N)c1[N+](=O)[O-]>O.CS(=O)C>Cc1cc(N2C=NCCC2)cc(N)c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7e6494fa8f7460c91b889ba606e119f | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C>>Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C | [Cl-].[NH4+].[H-].[Na+].C(C)OC(CNC(CC1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)=O)=O.C(C)(=O)OCC>>OC1=C(C(NC1)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2 | CCO[C:17](=[O:18])[CH2:19][NH:20][C:21]([CH2:16][c:15]1[n:14][c:13]2[c:2]([CH3:1])[cH:3][c:4]([N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[cH:11][c:12]2[n:23]1[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:22]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]2[c:13]1[n:14][c:1... | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C | null | null | O1CCCC1.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 2a6ece8886ad883f7558adcc6d9b0042824d924f877e287882f270a1578f5b9a | 0659373f3fa6d9cff47a4c1440102215d90e61b9fd30b7cb63f622f6bc940def | O=C1NCC=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:1-[C:13](-[#8:14])=[O;D1;H0:15]>>[#8:14]-[C:13](=[O;D1;H0:15])-[#7;a:12]1:[c:11]:[c:10]:[#7;a:9]:[c:8]:1-[C;H0;D3;+0:7]1=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[#7:4]-[C:5]-1=[O;D1;H0:6] | 59.3 | [{"value": 59.0, "product": "OC1=C(C(NC1)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "OC1=C(C(NC1)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2.5 | HOUR | To a stirred suspension of sodium hydride (60% in oil, 0.014 g, 0.352 mmol) in toluene (5 mL) was added [2-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-acetylamino]-acetic acid ethyl ester (0.135 g, 0.293 mmol) in tetrahydrofuran (5 mL) over 5 minutes. The mixture was stirred at 90–100° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Enol | null | C1=CCNC1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1.C1=CCNC1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | 0 | 2.5 | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C>O1CCCC1.C1(=CC=CC=C1)C>Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdb229fb52504c7c865515f1f76e0f50 | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C>>Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(O)CNC3=O)nc12 | Cl.[H-].[Na+].C(C)OC(CNC(CC1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)=O)=O.C(C)(=O)OCC>>OC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2 | CCO[C:16](=[O:17])[CH2:18][NH:19][C:20]([CH2:15][c:14]1[n:13](C(=O)OC(C)(C)C)[c:12]2[cH:11][c:4]([N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[cH:3][c:2]([CH3:1])[c:23]2[n:22]1)=[O:21]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][c:12]2[nH:13][c:14]([C:15]3=[C:16]([OH:17])[CH2:18][NH:19][C:2... | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C | Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(O)CNC3=O)nc12 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 8db06172dbb34aa0e1e2ef5fa4b1974ae30ad05d61dcbdc6732e881989252889 | fa217a357031eb0909b8083e1a82e4044635db92e294ecf44cb04195dc70c434 | O=C1NCC=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[c:8]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[n;H0;D3;+0:14]:1-C(=O)-O-C(-C)(-C)-C>>[O;D1;H0:6]=[C:5]1-[#7:4]-[C:3]-[C;H0;D3;+0:1](-[OH;D1;+0:2])=[C;H0;D3;+0:7]-1-[c:8]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[nH;D2;+0:14]:1 | 69 | [{"value": 69.0, "product": "OC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.7, "product": "OC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | HOUR | To a stirred suspension of sodium hydride (60% in oil, 0.003 g, 0.044 mmol) in toluene (1 mL) was added [2-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-acetylamino]-acetic acid ethyl ester (0.135 g, 0.293 mmol) in tetrahydrofuran (2 mL) over 5 minutes. The mixture was stirred at 90–100° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Boc | Enol | c1ccc2nc[nH]c2c1 | c1ccc2[nH]cnc2c1.C1=CCNC1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1.C1=CCNC1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | 0 | 5 | CCOC(=O)CNC(=O)Cc1nc2c(C)cc(N3CCOCC3)cc2n1C(=O)OC(C)(C)C>O1CCCC1.C1(=CC=CC=C1)C>Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(O)CNC3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f8344c2ce4648658b0b21935e1e0164 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.N[C@H](CO)c1ccccc1>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)c4ccccc4)cc[nH]c3=O)nc12 | N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2I)=O)C1)C.C1(=CC=CC=C1)[C@H](N)CO.CN1CCOCC1>>OC[C@H](C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2 | I[c:15]1[c:14](-[c:13]2[nH:12][c:11]3[cH:10][c:4](-[n:5]4[cH:6][cH:7][n:8][cH:9]4)[cH:3][c:2]([CH3:1])[c:32]3[n:31]2)[c:29](=[O:30])[nH:28][cH:27][cH:26]1.[NH2:16][C@H:17]([CH2:18][OH:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:12][c:13](-[... | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.N[C@H](CO)c1ccccc1 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)c4ccccc4)cc[nH]c3=O)nc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e72e852090cf7435e97b85905772f4450e91af32c902e1e774d793ceb6479b9b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]ccc(NCc2ccccc2)c1-c1nc2ccc(-n3ccnc3)cc2[nH]1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[C:11]-[C:12](-[NH2;D1;+0:13])-[c:14]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](=[O;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12](-[C:11])-[c:14]):[#7;a:10] | 52.1 | [{"value": 52.0, "product": "OC[C@H](C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.1, "product": "OC[C@H](C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one (30 mg, 0.072 mmol) in DMF (1 mL) were added (S)-(−)-2-phenylglycinol (26 mg, 0.18 mmol) and N-methylmorpholine (0.1 mL). The reaction mixture was heated to 80° C. for 6 h and cooled to room temperature. The solvent was removed u... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cccnc1 | c1cccnc1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HI | CN(C)C=O | 80 | null | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.N[C@H](CO)c1ccccc1>CN(C)C=O>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)c4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f8cf0098830427dbd7603dfff6765ca | CO.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.c1ccncc1>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(OCc4ccccn4)cc[nH]c3=O)nc12 | N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2I)=O)C1)C.CO.N1=CC=CC=C1.[F-].[Cs+]>>N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2OCC2=NC=CC=C2)=O)C1)C | [OH:16][CH3:17].I[c:15]1[c:14](-[c:13]2[nH:12][c:11]3[cH:10][c:4](-[n:5]4[cH:6][cH:7][n:8][cH:9]4)[cH:3][c:2]([CH3:1])[c:30]3[n:29]2)[c:27](=[O:28])[nH:26][cH:25][cH:24]1.[cH:18]1[cH:19][cH:21][cH:20][cH:22][n:23]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:12][c:13](-[c:14]3[c:15]([O:1... | CO.