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-1e238da9ec0441dc8fe8397dcb8c5375 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C)F>>C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F | [CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | [Pd] | C(C)O | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 92.1 | [{"value": 92.0, "product": "C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The product of Step C, 3,4-difluoro-2-[(4-ethynyl-2-fluorophenyl)amino]benzoic acid (300 mg, 1.03 mmol), was dissolved in absolute ethanol (30 mL) and 5% Pd/C (30 mg) added. This mixture was stirred under an atmosphere of hydrogen (60 psi) for 2 hours at room temperature. The Pd/C was removed over Celite®, which was wa... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)O | null | 2 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>[Pd].C(C)O>CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ecc0f5765204fb38ea527400b4d8bc4 | CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | [N-]1C=NC=C1.NOCCO.C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F | O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:25][c:23]2[F:24])[c:21]([F:22])[c:19]([F:20])[cH:18][cH:17]1)=[O:11].[NH2:12][O:13][CH2:14][CH2:15][OH:16]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2... | CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65 | [{"value": 65.0, "product": "C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | The title compound was prepared from the reaction of the product of Step D, 2-[(4-ethyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acid (93 mg, 0.32 mmol) dissolved in dry THF (5 mL), and carbonyldiimidazole (CDI) (102 mg, 0.63 mmol). Within 10 minutes, a bright yellow solution was obtained and conversion to the imidazo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 0.166667 | CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>C1CCOC1>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-899d1d4e9b5d4a96af3a362160180f80 | O=C(O)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F>>O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | ClC1=C(C=CC(=C1)I)NC1=C(C(=O)O)C=CC(=C1F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)O)C=CC(=C1F)F.N1=CC=CC=C1.FC(C(=O)OC1=C(C(=C(C(=C1F)F)F)F)F)(F)F>>FC1=C(C(=C(C(=C1OC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)I)Cl)=O)F)F)F)F | O=C(O)[c:15]1[cH:16][cH:17][c:18]([F:19])[c:20]([F:21])[c:22]1[NH:23][c:24]1[cH:25][cH:26][c:27]([I:28])[cH:29][c:30]1[Cl:31].FC(F)(F)[C:2](=[O:1])[O:3][c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[c:11]([F:12])[c:13]1[F:14]>>[O:1]=[C:2]([O:3][c:4]1[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[c:11]([F:12])[c:13]1[F:14])[c:15]1[... | O=C(O)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F | O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | null | null | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | a107b7fa240a00727def35d9f3f3d79f77e3bfda9f2cc9627f9211a6797e9acc | c8a900bd957c46e0c8e28722dfe9262f44e12b24af7a12a545c112943e69a54a | O=C(Oc1ccccc1)c1ccccc1Nc1ccccc1 | F-C(-F)(-F)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].O-C(=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[#7:9]):[c:10]>>[#7:9]-[c:8](:[c:10]):[c;H0;D3;+0:5](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4]):[c:6]:[c:7] | 91 | [{"value": 91.0, "product": "FC1=C(C(=C(C(=C1OC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)I)Cl)=O)F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the product of Example 2, Step A, 2-(2-chloro-4-iodophenylamino)-3,4-difluorobenzoic acid (10.0 g, 24.4 mmol), and pyridine (2.16 mL, 26.8 mmol) in anhydrous dimethylformamide (49 mL) was added pentafluorophenyl trifluoroacetate (5.35 mL, 30.5 mmol). The resultant solution was stirred at ambient temper... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Ester | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF | CN(C=O)C.C(C)(=O)OCC | null | null | O=C(O)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl.O=C(Oc1c(F)c(F)c(F)c(F)c1F)C(F)(F)F>CN(C=O)C.C(C)(=O)OCC>O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-67ba23b4a90d4811a82556d842bf0a11 | NOCCO.O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | C(C)(C)N(C(C)C)CC.FC1=C(C(=C(C(=C1OC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)I)Cl)=O)F)F)F)F.FC1=C(C(=C(C(=C1OC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)I)Cl)=O)F)F)F)F.NOCCO>>ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCCO)C=CC(=C1F)F | [NH2:3][O:4][CH2:5][CH2:6][OH:7].Fc1c(F)c(F)c(O[C:2](=[O:1])[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]2[NH:16][c:17]2[cH:18][cH:19][c:20]([I:21])[cH:22][c:23]2[Cl:24])c(F)c1F>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20](... | NOCCO.O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | null | null | CN(C=O)C | Acylation | Aminolysis of esters | bee80c17ba750e5b878660daaf03b34b83cc65c10d42a24fde7726a66e741f89 | f21fd5f8c88779686ca0dcd2a6ec464a4e9cd0b9a76d99bbd673ae535081dde3 | c1ccc(Nc2ccccc2)cc1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):c(-F):c:1-F.[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 90 | [{"value": 90.0, "product": "ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCCO)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the product of Example 2, Step B, 2-(2-chloro-4-iodo-phenylamino)-3,4-difluorobenzoic acid pentafluorophenyl ester (10.0 g, 17.4 mmol), in anhydrous dimethylformamide (36 mL) was added 2-(aminooxy)-ethanol [prepared by the literature procedure: Dhanak, D.; Reese, C. B., J. Chem. Soc., Perkin Trans. 198... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester.Primary amine | Secondary amide | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HF | CN(C=O)C | null | null | NOCCO.O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl>CN(C=O)C>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-73439d27f39b4390aed46e812a67376f | C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1>>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | ClC1=C(C=CC(=C1)C=C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F.ClC1=C(C=CC(=C1)C=C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F>>ClC1=C(C=CC(=C1)CC)NC1=C(C(=O)NOCCO)C=CC(=C1F)F | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:22])[c:23]([Cl:24])[cH:25]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F... | C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | null | [Pd] | O1CCCC1.CO | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccc(Nc2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 6 | HOUR | A solution of the product of Example 2, Step D, 2-(2-chloro-4-vinyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide (0.291 g, 0.789 mmol) in tetrahydrofuran (16 mL) was hydrogenated over 10% palladium on carbon (0.08 g) at 6900 psig at room temperature for 17 hours. The catalyst was removed by filtration and t... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].O1CCCC1.CO | null | 6 | C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1>[Pd].O1CCCC1.CO>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-652bcc1582d54f0ca58d7b36a9a67c78 | Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)C.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[c:18]([F:19])[cH:20]1.F[c:7]1[c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13][c:14]([F:15])[c:16]1[F:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[c:8]([C:9](=[O:10])[OH:11])[cH:12][cH:13][c:14]([F:15])[c:16]2[F:17])[c:18]([F:19])[cH:20]1 | Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9] | null | [] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and 2-fluoro-4-methylaniline were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, 3,4-difluoro-2-[2-fluoro-4-methylanilino]benzoic acid was isolated as a crude pale brown solid which was reacted directly with 2-(aminooxy)ethanol ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2bae50fd47ff4a1cbb15b2e0c82c7bc1 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | C(#C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F.N1=CC=CC2=CC=CC=C12>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C=C)F | [CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2] | C1CCOC1 | Reduction | Hydrogenation (triple to double) | 9fb9e3bcd1979ce1ec380a62b41fc2baa9493f4b62d173fd793175200be9b0be | d06db8777adee8a754da5dc5b637b0f3c536c729d38bcda44c5eb217b809e799 | c1ccc(Nc2ccccc2)cc1 | [CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 72 | [{"value": 72.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C=C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.5, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C=C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | The product of Example 1, Step C, 2-[(4-ethynyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acid (540 mg, 1.86 mmol) and quinoline (220 mg) were dissolved in THF (50 mL), then Lindlar catalyst (11 mg) added. This mixture was stirred under an atmosphere of hydrogen (60 psi) for 3 periods of 15 minutes and monitored carefu... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | Vinyl | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C1CCOC1 | null | 0.25 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>[Pd].CC(=O)[O-].CC(=O)[O-].[Pb+2].C1CCOC1>C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cd6518d59e44a37a1277486b0c0d90a | C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C=C)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C=C)F | O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:25][c:23]2[F:24])[c:21]([F:22])[c:19]([F:20])[cH:18][cH:17]1)=[O:11].[NH2:12][O:13][CH2:14][CH2:15][OH:16]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2... | C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78 | [{"value": 78.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C=C)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of the product of Example 4, Step A, 3,4-difluoro-2-[(2-fluoro-4-vinylphenyl)amino]benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E, then purified by flash column chromatography on silica gel (10% EtOAc/hexanes) to give 3,4-difluor... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | C=Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-05e03083de6c4618867870fed822e0e5 | COCCOC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)I)F.C(OC)COC.O.C(=O)([O-])[O-].[K+].[K+].O.[B]>>C(=C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F | COCCO[CH3:1].I[c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:22])[c:23]([F:24])[cH:25]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:... | COCCOC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | 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 | [Cl-].[Na+].O | C-C Coupling | OtherReaction | 63d3206d581071ef7b7bb23b8ca08334fbab0b6c6d066dc8a9ac56ee0ddb7824 | 23c65ae2aa282ff569a38af7d0cad288cbe289bcf57e497c7f4b894b7dbcb571 | c1ccc(Nc2ccccc2)cc1 | C-O-C-C-O-[CH3;D1;+0:1].I-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]>>[CH2;D1;+0:1]=[C:7]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6] | 76 | [{"value": 76.0, "product": "C(=C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (1.00 g, 2.21 mmol) was dissolved in dry dimethoxyethane (DME, 18 ml) under a nitrogen atmosphere, Pd(Ph3P)4 (0.13 g, 0.11 mmol) was added and the resulting yellow solution was stirred at ambient temperature for 20 min. K2CO3 (−325 mesh, 0.31 g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | 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.[Cl-].[Na+].O | null | 0.333333 | COCCOC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>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.[Cl-].[Na+].O>C=Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2dc6b170e3ac4f2cbf2e0c712791378e | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | Cl.O1CCOCC1.C(C=C)[Sn](CCCC)(CCCC)CCCC.FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)I)F>>C(C=C)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:3][CH:2]=[CH2:1].C[O:13][C:11]([c:10]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4](I)[cH:22][c:20]2[F:21])[c:18]([F:19])[c:16]([F:17])[cH:15][cH:14]1)=[O:12]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]([F:17])[c:18]2[F:19])[c:2... | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | 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 | O.CCO.[OH-].[Na+] | C-C Coupling | OtherReaction | 9844ab3c1e1bce74e59a0bb4609e30f2e92db385fb12d8c99463ca9efeaf158b | fe5f5a8472b016fdb14f74f8a0f437bcda3556c00d888a32c2afe280635279e6 | c1ccc(Nc2ccccc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])(-[CH2]-C-C-C)-[CH2]-C-C-C.C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].I-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | 77.2 | [{"value": 72.0, "product": "C(C=C)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "C(C=C)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Methyl 3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoate (1.00 g), 2.45 mmol) and (Ph3P)4Pd (568 mg, 0.49 mmol) were weighed into a dry flask which was fitted with a condensor and flushed with nitrogen. Dioxane (20 mL) and allyltributyltin (976 mg, 2.95 mmol) were added via syringe and the entire mixture heated at reflux... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Allyl.Tin | Carboxylic acid.Allyl | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.CCO.[OH-].[Na+] | null | 8 | C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.CCO.[OH-].[Na+]>C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bee613de47d04e23943809275f1c17bb | C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>C=CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | [Cl-].COC1=NC(=NC(=N1)OC)[N+]1(CCOCC1)C.NOCCO.C(C=C)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F.[Cl-].COC1=NC(=NC(=N1)OC)[N+]1(CCOCC1)C>>C(C=C)C1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F | O[C:11]([c:10]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([CH2:3][CH:2]=[CH2:1])[cH:26][c:24]2[F:25])[c:22]([F:23])[c:20]([F:21])[cH:19][cH:18]1)=[O:12].[NH2:13][O:14][CH2:15][CH2:16][OH:17]>>[CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][O:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20... | C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | C=CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | CO | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 88 | [{"value": 88.0, "product": "C(C=C)C1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "C(C=C)C1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 2-(4-Allyl-2-fluoroanilino)-3,4-difluorobenzoic acid (700 mg, 2.28 mmol) was dissolved in MeOH (20 mL) to which was added 2-(aminooxy)ethanol (263 mg, 3.42 mmol), followed by 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methymorpholinium chloride [DMT-MM, prepared according to the procedure of Kunishima et al [Tetrahedron, 5... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CO | null | 15 | C=CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>CO>C=CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-efdf57ef69424c9cb693f35b63f73eb8 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | [N-]1C=NC=C1.FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C)F.NOCCO.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(#C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F | O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([C:2]#[CH:1])[cH:25][c:23]2[F:24])[c:21]([F:22])[c:19]([F:20])[cH:18][cH:17]1)=[O:11].