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.c1ccncc1 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(OCc4ccccn4)cc[nH]c3=O)nc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 4bd4daeaae3d60d4e661cfa318109d3052f11b8772d8b92f15df5d6cd5788cf9 | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | O=c1[nH]ccc(OCc2ccccn2)c1-c1nc2ccc(-n3ccnc3)cc2[nH]1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[#7;a:11]1:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:1.[CH3;D1;+0:17]-[OH;D1;+0:18]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](=[O;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:18]-[CH2;D2;+0:17]-[... | 34.3 | [{"value": 34.0, "product": "N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2OCC2=NC=CC=C2)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.3, "product": "N1(C=NC=C1)C=1C=C(C2=C(NC(=N2)C=2C(NC=CC2OCC2=NC=CC=C2)=O)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | To a solution of 3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one (25 mg, 0.06 mmol) in DMF (2 mL) were added pyridine carbinol (26 mg, 0.24 mmol) and cesium fluoride (36 mg, 0.24 mmol). The reaction mixture was heated to 130° C. for 14 h and cooled to room temperature. After concentration in v... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1cccnc1.c1ccncc1 | c1ccncc1.c1cccnc1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1ccncc1.c1cccnc1 | HI | CN(C)C=O | 130 | null | CO.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(I)cc[nH]c3=O)nc12.c1ccncc1>CN(C)C=O>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(OCc4ccccn4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33537aaeca9247a58458ddeff6ad7439 | Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1>>Cc1cc(C#N)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | ClC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C.CN1CCOCC1.N[C@H](CO)CC1=CC=CC=C1>>OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C | Cl[c:12]1[c:11](-[c:10]2[nH:9][c:8]3[cH:7][c:4]([C:5]#[N:6])[cH:3][c:2]([CH3:1])[c:30]3[n:29]2)[c:27](=[O:28])[nH:26][cH:25][cH:24]1.[NH2:13][C@H:14]([CH2:15][OH:16])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][c:8]2[nH:9][c:10](-[c:11]3[c:12]([NH:13][C@H:14]([CH2:15]... | Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1 | Cc1cc(C#N)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | e72e852090cf7435e97b85905772f4450e91af32c902e1e774d793ceb6479b9b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](=[O;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[C:11]-[C:12](-[C:13])-[NH2;D1;+0:14]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](=[O;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:14]-[C:12](-[C:11])-[C:13]):[#7;a:10] | 68 | [{"value": 68.0, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 2-(4-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile (0.7 g, 2.19 mmol) in DMF (15 mL) were added N-methylmorpholine (0.66 g, 6.57 mmol) and (S)-(−)-2-amino-3-phenyl-1-propanol (0.40 g, 2.63 mmol). The reaction mixture was heated to 80° C. for 6 h and then cooled to room... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cccnc1 | c1cccnc1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HCl | CN(C)C=O | 80 | null | Cc1cc(C#N)cc2[nH]c(-c3c(Cl)cc[nH]c3=O)nc12.N[C@H](CO)Cc1ccccc1>CN(C)C=O>Cc1cc(C#N)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-edc45fb5b48a4647b0c6da69f1550dcb | CO.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12>>Cc1cc(N2CCN(C(=O)c3ccccc3)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2.CO>>OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCN(CC2)C(=O)C2=CC=CC=C2 | [CH3:9][OH:10].[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:17][CH2:18]2)[cH:19][c:20]2[nH:21][c:22](-[c:23]3[c:24]([NH:25][C@H:26]([CH2:27][OH:28])[CH2:29][c:30]4[cH:11][cH:15][cH:14][cH:13][cH:12]4)[cH:36][cH:37][nH:38][c:39]3=[O:40])[n:41][c:42]12>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](... | CO.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | Cc1cc(N2CCN(C(=O)c3ccccc3)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | C(C1=CC=CC=C1)(=O)Cl | null | Aromatic Heterocycle Formation | OtherReaction | 3d14998485e7ab3bf7be7d1955355ae5d042e5f0ef1052734609e4c495073893 | 8d86c688d267df2efa5d22f910acf32ce98e069bb28f67fb21d39c7d03924239 | O=C(c1ccccc1)N1CCN(c2ccc3nc(-c4c(NCCc5ccccc5)cc[nH]c4=O)[nH]c3c2)CC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[C:7]-[C:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1.[CH3;D1;+0:15]-[OH;D1;+0:16]>>[C:7]-[C:8]-[c;H0;D3;+0:9](:[c:17]:[c:18]):[c:19]:[c:20].[O;H0;D1;+0:16]=[C;H0;D3;+0:15](-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1)-[c;H0;D3;+0:10]1:... | 33 | [{"value": 33.0, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCN(CC2)C(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of (S)-4-(1-hydroxymethyl-2-phenyl-ethylamino)-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one (30 mg, 0.063 mmol) in methanol (2 mL) was added benzoyl chloride (1 drop). The reaction mixture was stirred for 5 min. and concentrated. The residue was purified by prep. HPLC to yield the t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Methanol | Tertiary amide | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | C(C1=CC=CC=C1)(=O)Cl | null | 0.083333 | CO.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12>C(C1=CC=CC=C1)(=O)Cl>Cc1cc(N2CCN(C(=O)c3ccccc3)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1499889cbbf4dbcb9bcba9dc3b39e9f | CC(C)=O.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12>>Cc1cc(N2CCN(C(C)C)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCNCC2.CC(=O)C.C1CCOC1.[BH3-]C#N.[Na+]>>OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCN(CC2)C(C)C | O=[C:9]([CH3:10])[CH3:11].[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:12][CH2:13]2)[cH:14][c:15]2[nH:16][c:17](-[c:18]3[c:19]([NH:20][C@H:21]([CH2:22][OH:23])[CH2:24][c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[cH:31][cH:32][nH:33][c:34]3=[O:35])[n:36][c:37]12>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][... | CC(C)=O.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | Cc1cc(N2CCN(C(C)C)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | 854fe88b501608b5d4145f9e8c3d87d2513f8a01d07d6ef74b399fc089a3703b | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(N3CCNCC3)cc2[nH]1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 44 | [{"value": 44.0, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCN(CC2)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (S)-4-(1-hydroxymethyl-2-phenyl-ethylamino)-3-(4-methyl-6-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyridin-2-one (25 mg, 0.054 mmol) in methanol (0.5 mL) was added acetone (0.25 mL) and 1 M THF solution of NaCNBH3 (0.2 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | CO | null | 1 | CC(C)=O.Cc1cc(N2CCNCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12>CO>Cc1cc(N2CCN(C(C)C)CC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-562fc9192226499b93ae0748e29277b4 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12.N[C@H](CO)Cc1ccccc1>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12 | ClC1=NC=NC(=C1C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2)Cl.N[C@H](CO)CC1=CC=CC=C1.C(C)N(CC)CC>>ClC1=C(C(=NC=N1)N[C@H](CO)CC1=CC=CC=C1)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2 | Cl[c:20]1[c:14](-[c:13]2[nH:12][c:11]3[cH:10][c:4](-[n:5]4[cH:6][cH:7][n:8][cH:9]4)[cH:3][c:2]([CH3:1])[c:33]3[n:32]2)[c:15]([Cl:16])[n:17][cH:18][n:19]1.