[NH2:12][O:13][CH2:14][CH2:15][OH:16]>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:2... | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 55.2 | [{"value": 55.0, "product": "C(#C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.2, "product": "C(#C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | The product of Example 1, Step C, 3,4-difluoro-2-[(4-ethynyl-2-fluorophenyl)amino]benzoic acid (349 mg, 1.20 mmol) was dissolved in dry THF (15 mL), to which was added carbonyldiimidazole (CDI) (389 mg, 2.40 mmol). Within 10 minutes, a bright yellow solution was obtained and conversion to the imidazolide was confirmed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 0.166667 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>C1CCOC1>C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-940f3b3425414b03972be03656888992 | C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | C(#C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F>>C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOCCO)C=CC(=C1F)F)F | [CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:22])[c:23]([F:24])[cH:25]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:22... | C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | [Pd] | CO.C1CCOC1 | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 14.8 | HOUR | A mixture of the product of Example 7A, 2-[(4-ethynyl-2-fluorophenyl)amino]-3,4-difluoro-N-(2-hydroxy-ethoxy)benzamide (11.0 g, 31.40 mmol), Pd—C (10%, 1.0 g) in THF (100 mL) and MeOH (100 mL) was subject to hydrogenation (25 psi) for 14.8 hrs (The reaction was followed by HPLC until all SM peak disappeared.). The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CO.C1CCOC1 | null | 14.8 | C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>[Pd].CO.C1CCOC1>CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1c05f4c5d514d3ca0e088de67bfd785 | C#C[Si](C)(C)C.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl>>C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCCO)C=CC(=C1F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCCO)C=CC(=C1F)F.C[Si](C)(C)C#C>>ClC1=C(C=CC(=C1)C#C[Si](C)(C)C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].I[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][O:17][CH2:18][CH2:19][OH:20])[cH:21][cH:22][c:23]([F:24])[c:25]2[F:26])[c:27]([Cl:28])[cH:29]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16]... | C#C[Si](C)(C)C.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)N(CC)CC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 76 | [{"value": 76.0, "product": "ClC1=C(C=CC(=C1)C#C[Si](C)(C)C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | The product of Example 2, Step C, 2-(2-chloro-4-iodo-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide (3.25 g, 6.93 mmol) and (trimethylsilyl)acetylene (1.10 mL, 7.78 mmol) were combined in triethylamine (17 mL). Dichlorobis(triphenylphosphine)-palladium(II) (0.120 g, 0.017 mol) and cuprous iodide (0.033 g, 0.1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)N(CC)CC | null | 0.333333 | C#C[Si](C)(C)C.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1Cl>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)N(CC)CC>C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abf0c5ff35c141c0a0a8eb3ff909fa59 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1>>C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | ClC1=C(C=CC(=C1)C#C[Si](C)(C)C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F.ClC1=C(C=CC(=C1)C#C[Si](C)(C)C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F.C(C)(=O)O.[F-].[Cs+]>>ClC1=C(C=CC(=C1)C#C)NC1=C(C(=O)NOCCO)C=CC(=C1F)F | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:22])[c:23]([Cl:24])[cH:25]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:... | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 | null | null | CO | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc(Nc2ccccc2)cc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | null | [] | null | null | 26 | HOUR | To a solution of the product of Example 8, Step A, 2-(2-Chloro-4-trimethylsilanylethynyl-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-benzamide (0.704 g, 1.60 mmol) in methanol (21 mL) was added acetic acid (0.1 mL) and cesium fluoride (0.600 g, 3.95 mmol). The resultant solution was stirred at ambient temperature. A... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 26 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1>CO>C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d409171efd4418290188d6fe86a4dd7 | C#CCN.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | C(C#C)N.FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)I)F>>NCC#CC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F | [NH2:1][CH2:2][C:3]#[CH:4].I[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20][c:21]([F:22])[c:23]2[F:24])[c:25]([F:26])[cH:27]1>>[NH2:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH:19][c... | C#CCN.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 100 | [{"value": 100.0, "product": "NCC#CC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by Sonogashira reaction of propargyl amine and 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide by the general procedure of Example 1, Step A. The orange oil resulting from workup was purified by chromatography on silica gel (10% MeOH/CH2Cl2 as eluant), to give... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | null | null | null | C#CCN.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ff016bab27144549569c92e42e28f21 | Nc1ccc(C#CCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F>>O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)C#CCOC1OCCCC1.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCOC1OCCCC1)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][O:26]2)[cH:27][c:28]1[F:29].F[c:11]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][c:7]([F:8])[c:9]1[F:10]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18... | Nc1ccc(C#CCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F | O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | C(#Cc1ccc(Nc2ccccc2)cc1)COC1CCCCO1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and 2-fluoro-4-[3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl]aniline were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, followed by purification by chromatography on silica gel (50% EtOAc/PE as eluant), 3,4-difluoro-2-{2-fluoro-4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CCOCC1 | HF | C1CCOC1 | null | null | Nc1ccc(C#CCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e3f5e894c964094bd2b7980d8d4d6f3 | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCOC1OCCCC1)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCOC1OCCCC1)F | [NH2:3][O:4][CH2:5][CH2:6][OH:7].O[C:2](=[O:1])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[C:22][CH2:23][O:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:30]2)[cH:31][c:32]1[F:33]>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:... | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C(#Cc1ccc(Nc2ccccc2)cc1)COC1CCCCO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 69 | [{"value": 69.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCOC1OCCCC1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of 3,4-difluoro-2-{2-fluoro-4-[3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl]anilino}benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E, then purified by column chromatography on silica gel (50% EtOAc/PE) as eluant), to give 3,4-difluor... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CCOCC1 | HO- | null | null | null | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-443998a5f675458886606cde78f87851 | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCOC1OCCCC1)F>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F | C1CCC([O:24][CH2:23][C:22]#[C:21][c:20]2[cH:19][cH:18][c:17]([NH:16][c:15]3[c:8]([C:2](=[O:1])[NH:3][O:4][CH2:5][CH2:6][OH:7])[cH:9][cH:10][c:11]([F:12])[c:13]3[F:14])[c:26]([F:27])[cH:25]2)OC1>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19... | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | null | Cl | O.CCO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccc(Nc2ccccc2)cc1 | [c:1]-[C:2]#[C:3]-[C:4]-[O;H0;D2;+0:5]-C1-C-C-C-C-O-1>>[OH;D1;+0:5]-[C:4]-[C:3]#[C:2]-[c:1] | 100 | [{"value": 100.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3,4-Difluoro-2-{2-fluoro-4-[3-(tetrahydro-2H-pyran-2-yloxy)-1-propynyl]anilino}-N-(2-hydroxyethoxy)benzamide (115 mg, 0.25 mmol) was dissolved in EtOH (4 mL) to which was added 1 M HCl (5 drops). This reaction mixture was stirred overnight at RT, then the mixture was diluted with water (50 mL) and extracted with EtOAc ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1ccccc1.c1ccccc1 | HO- | Cl.O.CCO | null | 8 | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCOC2CCCCO2)cc1F>Cl.O.CCO>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-17aba261fdd1485b9bacfe6e52bb4f75 | Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F>>O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)C#CCCOC1OCCCC1.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCCOC1OCCCC1)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]#[C:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:27]2)[cH:28][c:29]1[F:30].F[c:11]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][c:7]([F:8])[c:9]1[F:10]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]([C:1... | Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F | O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F | null | null | CCOCC.CCCCCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | C(#Cc1ccc(Nc2ccccc2)cc1)CCOC1CCCCO1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | null | [] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and 2-fluoro-4-[4-(tetrahydro-2H-pyran-2-yloxy)-1-butynyl]aniline were reacted in the presence of LiHMDS solution by the general procedure of Example 1, Step B. After workup, followed by purification by column chromatography on silica gel (50% EtOAc as eluant), unreacted aniline (26%), follo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CCOCC1 | HF | CCOCC.CCCCCC | null | null | Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(O)c1ccc(F)c(F)c1F>CCOCC.CCCCCC>O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56cd40aec004470d9237abd900b00daa | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(n1ccnc1)n1ccnc1>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCCOC1OCCCC1)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCCO)F.FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCCOC1OCCCC1)F | [NH2:31][O:32][CH2:33][CH2:34][OH:35].[O:1]=[C:2]([OH:4])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[C:22][CH2:23][CH2:24][O:25][CH:54]2[CH2:55][CH2:56][CH2:57][CH2:58][O:59]2)[cH:26][c:27]1[F:28].n1[cH:5][cH:43][n:44]([C:30]([n:3]2[cH:41]n[cH:48][cH:49]2)=[O:29])[cH... | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(n1ccnc1)n1ccnc1 | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F | null | null | null | Acylation | OtherReaction | 5fb95cee82a26dfaba6e7018d41e90867d30bb3af34775da82469a1c8bbc056d | 6d390f3343af917fc24ba1a240c9ee274754782a0537624e103b6f40d10d3dce | C(#Cc1ccc(Nc2ccccc2)cc1)CCOC1CCCCO1.c1ccc(Nc2ccccc2)cc1 | [C:1]#[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-[CH;D3;+0:6](-[#8:7]-[C:8])-[C:9]-[C:10].[O;D1;H0:11]=[C;H0;D3;+0:12](-[OH;D1;+0:13])-[c:14](:[c:15]):[c:16].[C:17]-[#8:18]-[NH2;D1;+0:19].[O;D1;H0:20]=[C;H0;D3;+0:21](-[n;H0;D3;+0:22]1:[cH;D2;+0:23]:n:[cH;D2;+0:24]:[cH;D2;+0:25]:1)-[n;H0;D3;+0:26]1:[cH;D2;+0:27]:[cH;D2;+0:28]:n:[... | null | [] | null | null | null | null | The title compound was prepared by reaction of 3,4-difluoro-2-{2-fluoro-4-[4-(tetrahydro-2H-pyran-2-yloxy)-1-butynyl]anilino}benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E, then purified by column chromatography on silica gel (50% EtOAc/PE as eluant) to give 3,4-difluoro-2-{... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Secondary amide.Secondary amide.Primary alcohol.Primary alcohol.Secondary amine.Alkyne | C1CCOCC1.c1c[nH]cn1.c1c[nH]cn1 | c1ccccc1.c1ccccc1.C1CCOCC1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCOCC1 | null | null | null | null | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F.O=C(n1ccnc1)n1ccnc1>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCOC2CCCCO2)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2309c2bbab4d4155a5295bdf10122a8d | C#CC(C)(C)O.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)I)F.CC(C)(C#C)O>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(C)(C)O)F | [CH3:1][C:2]([CH3:3])([OH:4])[C:5]#[CH:6].I[c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][O:17][CH2:18][CH2:19][OH:20])[cH:21][cH:22][c:23]([F:24])[c:25]2[F:26])[c:27]([F:28])[cH:29]1>>[CH3:1][C:2]([CH3:3])([OH:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][O:17... | C#CC(C)(C)O.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | [Cu]I | CCOCC.CO | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 97 | [{"value": 97.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(C)(C)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide, which can be prepared according to the procedure in PCT Publication No. WO 00/41505, and 2-methyl-3-butyn-2-ol were reacted in the presence of CuI and (PhP3)2Cl2 by the general procedure of Example 1, Step A, and the mixture stirred at RT for 4 h. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | [Cu]I.CCOCC.CO | null | 4 | C#CC(C)(C)O.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>[Cu]I.CCOCC.CO>CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93773aa78aea4709b88b8a4e3c2a60c6 | C#CC(C)(O)CC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)I)F.CC(C#C)(CC)O>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(CC)(C)O)F | [CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[C:6]#[CH:7].I[c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[c:14]([C:15](=[O:16])[NH:17][O:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23][c:24]([F:25])[c:26]2[F:27])[c:28]([F:29])[cH:30]1>>[CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[C:6]#[C:7][c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[c:14]([C:15](=[O:... | C#CC(C)(O)CC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | [Cu]I | CCOCC.CO | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 77 | [{"value": 77.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(CC)(C)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide which can be prepared according to the procedure in PCT Publication No. WO 00/41505, and 3-methyl-1-pentyn-3-ol were reacted in the presence of CuI and (PhP3)2PdCl2 by the general procedure of Example 1, Step A, and the mixture stirred at RT for 4 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | [Cu]I.CCOCC.CO | null | 4 | C#CC(C)(O)CC.O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>[Cu]I.CCOCC.CO>CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-703e0c7bf0ba48d2916d2a4a288c816a | NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>>NCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | NCC#CC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F>>NCCCC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F | [NH2:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH:19][cH:20][c:21]([F:22])[c:23]2[F:24])[c:25]([F:26])[cH:27]1>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH:19][c... | NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | NCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | [Pd].CCO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [N;D1;H2:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H2:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 46 | [{"value": 46.0, "product": "NCCCC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 9, 2-[4-(3-amino-1-propynyl)-2-fluoroanilino]-3,4-difluoro-N-(2-hydroxyethoxy)benzamide was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the general procedure of Example 1, Step D. Purification of the resulting oil was carried out by column chromatography on silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CCO | null | null | NCC#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>[Pd].CCO>NCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d3cfd5131e3410bbcdb5fd0eff6d6d5 | C#CCO.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | C(C#C)O.FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)I)F>>FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F | [CH:18]#[C:19][CH2:20][OH:21].I[c:17]1[cH:16][cH:15][c:14]([NH:13][c:12]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([F:9])[c:10]2[F:11])[c:23]([F:24])[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[c:12]1[NH:13][c:14]1[cH:15][cH:16][c:17]([C:18]#[C:19][CH2:20][OH:21])[cH:22][c:23]... | C#CCO.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F | COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | null | null | null | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(Nc2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 94 | [{"value": 94.0, "product": "FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by Sonogashira reaction of propargyl alcohol and methyl 3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoate by the general procedure of Example 1, Step A. The oil resulting from workup was purified by chromatography on silica gel (20% EtOAc/PE as eluant), to give methyl 3,4-difluoro-2-[2-flu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HI | null | null | null | C#CCO.COC(=O)c1ccc(F)c(F)c1Nc1ccc(I)cc1F>>COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2fd9b05bc69478ca881d4e35f1b42be | COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F>>COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F>>FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)CCCO)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[c:12]1[NH:13][c:14]1[cH:15][cH:16][c:17]([C:18]#[C:19][CH2:20][OH:21])[cH:22][c:23]1[F:24]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[c:12]1[NH:13][c:14]1[cH:15][cH:16][c:17]([CH2:18][CH2:19][CH2:20][OH:21])[cH:22][c:23]1[... | COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | null | null | [Pd].CCO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [O;D1;H1:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H1:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 93 | [{"value": 93.0, "product": "FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)CCCO)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]benzoate was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the general procedure of Example 1, Step D. Purification of the resulting oil was carried out by column chromatography on silica gel (20% EtOAc/PE as eluant) to give met... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CCO | null | null | COC(=O)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F>[Pd].CCO>COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b48c2cfe1c3e42d2a0c217f5c156ec51 | C=COCCON.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F>>C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCCO)F.NOCCOC=C.C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]>>FC=1C(=C(C(=O)NOCCOC=C)C=CC1F)NC1=C(C=C(C=C1)CCCO)F | [CH2:1]=[CH:2][O:3][CH2:4][CH2:5][O:6][NH2:7].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[c:17]1[NH:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][CH2:24][CH2:25][OH:26])[cH:27][c:28]1[F:29]>>[CH2:1]=[CH:2][O:3][CH2:4][CH2:5][O:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([F:16])[c:17]1[N... | C=COCCON.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 46 | [{"value": 46.0, "product": "FC=1C(=C(C(=O)NOCCOC=C)C=CC1F)NC1=C(C=C(C=C1)CCCO)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]benzoic acid with 1-[2-(aminooxy)ethoxy]ethylene and DMT-MM by the general procedure of Example 6, Step B, then purified by column chromatography on silica gel (20% EtOAc/PE as eluant) to give 3,4-difluoro-2-[2-fluoro-4... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | C=COCCON.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F>>C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a17282e9a7c047d2bd19b7693a12a426 | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CNC>>CN(C)CCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | C(=O)([O-])[O-].[K+].[K+].CNC.Cl.[Na+].[Cl-].FC=1C(=C(C(=O)NOCCOC=C)C=CC1F)NC1=C(C=C(C=C1)CCCI)F>>CN(CCCC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F)C | C=C[O:20][CH2:19][CH2:18][O:17][NH:16][C:14]([c:13]1[c:12]([NH:11][c:10]2[cH:9][cH:8][c:7]([CH2:6][CH2:5][CH2:4]I)[cH:29][c:27]2[F:28])[c:25]([F:26])[c:23]([F:24])[cH:22][cH:21]1)=[O:15].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][... | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CNC | CN(C)CCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | O.CC(=O)N(C)C.CCO | Heteroatom Alkylation and Arylation | OtherReaction | ec14f640305641a4a365da0f794c766899026d32803845716c9aad4957b3e910 | 7b457ef06260012b6a578b0b100111ddb70017121857acb4be1c04046ed64590 | c1ccc(Nc2ccccc2)cc1 | C=C-[O;H0;D2;+0:1]-[C:2]-[C:3].I-[CH2;D2;+0:4]-[C:5]-[C:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C:6]-[C:5]-[CH2;D2;+0:4]-[N;H0;D3;+0:8](-[C;D1;H3:7])-[C;D1;H3:9].[C:3]-[C:2]-[OH;D1;+0:1] | 36 | [{"value": 36.0, "product": "CN(CCCC1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | 3,4-Difluoro-2-[2-fluoro-4-(3-iodopropyl)anilino]-N-[2-(vinyloxy)ethoxy]benzamide (200 mg, 0.39 mmol) was dissolved in DMA (10 mL), to which was added dimethylamine (0.15 mL of a 40% solution in water). This mixture was stirred at RT for 15 hours, then the DMA removed under reduced pressure, affording a yellow oil. Thi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amine.Vinyl | Primary alcohol.Tertiary amine | null | null | c1ccccc1.c1ccccc1 | HI | O.CC(=O)N(C)C.CCO | null | 15 | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CNC>O.CC(=O)N(C)C.CCO>CN(C)CCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25003a94f8114147ba64c74b46faf942 | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CN>>CNCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCOC=C)C=CC1F)NC1=C(C=C(C=C1)CCCI)F.CN>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCNC)F | C=C[O:19][CH2:18][CH2:17][O:16][NH:15][C:13]([c:12]1[c:11]([NH:10][c:9]2[cH:8][cH:7][c:6]([CH2:5][CH2:4][CH2:3]I)[cH:28][c:26]2[F:27])[c:24]([F:25])[c:22]([F:23])[cH:21][cH:20]1)=[O:14].[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13](=[O:14])[NH:15][O:16][CH2:17][CH... | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CN | CNCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e35ad961f1e6d9861787b321abc3cacad15211219fc7a442b2c63e9cc68174b1 | e6f261fd8878f8a8d14bee33bef7e6af925a72342ff9d3817ff3eacc59eda654 | c1ccc(Nc2ccccc2)cc1 | C=C-[O;H0;D2;+0:1]-[C:2]-[C:3].I-[CH2;D2;+0:4]-[C:5]-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:6]-[C:5]-[CH2;D2;+0:4]-[NH;D2;+0:8]-[C;D1;H3:7].[C:3]-[C:2]-[OH;D1;+0:1] | 32 | [{"value": 32.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCNC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 15, Step E, 3,4-Difluoro-2-[2-fluoro-4-(3-iodopropyl)anilino]-N-[2-(vinyloxy)ethoxy]benzamide was reacted with methylamine and then deprotected according to the general procedure of Example 15, Step F, to afford 3,4-difluoro-2-{2-fluoro-4-[3-(methylamino)propyl] anilino}-N-(2-hydroxyethoxy)benzam... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine.Vinyl | Primary alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1 | HI | null | null | null | C=COCCONC(=O)c1ccc(F)c(F)c1Nc1ccc(CCCI)cc1F.CN>>CNCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85064afb2c2d4ee08e4b9df3eb3468d1 | COC(=O)c1ccc(N)cc1.O=C(O)c1ccc(F)c(F)c1F>>COC(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)cc1 | FC1=C(C(=O)O)C=CC(=C1F)F.NC1=CC=C(C(=O)OC)C=C1.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=CC=C(C=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:21][cH:22]1.F[c:10]1[c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16][c:17]([F:18])[c:19]1[F:20]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16][c:17]([F:18])[c:19]2[F:20])[cH:21][cH:22]1 | COC(=O)c1ccc(N)cc1.O=C(O)c1ccc(F)c(F)c1F | COC(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | null | [] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and methyl 4-aminobenzoate were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B, to afford after workup, crude 3,4-difluoro-2-[[4-(methoxycarbonyl)-phenyl]amino]benzoic acid as a cream solid. This material was then coupled directly with 2-(amin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | COC(=O)c1ccc(N)cc1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>COC(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d18dcc7634a42be912c43fc3087cdf0 | COC(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1>>O=C(O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1 | Cl.FC1=C(C(=CC=C1F)C(=O)NOCCO)NC1=CC=C(C(=O)OC)C=C1.[OH-].[Na+]>>FC1=C(C(=CC=C1F)C(=O)NOCCO)NC1=CC=C(C(=O)O)C=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][O:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20]([F:21])[c:22]2[F:23])[cH:24][cH:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][O:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20]([F:21])[c:22... | COC(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1 | O=C(O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1 | null | null | C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 57 | [{"value": 57.0, "product": "FC1=C(C(=CC=C1F)C(=O)NOCCO)NC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "FC1=C(C(=CC=C1F)C(=O)NOCCO)NC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | The product of Example 17, Step A, methyl 4-[[2,3-difluoro-6-[[(2-hydroxyethoxy)amino]carbonyl]phenyl]amino]benzoate (306 mg, 0.84 mmol) was dissolved in ethanol (40 mL), to which was added 1 M NaOH solution (40 mL). This mixture was stirred at room temperature for 15 hours, then poured into 1 M HCl solution (100 mL). ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | null | 15 | COC(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1>C(C)O>O=C(O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84f9ed7f26984a379b554b4c90bb3f70 | O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CO)cc1 | Cl.FC1=C(C(=CC=C1F)C(=O)NOCCO)NC1=CC=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=C1.[BH4-].[Na+]>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=CC=C(C=C1)CO | Fc1c(F)c(F)c(O[C:21]([c:20]2[cH:19][cH:18][c:17]([NH:16][c:15]3[c:8]([C:2](=[O:1])[NH:3][O:4][CH2:5][CH2:6][OH:7])[cH:9][cH:10][c:11]([F:12])[c:13]3[F:14])[cH:24][cH:23]2)=[O:22])c(F)c1F>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]... | O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1 | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CO)cc1 | null | null | O.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | b575eec76a4c9ad8acb617ea1e7a79320fb3fbdc661ff7c5ebff9aea18f305c7 | b3072e135d22925398f326e6f6481a4c91699920b3f0efb5c65dcb31aeadb549 | c1ccc(Nc2ccccc2)cc1 | F-c1:c(-F):c(-F):c(-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]):c(-F):c:1-F>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 37 | [{"value": 37.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=CC=C(C=C1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.7, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=CC=C(C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The product of Example 17, Step C, 2,3,4,5,6-pentafluorophenyl 4-[[2,3-difluoro-6-[[(2-hydroxyethoxy)amino]carbonyl]phenyl]amino]benzoate (150 mg, 0.29 mmol) was dissolved in THF (2 mL), then added dropwise to a solution of NaBH4 (110 mg, 2.90 mmol) in water (2 mL). This mixture was stirred at room temperature for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester | Primary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | O.C1CCOC1 | null | 2 | O=C(Oc1c(F)c(F)c(F)c(F)c1F)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)cc1>O.C1CCOC1>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CO)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a93240bc8b454d4bb2f7365f9cfe6b9f | COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F>>O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | FC=1C(=C(C(=O)OC)C=CC1F)NC1=C(C=C(C=C1)CCO)F>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCO)F | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][OH:19])[cH:20][c:21]1[F:22]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][OH:19])[cH:20][c:21]1[F:22] | COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | null | null | CCO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 93 | [{"value": 93.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCO)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 3,4-difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoate was deprotected using EtOH/1 M NaOH as above to afford 3,4-difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoic acid as a crystalline cream solid (93%); m.p. (EtOAc/hexane) 196–200° C. 1H NMR [400 MHz, (CD3)2SO] δ 13.67 (v br s, 1 H), 9.28 (br s, 1 H)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | CCO | null | null | COC(=O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F>CCO>O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f15fc43c037f4f37b8ec705d194eed15 | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCO)F.NOCCO.C[N+]1(CCOCC1)C2=NC(=NC(=N2)OC)OC.[Cl-]>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCO)F | [NH2:3][O:4][CH2:5][CH2:6][OH:7].O[C:2](=[O:1])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([CH2:21][CH2:22][OH:23])[cH:24][c:25]1[F:26]>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([CH2:... | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F | null | null | CO | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 57 | [{"value": 57.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,4-Difluoro-2-[2-fluoro-4-(2-hydroxyethyl)anilino]benzoic acid was dissolved in MeOH and prepared from reaction with 2(aminooxy)ethanol and DMT-MM by the general procedure of Example 6, Step B, affording a crude yellow oil after workup which was purified by filtration through a plug of silica gel (100% EtOAc as eluant... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CO | null | null | NOCCO.O=C(O)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F>CO>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac5dfe3769464fd4a6214661ea172ebc | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCO)F>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCO)F | [O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[C:22][CH2:23][OH:24])[cH:25][c:26]1[F:27]>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([CH... | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F | null | [Pd] | CCO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [O;D1;H1:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[O;D1;H1:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 73 | [{"value": 73.