[NH2:21][C@H:22]([CH2:23][OH:24])[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:12][c... | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12.N[C@H](CO)Cc1ccccc1 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCNc2ncncc2-c2nc3ccc(-n4ccnc4)cc3[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8](:[#7;a:9]):[#7;a:10].[C:11]-[C:12](-[C:13])-[NH2;D1;+0:14]>>[#7;a:9]:[c:8](-[c:7]1:[c:5](-[Cl;D1;H0:6]):[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:14]-[C:12](-[C:11])-[C:13]):[#7;a:10] | null | [] | 80 | CELSIUS | null | null | To a solution of 2-(4,6-dichloro-pyrimidin-5-yl)-6-imidazol-1-yl-4-methyl-1H-benzimidazole (40 mg, 0.16 mmol) in isopropanol (5 mL) was added (S)-(−)-2-amino-3-phenyl-propanol (35 mg, 0.23 mmol) and triethylamine (0.5 mL). The reaction mixture was heated to 80° C. for 4 h, cooled to room temperature and concentrated wi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1cncnc1.c1ccccc1 | HCl | C(C)(C)O | 80 | null | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3Cl)nc12.N[C@H](CO)Cc1ccccc1>C(C)(C)O>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc542426718546258840318a9ecddafe | CC(=O)O.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12>>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)nc[nH]c3=O)nc12 | ClC1=C(C(=NC=N1)N[C@H](CO)CC1=CC=CC=C1)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2.C(C)(=O)O.N>>OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=N1)=O)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2 | CC(O)=[O:31].Cl[c:30]1[c:14](-[c:13]2[nH:12][c:11]3[cH:10][c:4](-[n:5]4[cH:6][cH:7][n:8][cH:9]4)[cH:3][c:2]([CH3:1])[c:33]3[n:32]2)[c:15]([NH:16][C@H:17]([CH2:18][OH:19])[CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[n:27][cH:28][n:29]1>>[CH3:1][c:2]1[cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][cH:9]2)[cH:10][c:11]2[nH:1... | CC(=O)O.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12 | Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)nc[nH]c3=O)nc12 | null | O | Cl.CO | Miscellaneous | OtherReaction | 427b6563884bf6ecad006f18b561981182d366777c7ccaba473cc0c61768fa05 | 3fbb180061815c1a91daf750f59d95354663c01e4c6076719644d5369bdccd52 | O=c1[nH]cnc(NCCc2ccccc2)c1-c1nc2ccc(-n3ccnc3)cc2[nH]1 | C-C(-O)=[O;H0;D1;+0:1].Cl-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[c:9](:[#7;a:10]):[#7;a:11]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[nH;D2;+0:3]:[c;H0;D3;+0:2](=[O;H0;D1;+0:1]):[c:8]:1-[c:9](:[#7;a:10]):[#7;a:11] | 37 | [{"value": 37.0, "product": "OC[C@H](CC1=CC=CC=C1)NC1=C(C(NC=N1)=O)C1=NC2=C(N1)C=C(C=C2C)N2C=NC=C2", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of (S)-2-[6-chloro-5-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-pyrimidin-4-ylamino]-3-phenyl-propan-1-ol in 4 N HCl (0.5 mL) and acetic acid (0.5 mL) was added two drops of water. The reaction mixture was heated to 100° C. for 8 h, cooled to room temperature, and neutralized with ammonia in methanol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid | null | c1cncnc1 | c1cncnc1 | c1c[nH]cn1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cncnc1 | HCl | O.Cl.CO | 100 | null | CC(=O)O.Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(Cl)ncnc3N[C@H](CO)Cc3ccccc3)nc12>O.Cl.CO>Cc1cc(-n2ccnc2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)nc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-338637abc7114f259ff64c6c0c320f6e | CNC(=N)c1cc(C)c2nc(-c3c(NCC(OC)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1>>CNC(=N)c1cc(C)c2nc(-c3c(NCC(O)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1 | ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C(=N)NC)C)OC.[OH-].[Na+]>>ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C(=N)NC)C)O | C[O:17][CH:16]([CH2:15][NH:14][c:13]1[c:12](-[c:11]2[n:10][c:9]3[c:7]([CH3:8])[cH:6][c:5]([C:3]([NH:2][CH3:1])=[NH:4])[cH:34][c:33]3[nH:32]2)[c:30](=[O:31])[nH:29][cH:28][cH:27]1)[c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[c:24]([Cl:25])[cH:26]1>>[CH3:1][NH:2][C:3](=[NH:4])[c:5]1[cH:6][c:7]([CH3:8])[c:9]2[n:10][c:11](-... | CNC(=N)c1cc(C)c2nc(-c3c(NCC(OC)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1 | CNC(=N)c1cc(C)c2nc(-c3c(NCC(O)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1 | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | dcaefb482d0d4070854ae2f21edb78f004963f26f985f41a9781ad20aca44e4e | 32e9a9ca3191eb6608eee26da72fef0d2c2afd087eefdbcc65ce4c46772064f8 | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[c:4] | 19 | [{"value": 19.0, "product": "ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C(=N)NC)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.7, "product": "ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C(=N)NC)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 2-{4-[2-(3-chloro-4-methoxy-phenyl)-2-methoxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7,N-dimethyl-3H-benzimidazole-5-carboxamidine (40 mg, 0.08 mmol) in methanol (5 mL) was added 2 N NaOH (0.5 mL) and the reaction mixture was stirred at room temperature for 14 h. After concentration in vacuo, the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | null | null | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | CO | null | 14 | CNC(=N)c1cc(C)c2nc(-c3c(NCC(OC)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1>CO>CNC(=N)c1cc(C)c2nc(-c3c(NCC(O)c4ccc(OC)c(Cl)c4)cc[nH]c3=O)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e74e704a8844e3eaad4c028ece33304 | Cc1cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12>>Cc1cc(C(=O)N2CCNCC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C1=CC2=C(N=C(N2)C=2C(NC=CC2NCC(O)C2=CC(=CC=C2)Cl)=O)C(=C1)C.O1CCOCC1.Cl>>ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C(=O)N2CCNCC2)O | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([C:5]([c:4]2[cH:3][c:2]([CH3:1])[c:36]3[c:14]([cH:13]2)[nH:15][c:16](-[c:17]2[c:18]([NH:19][CH2:20][CH:21]([OH:22])[c:23]4[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]4)[cH:30][cH:31][nH:32][c:33]2=[O:34])[n:35]3)=[O:6])[CH2:12][CH2:11]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[N:7... | Cc1cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | Cc1cc(C(=O)N2CCNCC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | null | null | CO | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(c1ccc2nc(-c3c(NCCc4ccccc4)cc[nH]c3=O)[nH]c2c1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 63 | [{"value": 63.0, "product": "ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C(=O)N2CCNCC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.6, "product": "ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C(=O)N2CCNCC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of (±)-4-[1-(2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazol-5-yl)-methanoyl]-piperazine-1-carboxylic acid tert-butyl ester (40 mg, 0.06 mmol) in methanol (5 mL) was added 4.0 M HCl dioxane solution (0.1 mL, excess). The reaction mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HO- | CO | null | 14 | Cc1cc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12>CO>Cc1cc(C(=O)N2CCNCC2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-206e81d9f3434b4fa34c3bb75a51c123 | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.NCCS>>Cc1cc(C2=NCCS2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C)O.Cl.NCCS.C(C)N(CC)CC>>ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C=2SCCN2)O | N#[C:5][c:4]1[cH:3][c:2]([CH3:1])[c:33]2[c:11]([cH:10]1)[nH:12][c:13](-[c:14]1[c:15]([NH:16][CH2:17][CH:18]([OH:19])[c:20]3[cH:21][cH:22][cH:23][c:24]([Cl:25])[cH:26]3)[cH:27][cH:28][nH:29][c:30]1=[O:31])[n:32]2.