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 10, Step D, 3,4-Difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]-N-(2-hydroxyethoxy)-benzamide was hydrogenated in absolute EtOH in the presence of 5% Pd/C by the procedure of Example 1, Step D. An off-white solid was isolated which was purified by filtration through a plug of silica gel (Et... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CCO | null | null | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCO)cc1F>[Pd].CCO>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3eb01a097864b2887c7d147dccbe10d | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F>>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCCO)cc1F | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CCCO)F>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCCO)F | [O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c:20]([C:21]#[C:22][CH2:23][CH2:24][OH:25])[cH:26][c:27]1[F:28]>>[O:1]=[C:2]([NH:3][O:4][CH2:5][CH2:6][OH:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][c... | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCCO)cc1F | null | [Pd] | CCO | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 46 | [{"value": 46.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCCO)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 11, 3,4-Difluoro-2-[2-fluoro-4-(4-hydroxy-1-butynyl)anilino]-N-(2-hydroxyethoxy)-benzamide was hydrogenated in absolute EtOH in the presence of 5% Pd/C by the procedure of Example 1, Step D. Purification of the resulting oil was carried out by filtration through a plug of silica gel (EtOAc as elu... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].CCO | null | null | O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(C#CCCO)cc1F>[Pd].CCO>O=C(NOCCO)c1ccc(F)c(F)c1Nc1ccc(CCCCO)cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96917a0bbab24ac9829bc12390da4106 | CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>>CC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(C)(C)O)F>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCC(C)(C)O)F | [CH3:1][C:2]([CH3:3])([OH:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][O:17][CH2:18][CH2:19][OH:20])[cH:21][cH:22][c:23]([F:24])[c:25]2[F:26])[c:27]([F:28])[cH:29]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[NH:16][O:17... | CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | CC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | [Pd] | C(C)O | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[C;H0;D2;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99 | [{"value": 99.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCC(C)(C)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 12, 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-butynyl)anilino]-N-(2-hydroxyethoxy)benzamide was hydrogenated in absolute ethanol in the presence of 5% Pd/C by the general procedure of Example 1, Step D. The resulting crude solid was purified by filtration through a plug of silica (MeOH as ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)O | null | null | CC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>[Pd].C(C)O>CC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4595e47307364b58b48b58bd2015dbac | CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>>CCC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)C#CC(CC)(C)O)F>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCC(CC)(C)O)F | [CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[C:6]#[C:7][c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[c:14]([C:15](=[O:16])[NH:17][O:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23][c:24]([F:25])[c:26]2[F:27])[c:28]([F:29])[cH:30]1>>[CH3:1][CH2:2][C:3]([CH3:4])([OH:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[c:14]([C:15](=[O:... | CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | CCC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | [Pd] | C(C)O | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[C;H0;D2;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2](-[C;D1;H3:3])(-[O;D1;H1:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | 98 | [{"value": 98.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCC(CC)(C)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 13, 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-3-methyl-1-pentynyl)anilino]-N-(2-hydroxyethoxy)benzamide was hydrogenated in absolute ethanol in the presence of 5% Pd/C by the general procedure of Example 1, Step D. The resulting crude solid was purified by filtration through a plug of silica (MeOH as... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)O | null | null | CCC(C)(O)C#Cc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1>[Pd].C(C)O>CCC(C)(O)CCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c439634243f14a188004ab61d850db02 | COCC#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)C#CCOC.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCOC)F | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[c:22]([F:23])[cH:24]1.F[c:11]1[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]([F:19])[c:20]1[F:21]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]([F:19])[c:20]2[F:21])[c:22]([F:23]... | COCC#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | null | [] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and the product of Example 25, Step A, 2-fluoro-4-(3-methoxy-1-propynyl)aniline, were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, followed by purification by chromatography on silica gel (10% EtOAc/hexanes as eluant), 3,4-dif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | COCC#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4eaf013c6c34739bc3f9746bb483624 | COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#CCOC)F>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCCOC)F | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]([F:19])[c:20]2[F:21])[c:22]([F:23])[cH:24]1>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]([F:19])[c:20]2[F:21])[c:22]([F:23]... | COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | [Pd] | C(C)O | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1ccc(Nc2ccccc2)cc1 | [#8:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 65 | [{"value": 65.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCCOC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 25, Step B, 3,4-difluoro-2-[[2-fluoro-4-(3-methoxy-1-propynyl)phenyl]amino]benzoic acid, was hydrogenated in absolute ethanol in the presence of 5% Pd/C as above in Example 1, Step D. The resulting crude solid was purified by filtration through a plug of silica gel (50% EtOAc/hexanes as eluant) t... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)O | null | null | COCC#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>[Pd].C(C)O>COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21ffa39c779d46b29f1fddda419cf3ee | COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>COCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)CCCOC)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCOC)F | O[C:13]([c:12]1[c:11]([NH:10][c:9]2[cH:8][cH:7][c:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[cH:28][c:26]2[F:27])[c:24]([F:25])[c:22]([F:23])[cH:21][cH:20]1)=[O:14].[NH2:15][O:16][CH2:17][CH2:18][OH:19]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[c:12]([C:13](=[O:14])[NH:15][O:16][CH2:17][CH2:18... | COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | COCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 69 | [{"value": 69.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)CCCOC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of the product of Example 25, Step C, 3,4-difluoro-2-[[2-fluoro-4-(3-methoxypropyl)phenyl]amino]benzoic acid with CDI and 2-(aminooxy)ethanol, by the general procedure of Example 1, Step E, then purified by flash column chromatography on silica gel (50% EtOAc/hexanes) to gi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>COCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d5a5d07896b4feea0298b3cb0ee8fb8 | N#C[S-].Nc1ccccc1F>>N#CSc1ccc(N)c(F)c1 | C(=O)([O-])[O-].[Na+].[Na+].BrBr.FC1=C(N)C=CC=C1.[S-]C#N.[K+]>>NC1=C(C=C(C=C1)SC#N)F | [N:1]#[C:2][S-:3].[cH:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11]1>>[N:1]#[C:2][S:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11]1 | N#C[S-].Nc1ccccc1F | N#CSc1ccc(N)c(F)c1 | null | null | O.[Br-].[Na+].CO | Heteroatom Alkylation and Arylation | OtherReaction | 29d483be92b78aea9894649c5ff004e9773d34416f95eeab1829acdbdeaacc59 | 21e67be598c63344ea1fea503581f1ce4855b092ed4079749b71ebb3b04166d6 | c1ccccc1 | [N;D1;H0:1]#[C:2]-[S-;H0;D1:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[N;D1;H0:1]#[C:2]-[S;H0;D2;+0:3]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:5]:[c:4] | 53 | [{"value": 53.0, "product": "NC1=C(C=C(C=C1)SC#N)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "NC1=C(C=C(C=C1)SC#N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of bromine (3.02 g, 18.9 mmol) in sodium bromide-saturated methanol (11 mL) was added dropwise to a solution of 2-fluoroaniline (2.00 g, 18.0 mmol) and potassium thiocyanate (5.25 g, 54.0 mmol) in methanol (45 mL). The mixture was stirred for 0.5 hours, at room temperature, poured into water (300 mL) and mad... | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O.[Br-].[Na+].CO | null | 0.5 | N#C[S-].Nc1ccccc1F>O.[Br-].[Na+].CO>N#CSc1ccc(N)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-627d2afbdee44368942c36f3c6bcaed6 | CI.N#CSc1ccc(N)c(F)c1>>CSc1ccc(N)c(F)c1 | CI.NC1=C(C=C(C=C1)SC#N)F.NC1=C(C=C(C=C1)SC#N)F.O.[S-2].[Na+].[Na+]>>FC1=C(N)C=CC(=C1)SC | I[CH3:1].N#C[S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([F:9])[cH:10]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([F:9])[cH:10]1 | CI.N#CSc1ccc(N)c(F)c1 | CSc1ccc(N)c(F)c1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 814eda62f542c6c8a8489fc07e9c3a90fd7f13ede724ebe06dfb3edcf3916fdf | 811ffad760b193ef7d543b0a95fb44c366861bf32d67304b457c7f95b7fc4f13 | c1ccccc1 | I-[CH3;D1;+0:1].N#C-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 87 | [{"value": 87.0, "product": "FC1=C(N)C=CC(=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | A solution of the product of Example 26, Step A, 4-amino-3-fluorophenyl thiocyanate (500 mg, 2.97 mmol), in ethanol (7.5 mL) was added to a solution of sodium sulfide monohydrate (714 mg, 2.97 mmol) in water (1.5 mL) and the mixture heated at 50° C. for 2 hours. Methyl iodide (464 mg, 3.27 mmol) in ethanol (0.5 mL) was... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Monosulfide | Monosulfide | null | null | c1ccccc1 | I- | O.C(C)O | 50 | 4 | CI.N#CSc1ccc(N)c(F)c1>O.C(C)O>CSc1ccc(N)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32e71b0cf85c4ae48b219b6ae0e5c41b | CSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)SC.FC1=C(N)C=CC(=C1)SC.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SC)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:19]([F:20])[cH:21]1.F[c:8]1[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]1[F:18]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1 | CSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9] | 52 | [{"value": 52.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and the product of Example 26, Step B, 2-fluoro-4-methylthioaniline, were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, this material was purified by dry flash column chromatography on silica (0.5% Et2O in 1:1 CH2Cl2/hexanes as... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | CSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32b5d7eabf2d45a28e6a0c51f337a23b | CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SC)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)SC)F | O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:25][c:23]2[F:24])[c:21]([F:22])[c:19]([F:20])[cH:18][cH:17]1)=[O:11].[NH2:12][O:13][CH2:14][CH2:15][OH:16]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]2[F:2... | CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | CSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 80 | [{"value": 80.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)SC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of the product of Example 26, Step C, 3,4-difluoro-2-[[2-fluoro-4-(methylthio)phenyl]amino]benzoic acid, with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E. Then, after workup, the crude solid triturated with Et2O and washed with pentane to affor... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0951191161c74f289d2fe6513a0f5e04 | CCI.N#CSc1ccc(N)c(F)c1>>CCSc1ccc(N)c(F)c1 | C(C)I.NC1=C(C=C(C=C1)SC#N)F.NC1=C(C=C(C=C1)SC#N)F>>FC1=C(N)C=CC(=C1)SCC | I[CH2:2][CH3:1].N#C[S:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11]1>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:9]([F:10])[cH:11]1 | CCI.N#CSc1ccc(N)c(F)c1 | CCSc1ccc(N)c(F)c1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 7a537837424ff035199d862c139991b73a0343ed1d8917ad14792f97a1d81ece | d9ceb7062b176f3e6428d11b6c9b4fb9a42d21fd0f34ba5ae00249f992efd6c5 | c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].N#C-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 92 | [{"value": 92.0, "product": "FC1=C(N)C=CC(=C1)SCC", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | A solution of the product of Example 26, Step A, 4-amino-3-fluorophenyl thiocyanate (500 mg, 2.97 mmol), in ethanol (7 mL) was added dropwise to a solution of Na2S.9H2O (714 mg, 2.97 mmol) in water (1.5 mL) and the resulting mixture stirred at 50° C. for 1 hour. A solution of ethyl iodide (510 mg, 3.27 mmol) in ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile.Monosulfide | Monosulfide | null | null | c1ccccc1 | I- | O.C(C)O | 50 | 1 | CCI.N#CSc1ccc(N)c(F)c1>O.C(C)O>CCSc1ccc(N)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abfaeb570e064d149175c8c236dc2def | CCSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1F)F.FC1=C(N)C=CC(=C1)SCC.FC1=C(N)C=CC(=C1)SCC.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SCC)F | [CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:20]([F:21])[cH:22]1.F[c:9]1[c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]([F:17])[c:18]2[F:19])[c:20]([F:21])[cH:22]1 | CCSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | 55 | [{"value": 55.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SCC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and the product of Example 27, Step A, 2-fluoro-4-ethylthioaniline, were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, a yellow solid was obtained which was purified by dry flash column chromatography on silica (0.5% Et2O in 1:... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | CCSc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cafa73904e494338b7ca5974bfa59ba8 | CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CCSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)SCC)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)SCC)F | O[C:11]([c:10]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([S:3][CH2:2][CH3:1])[cH:26][c:24]2[F:25])[c:22]([F:23])[c:20]([F:21])[cH:19][cH:18]1)=[O:12].