[NH2:6][CH2:7][CH2:8][SH:9]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]2=[N:6][CH2:7][CH2:8][S:9]2)[cH:10][c:11]2[nH:12]... | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.NCCS | Cc1cc(C2=NCCS2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 8bfbb26c81f477c00edcdc859f846785b4e9291c5091b005d109f7dc24702a58 | 3c08085a6d1a63d4de2eb84f83da9f89152a7592be88f0cad516baac8a24ffab | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(C3=NCCS3)cc2[nH]1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[NH2;D1;+0:7]-[C:8]-[C:9]-[SH;D1;+0:10]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1]1=[N;H0;D2;+0:7]-[C:8]-[C:9]-[S;H0;D2;+0:10]-1):[c:3] | 66 | [{"value": 66.0, "product": "ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C=2SCCN2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C=2SCCN2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (±)-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carbonitrile (100 mg, 0.24 mmol) in methanol (20 mL) was added 2-aminoethanethiol hydrochloride (41 mg, 0.36 mmol) and triethylamine (0.1 mL, excess). The reaction mixture was heated to reflu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Aliphatic thiol | Monosulfide | null | C1=NCCS1 | C1=NCCS1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | CO | null | null | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.NCCS>CO>Cc1cc(C2=NCCS2)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d307fd90bd6d49408d0461f8c4eec9d0 | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.O>>Cc1cc(C=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | O.C(C(C)C)[Al]CC(C)C.ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C#N)C)O.C(C)(=O)OCC>>ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C=O)C)O | N#[C:5][c:4]1[cH:3][c:2]([CH3:1])[c:30]2[c:8]([cH:7]1)[nH:9][c:10](-[c:11]1[c:12]([NH:13][CH2:14][CH:15]([OH:16])[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[cH:24][cH:25][nH:26][c:27]1=[O:28])[n:29]2.[OH2:6]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]=[O:6])[cH:7][c:8]2[nH:9][c:10](-[c:11]3[c:12]([NH:13][CH2:14][CH:15]([... | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.O | Cc1cc(C=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[OH2;D0;+0:7]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH;D2;+0:1]=[O;H0;D1;+0:7]):[c:3] | 2.5 | [{"value": 2.5, "product": "ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C=O)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a suspension of (±)-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl }-7-methyl-3H-benzimidazole-5-carbonitrile (76 mg, 0.18 mmol) in toluene (anhydrous, 20 mL) was added diisobutylaluminium (1.4 M toluene solution) (0.65 mL, 0.97 mmol) at −78° C. under nitrogen. The mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | C1(=CC=CC=C1)C | null | 6 | Cc1cc(C#N)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12.O>C1(=CC=CC=C1)C>Cc1cc(C=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb2391b5125742e28ea0f4edae1dc953 | Cc1cc(C(N)=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12>>Cc1cc(CN)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | ClC=1C=C(C=CC1)C(CNC1=C(C(NC=C1)=O)C=1NC2=C(N1)C(=CC(=C2)C(=O)N)C)O>>NCC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2NCC(O)C2=CC(=CC=C2)Cl)=O)C1)C | O=[C:5]([c:4]1[cH:3][c:2]([CH3:1])[c:30]2[c:8]([cH:7]1)[nH:9][c:10](-[c:11]1[c:12]([NH:13][CH2:14][CH:15]([OH:16])[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[cH:24][cH:25][nH:26][c:27]1=[O:28])[n:29]2)[NH2:6]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][NH2:6])[cH:7][c:8]2[nH:9][c:10](-[c:11]3[c:12]([NH:13][CH2:14][CH:15... | Cc1cc(C(N)=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | Cc1cc(CN)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | null | null | C1CCOC1 | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccccc2[nH]1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:1]-[N;D1;H2:2]):[c:4] | 60 | [{"value": 60.0, "product": "NCC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2NCC(O)C2=CC(=CC=C2)Cl)=O)C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "NCC=1C=C(C2=C(NC(=N2)C=2C(NC=CC2NCC(O)C2=CC(=CC=C2)Cl)=O)C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a solution of (±)-2-{4-[2-(3-Chloro-phenyl)-2-hydroxyethyl amino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carboxylic acid amide (20 mg, 0.046 mmol) in THF (1 mL) was added borane-tetrahydrofuran complex (1 M solution) (0.45 mL, 0.45 mmol). The reaction mixture was stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | Other | C1CCOC1 | null | 10 | Cc1cc(C(N)=O)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12>C1CCOC1>Cc1cc(CN)cc2[nH]c(-c3c(NCC(O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ae23718e7aa4596a65986ea647e0ce5 | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12.OB(O)c1ccccc1>>Cc1cc(-c2ccccc2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | C(C1=CC=CC=C1)[C@@H](COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C2=CC=CC=C2 | Br[c:4]1[cH:3][c:2]([CH3:1])[c:34]2[c:12]([cH:11]1)[nH:13][c:14](-[c:15]1[c:16]([NH:17][C@H:18]([CH2:19][O:20]C(c3ccccc3)(c3ccccc3)c3ccccc3)[CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][nH:30][c:31]1=[O:32])[n:33]2.OB(O)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][... | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12.OB(O)c1ccccc1 | Cc1cc(-c2ccccc2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | 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 | C(Cl)Cl.C1CCOC1 | C-C Coupling | OtherReaction | afa2967cd6cfa90907cacc9db0b4020ddf2593fff80fec2a65bfcf628dc90103 | 9813dfd61e5b23fc207abc2f1b5b582107ee9cff82209022f6e85dc6d65f6dc2 | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(-c3ccccc3)cc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[O;H0;D2;+0:12]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[C:10]-[C:11]-[OH;D1;+0:12].[c:17]:[c:16]:[c;H0;D3;+0:13](-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7... | 52.4 | [{"value": 34.0, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.4, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (S)-4-(1-benzyl-2-trityloxy-ethylamino)-3-[6-bromo-4-methyl-1H-benzimidazole-2-yl]-1H-pyridin-2-one (50 mg, 0.072 mmol), phenylboronic acid (13 mg, 0.11 mmol), and 2 M K2CO3 (0.108 mL, 0.22 mmol) in THF (5 mL) was added Pd(PPh3)4 (8.3 mg, 0.007 mmol). The mixture was heated to reflux 14 h. Upon cooling... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Boronic acid | Primary alcohol | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HBr.B | 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.C(Cl)Cl.C1CCOC1 | null | null | Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12.OB(O)c1ccccc1>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.C(Cl)Cl.C1CCOC1>Cc1cc(-c2ccccc2)cc2[nH]c(-c3c(N... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68323d92230442dfaae55347f4251932 | C1COCCN1.Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12>>Cc1cc(N2CCOCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | C(C1=CC=CC=C1)[C@@H](COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)Br.N1CCOCC1.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[Na+].O1CCOCC1.Cl>>C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[c:4]1[cH:3][c:2]([CH3:1])[c:34]2[c:12]([cH:11]1)[nH:13][c:14](-[c:15]1[c:16]([NH:17][C@H:18]([CH2:19][O:20]C(c3ccccc3)(c3ccccc3)c3ccccc3)[CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][nH:30][c:31]1=[O:32])[n:33]2>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][C... | C1COCCN1.Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12 | Cc1cc(N2CCOCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 28ca84ddeb7904ab5e67d3ac0fe92f6e14d4f0a6629e67633a41e0c1a4a94893 | 642417fb39951d82c019f2a0f9132eeb9588d3fabe5b026a631b7cc9431a9073 | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(N3CCOCC3)cc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[C:10]-[C:11]-[O;H0;D2;+0:12]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[#8:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[#7;a:4]1:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[c;H0;D3;+0:1](-[N;H0;D3;+0:16]3-[C:17]-[C:18]-[#8:13]-[C:14]-[... | 18.1 | [{"value": 18.0, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.1, "product": "C(C1=CC=CC=C1)[C@@H](CO)NC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of (S)-4-(1-benzyl-2-trityloxy-ethylamino)-3-[6-bromo-4-methyl-1H-benzimidazol-2-yl]-1H-pyridin-2-one (150 mg, 0.216 mmol), morpholine (28.2 mg, 0.324 mmol), palladium acetate (2.4 mg, 0.01 mmol), tri-tert-buylphosphine (4.4 mg, 0.02 mmol), and sodium tert-butoxide (104 mg, 1.08 mmol) in toluene (5 mL) was he... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amine | Primary alcohol.Tertiary amine | C1COCCN1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C.CCOC(=O)C | 100 | null | C1COCCN1.Cc1cc(Br)cc2[nH]c(-c3c(N[C@H](COC(c4ccccc4)(c4ccccc4)c4ccccc4)Cc4ccccc4)cc[nH]c3=O)nc12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C.CCOC(=O)C>Cc1cc(N2CCOCC2)cc2[nH]c(-c3c(N[C@H](CO)Cc4ccccc4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33034dc610184844a7c12e8c1cd62ff1 | NC(=O)Cl.NC1CCNCC1>>NC(=O)C1CCN(N)CC1 | NC1CCNCC1.CCN(C(C)C)C(C)C.C(N)(=O)Cl>>C(N)(=O)C1CCN(CC1)N | Cl[C:2]([NH2:1])=[O:3].[CH:4]1([NH2:8])[CH2:5][CH2:6][NH:7][CH2:9][CH2:10]1>>[NH2:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][N:7]([NH2:8])[CH2:9][CH2:10]1 | NC(=O)Cl.NC1CCNCC1 | NC(=O)C1CCN(N)CC1 | null | null | CO | C-C Coupling | OtherReaction | 19dab72856335101e04553fa3203adf6758f5225a3027c8737bbc69f4c776089 | 8af179218b5e47386544b64b515e8e793746d3aa61eaa2708c1a752575ae95e7 | C1CCNCC1 | Cl-[C;H0;D3;+0:1](-[N;D1;H2:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[CH;D3;+0:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[N;D1;H2:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[CH;D3;+0:5]1-[C:6]-[C:7]-[N;H0;D3;+0:8](-[NH2;D1;+0:4])-[C:9]-[C:10]-1 | null | [] | null | null | 8 | HOUR | A solution of the 4-amino-piperidine compound (˜50–100 umol) in 5 ml MeOH is cooled to 0° C. Then 10 equivalent of Huenigs base and ˜3 equivalent of carbamoyl chloride are added. The vial is shaken once and allowed to stand at ambient temperature overnight. Evaporation of volatiles and purification by prep. HPLC gives ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amide.Primary amine.Secondary amine | Hydrazine.Primary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | CO | null | 8 | NC(=O)Cl.NC1CCNCC1>CO>NC(=O)C1CCN(N)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9de6242fa83b44d2bf38ec6206d1b02c | C1COCCN1.O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1>>O=c1[nH]ccc(NC[C@@H](O)c2cccc(Cl)c2)c1-c1nc2c(Br)cc(CN3CCOCC3)cc2[nH]1 | [BH3-]C#N.[Na+].BrC1=CC(=CC2=C1N=C(N2)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)C=O.N1CCOCC1>>BrC1=CC(=CC=2NC(=NC21)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)CN2CCOCC2 | [NH:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1.O=[CH:26][c:25]1[cH:24][c:22]([Br:23])[c:21]2[n:20][c:19](-[c:18]3[c:2](=[O:1])[nH:3][cH:4][cH:5][c:6]3[NH:7][CH2:8][C@@H:9]([OH:10])[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[nH:35][c:34]2[cH:33]1>>[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:6]([NH:7][CH2:8][C@@H:9]([OH:1... | C1COCCN1.O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1 | O=c1[nH]ccc(NC[C@@H](O)c2cccc(Cl)c2)c1-c1nc2c(Br)cc(CN3CCOCC3)cc2[nH]1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | 073d98e7dcd77aafeef71a76da7e61b2751c934600f6fff04db700a08f3e4453 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(CN3CCOCC3)cc2[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6].[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-1):[c:3] | 45 | [{"value": 45.0, "product": "BrC1=CC(=CC=2NC(=NC21)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)CN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (S)-7-Bromo-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzimidazole-5-carbaldehyde (130 mg, 0.27 mmol) in methanol (60 mL) was added morpholine (0.2 mL, excess). The reaction mixture was stirred 1 h at room temperature. Then NaCNBH3 (1M THF solution, 1.35 mL, 1.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1cccnc1.c1ccccc1.c1ccc2[nH]cnc2c1.C1COCC[NH]1 | Other | CO | null | 1 | C1COCCN1.O=Cc1cc(Br)c2nc(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)[nH]c2c1>CO>O=c1[nH]ccc(NC[C@@H](O)c2cccc(Cl)c2)c1-c1nc2c(Br)cc(CN3CCOCC3)cc2[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25e7603e3e8f415fab1e2c2360534542 | CN1CCN(Cc2cc(Br)c3nc(-c4c(NC[C@@H](O)c5cccc(Cl)c5)cc[nH]c4=O)[nH]c3c2)CC1.[CH3][Sn]([CH3])([CH3])[CH3]>>Cc1cc(CN2CCN(C)CC2)cc2[nH]c(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | BrC1=CC(=CC=2NC(=NC21)C=2C(NC=CC2NC[C@@H](O)C2=CC(=CC=C2)Cl)=O)CN2CCN(CC2)C.C[Sn](C)(C)C.[F-].[K+]>>ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)CN2CCN(CC2)C)O | Br[c:2]1[cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)[cH:13][c:14]2[nH:15][c:16](-[c:17]3[c:18]([NH:19][CH2:20][C@@H:21]([OH:22])[c:23]4[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]4)[cH:30][cH:31][nH:32][c:33]3=[O:34])[n:35][c:36]12.[CH3][Sn]([CH3])([CH3])[CH3:1]>>[CH3:1][c:2]1[cH:3][c:4]([CH2... | CN1CCN(Cc2cc(Br)c3nc(-c4c(NC[C@@H](O)c5cccc(Cl)c5)cc[nH]c4=O)[nH]c3c2)CC1.