[NH2:13][O:14][CH2:15][CH2:16][OH:17]>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[c:10]([C:11](=[O:12])[NH:13][O:14][CH2:15][CH2:16][OH:17])[cH:18][cH:19][c:20]([F... | CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | CCSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65 | [{"value": 65.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)SCC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of the product of Example 27, Step B, 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E. Then, after workup, the crude solid triturated with Et2O and washed with pentane to afford ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCSc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CCSc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1b37f0aa5984735a6aee631497d85bc | CS(=O)(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CS(=O)(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)S(=O)(=O)C)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)S(=O)(=O)C)F | O[C:12]([c:11]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:27][c:25]2[F:26])[c:23]([F:24])[c:21]([F:22])[cH:20][cH:19]1)=[O:13].[NH2:14][O:15][CH2:16][CH2:17][OH:18]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH... | CS(=O)(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | CS(=O)(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 52 | [{"value": 52.0, "product": "FC=1C(=C(C(=O)NOCCO)C=CC1F)NC1=C(C=C(C=C1)S(=O)(=O)C)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of the product of Example 28, Step A, 3,4-difluoro-2-[[2-fluoro-4-(methylsulfonyl)phenyl]amino]benzoic acid, with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E. Then, after workup, the crude solid purified by dry flash column chromatography on si... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CS(=O)(=O)c1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CS(=O)(=O)c1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4c682bcb2c3452aabe8dcc2de953953 | Nc1ccc(I)cc1F.[Li][CH2]CCC>>CCCCc1ccc(N)c(F)c1 | [Li]CCCC.FC1=C(N)C=CC(=C1)I>>C(CCC)C1=CC(=C(N)C=C1)F | I[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([F:11])[cH:12]1.[Li][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([F:11])[cH:12]1 | Nc1ccc(I)cc1F.[Li][CH2]CCC | CCCCc1ccc(N)c(F)c1 | 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.[Cl-].[Cl-].[Zn+2] | C1CCOC1 | C-C Coupling | Reaction of alkyl halides with organometallic coumpounds | 0066f9b754d2f38fc3a3e00bd00efaa68e272a14d59eb48de899b8731ef9f439 | 191bc7600fa9483952eddd0040b2b21cf731d54d9c6629540e93105469ea07da | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[Li]>>[C:6]-[C:7]-[CH2;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 30 | [{"value": 30.0, "product": "C(CCC)C1=CC(=C(N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.1, "product": "C(CCC)C1=CC(=C(N)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | ZnCl2 (5.17 g, 38.0 mmol) was weighed into a flask, which was then flame dried and flushed with N2. Anhydrous THF (20 ml) was then added at 0° C., followed by 2.5 M nBuLi (15.2 ml, 38.0 mmol). The reaction mixture was stirred at 0° C. for 15 min, after which 2-fluoro-4-iodoaniline (3.00 g, 12.7 mmol) in anhydrous THF (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyl lithium | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | I-.Li | 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.[Cl-].[Cl-].[Zn+2].C1CCOC1 | 0 | 0.25 | Nc1ccc(I)cc1F.[Li][CH2]CCC>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.[Cl-].[Cl-].[Zn+2].C1CCOC1>CCCCc1ccc(N)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6599587cad34dc3995cc971754ba0f6 | CCCCc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1F)F.C(CCC)C1=CC(=C(N)C=C1)F.[Li+].C[Si](C)(C)[N-][Si](C)(C)C>>C(CCC)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:21]([F:22])[cH:23]1.F[c:10]1[c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16][c:17]([F:18])[c:19]1[F:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[OH:14])[cH:15][cH:16][c:17]([F:18])[c:19]2[F:20])[c:21]([F:22])[cH:2... | CCCCc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | 40 | [{"value": 40.0, "product": "C(CCC)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluorobenzoic acid and 4-butyl-2-fluoroaniline were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B, affording crude 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid after workup. The crude material was further purified by flash chromatography on silica (10% ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | null | null | CCCCc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6315cdb1a03b4202a2e59ded1d397c50 | CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | C(CCC)C1=CC(=C(NC2=C(C(=O)O)C=CC(=C2F)F)C=C1)F.C1=CN(C=N1)C(=O)N2C=CN=C2.NOCCO>>C(CCC)C1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F | O[C:12]([c:11]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[cH:27][c:25]2[F:26])[c:23]([F:24])[c:21]([F:22])[cH:20][cH:19]1)=[O:13].[NH2:14][O:15][CH2:16][CH2:17][OH:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[c:11]([C:12](=[O:13])[NH:14][O:15][CH2:16][CH2:17][OH:18])[cH... | CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO | CCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 68 | [{"value": 68.0, "product": "C(CCC)C1=CC(=C(NC2=C(C(=O)NOCCO)C=CC(=C2F)F)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from reaction of 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid with CDI and 2-(aminooxy)ethanol by the general procedure of Example 1, Step E, then purified by flash column chromatography on silica (50% EtOAc/Hexane as eluant) to give 2-(4-butyl-2-fluoroanilino)-3,4-difluoro-N-(2-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCCCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1.NOCCO>>CCCCc1ccc(Nc2c(C(=O)NOCCO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-34126a20ba3d4ddfa296dac0bad17c99 | COC(C)(C)OC.COC(C)(C)OC.OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>CC1(C)OC[C@H]([C@@H](O)[C@H](O)[C@H]2COC(C)(C)O2)O1 | C([O-])(O)=O.[Na+].C([C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)O.O1CCCC1.COC(C)(C)OC.COC(C)(C)OC>>CC1(OC[C@@H](O1)[C@H]([C@@H]([C@H]2COC(O2)(C)C)O)O)C | CO[C:2](OC)([CH3:1])[CH3:3].CO[C:14](OC)([CH3:15])[CH3:16].[OH:4][CH2:5][C@H:6]([C@@H:7]([OH:8])[C@H:9]([OH:10])[C@@H:11]([CH2:12][OH:13])[OH:17])[OH:18]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([C@@H:7]([OH:8])[C@H:9]([OH:10])[C@H:11]2[CH2:12][O:13][C:14]([CH3:15])([CH3:16])[O:17]2)[O:18]1 | COC(C)(C)OC.COC(C)(C)OC.OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | CC1(C)OC[C@H]([C@@H](O)[C@H](O)[C@H]2COC(C)(C)O2)O1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0831c7a204680ca83961aa9a34164020828b2a20dbbfc68e726a72ec22e7e46c | 12d66e1e985804ee9752178b3b686e5b66d21e9126fae4c7a6d479ea827147a5 | C1OC[C@H](CC[C@H]2COCO2)O1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.C-O-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[C;D1;H3:6])-O-C.[OH;D1;+0:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]-[C:12]-[C:13](-[OH;D1;+0:14])-[C:15]-[OH;D1;+0:16]>>[C;D1;H3:5]-[C;H0;D4;+0:4]1(-[C;D1;H3:6])-[O;H0;D2;+0:7]-[C:8]-[C:9](-[C:11]-[C:12]-[C:13]2-[C:15]-[O;H0;D2;+0:16]-[C;... | 47.3 | [{"value": 47.3, "product": "CC1(OC[C@@H](O1)[C@H]([C@@H]([C@H]2COC(O2)(C)C)O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a stirring suspension of D-Mannitol (1.82 g, 10.0 mmol) in tetrahydrofuran (21 mL) and dimethylformamide (9 mL) was added p-toluenesulfonic acid monohydrate (0.02 g, 0.1 mmol,) at ambient temperature, followed by 2,2-dimethoxypropane (2.8 mL, 0.023 mol). The reaction mixture was stirred for 18 hours at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether.Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol | Ether.Ether.Ether.Ether | null | C1COCO1.C1COCO1 | C1COCO1.C1COCO1 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CN(C=O)C | null | 18 | COC(C)(C)OC.COC(C)(C)OC.OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CN(C=O)C>CC1(C)OC[C@H]([C@@H](O)[C@H](O)[C@H]2COC(C)(C)O2)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b64bb33cef24f6e8fe907b906eadc38 | CC1(C)OC[C@H](CO)O1.O=C1c2ccccc2C(=O)N1O>>CC1(C)OC[C@H](CON2C(=O)c3ccccc3C2=O)O1 | CC1(OC[C@@H](O1)CO)C.ON1C(C=2C(C1=O)=CC=CC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC.CC1(OC[C@@H](O1)CO)C>>CC1(OC[C@@H](O1)CON1C(C2=CC=CC=C2C1=O)=O)C | O[CH2:7][C@H:6]1[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:20]1.[OH:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([CH2:7][O:8][N:9]2[C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]2=[O:19])[O:20]1 | CC1(C)OC[C@H](CO)O1.O=C1c2ccccc2C(=O)N1O | CC1(C)OC[C@H](CON2C(=O)c3ccccc3C2=O)O1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0fcd381b777d6629b0c9e6356597dd7aaabef76c7dfe47721d8d10b5fc8adb37 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | O=C1c2ccccc2C(=O)N1OC[C@H]1COCO1 | O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[#8:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[#7:13]-1-[OH;D1;+0:14]>>[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[#7:13]-1-[O;H0;D2;+0:14]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-[#8:5]-[C:6]-1 | 97 | [{"value": 97.0, "product": "CC1(OC[C@@H](O1)CON1C(C2=CC=CC=C2C1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A 3-L round-bottomed flask equipped with mechanical stirrer and additional funnel was charged with N-hydroxyphthalimide (68.0 g, 0.416 mol) and tetrahydrofuran (1.2 L) under nitrogen atmosphere. To this solution was added triphenylphosphine (109.2 g, 0.416 mol) and the product of Example 31, Step B, (S)-(2,2-dimethyl-[... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | C1COCO1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 18 | CC1(C)OC[C@H](CO)O1.O=C1c2ccccc2C(=O)N1O>O1CCCC1>CC1(C)OC[C@H](CON2C(=O)c3ccccc3C2=O)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f5b4bb3d9eb4f009cf884288ecb6d46 | CC1(C)OC[C@@H](CNO)O1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1 | C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F.CC1(OC[C@H](O1)CNO)C.CC1(OCC[C@@H](O1)CON)C.C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N2CCCC2)(N2CCCC2)N2CCCC2>>CC1(OC[C@@H](O1)CONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)C | [NH:12]([OH:13])[CH2:14][C@@H:15]1[CH2:16][O:17][C:18]([CH3:19])([CH3:20])[O:21]1.O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:30][c:28]2[F:29])[c:26]([F:27])[c:24]([F:25])[cH:23][cH:22]1)=[O:11]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][C@H:15... | CC1(C)OC[C@@H](CNO)O1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1 | null | null | ClCCl | Acylation | OtherReaction | 5a5ff76e01d051a03a2c77088c884912413ce09f49ca50e186c0fb9c62ad0bd2 | 9b702924f2df230008ea1edd297d6a4305f6e78d7804dff7e838c4286e010bf9 | O=C(NOC[C@H]1COCO1)c1ccccc1Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[C:9]1-[#8:10]-[C:11]-[#8:12]-[C:13]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:7]-[O;H0;D2;+0:6]-[CH2;D2;+0:8]-[C:9]1-[#8:10]-[C:11]-[#8:12]-[C:13]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 90 | MINUTE | To a stirring solution of the product of Example 1, Step D, 2-[(4-ethyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acid (0.480 g, 1.626 mmol) in dichloromethane (25 mL) is added to the product of Example 31, Step D, (R)—O-(2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-hydroxylamine (0.38 g, 2.57 mmol), triethylamine (0.54 mL, 3.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Secondary amide | null | null | c1ccccc1.C1COCO1.c1ccccc1 | HO- | ClCCl | null | 1.5 | CC1(C)OC[C@@H](CNO)O1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>ClCCl>CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7c280b71af1a4325818d2a3341d881cc | CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)NOC[C@H](O)CO)ccc(F)c2F)c(F)c1 | CC1(OC[C@@H](O1)CONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>O[C@@H](CONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)CO | CC1(C)[O:16][C@@H:15]([CH2:14][O:13][NH:12][C:10]([c:9]2[c:8]([NH:7][c:6]3[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:27][c:25]3[F:26])[c:23]([F:24])[c:21]([F:22])[cH:20][cH:19]2)=[O:11])[CH2:17][O:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH2:14][C@H:15]([OH:16])[CH2:17][OH:18... | CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)NOC[C@H](O)CO)ccc(F)c2F)c(F)c1 | null | null | O.CO | Deprotection | Acetal hydrolysis to diol | 5f7e1daa6b91d1ca6716348acae46f804565b19cb8bd8a05be2ed6c083743e87 | d0de49ebcb43eafba55a762f6d5237c53d7a87b3a882d6753f793a17a3c3a120 | c1ccc(Nc2ccccc2)cc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[O;H0;D2;+0:5]-1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[OH;D1;+0:5] | 94.4 | [{"value": 94.4, "product": "O[C@@H](CONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "O[C@@H](CONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | To a stirring solution of the product of Example 31, Step E, N-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-benzamide (0.515 g, 1.213 mmol) in methanol (10 mL) and water (1 mL) was added p-toluenesulfonic acid (0.115 g, 0.607 mmol). After stirring for 17 hours the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Secondary alcohol | C1COCO1 | null | c1ccccc1.c1ccccc1 | Other | O.CO | null | 17 | CCc1ccc(Nc2c(C(=O)NOC[C@H]3COC(C)(C)O3)ccc(F)c2F)c(F)c1>O.CO>CCc1ccc(Nc2c(C(=O)NOC[C@H](O)CO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc05ac99a34448169fb70c3de32d753e | O=C1O[C@H]([C@@H](O)CO)C(O)=C1O>>O=C1O[C@H]([C@@H](O)CO)[C@H](O)[C@@H]1O | O=C1C(O)=C(O)[C@H](O1)[C@@H](O)CO>>C([C@@H]([C@@H]1[C@@H]([C@@H](C(=O)O1)O)O)O)O | [O:1]=[C:2]1[O:3][C@H:4]([C@@H:5]([OH:6])[CH2:7][OH:8])[C:9]([OH:10])=[C:11]1[OH:12]>>[O:1]=[C:2]1[O:3][C@H:4]([C@@H:5]([OH:6])[CH2:7][OH:8])[C@H:9]([OH:10])[C@@H:11]1[OH:12] | O=C1O[C@H]([C@@H](O)CO)C(O)=C1O | O=C1O[C@H]([C@@H](O)CO)[C@H](O)[C@@H]1O | null | [Pd] | O | Reduction | Hydrogenation (double to single) | 35bffc355da56b2729c3211f6da20eac560b68f89a9052680c16e18701c1de1e | f2f3dceb2fa4db8d2652a67eb089edbb1d41f08fc254b9c5ab3d7362315d197c | O=C1CCCO1 | [C:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[C;H0;D3;+0:6](-[O;D1;H1:7])=[C;H0;D3;+0:8]-1-[O;D1;H1:9]>>[C:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[C@@H;D3;+0:6](-[O;D1;H1:7])-[C@H;D3;+0:8]-1-[O;D1;H1:9] | null | [] | null | null | 2.5 | DAY | To a solution of L-ascorbic acid in water is added Pd/C (10%). The mixture is subjected to hydrogenation in a Parr hydrogenator at 48 psi, 18° C. for about 2 to 3 days. The reaction mixture is filtered and the filtrate is concentrated in vacuo to afford L-gulonic γ-lactone, after drying at 50° C. in a vacuum oven for a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Enol.Enol | Ester.Secondary alcohol.Secondary alcohol | C1=CCOC1 | C1CCOC1 | C1CCOC1 | null | [Pd].O | null | 60 | O=C1O[C@H]([C@@H](O)CO)C(O)=C1O>[Pd].O>O=C1O[C@H]([C@@H](O)CO)[C@H](O)[C@@H]1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9727f0de925b491185083a8b87351762 | CC1(C)OC[C@@H]([C@H]2OC(=O)[C@@H](O)[C@H]2O)O1>>CC1(C)OC[C@@H](CO)O1 | [OH-].[Na+].I(=O)(=O)(=O)[O-].