[CH3][Sn]([CH3])([CH3])[CH3] | Cc1cc(CN2CCN(C)CC2)cc2[nH]c(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 | null | null | CN(C)C=O | C-C Coupling | Stille reaction_other | 67cae9395236f76d71cd1c9cfc6def0d0c8bc8fcb4fc867ab6b50d5f00aa9211 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=c1[nH]ccc(NCCc2ccccc2)c1-c1nc2ccc(CN3CCNCC3)cc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[CH3;D1;+0:10]-[Sn](-[CH3])(-[CH3])-[CH3]>>[CH3;D1;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 48 | [{"value": 48.0, "product": "ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC=C1)=O)C1=NC2=C(N1)C=C(C=C2C)CN2CCN(CC2)C)O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Through a mixture of (S)-3-[4-Bromo-6-(4-methyl-piperazin-1-ylmethyl)-1H-benzimidazol-2-yl]-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-one (80 mg, 0.14 mmol), tetramethyl tin (2.5 mL, excess), PdCl2 (PPh3)4 (10 mg, 0.014 mmol), and KF (40 mg, 0.7 mmol) in DMF (2 mL) in a vial was bubbled nitrogen, sealed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | C1C[NH]CC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1.c1cccnc1 | HBr.Sn | CN(C)C=O | 100 | null | CN1CCN(Cc2cc(Br)c3nc(-c4c(NC[C@@H](O)c5cccc(Cl)c5)cc[nH]c4=O)[nH]c3c2)CC1.[CH3][Sn]([CH3])([CH3])[CH3]>CN(C)C=O>Cc1cc(CN2CCN(C)CC2)cc2[nH]c(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-726b6a0725b1421a8ba3f63c4b0f73c4 | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C.Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C>>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl | OC1=C(C(NC1)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2.ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O>>ClC=1C=C(C=CC1OC)C(CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O | [cH:3]1[cH:4][cH:5][c:6]([C@H:7]([OH:8])[CH2:9][NH:10][C:11]2=[C:12]([c:13]3[n:14][c:15]4[c:16]([CH3:17])[cH:18][c:19]([N:20]5[CH2:21][CH2:22][O:23][CH2:24][CH2:25]5)[cH:26][c:27]4[n:28]3[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[C:36](=[O:37])[N:38]([S:39](=[O:40])(=[O:41])[C:42]([F:43])([F:44])[F:45])[C... | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C.Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 4515a50e14267aca11ea1959a285f9440c16001837a98e5f78bf1b63e016508a | 8cf563015e64cb43f3591e9989d682e9691b3ada12c6d21e1870366f30219534 | O=C1NCC(NCCc2ccccc2)=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-c1:c:c(-N2-C-C-O-C-C-2):c:c2:c:1:n:c(-C1=[C;H0;D3;+0:1](-[OH;D1;+0:2])-C-N-C-1=O):n:2-C(=O)-O-C(-C)(-C)-C.[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](-[Cl;D1;H0:3]):[c:5] | 35 | [{"value": 35.0, "product": "ClC=1C=C(C=CC1OC)C(CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1,5-dihydro-pyrrol-2-one (0.032 g, 0.059 mmol) was reacted as described in the procedure used to synthesize (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide.Enol.Tertiary amine.Boc | Ether | c1ccccc1.C1COCCN1.c1ccc2[nH]cnc2c1.C1=CCNC1 | c1ccccc1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1COCC[NH]1.C1=CC[NH]C1 | HO- | C(C)#N | null | null | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C.Cc1cc(N2CCOCC2)cc2c1nc(C1=C(O)CNC1=O)n2C(=O)OC(C)(C)C>C(C)#N>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8bc663c636c34e30b341ffef7a30b772 | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl>>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Cl | ClC=1C=C(C=CC1OC)C(CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O.ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O>>ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O | CC(C)(C)OC(=O)[n:28]1[c:13]([C:12]2=[C:11]([NH:10][CH2:9][CH:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:34]([Cl:35])[cH:33]3)[OH:8])[CH2:32][N:31](S(=O)(=O)C(F)(F)F)[C:29]2=[O:30])[n:14][c:15]2[c:16]([CH3:17])[cH:18][c:19]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[cH:26][c:27]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:... | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Cl | null | null | null | Reduction | OtherReaction | 2f11a948f4e357206835e0387eaef9d4eff33ee011003551d4339449b953a4e0 | 3c18ba9ff13d6939ae55af454539aa1d409cfd52b5cc70c0158f2cca2d3a298a | O=C1NCC(NCCc2ccccc2)=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]2=[C:4](-[#7:5])-[C:6]-[N;H0;D3;+0:7](-S(=O)(=O)-C(-F)(-F)-F)-[C:8]-2=[O;D1;H0:9]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14]>>[#7:5]-[C:4]1=[C:3](-[c:2]2:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[nH;D2;+0:1]:2)-[C:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:6]-1 | 60.2 | [{"value": 59.0, "product": "ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.2, "product": "ClC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[2-(3-Chloro-4-methoxy-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1-trifluoromethanesulfonyl-1,5-dihydro-pyrrol-2-one (0.017 g, 0.023 mmol) was reacted according to the procedure used to synthesize (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-met... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ether.Tertiary amide.Boc | Secondary amide | C1=CC[NH]C1.c1ccc2nc[nH]c2c1 | c1ccc2[nH]cnc2c1.C1=CCNC1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1COCC[NH]1.C1=CCNC1 | HF | null | null | null | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Cl>>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-70e0ffd8e5a940b28702b704dfc02679 | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Br>>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Br | BrC=1C=C(C=CC1OC)C(CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O.ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O>>BrC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O | CC(C)(C)OC(=O)[n:28]1[c:13]([C:12]2=[C:11]([NH:10][CH2:9][CH:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:34]([Br:35])[cH:33]3)[OH:8])[CH2:32][N:31](S(=O)(=O)C(F)(F)F)[C:29]2=[O:30])[n:14][c:15]2[c:16]([CH3:17])[cH:18][c:19]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[cH:26][c:27]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:... | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Br | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Br | null | null | null | Reduction | OtherReaction | 2f11a948f4e357206835e0387eaef9d4eff33ee011003551d4339449b953a4e0 | 3c18ba9ff13d6939ae55af454539aa1d409cfd52b5cc70c0158f2cca2d3a298a | O=C1NCC(NCCc2ccccc2)=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](-[C:3]2=[C:4](-[#7:5])-[C:6]-[N;H0;D3;+0:7](-S(=O)(=O)-C(-F)(-F)-F)-[C:8]-2=[O;D1;H0:9]):[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14]>>[#7:5]-[C:4]1=[C:3](-[c:2]2:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[nH;D2;+0:1]:2)-[C:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:6]-1 | 54.5 | [{"value": 54.0, "product": "BrC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "BrC=1C=C(C=CC1OC)C(CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[2-(3-Bromo-4-methoxy-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1-trifluoromethanesulfonyl-1,5-dihydro-pyrrol-2-one (0.018 g, 0.023 mmol) was reacted according to the procedure used to synthesize (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-meth... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ether.Tertiary amide.Boc | Secondary amide | C1=CC[NH]C1.c1ccc2nc[nH]c2c1 | c1ccc2[nH]cnc2c1.C1=CCNC1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1COCC[NH]1.C1=CCNC1 | HF | null | null | null | COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4n3C(=O)OC(C)(C)C)C(=O)N(S(=O)(=O)C(F)(F)F)C2)cc1Br>>COc1ccc(C(O)CNC2=C(c3nc4c(C)cc(N5CCOCC5)cc4[nH]3)C(=O)NC2)cc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d863f6bcdd0446a9923caa55a7dc45dc | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C>>Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(NC[C@@H](O)c4cccc(Cl)c4)CNC3=O)nc12 | Cl.ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(N(C1)S(=O)(=O)C(F)(F)F)=O)C1=NC2=C(N1C(=O)OC(C)(C)C)C=C(C=C2C)N2CCOCC2)O.O.ClCCl>>ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O | CC(C)(C)OC(=O)[n:13]1[c:12]2[cH:11][c:4]([N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[cH:3][c:2]([CH3:1])[c:33]2[n:32][c:14]1[C:15]1=[C:16]([NH:17][CH2:18][C@@H:19]([OH:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28][N:29](S(=O)(=O)C(F)(F)F)[C:30]1=[O:31]>>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:... | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C | Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(NC[C@@H](O)c4cccc(Cl)c4)CNC3=O)nc12 | null | C([O-])(O)=O.[Na+] | CN(C=O)C | Reduction | OtherReaction | 2f11a948f4e357206835e0387eaef9d4eff33ee011003551d4339449b953a4e0 | 3c18ba9ff13d6939ae55af454539aa1d409cfd52b5cc70c0158f2cca2d3a298a | O=C1NCC(NCCc2ccccc2)=C1c1nc2ccc(N3CCOCC3)cc2[nH]1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:1-[C:8]1=[C:9](-[#7:10])-[C:11]-[N;H0;D3;+0:12](-S(=O)(=O)-C(-F)(-F)-F)-[C:13]-1=[O;D1;H0:14]>>[#7:10]-[C:9]1=[C:8](-[c:7]2:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[nH;D2;+0:1]:2)-[C:13](=[O;D1;H0:14])-[NH;D2;+0:12]-[C:11]-1 | 138.9 | [{"value": 138.9, "product": "ClC=1C=C(C=CC1)[C@@H](CNC1=C(C(NC1)=O)C1=NC2=C(N1)C=C(C=C2C)N2CCOCC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a stirred solution of (S)-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1-trifluoromethanesulfonyl-1,5-dihydro-pyrrol-2-one (0.014 g, 0.020 mmol) in N,N-dimethylformamide (2 mL) was added saturated sodium bicarbonate (10 drops) and this was h... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ether.Tertiary amide.Boc | Secondary amide | c1ccc2nc[nH]c2c1.C1=CC[NH]C1 | c1ccc2[nH]cnc2c1.C1=CCNC1 | C1COCC[NH]1.c1ccc2[nH]cnc2c1.c1ccccc1.C1=CCNC1 | HF | C([O-])(O)=O.[Na+].CN(C=O)C | 80 | 2 | Cc1cc(N2CCOCC2)cc2c1nc(C1=C(NC[C@@H](O)c3cccc(Cl)c3)CN(S(=O)(=O)C(F)(F)F)C1=O)n2C(=O)OC(C)(C)C>C([O-])(O)=O.[Na+].CN(C=O)C>Cc1cc(N2CCOCC2)cc2[nH]c(C3=C(NC[C@@H](O)c4cccc(Cl)c4)CNC3=O)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07f9970c50e64af1ab131f98a6014d5c | C1COCCN1.O=C(O)c1cccc(O)c1>>C1COCC[NH2+]1.O=C([O-])c1cccc(O)c1 | N1CCOCC1.OC=1C=C(C(=O)O)C=CC1.N1CCOCC1>>OC=1C=C(C(=O)[O-])C=CC1.[NH2+]1CCOCC1 | [CH2:1]1[CH2:2][O:3][CH2:4][CH2:5][NH:6]1.[O:7]=[C:8]([OH:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1>>[CH2:1]1[CH2:2][O:3][CH2:4][CH2:5][NH2+:6]1.[O:7]=[C:8]([O-:9])[c:10]1[cH:11][cH:12][cH:13][c:14]([OH:15])[cH:16]1 | C1COCCN1.O=C(O)c1cccc(O)c1 | C1COCC[NH2+]1.O=C([O-])c1cccc(O)c1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | a814cc1a011593e2c68585e2731f099af1d517de1fcd3feca16c306f99ada8f5 | 02cc035f718d8b0360e817e412bd90c19b45bf9577e942246522aa40ca6fc5a8 | C1COCC[NH2+]1.c1ccccc1 | [#8:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8](-[OH;D1;+0:9])-[c:10]>>[#8:1]1-[C:2]-[C:3]-[NH2+;D2:4]-[C:5]-[C:6]-1.[O-;H0;D1:9]-[C:8](=[O;D1;H0:7])-[c:10] | 70 | [{"value": 70.0, "product": "OC=1C=C(C(=O)[O-])C=CC1.[NH2+]1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a conical flask, cold absolute ethanol (ca. 40 ml) was added to 99% pure 3-hydroxybenzoic acid (1.8495 g; 13.39 mmol). Dissolution of the acid was achieved at room temperature by constant stirring. Morpholine (1.1653 g, 13.39 mmol) was added dropwise to the acid solution. The reaction was exothermic and some white f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | C1COCCN1 | C1COCC[NH+]1 | C1COCC[NH+]1.c1ccccc1 | null | C(C)O | null | null | C1COCCN1.O=C(O)c1cccc(O)c1>C(C)O>C1COCC[NH2+]1.O=C([O-])c1cccc(O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40e5334c84874430bb136034050caaff | COc1ccc(C(CC(N)=O)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1>>COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC(=O)N)C3=CC(=C(C=C3)OC)OC3CCCC3.C(CC)(=O)N.C(CC)(=O)N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC(=O)N)C3=CC(=C(C=C3)OC3CCCCC3)OCC.C(CC)(=O)N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC(=O)N)C3=CC(=C(C=C3)OC3CCCC3)OCC.C(CC)(=O)N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC(=O)N)C3=CC(=C(C=C3)OCC)O... | c1c2c(c[c:20]3[c:15]1[C:13](=[O:14])[N:12]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)[cH:23]1)[CH2:8][C:9]([NH2:10])=[O:11])[C:21]3=[O:22])[cH:19][cH:18][cH:17][cH:16]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9]([NH2:10])=[O:11])[N:12]2[C:13](=[O:14... | COc1ccc(C(CC(N)=O)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1 | COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 | null | null | null | Miscellaneous | OtherReaction | 10fe611be61ee72097578a5d4ed1558302454ebef747e299e4f22b2923657470 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1Cc1cccc(OC2CCCC2)c1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]2:c:c3:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:c:3:c:[c;H0;D3;+0:10]:2-[C:11]-1=[O;D1;H0:12]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[c:7]:[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10]:2-[C:11]-1=[O;D1;H0:12] | null | [] | null | null | null | null | Similarly from equivalent amounts of 3-(1,3-dioxobenzo[f]isoindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid, 3-(1,3-dioxo-4-azaindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid, 3-(1,3-dioxo-5-azaindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid, 3-(1,3-dioxobenzo[f]isoind... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2cc3c(cc2c1)C[NH]C3 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CCCC1 | Other | null | null | null | COc1ccc(C(CC(N)=O)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1>>COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c42df188bae344b0b40a7326cdfc01b4 | CCOc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1.CCOc1ccc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1.COc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1>>CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC | O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC#N)C3=CC(=C(C=C3)OC)OC3CCCC3.C(CC)#N.C(CC)#N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC#N)C3=CC(=C(C=C3)OC3CCCCC3)OCC.C(CC)#N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC#N)C3=CC(=C(C=C3)OC3CCCC3)OCC.C(CC)#N.O=C1N(C(C=2C=C3C(=CC12)C=CC=C3)=O)C(CC#N)C3=CC(=C(C=C3)OCC)OC3CCCC3.C(CC)#N.O=C1N(C(... | N#CCC(c1ccc(OC2CCCCC2)c(O[CH2:26][CH3:27])c1)N1C(=O)c2cc3ccccc3cc2C1=O.c1ccc2c(c1)c[c:20]1[c:15]([cH:16]2)[C:13](=[O:14])[N:12]([CH:8]([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24]([O:25]C3CCCC3)[cH:23]2)[CH2:9][C:10]#[N:11])[C:21]1=[O:22].COc1cc(C(CC#N)N2C(=O)c3cc4c[cH:17][cH:18][cH:19]c4cc3C2=O)ccc1OC1CCCCC1>>[C... | CCOc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1.CCOc1ccc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1.COc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1 | CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | adaa67294eb78ea68a7fc4765fca71212b1bd5e899888e9a3e6d29f88097d446 | 84975d4bc70f363124ea54454eaaa83f471369b28468215e592bc4b99012ea98 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | C-O-c1:c:c(-C(-C-C#N)-N2-C(=O)-c3:c:c4:[cH;D2;+0:1]:[c:2]:[cH;D2;+0:3]:c:c:4:c:c:3-C-2=O):c:c:c:1-O-C1-C-C-C-C-C-1.N#C-C-C(-N1-C(=O)-c2:c:c3:c:c:c:c:c:3:c:c:2-C-1=O)-c1:c:c:c(-O-C2-C-C-C-C-C-2):c(-O-[CH2;D2;+0:4]-[C;D1;H3:5]):c:1.