[Na+].CC1(OC[C@H](O1)[C@@H]2[C@@H]([C@@H](C(=O)O2)O)O)C>>CC1(OC[C@H](O1)CO)C | O=C1[C@@H](O)[C@@H](O)[C@@H:7]([C@@H:6]2[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:9]2)[O:8]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([CH2:7][OH:8])[O:9]1 | CC1(C)OC[C@@H]([C@H]2OC(=O)[C@@H](O)[C@H]2O)O1 | CC1(C)OC[C@@H](CO)O1 | null | null | O | Reduction | OtherReaction | 6adaba872e9713768203b196c0cf2cb300b19c2d72944709c486be13cfa01fe8 | 8d479d153d636eb896155cd1db0f6fdb2f1c31c6d77c5d37d63519469c22f311 | C1COCO1 | O-[C@@H]1-C(=O)-[O;H0;D2;+0:1]-[C@H;D3;+0:2](-[C:3]2-[#8:4]-[C:5]-[#8:6]-[C:7]-2)-[C@@H]-1-O>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[C:3]1-[#8:4]-[C:5]-[#8:6]-[C:7]-1 | null | [] | null | null | 2 | HOUR | To a stirring suspension of the product of Example 32, Step B, 5,6-O-isopropylidene-L-gulono-1,4-lactone, in water is added solid sodium periodate in small portions at 3° C. to 5° C. The pH of the mixture is adjusted to 5.5 with 1N aqueous sodium hydroxide. The suspension is stirred for 2 hours at ambient temperature, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Secondary alcohol | Primary alcohol | C1CCOC1 | null | C1COCO1 | HO- | O | null | 2 | CC1(C)OC[C@@H]([C@H]2OC(=O)[C@@H](O)[C@H]2O)O1>O>CC1(C)OC[C@@H](CO)O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b473736acb5643f9a894944ec78dad40 | CC1(C)OCC(O)CO1.CCOC(=O)N=NC(=O)OCC.O=C1c2ccccc2C(=O)N1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CC1(C)OCC(O)CO1.CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1 | CC1(OCC(CO1)O)C.ON1C(C=2C(C1=O)=CC=CC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC>>CC1(OCC(CO1)O)C.CC1(OCC(CO1)ON1C(C2=CC=CC=C2C1=O)=O)C | [OH:7][CH:15]1[CH2:14][O:13][C:11]([CH3:10])([CH3:12])[O:29][CH2:28]1.CCO[C:6](=O)N=N[C:5]([O:4][CH2:2][CH3:1])=[O:9].[OH:16][N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27].c1ccc(P(c2ccccc2)c2[cH:3]ccc[cH:8]2)cc1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([OH:7])[CH2:8][O:9]1.[CH3:10][C:11... | CC1(C)OCC(O)CO1.CCOC(=O)N=NC(=O)OCC.O=C1c2ccccc2C(=O)N1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CC1(C)OCC(O)CO1.CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | cdb1b139b51253c38c7ac24540a762bcfaf4b35d0b6aac4cfd10cae406f48953 | 5bffd1bf565f92a8cda300ddd1a2f28d7a2dd65284aba9d48791cfd6639e680e | C1COCOC1.O=C1c2ccccc2C(=O)N1OC1COCOC1 | C-C-O-[C;H0;D3;+0:1](=O)-N=N-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[#8:4]-[CH2;D2;+0:5]-[C;D1;H3:6].[O;D1;H0:7]=[C:8]1-[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[#7:13]-1-[OH;D1;+0:14].[OH;D1;+0:15]-[CH;D3;+0:16]1-[C:17]-[#8:18]-[C:19]-[#8:20]-[C:21]-1.[cH;D2;+0:22]1:c:c:c:[cH;D2;+0:23]:c:1-P(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;... | null | [] | null | null | 3 | HOUR | 2,2-Dimethyl-[1,3]dioxan-5-ol was prepared as described previously (Forbes, D. C. et al.; Synthesis, 1998; 6:879–882). 1H NMR (400 MHz; DMSO-d6) δ 4.91 (d, 1H, J=5.1), 3.70–3.75 (m, 2 H), 3.41–3.46 (m, 3 H), 1.30 (s, 3 H), 1.24 (s, 3 H); MS (APCI+)=132.9. To a stirring solution of 2,2-dimethyl-[1,3]dioxan-5-ol (1.50 g,... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Secondary alcohol | Ether.Ether.Secondary alcohol | C1COCOC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1COCOC1.C1COCOC1 | C1COCOC1.C1COCOC1.c1ccc2c(c1)C[NH]C2 | HO- | O1CCCC1 | null | 3 | CC1(C)OCC(O)CO1.CCOC(=O)N=NC(=O)OCC.O=C1c2ccccc2C(=O)N1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>O1CCCC1>CC1(C)OCC(O)CO1.CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-098cba35338843238638a834ddd05bba | CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1>>CC1(C)OCC(ON)CO1 | CC1(OCC(CO1)ON1C(C2=CC=CC=C2C1=O)=O)C.CNN>>CC1(OCC(CO1)ON)C | O=C1c2ccccc2C(=O)[N:8]1[O:7][CH:6]1[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:10][CH2:9]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH:6]([O:7][NH2:8])[CH2:9][O:10]1 | CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1 | CC1(C)OCC(ON)CO1 | null | null | ClCCl | Reduction | Phthalimide deprotection | 8c6c904eae7a7d528fa3eeedb7e9706448ab9f7df249a16fa865a9210a6adc85 | 892f9aeb7d80035b81a0f5a363c9ed6a90780ba9faa3f0708093fa283b8c9a24 | C1COCOC1 | O=C1-[N;H0;D3;+0:1](-[#8:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[#8:2]-[NH2;D1;+0:1] | 106.3 | [{"value": 100.0, "product": "CC1(OCC(CO1)ON)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.3, "product": "CC1(OCC(CO1)ON)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirring solution of the product of Example 33, Step A, 2-(2,2-dimethyl-[1,3]dioxan-5-yloxy)-isoindole-1,3-dione (1.72 g, 6.20 mmol), in dichloromethane (15 mL) at 0° C. under nitrogen was added methylhydrazine (0.36 mL, 6.82 mmol) and allowed to warm to room temperature. After stirring for 2 hours the reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1COCOC1 | HO- | ClCCl | null | 2 | CC1(C)OCC(ON2C(=O)c3ccccc3C2=O)CO1>ClCCl>CC1(C)OCC(ON)CO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a79ecd9c5da346269ed328d3e15ee622 | CC1(C)OCC(ON)CO1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1 | C(C)C1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1F)F)F.CC1(OCC(CO1)ON)C.CC1(OCC(CO1)ON)C.C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N2CCCC2)(N2CCCC2)N2CCCC2>>CC1(OCC(CO1)ONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)C | [NH2:12][O:13][CH:14]1[CH2:15][O:16][C:17]([CH3:18])([CH3:19])[O:20][CH2:21]1.O[C:10]([c:9]1[c:8]([NH:7][c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:30][c:28]2[F:29])[c:26]([F:27])[c:24]([F:25])[cH:23][cH:22]1)=[O:11]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH:14]3[CH2:15][O:... | CC1(C)OCC(ON)CO1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NOC1COCOC1)c1ccccc1Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 61.4 | [{"value": 61.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 75 | MINUTE | To a stirring solution of the product of Example 1, Step D, 2-[(4-ethyl-2-fluorophenyl)amino]-3,4-difluorobenzoic acid (0.480 g, 1.626 mmol) in dichloromethane (15 mL) is added the product of Example 33, Step B, O-(2,2-dimethyl-[1,3]dioxan-5-yl)-hydroxylamine (0.287 g, 1.951 mmol), triethylamine (0.41 mL, 2.927 mmol), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCOC1.c1ccccc1 | HO- | ClCCl | null | 1.25 | CC1(C)OCC(ON)CO1.CCc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>ClCCl>CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7104acbbd12461a8b874be5fbda6497 | CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1>>CCc1ccc(Nc2c(C(=O)NOC(CO)CO)ccc(F)c2F)c(F)c1 | CC1(OCC(CO1)ONC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)CC)F)=O)C.Cl>>C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOC(CO)CO)C=CC(=C1F)F)F | CC1(C)[O:16][CH2:15][CH:14]([O:13][NH:12][C:10]([c:9]2[c:8]([NH:7][c:6]3[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:27][c:25]3[F:26])[c:23]([F:24])[c:21]([F:22])[cH:20][cH:19]2)=[O:11])[CH2:17][O:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[NH:12][O:13][CH:14]([CH2:15][OH:16])[CH2:17][OH:18])[... | CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1 | CCc1ccc(Nc2c(C(=O)NOC(CO)CO)ccc(F)c2F)c(F)c1 | null | null | C(C)O | Deprotection | Ether cleavage to primary alcohol | db60f3679fcc60468c35d46ab68797e1b8f177a1be5585affc59e7a3cf3777b0 | 2f23bf710218006c93ff728dc99485ec1b0a0e5cb41fb3252e62eb1ed984c4ac | c1ccc(Nc2ccccc2)cc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[O;H0;D2;+0:5]-1>>[OH;D1;+0:1]-[C:2]-[C:3]-[C:4]-[OH;D1;+0:5] | 84.6 | [{"value": 84.6, "product": "C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOC(CO)CO)C=CC(=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "C(C)C1=CC(=C(C=C1)NC1=C(C(=O)NOC(CO)CO)C=CC(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirring solution of the product of Example 33, Step C, N-(2,2-dimethyl-[1,3]dioxan-5-yloxy)-2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-benzamide (0.416 g, 0.980 mmol) in ethanol (5 mL) was added 1 molar aqueous hydrochloric acid solution (1 mL). After stirring for 1 hour at ambient temperature the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Primary alcohol | C1COCOC1 | null | c1ccccc1.c1ccccc1 | Other | C(C)O | null | 1 | CCc1ccc(Nc2c(C(=O)NOC3COC(C)(C)OC3)ccc(F)c2F)c(F)c1>C(C)O>CCc1ccc(Nc2c(C(=O)NOC(CO)CO)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7ccd6d335ce448838225837d6fa2e989 | CCOC(=O)Oc1c2[nH]c3ccc(C(=O)OCC)cc3c2cc2c1[nH]c1ccc(C(=O)OCC)cc12.CCOC(=O)Oc1c2c(cc3c4cc(Br)ccc4n(C(=O)OC(C)(C)C)c13)c1cc(Br)ccc1n2C(=O)OC(C)(C)C>>CCOC(=O)Oc1c2c(cc3c1=Nc1ccc(C(=O)OCC)c(C(=O)OC(C)(C)C)c1-3)=c1cc(C(=O)OC(C)C(=O)OC(C)(C)C)ccc1=N2 | [Li]C(C)(C)C.CCCCC.BrC=1C=C2C=3C=C4C(=C(C3N(C2=CC1)C(=O)OC(C)(C)C)OC(=O)OCC)N(C=1C=CC(=CC14)Br)C(=O)OC(C)(C)C.[NH4+].[Cl-].C(=O)(OCC)C=1C=C2C=3C=C4C(=C(C3NC2=CC1)OC(=O)OCC)NC=1C=CC(=CC14)C(=O)OCC.ClC(=O)OCC>>C(=O)(OC(C)(C)C)C1=C2C3=CC=4C(=C(C3=NC2=CC=C1C(=O)OCC)OC(=O)OCC)N=C1C=CC(=CC14)C(=O)OC(C)C(=O)OC(C)(C)C | CCOC(=O)Oc1c2[nH]c3ccc([C:18](=[O:19])[O:20][CH2:21][CH3:22])cc3c2cc2c1[nH]c1ccc([C:35](=[O:36])[O:37][CH2:38][CH3:39])cc12.Br[c:17]1[cH:16][cH:15][c:14]2[n:13]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[c:12]3[c:7]([O:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]4[c:9]([cH:10][c:11]3[c:31]2[cH:23]1)[c:32]1[cH... | CCOC(=O)Oc1c2[nH]c3ccc(C(=O)OCC)cc3c2cc2c1[nH]c1ccc(C(=O)OCC)cc12.CCOC(=O)Oc1c2c(cc3c4cc(Br)ccc4n(C(=O)OC(C)(C)C)c13)c1cc(Br)ccc1n2C(=O)OC(C)(C)C | CCOC(=O)Oc1c2c(cc3c1=Nc1ccc(C(=O)OCC)c(C(=O)OC(C)(C)C)c1-3)=c1cc(C(=O)OC(C)C(=O)OC(C)(C)C)ccc1=N2 | null | null | CCOC(=O)C.CCCCCC.C1CCOC1 | C-C Coupling | OtherReaction | d354052b5a19e91e3692a64042437acc2acc1c94e80c9a5e8ef7c022611012ac | 78d8ffa0c4678aa2c77d69612c39175aa3885ae8e5b78b421fcfc250fa0c0671 | c1ccc2c(c1)N=c1cc3c(cc1-2)=c1ccccc1=N3 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c;H0;D3;+0:5](:[cH;D2;+0:6]:1):[c;H0;D3;+0:7]1:[c:8]:[c;H0;D3;+0:9]3:[c:10](:[c:11](-[#8:12]-[C:13]=[O;D1;H0:14]):[c;H0;D3;+0:15]:1:[n;H0;D3;+0:16]:2-[C;H0;D3;+0:17](=[O;D1;H0:18])-[#8:19]-[C:20](-[C;D1;H3:21])(-[C;D1;H3:22])-[C;D1;H3:23]):[n;H0;D3;+0:24](-[C;H0;D3;+0:25](=[O;D1;H... | 89 | [{"value": 89.0, "product": "C(=O)(OC(C)(C)C)C1=C2C3=CC=4C(=C(C3=NC2=CC=C1C(=O)OCC)OC(=O)OCC)N=C1C=CC(=CC14)C(=O)OC(C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 10 | MINUTE | 2,10-Dicarbethoxy-6-ethoxycarbonyloxy-5,7-dihydro-indolo [2,3-b]carbazole (63). To a solution of 1.7 M t-BuLi in pentane (32.3 mL, 54.8 mmol) in THF (200 mL) at −100° C. under argon was added 61 (7.0 g, 9.97 mmol) in THF (20 mL), and stirred for 10 min. ClCO2CH2CH3 (30 mL) was added and the mixture was slowly warmed to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Ester.Ether.Ether.Ether.Ether.Boc.Boc | Ester.Ester.Ester.Ester.Boc.Boc | c1ccc2c(c1)nc1cc3nc4ccccc4c3cc12.c1ccc2c(c1)N=c1cc3c(cc12)c1ccccc1=N3 | c1ccc2c(c1)N=c1cc3c(cc12)c1ccccc1=N3 | c1ccc2c(c1)N=c1cc3c(cc12)c1ccccc1=N3 | HBr | CCOC(=O)C.CCCCCC.C1CCOC1 | -10 | 0.166667 | CCOC(=O)Oc1c2[nH]c3ccc(C(=O)OCC)cc3c2cc2c1[nH]c1ccc(C(=O)OCC)cc12.CCOC(=O)Oc1c2c(cc3c4cc(Br)ccc4n(C(=O)OC(C)(C)C)c13)c1cc(Br)ccc1n2C(=O)OC(C)(C)C>CCOC(=O)C.CCCCCC.C1CCOC1>CCOC(=O)Oc1c2c(cc3c1=Nc1ccc(C(=O)OCC)c(C(=O)OC(C)(C)C)c1-3)=c1cc(C(=O)OC(C)C(=O)OC(C)(C)C)ccc1=N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3672edfb92dc40a3a074c125d9de4add | CCC(=O)C(Cl)C(=O)OC.Nc1nccnc1Cl>>CCc1nc2c(Cl)nccn2c1C(=O)OC | ClC=1C(=NC=CN1)N.ClC(C(=O)OC)C(CC)=O>>COC(=O)C1=C(N=C2N1C=CN=C2Cl)CC | O=[C:3]([CH2:2][CH3:1])[CH:12](Cl)[C:13](=[O:14])[O:15][CH3:16].[NH2:4][c:5]1[c:6]([Cl:7])[n:8][cH:9][cH:10][n:11]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][cH:10][n:11]2[c:12]1[C:13](=[O:14])[O:15][CH3:16] | CCC(=O)C(Cl)C(=O)OC.Nc1nccnc1Cl | CCc1nc2c(Cl)nccn2c1C(=O)OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9ef3f8c7d8012f16862df6e6d5d64f5e5c28836502935c9f0f51594189d35521 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1cn2ccnc2cn1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8].[Cl;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[n;H0;D2;+0:14]:[c:15]:1-[NH2;D1;+0:16]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:6](-[C:7]-[C;D1;H3:8]):[n;H0;D2;+0:16]:[c:15]2:[c:10](-[Cl;D1;H0:9]):[#7;... | 25.5 | [{"value": 25.5, "product": "COC(=O)C1=C(N=C2N1C=CN=C2Cl)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | 2 | HOUR | 3-Chloro-2-aminopyrazine (2.1 g, 16.2 mmol) and methyl 2-chloro-3-oxopentanoate (6.7 mL, 48.6 mmol) were mixed, and heated under stirring at 170° C. for 2 hours. After being allowed to cool, the unnecessary materials were filtered off and washed with ethyl acetate, and then filtrates were combined and evaporated. The r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1cnccn1 | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | HCl | null | 170 | 2 | CCC(=O)C(Cl)C(=O)OC.Nc1nccnc1Cl>>CCc1nc2c(Cl)nccn2c1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af52f131170f4f0b925451eb64c45d74 | Nc1nccnc1-c1ccc(Cl)cc1Cl.O=C1CCC(=O)N1Cl>>Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl | ClC1=C(C=CC(=C1)Cl)C=1C(=NC=CN1)N.ClN1C(CCC1=O)=O.O>>ClC=1N=C(C(=NC1)N)C1=C(C=C(C=C1)Cl)Cl | [NH2:1][c:2]1[n:3][cH:4][cH:5][n:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16].O=C1CCC(=O)N1[Cl:6]>>[NH2:1][c:2]1[n:3][cH:4][c:5]([Cl:6])[n:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16] | Nc1nccnc1-c1ccc(Cl)cc1Cl.O=C1CCC(=O)N1Cl | Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | bc1f7cfdae813ebe8c69faae7323293eaef048ef481216eb2be3204f184b46ec | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2cnccn2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[cH;D2;+0:6]:[c:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c:7]:1 | 93.5 | [{"value": 93.5, "product": "ClC=1N=C(C(=NC1)N)C1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(2,4-Dichlorophenyl)-2-pyrazinamine (1.43 g, 6.0 mmol) was dissolved in chloroform (9 mL), N-chlorosuccinimide (0.96 g, 7.2 mmol) was added thereto, and the mixture was stirred by heating under reflux for 4 hours. After being allowed to cool, water was added to the reaction mixture, which was extracted with ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cnccn1.C1CCNC1 | c1cnccn1 | c1cnccn1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | Nc1nccnc1-c1ccc(Cl)cc1Cl.O=C1CCC(=O)N1Cl>C(Cl)(Cl)Cl>Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f8d44ee9da14af286866a53df2b00c2 | CCC(=O)C(Cl)C(=O)OC.Cc1cnc(N)c(Br)n1>>CCc1nc2c(Br)nc(C)cn2c1C(=O)OC | BrC=1C(=NC=C(N1)C)N.ClC(C(=O)OC)C(CC)=O>>COC(=O)C1=C(N=C2N1C=C(N=C2Br)C)CC | O=[C:3]([CH2:2][CH3:1])[CH:13](Cl)[C:14](=[O:15])[O:16][CH3:17].[NH2:4][c:5]1[c:6]([Br:7])[n:8][c:9]([CH3:10])[cH:11][n:12]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Br:7])[n:8][c:9]([CH3:10])[cH:11][n:12]2[c:13]1[C:14](=[O:15])[O:16][CH3:17] | CCC(=O)C(Cl)C(=O)OC.Cc1cnc(N)c(Br)n1 | CCc1nc2c(Br)nc(C)cn2c1C(=O)OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9ef3f8c7d8012f16862df6e6d5d64f5e5c28836502935c9f0f51594189d35521 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1cn2ccnc2cn1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8].[Br;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12](-[C;D1;H3:13]):[c:14]:[n;H0;D2;+0:15]:[c:16]:1-[NH2;D1;+0:17]>>[Br;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12](-[C;D1;H3:13]):[c:14]:[n;H0;D3;+0:15]2:[c:16]:1:[n;H0;D2;+0:17]:[c;H0;D3;+0:6](-[C:7]-[... | 5.8 | [{"value": 5.8, "product": "COC(=O)C1=C(N=C2N1C=C(N=C2Br)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 1 | HOUR | 3-Bromo-5-methyl-2-pyrazineamine (3.5 g, 18.6 mmol) and methyl 2-chloro-3-oxopentanoate (6.7 mL, 48.6 mmol) were mixed, and the mixture was heated under stirring at 130° C. for 1 hour. After being allowed to cool, the unnecessary materials were filtered off and washed with ethyl acetate, and then the filtrates were com... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1cnccn1 | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | HCl | null | 130 | 1 | CCC(=O)C(Cl)C(=O)OC.Cc1cnc(N)c(Br)n1>>CCc1nc2c(Br)nc(C)cn2c1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e51d2344008247c5826386b93d8b5392 | CCc1cn2ccnc(Cl)c2n1.CN(C)C=O>>CCc1nc2c(Cl)nccn2c1C=O | ClC=1C=2N(C=CN1)C=C(N2)CC.CN(C=O)C.P(=O)(Cl)(Cl)Cl>>ClC=1C=2N(C=CN1)C(=C(N2)CC)C=O | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][cH:10][n:11]2[cH:12]1.CN(C)[CH:13]=[O:14]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][cH:10][n:11]2[c:12]1[CH:13]=[O:14] | CCc1cn2ccnc(Cl)c2n1.CN(C)C=O | CCc1nc2c(Cl)nccn2c1C=O | null | null | null | C-C Coupling | OtherReaction | e72235189db37a417e31189cefe09560ddeac4330840d64763923712813d11ed | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1cn2ccnc2cn1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:2:[cH;D2;+0:12]:1>>[C:3]-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]:2:[c;H0;D3;+0:12]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | 90 | CELSIUS | 2 | HOUR | 8-Chloro-2-ethylimidazo[1,2-a]pyrazine (600 mg, 3.3 mmol) was dissolved in N,N-dimethylformamide (3.3 mL), phosphorus oxychloride (1.2 mL, 13.2 mmol) was added dropwise at room temperature, and the mixture was heated under stirring at 90° C. for 2 hours. After being allowed to cool, the reaction mixture was poured into... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | Other | null | 90 | 2 | CCc1cn2ccnc(Cl)c2n1.CN(C)C=O>>CCc1nc2c(Cl)nccn2c1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7cbd6c8b578408b9693bca3dfa726d9 | CCCC(O)c1c(CC)nc2c(Cl)nccn12.CCI>>CCCC(OCC)c1c(CC)nc2c(Cl)nccn12 | O.ICC.[H-].[Na+].ClC=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)O>>C(C)OC(CCC)C1=C(N=C2N1C=CN=C2Cl)CC | [CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14]([Cl:15])[n:16][cH:17][cH:18][n:19]12.I[CH2:6][CH3:7]>>[CH3:1][CH2:2][CH2:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14]([Cl:15])[n:16][cH:17][cH:18][n:19]12 | CCCC(O)c1c(CC)nc2c(Cl)nccn12.CCI | CCCC(OCC)c1c(CC)nc2c(Cl)nccn12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2e63de7b1f097c059f31781c5dec3b7812b761a1b3812b5238753f554cfa0846 | 9d3e82e8fa4f4bc62c1019e0bd869bdb0cf4748977f3c0b945b8ffdfc70126be | c1cn2ccnc2cn1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4]:[c:5](-[C:6](-[C:7])-[OH;D1;+0:8]):[#7;a:9]>>[#7;a:3]:[c:4]:[c:5](-[C:6](-[C:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2]):[#7;a:9] | null | [] | null | null | 3 | HOUR | The resulting 1-(8-chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanol was dissolved in N,N-dimethylformamide (2.2 mL), then iodoethane (0.079 mL, 0.99 mmol) and sodium hydride (65% in oil; 49 mg, 1.32 mmol) were added thereto under ice-cooling, and the mixture was stirred for 3 hours. Water was added to the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Ether | null | null | c1cn2ccnc2cn1 | HI | CN(C=O)C | null | 3 | CCCC(O)c1c(CC)nc2c(Cl)nccn12.CCI>CN(C=O)C>CCCC(OCC)c1c(CC)nc2c(Cl)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72159f0f66b74005a17e9d77b719b034 | CCCC(O)c1c(CC)nc2c(Cl)nccn12>>CCCC(=O)c1c(CC)nc2c(Cl)nccn12 | ClC=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)O>>ClC=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)=O | [CH3:1][CH2:2][CH2:3][CH:4]([OH:5])[c:6]1[c:7]([CH2:8][CH3:9])[n:10][c:11]2[c:12]([Cl:13])[n:14][cH:15][cH:16][n:17]12>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH3:9])[n:10][c:11]2[c:12]([Cl:13])[n:14][cH:15][cH:16][n:17]12 | CCCC(O)c1c(CC)nc2c(Cl)nccn12 | CCCC(=O)c1c(CC)nc2c(Cl)nccn12 | null | [O-2].[Mn+4].[O-2] | C(Cl)Cl.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1cn2ccnc2cn1 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5]1:[#7;a:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[#7;a:12]:[c:13]:1-[C:14]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[#7;a:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[#7;a:12]:[c:13]:1-[C:14] | null | [] | 60 | CELSIUS | 5 | HOUR | The resulting 1-(8-chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanol was dissolved in ethyl acetate (4 mL) and methylene chloride (1 mL), then activated manganese (IV) oxide (3 g) was added thereto, and the mixture was heated under stirring at 60° C. for 5 hours. After being allowed to cool, the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1cn2ccnc2cn1 | null | [O-2].[Mn+4].[O-2].C(Cl)Cl.C(C)(=O)OCC | 60 | 5 | CCCC(O)c1c(CC)nc2c(Cl)nccn12>[O-2].[Mn+4].[O-2].C(Cl)Cl.C(C)(=O)OCC>CCCC(=O)c1c(CC)nc2c(Cl)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a208b4e824e9469ab599b6b4e775f6d6 | CC(=O)/C=C/c1ccc(C)cc1C.[C-]#N>>CC(=O)CC(C#N)c1ccc(C)cc1C | [Cl-].[NH4+].[C-]#N.[K+].CC1=C(C=CC(=C1)C)/C=C/C(C)=O.CN(C=O)C>>CC1=C(C=CC(=C1)C)C(CC(C)=O)C#N | [CH3:1][C:2](=[O:3])/[CH:4]=[CH:5]/[c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]1[CH3:15].[C-:6]#[N:7]>>[CH3:1][C:2](=[O:3])[CH2:4][CH:5]([C:6]#[N:7])[c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]1[CH3:15] | CC(=O)/C=C/c1ccc(C)cc1C.[C-]#N | CC(=O)CC(C#N)c1ccc(C)cc1C | null | null | O | C-C Coupling | OtherReaction | 876100d9029380276bad4bfffd336e941029e62a60aedd8b2e7be808cdf4dbf7 | 491da00d5858e1f2efb2cb52ad5e0bdc63f42de65d8d378a501175351ff676a5 | c1ccccc1 | [C-;H0;D1:1]#[N;D1;H0:2].[C;D1;H3:3]-[C:4](=[O;D1;H0:5])/[CH;D2;+0:6]=[CH;D2;+0:7]/[c:8](:[c:9]):[c:10]>>[C;D1;H3:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[CH;D3;+0:7](-[C;H0;D2;+0:1]#[N;D1;H0:2])-[c:8](:[c:9]):[c:10] | 48 | [{"value": 48.0, "product": "CC1=C(C=CC(=C1)C)C(CC(C)=O)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ammonium chloride (6.84 g, 0.126 mol) and potassium cyanide (13.68 g, 0.210 mol) were added to a mixed solution (100 mL) of a 15% aqueous solution of (E)-4-(2,4-dimethylphenyl)-3-butene-2-one (18.32 g, 0.105 mol) and N,N-dimethylformamide, and the mixture was heated under reflux for 6 hours. Water was added to the reac... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Nitrile | null | null | c1ccccc1 | null | O | null | null | CC(=O)/C=C/c1ccc(C)cc1C.[C-]#N>O>CC(=O)CC(C#N)c1ccc(C)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4cc3645b2fc3406b990ff55a9ee5e30d | BrBr.Nc1ccc(Cl)nn1>>Nc1nnc(Cl)cc1Br | C([O-])(O)=O.[Na+].BrBr.NC=1N=NC(=CC1)Cl>>BrC1=C(N=NC(=C1)Cl)N | Br[Br:9].[NH2:1][c:2]1[n:3][n:4][c:5]([Cl:6])[cH:7][cH:8]1>>[NH2:1][c:2]1[n:3][n:4][c:5]([Cl:6])[cH:7][c:8]1[Br:9] | BrBr.Nc1ccc(Cl)nn1 | Nc1nnc(Cl)cc1Br | null | null | CO | Functional Group Interconversion | Bromination | 3b22a5d23572bfe9ad1502a182eb9a0357f308a16eb4f4f5e1618044bed6ab38 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccnnc1 | Br-[Br;H0;D1;+0:1].[Cl;D1;H0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6](-[N;D1;H2:7]):[cH;D2;+0:8]:[c:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:9]:[c:3](-[Cl;D1;H0:2]):[#7;a:4]:[#7;a:5]:[c:6]:1-[N;D1;H2:7] | 53 | [{"value": 53.0, "product": "BrC1=C(N=NC(=C1)Cl)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "BrC1=C(N=NC(=C1)Cl)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Sodium bicarbonate (13.0 g, 155 mmol) and bromine (4.0 mL, 78 mmol) were added to a solution of 3-amino-6-chloropyridazine (10.0 g, 78 mmol) in methanol (150 mL) at room temperature, and the mixture was stirred for 15 hours. The reaction mixture was filtered, and the solvent was evaporated. Water was added thereto, whi... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | HBr | CO | null | 15 | BrBr.Nc1ccc(Cl)nn1>CO>Nc1nnc(Cl)cc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-18ffd5812c2a41f39e974886d5d3b71a | CCO.Cc1ccccc1.Nc1nnc(Cl)cc1Br>>Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | C(C)O.C([O-])([O-])=O.[Na+].[Na+].NC=1N=NC(=CC1Br)Cl.C1(=CC=CC=C1)C.O>>ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)C)C | OC[CH3:15].[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:14][cH:16]1.Br[c:6]1[cH:7][c:8]([Cl:9])[n:10][n:11][c:12]1[NH2:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10][n:11][c:12]2[NH2:13])[c:14]([CH3:15])[cH:16]1 | CCO.Cc1ccccc1.Nc1nnc(Cl)cc1Br | Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | null | null | null | C-C Coupling | OtherReaction | 378e6cf61b1154372bf750950dd7ae6cbdcca521fb592851187e74793d6227b8 | af1238a0d333620701e826be7a9367863896c568351b293f0287634647ec2581 | c1ccc(-c2ccnnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8].O-C-[CH3;D1;+0:9].[c:10]1:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[CH3;D1;+0:9]-[c;H0;D3;+0:15]1:[c:10]:[c:11]:[c:12]:[c:13]:[c;H0;D3;+0:14]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8] | 82 | [{"value": 82.0, "product": "ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Ethanol (8 mL), a 2M aqueous sodium carbonate solution (4 mL), 2,4-dimethylbenzeneboric acid (650 mg, 4.3 mmol) and tetrakistriphenylphosphine palladium complex (456 mg, 0.39 mmol) were added to a solution of 3-amino-4-bromo-6-chloropyridazine (822 mg, 3.9 mmol) in toluene (40 mL), and the mixture was heated at 100° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | null | c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1 | HBr | null | 100 | null | CCO.Cc1ccccc1.Nc1nnc(Cl)cc1Br>>Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2efd3e9c6be4ff4b11581754d31d024 | Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1>>Cc1ccc(-c2ccnnc2N)c(C)c1 | C(=O)[O-].[NH4+].ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)C)C>>CC1=C(C=CC(=C1)C)C1=C(N=NC=C1)N | Cl[c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:15][c:13]2[CH3:14])[c:11]([NH2:12])[n:10][n:9]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][n:9][n:10][c:11]2[NH2:12])[c:13]([CH3:14])[cH:15]1 | Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | Cc1ccc(-c2ccnnc2N)c(C)c1 | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 11fec97dc22aabf340de6dd16bd9ed47791a1ff823f957f6e3aa8baf8018c49f | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccnnc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1>>[#7;a:3]1:[#7;a:2]:[cH;D2;+0:1]:[c:6]:[c:5]:[c:4]:1 | 100.4 | [{"value": 99.0, "product": "CC1=C(C=CC(=C1)C)C1=C(N=NC=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.4, "product": "CC1=C(C=CC(=C1)C)C1=C(N=NC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10% Pd—C (759 mg, 50 wt %) and ammonium formate (1.23 g, 19 mmol) were added to a solution of 6-chloro-4-(2,4-dimethylphenyl)-3-pyridazineamine (759 mg, 3.2 mmol) in methanol (40 mL), and the mixture was heated under reflux for 1 hour. The reaction solution was filtered through Celite, and the solvent was evaporated. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccnnc1 | c1ccnnc1 | c1ccccc1.c1ccnnc1 | Other | [Pd].CO | null | null | Cc1ccc(-c2cc(Cl)nnc2N)c(C)c1>[Pd].CO>Cc1ccc(-c2ccnnc2N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-caf162bcebbc4f10bff043f94df86b92 | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2ccnnc2N)c(C)c1>>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC | ClC(C(=O)OC)C(CC)=O.CC1=C(C=CC(=C1)C)C1=C(N=NC=C1)N>>COC(=O)C1=C(N=C2N1N=CC=C2C2=C(C=C(C=C2)C)C)CC | O=[C:3]([CH2:2][CH3:1])[CH:19](Cl)[C:20](=[O:21])[O:22][CH3:23].[NH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]2[CH3:14])[cH:15][cH:16][n:17][n:18]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][cH:16][n:17][n:18]2[c:19]1[C:20](=[O:21])[O:22]... | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2ccnnc2N)c(C)c1 | CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | e9a3a6063b8692570315ac7f7821b744f54b8f587cd5476dacd07314c341cb27 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1ccc(-c2ccnn3ccnc23)cc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[#7;a:13]:[c:14]>>[C;D1;H3:8]-[C:7]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:9]:[c:10](:[c:11]):[n;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5] | 37 | [{"value": 37.0, "product": "COC(=O)C1=C(N=C2N1N=CC=C2C2=C(C=C(C=C2)C)C)CC", "details": "PERCENTYIELD", "is_desired": false}] | 155 | CELSIUS | null | null | Methyl 2-chloro-3-oxopentanoate (5 mL) was added to 4-(2,4-dimethylphenyl)-3-pyridazineamine (640 mg, 3.2 mmol), and the mixture was heated at 155° C. for 30 minutes. Water was added to the resulting reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 5N aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1ccnnc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HCl | O | 155 | null | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2ccnnc2N)c(C)c1>O>CCc1nc2c(-c3ccc(C)cc3C)ccnn2c1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ddb96ed4486247d3b9e4c63487fdc840 | CCOC(=O)CBr.CSC(=Nc1ncc(C)cc1Br)SC>>CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12 | BrCC(=O)OCC.BrC=1C(=NC=C(C1)C)N=C(SC)SC.C(C)N(CC)CC>>C(C)OC(=O)C1=C(N=C2N1C=C(C=C2Br)C)SC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CS[C:7]([S:8][CH3:9])=[N:10][c:11]1[c:12]([Br:13])[cH:14][c:15]([CH3:16])[cH:17][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([S:8][CH3:9])[n:10][c:11]2[c:12]([Br:13])[cH:14][c:15]([CH3:16])[cH:17][n:18]12 | CCOC(=O)CBr.CSC(=Nc1ncc(C)cc1Br)SC | CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | ea4a591bb663a1a0c0d4cef4431d53eb59d599cc9e7e27e70212973e585b65fb | f7e1f7b75eaaa242da7c0fbcc1aa8ff0732ddd85decf84eb68979986ec93c0bd | c1ccn2ccnc2c1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-S-[C;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8])=[N;H0;D2;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[c:13]:[c:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8]):[n;H0;D2;+0:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1:[c:13]:[c:14] | null | [] | 60 | CELSIUS | 4 | HOUR | Ethyl bromoacetate (5.4 g) was added to methyl N-(3-bromo-5-methyl-2-pyridyl)(methylsulfanyl)methaneimidothioate, and the mixture was stirred at 60° C. for 4 hours. After cooled to room temperature, triethylamine was added to treat the material, and water was further added thereto. The reaction mixture was extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Monosulfide.Monosulfide | Ester.Monosulfide | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | O | 60 | 4 | CCOC(=O)CBr.CSC(=Nc1ncc(C)cc1Br)SC>O>CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61a7d60a91a74ecf9ad599979327e9da | CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12>>CSc1nc2c(Br)cc(C)cn2c1C(=O)O | C(C)OC(=O)C1=C(N=C2N1C=C(C=C2Br)C)SC.[OH-].[Na+].Cl>>BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)C(=O)O | CC[O:16][C:14]([c:13]1[c:3]([S:2][CH3:1])[n:4][c:5]2[c:6]([Br:7])[cH:8][c:9]([CH3:10])[cH:11][n:12]21)=[O:15]>>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([Br:7])[cH:8][c:9]([CH3:10])[cH:11][n:12]2[c:13]1[C:14](=[O:15])[OH:16] | CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12 | CSc1nc2c(Br)cc(C)cn2c1C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccn2ccnc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | 90.4 | [{"value": 90.4, "product": "BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-carboxylic acid ethyl ester (1.33 g) was dissolved in ethanol (50 mL), then a 5N aqueous sodium hydroxide solution (3 mL) was added thereto, and the mixture was stirred under reflux for 1 hour. Ice was added to the reaction mixture, then 2N hydrochloric acid (8... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccn2ccnc2c1 | Other | C(C)O | null | null | CCOC(=O)c1c(SC)nc2c(Br)cc(C)cn12>C(C)O>CSc1nc2c(Br)cc(C)cn2c1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e26e30ffe1064f57b436a8732bb972fc | CCCI.CSc1nc2c(Br)cc(C)cn2c1NC(=O)OC(C)(C)C>>CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12 | O.