[C:6]-[#7:7]1-[C:8](=[O;D1;H0:9])-[c:10]2:[cH;D2;+0:11]:c3:c:c:c:c:c:3:c:[c;H0;D3;+0:12]:2... | null | [] | null | null | null | null | Similarly obtained from 3-(1,3-dioxobenzo[f] isoindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionamide, 3-(1,3-dioxo-4-azaindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionamide, 3-(1,3-dioxo-5-azaindolin-2-yl)-3-(3-cyclopentyloxy-4-methoxyphenyl)propionamide, 3-(1,3-dioxobenzo[f]isoindolin-2-yl)-3-(3-et... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether.Ether.Substituted dicarboximide.Substituted dicarboximide.Nitrile.Nitrile | Ether | c1ccccc1.C1CCCCC1.c1ccc2cc3c(cc2c1)CNC3.c1ccc2cc3c(cc2c1)C[NH]C3.C1CCCC1.c1ccccc1.c1ccc2cc3c(cc2c1)CNC3.C1CCCCC1 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | null | null | null | CCOc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1.CCOc1ccc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)cc1OC1CCCC1.COc1cc(C(CC#N)N2C(=O)c3cc4ccccc4cc3C2=O)ccc1OC1CCCCC1>>CCOc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09886d22a7e74f5ea13173d30ce9b9e8 | COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC>>COc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OC | C1(C=2C(C(N1C(CC(=O)N)C1=CC(=C(C=C1)OC)OC)=O)=CC=CC2)=O.CN1CCOCC1.S(=O)(Cl)Cl>>C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OC)OC)=O)=CC=CC2)=O | O=[C:9]([CH2:8][CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[cH:22]1)[N:11]1[C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[C:20]1=[O:21])[NH2:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([CH2:8][C:9]#[N:10])[N:11]2[C:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[C:20]2=[O:21]... | COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC | COc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OC | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[C;H0;D2;+0:1]#[N;H0;D1;+0:2] | 79 | [{"value": 79.0, "product": "C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OC)OC)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "C1(C=2C(C(N1C(CC#N)C1=CC(=C(C=C1)OC)OC)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To an ice bath cooled stirred suspension of 3-phthalimido-3-(3,4-dimethoxyphenyl)propionamide (1.77 g, 5.00 mmol) and 4-methylmorpholine (1.3 mL, 12 mmol) in dimethyformamide (17 mL) under nitrogen, was added thionyl chloride (0.7 mL, 9.6 mmol) dropwise via a syringe. There was a slight exotherm and after 30 minutes, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | CN(C=O)C | null | 0.5 | COc1ccc(C(CC(N)=O)N2C(=O)c3ccccc3C2=O)cc1OC>CN(C=O)C>COc1ccc(C(CC#N)N2C(=O)c3ccccc3C2=O)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5592d5b86ad447fe92d882c35b63be43 | NC(CC(=O)O)c1ccccc1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>>O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O | NC(CC(=O)O)C1=CC=CC=C1.[C@@H]12[C@@H](CCCC1)C(=O)OC2=O>>C1([C@H]2[C@@H](C(N1C(CC(=O)O)C1=CC=CC=C1)=O)CCCC2)=O | [O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH2:12].O1[C:13](=[O:14])[C@@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@@H:20]2[C:21]1=[O:22]>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[N:12]1[C:13](=[O:14])[C@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]2[C:21]1=... | NC(CC(=O)O)c1ccccc1.O=C1OC(=O)[C@@H]2CCCC[C@H]12 | O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O | null | null | C(C)(=O)O | Acylation | OtherReaction | e31ab6bc2910da58d432cb5913ab0c5fdac34539ca9cc021c162ad6628b3e161 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1[C@H]2CCCC[C@H]2C(=O)N1Cc1ccccc1 | [C:1]-[C:2]1-[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-[C;H0;D3;+0:7]-1=[O;D1;H0:8].[NH2;D1;+0:9]-[C:10](-[c:11])-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[C:1]-[C:2]1-[C:3](-[C:4])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9](-[C:10](-[c:11])-[C:12]-[C:13](=[O;D1;H0:14])-[O;D1;H1:15])-[C;H0;D3;+0:7]-1=[O;D1;H0:8] | 58 | [{"value": 58.0, "product": "C1([C@H]2[C@@H](C(N1C(CC(=O)O)C1=CC=CC=C1)=O)CCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture 3-amino-3-phenylpropionic acid and cis-1,2-cyclohexanedicarboxylic anhydride in 10 mL of acetic acid under nitrogen was heated to reflux for 4 h and then allowed to cool to room temperature. The resulting mixture was concentrated to an orange yellow oil. This oil was crystallized from a 1/1 mixture of... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1CC[C@H]2COC[C@H]2C1 | C1CC[C@H]2C[NH]C[C@H]2C1 | c1ccccc1.C1CC[C@H]2C[NH]C[C@H]2C1 | HO- | C(C)(=O)O | null | null | NC(CC(=O)O)c1ccccc1.O=C1OC(=O)[C@@H]2CCCC[C@H]12>C(C)(=O)O>O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9086107146894d009a71b526bc30e351 | O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O.[NH4+]>>NC(=O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O | C1([C@H]2[C@@H](C(N1C(CC(=O)O)C1=CC=CC=C1)=O)CCCC2)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.[OH-].[NH4+]>>C1([C@H]2[C@@H](C(N1C(CC(=O)N)C1=CC=CC=C1)=O)CCCC2)=O | O[C:2](=[O:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[N:12]1[C:13](=[O:14])[C@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]2[C:21]1=[O:22].[NH4+:1]>>[NH2:1][C:2](=[O:3])[CH2:4][CH:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[N:12]1[C:13](=[O:14])[C@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]2[C:21]1=[... | O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O.[NH4+] | NC(=O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O | null | null | O1CCCC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1[C@H]2CCCC[C@H]2C(=O)N1Cc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 23.3 | [{"value": 23.3, "product": "C1([C@H]2[C@@H](C(N1C(CC(=O)N)C1=CC=CC=C1)=O)CCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3-(cis-hexahydrophthalimido)-3-phenylpropionic acid (0.903 g, 3.00 mmol) and carbonyldiimidazole (0.525 g, 3.75 mmol) in 13 mL of anhydrous tetrahydrofuran under nitrogen was stirred for 1 hour, then 0.25 mL of concentrated ammonium hydroxide was added to the reaction solution. After 20 minutes, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1CC[C@H]2C[NH]C[C@H]2C1 | HO- | O1CCCC1 | null | 1 | O=C(O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O.[NH4+]>O1CCCC1>NC(=O)CC(c1ccccc1)N1C(=O)[C@H]2CCCC[C@H]2C1=O |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.