[H-].[Na+].BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)NC(OC(C)(C)C)=O.ICCC>>BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(C(OC(C)(C)C)=O)CCC | I[CH2:3][CH2:2][CH3:1].[NH:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]1[c:13]([S:14][CH3:15])[n:16][c:17]2[c:18]([Br:19])[cH:20][c:21]([CH3:22])[cH:23][n:24]12>>[CH3:1][CH2:2][CH2:3][N:4]([C:5](=[O:6])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[c:12]1[c:13]([S:14][CH3:15])[n:16][c:17]2[c:18]([Br:19])[cH:20]... | CCCI.CSc1nc2c(Br)cc(C)cn2c1NC(=O)OC(C)(C)C | CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | c1ccn2ccnc2c1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:1-[NH;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]>>[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:1-[N;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3])-[C:12](=[O;D1;H0:13])-[#8:14]... | 97.1 | [{"value": 97.1, "product": "BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(C(OC(C)(C)C)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | tert-Butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]carbamate (123 mg) was dissolved in N,N-dimethylformamide (10 mL), then sodium hydride (65% in oil; 15 mg) was added thereto under ice-cooling, and the mixture was stirred for 10 minutes. Iodopropane (67 mg) was added thereto under ice-cooling,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | c1ccn2ccnc2c1 | HI | CN(C=O)C | null | 0.166667 | CCCI.CSc1nc2c(Br)cc(C)cn2c1NC(=O)OC(C)(C)C>CN(C=O)C>CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7aa3a44957624ee9a9e210aa85916a72 | CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12>>CCCNc1c(SC)nc2c(Br)cc(C)cn12 | BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(C(OC(C)(C)C)=O)CCC.Cl.C(C)(=O)OCC.[OH-].[Na+]>>BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)NCCC | CC(C)(C)OC(=O)[N:4]([CH2:3][CH2:2][CH3:1])[c:5]1[c:6]([S:7][CH3:8])[n:9][c:10]2[c:11]([Br:12])[cH:13][c:14]([CH3:15])[cH:16][n:17]12>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[c:6]([S:7][CH3:8])[n:9][c:10]2[c:11]([Br:12])[cH:13][c:14]([CH3:15])[cH:16][n:17]12 | CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12 | CCCNc1c(SC)nc2c(Br)cc(C)cn12 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccn2ccnc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4]1:[#7;a:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]:1-[#16:10]>>[#16:10]-[c:9]1:[#7;a:8]:[c:7]:[#7;a:5](:[c:6]):[c:4]:1-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 20 | HOUR | tert-Butyl N-[8-bromo-6-methyl-2-(methysulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylcarbamate was dissolved in ethyl acetate (5 mL), then a 4N hydrochloric acid-ethyl acetate solution (10 mL) was added thereto at room temperature, and the mixture was stirred at room temperature for 20 hours. Under ice-cooling, a 5N aqu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccn2ccnc2c1 | HO- | C(C)(=O)OCC | null | 20 | CCCN(C(=O)OC(C)(C)C)c1c(SC)nc2c(Br)cc(C)cn12>C(C)(=O)OCC>CCCNc1c(SC)nc2c(Br)cc(C)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-714abe1a9d0f4f08a934c9727575f9bf | CCC=O.CCCNc1c(SC)nc2c(Br)cc(C)cn12>>CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12 | [BH4-].[Na+].BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)NCCC.C(CC)=O.[OH-].[Na+].S(O)(O)(=O)=O>>BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(CCC)CCC | O=[CH:5][CH2:6][CH3:7].[CH3:1][CH2:2][CH2:3][NH:4][c:8]1[c:9]([S:10][CH3:11])[n:12][c:13]2[c:14]([Br:15])[cH:16][c:17]([CH3:18])[cH:19][n:20]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([S:10][CH3:11])[n:12][c:13]2[c:14]([Br:15])[cH:16][c:17]([CH3:18])[cH:19][n:20]12 | CCC=O.CCCNc1c(SC)nc2c(Br)cc(C)cn12 | CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12 | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccn2ccnc2c1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]>>[#16:4]-[c:5]1:[#7;a:6]:[c:7]:[#7;a:8](:[c:9]):[c:10]:1-[N;H0;D3;+0:11](-[C:12]-[C:13])-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | 67.6 | [{"value": 67.6, "product": "BrC=1C=2N(C=C(C1)C)C(=C(N2)SC)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine (103 mg) and propionaldehyde (57 mg) were dissolved in tetrahydrofuran (1.2 mL), then 3M sulfuric acid (0.24 mL) was added thereto, follwed by adding sodium borohydride (24 mg) under ice-cooling, and then the mixture was stirred for 3 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccn2ccnc2c1 | Other | O1CCCC1.O | null | 3 | CCC=O.CCCNc1c(SC)nc2c(Br)cc(C)cn12>O1CCCC1.O>CCCN(CCC)c1c(SC)nc2c(Br)cc(C)cn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53f8dfa59be24e519705658fa14c16ab | CCOC(=O)CBr.COc1nccnc1N=C(SC)SC>>CCOC(=O)c1c(SC)nc2c(OC)nccn12 | O.BrCC(=O)OCC.COC=1C(=NC=CN1)N=C(SC)SC>>COC=1C=2N(C=CN1)C(=C(N2)SC)C(=O)OCC | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CS[C:7]([S:8][CH3:9])=[N:10][c:11]1[c:12]([O:13][CH3:14])[n:15][cH:16][cH:17][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([S:8][CH3:9])[n:10][c:11]2[c:12]([O:13][CH3:14])[n:15][cH:16][cH:17][n:18]12 | CCOC(=O)CBr.COc1nccnc1N=C(SC)SC | CCOC(=O)c1c(SC)nc2c(OC)nccn12 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 3c267dccfae8261a70f72143b4e4810b305c259e0418e4dd3527c59c22d14363 | f7e1f7b75eaaa242da7c0fbcc1aa8ff0732ddd85decf84eb68979986ec93c0bd | c1cn2ccnc2cn1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-S-[C;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8])=[N;H0;D2;+0:9]-[c:10]1:[n;H0;D2;+0:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1-[#8:16]>>[#8:16]-[c:15]1:[#7;a:14]:[c:13]:[c:12]:[n;H0;D3;+0:11]2:[c:10]:1:[n;H0;D2;+0:9]:[c;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8]):[c;H0;D3;+0:1]:2-[C:2](=[O;D1;... | null | [] | 100 | CELSIUS | 14 | HOUR | Ethyl bromoacetate (18.5 mL) and iso-dipropylethylamine (29 mL) were added to a solution of methyl N-(3-methoxy-2-pyrazinyl)-(methylsulfanyl)methaneimidothioate (19.1 g) in acetonitrile (42 mL), and the mixture was heated under stirring at 100° C. for 14 hours. After the reaction mixture was cooled to room temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Monosulfide.Monosulfide | Ester.Monosulfide | c1cnccn1 | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | HBr | C(C)#N | 100 | 14 | CCOC(=O)CBr.COc1nccnc1N=C(SC)SC>C(C)#N>CCOC(=O)c1c(SC)nc2c(OC)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7abdf09d550e4ee88ce0c2159dad6a0b | COc1ccc(B(O)O)c(C)c1.Nc1nnc(Cl)cc1Br>>COc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | BrC1=C(N=NC(=C1)Cl)N.COC1=CC(=C(C=C1)B(O)O)C.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)OC)C | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][c:15]1[CH3:16].Br[c:7]1[cH:8][c:9]([Cl:10])[n:11][n:12][c:13]1[NH2:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([Cl:10])[n:11][n:12][c:13]2[NH2:14])[c:15]([CH3:16])[cH:17]1 | COc1ccc(B(O)O)c(C)c1.Nc1nnc(Cl)cc1Br | COc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | null | null | C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | adacd3669bc1a24c4361e5305292c80a681bc380fae785e3ebcb5b72415c1784 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccnnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[C;D1;H3:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8]):[c:10]:[c:11] | 54.9 | [{"value": 54.9, "product": "ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 12 | HOUR | 4-Bromo-6-chloro-3-pyridazineamine (12 g) and 4-methoxy-2-methylphenylboronic acid (10.5 g) were dissolved in a mixed solvent of toluene (240 mL) and ethanol (45 mL), then tetrakistriphenylphosphine palladium complex (6.7 g) and a 2M aqueous sodium carbonate solution (24 mL) were added thereto, and the mixture was heat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1 | c1ccccc1.c1ccnnc1 | HBr.B | C1(=CC=CC=C1)C.C(C)O | 100 | 12 | COc1ccc(B(O)O)c(C)c1.Nc1nnc(Cl)cc1Br>C1(=CC=CC=C1)C.C(C)O>COc1ccc(-c2cc(Cl)nnc2N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07a7055c4d7c49e6ac9330386c5fda72 | COc1ccc(-c2cc(Cl)nnc2N)c(C)c1>>COc1ccc(-c2ccnnc2N)c(C)c1 | C(=O)[O-].[NH4+].ClC1=CC(=C(N=N1)N)C1=C(C=C(C=C1)OC)C>>COC1=CC(=C(C=C1)C1=C(N=NC=C1)N)C | Cl[c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][c:14]2[CH3:15])[c:12]([NH2:13])[n:11][n:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][n:11][c:12]2[NH2:13])[c:14]([CH3:15])[cH:16]1 | COc1ccc(-c2cc(Cl)nnc2N)c(C)c1 | COc1ccc(-c2ccnnc2N)c(C)c1 | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 11fec97dc22aabf340de6dd16bd9ed47791a1ff823f957f6e3aa8baf8018c49f | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccnnc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1>>[#7;a:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:1]:1 | 90.6 | [{"value": 90.6, "product": "COC1=CC(=C(C=C1)C1=C(N=NC=C1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10% Pd—C (hydrous product; 7.89 g) and ammonium formate (11.96 g) were added to a solution of 6-chloro-4-(4-methoxy-2-methylphenyl)-3-pyridazineamine (7.89 g) in methanol (100 mL), and the mixture was heated under reflux for 1.5 hours. The reaction mixture was filtered through Celite, and the solvent was evaporated. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccnnc1 | c1ccnnc1 | c1ccccc1.c1ccnnc1 | Other | [Pd].CO | null | null | COc1ccc(-c2cc(Cl)nnc2N)c(C)c1>[Pd].CO>COc1ccc(-c2ccnnc2N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d011a34f340141d78c8d6e01cd5e9f78 | CCOC(=O)CBr.COc1ccc(-c2ccnnc2N=C(SC)SC)c(C)c1>>CCOC(=O)c1c(SC)nc2c(-c3ccc(OC)cc3C)ccnn12 | O.BrCC(=O)OCC.C(C)N(C(C)C)C(C)C.COC1=CC(=C(C=C1)C1=C(N=NC=C1)N=C(SC)SC)C>>COC1=CC(=C(C=C1)C=1C=2N(N=CC1)C(=C(N2)SC)C(=O)OCC)C | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CS[C:7]([S:8][CH3:9])=[N:10][c:11]1[c:12](-[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]2[CH3:21])[cH:22][cH:23][n:24][n:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([S:8][CH3:9])[n:10][c:11]2[c:12](-[c:13]3[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][c:20]3[CH3:... | CCOC(=O)CBr.COc1ccc(-c2ccnnc2N=C(SC)SC)c(C)c1 | CCOC(=O)c1c(SC)nc2c(-c3ccc(OC)cc3C)ccnn12 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | bc7c29467fce76f06e95a31f2573538d88769b2abbf0dae6a32a1db90239edc4 | f7e1f7b75eaaa242da7c0fbcc1aa8ff0732ddd85decf84eb68979986ec93c0bd | c1ccc(-c2ccnn3ccnc23)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-S-[C;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8])=[N;H0;D2;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[#7;a:13]:[c:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:6](-[#16:7]-[C;D1;H3:8]):[n;H0;D2;+0:9]:[c:10](:[c:11]):[n;H0;D3;+0:12]:1:[#7;a:13]:[c:14] | null | [] | 100 | CELSIUS | 14 | HOUR | Ethyl bromoacetate (0.87 mL) and i-Pr2EtN (1.36 mL) were added to a solution of methyl N-[4-(4-methoxy-2-methylphenyl)-3-pyridazinyl]-(methylsulfanyl)methaneimidothioate (1.25 g) in acetonitrile (10 mL), and the mixture was heated under stirring at 100° C. for 14 hours. The reaction mixture was cooled to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Monosulfide.Monosulfide | Ester.Monosulfide | c1ccnnc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HBr | C(C)#N | 100 | 14 | CCOC(=O)CBr.COc1ccc(-c2ccnnc2N=C(SC)SC)c(C)c1>C(C)#N>CCOC(=O)c1c(SC)nc2c(-c3ccc(OC)cc3C)ccnn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3ef0ed44cec4ad4b299aee980ab90e1 | CCC(N)CO.Clc1cc(Cl)ncn1>>CCC(CO)Nc1cc(Cl)ncn1 | ClC1=NC=NC(=C1)Cl.NC(CO)CC>>ClC1=CC(=NC=N1)NC(CO)CC | [CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[NH2:6].Cl[c:7]1[cH:8][c:9]([Cl:10])[n:11][cH:12][n:13]1>>[CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[NH:6][c:7]1[cH:8][c:9]([Cl:10])[n:11][cH:12][n:13]1 | CCC(N)CO.Clc1cc(Cl)ncn1 | CCC(CO)Nc1cc(Cl)ncn1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | 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]-[C:9](-[C:10])-[NH2;D1;+0:11]>>[C:8]-[C:9](-[C:10])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1 | null | [] | null | null | null | null | 4,6-Dichloropyrimidine (5.0 g) and 2-amino-1-butanol (6.5 mL) were heated under reflux in 1,4-dioxane (26 mL) for 1 hour. The reaction mixture was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10) to give the title compound (5.6 g) as a pale orange oil.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCOCC1 | null | null | CCC(N)CO.Clc1cc(Cl)ncn1>O1CCOCC1>CCC(CO)Nc1cc(Cl)ncn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7aeaa9b5e887432ea2aa67e82af68d84 | CCC(CO)Nc1cc(Cl)ncn1>>CCC(CO)Nc1ccncn1 | ClC1=CC(=NC=N1)NC(CO)CC.[OH-].[Na+]>>N1=CN=C(C=C1)NC(CO)CC | Cl[c:9]1[cH:8][c:7]([NH:6][CH:3]([CH2:2][CH3:1])[CH2:4][OH:5])[n:12][cH:11][n:10]1>>[CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[NH:6][c:7]1[cH:8][cH:9][n:10][cH:11][n:12]1 | CCC(CO)Nc1cc(Cl)ncn1 | CCC(CO)Nc1ccncn1 | null | [Pd].[Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 76895d15d2d466b89a30aacc2ef4edbb246f8c7b092db05f2443e4acbf4f85b3 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:7]:1 | null | [] | null | null | null | null | 2-[(6-Chloro-4-pyrimidinyl)amino]-1-butanol was dissolved in ethanol (110 mL), which was sequentially added with a 5N aqueous sodium hydroxide solution (5.5 mL) and Pd—C (hydrous product; 0.55 g), and hydrogenation was performed under hydrogen atmosphere at a normal temperature and a normal pressure. After completion o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1 | Other | [Pd].[Pd].C(C)O | null | null | CCC(CO)Nc1cc(Cl)ncn1>[Pd].[Pd].C(C)O>CCC(CO)Nc1ccncn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ce564191dcc48cfa674d17d783155ab | CCC(CO)Nc1ncncc1Br>>CCC1CN2C=NC=C(Br)C2=N1 | BrC=1C(=NC=NC1)NC(CO)CC.S(=O)(Cl)Cl>>BrC=1C=2N(C=NC1)CC(N2)CC | O[CH2:4][CH:3]([CH2:2][CH3:1])[NH:12][c:11]1[n:5][cH:6][n:7][cH:8][c:9]1[Br:10]>>[CH3:1][CH2:2][CH:3]1[CH2:4][N:5]2[CH:6]=[N:7][CH:8]=[C:9]([Br:10])[C:11]2=[N:12]1 | CCC(CO)Nc1ncncc1Br | CCC1CN2C=NC=C(Br)C2=N1 | null | null | C=1(C(=CC=CC1)C)C | Reduction | OtherReaction | 6a2ef22bb6c74569235803d2ce7a2fea50e3f12dac8dc022e2ff3ebc53e59331 | 9374feb200a4832853bbfb58e352f944bf17983311287662fa53041448433835 | C1=CC2=NCCN2C=N1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[NH;D2;+0:4]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[cH;D2;+0:9]:[c;H0;D3;+0:10]:1-[Br;D1;H0:11]>>[Br;D1;H0:11]-[C;H0;D3;+0:10]1=[CH;D2;+0:9]-[N;H0;D2;+0:8]=[CH;D2;+0:7]-[N;H0;D3;+0:6]2-[CH2;D2;+0:1]-[C:2](-[C:3])-[N;H0;D2;+0:4]=[C;H0;D3;+0:5]-1-2 | 98.1 | [{"value": 98.1, "product": "BrC=1C=2N(C=NC1)CC(N2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | DAY | 2-[(5-Bromo-4-pyrimidinyl)amino]-1-butanol (3.3 g) was dissolved in xylene (27 mL), then thionyl chloride (4.9 mL) was added thereto, and the mixture was heated under stirring at 100° C. for 1 day. The precipitated crystals were collected by filtration and suspended in a 1M aqueous sodium carbonate solution. This mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Secondary amine | Alkenyl halide.Tertiary amine | c1cncnc1 | C1=CC2=NCCN2C=N1 | C1=CC2=NCCN2C=N1 | HO- | C=1(C(=CC=CC1)C)C | 100 | 24 | CCC(CO)Nc1ncncc1Br>C=1(C(=CC=CC1)C)C>CCC1CN2C=NC=C(Br)C2=N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f6be0fdcc7454cd9853af08eab5f7538 | CCC1CN2C=NC=C(Br)C2=N1>>CCc1cn2cncc(Br)c2n1 | BrC=1C=2N(C=NC1)CC(N2)CC>>BrC=1C=2N(C=NC1)C=C(N2)CC | [CH3:1][CH2:2][CH:3]1[CH2:4][N:5]2[CH:6]=[N:7][CH:8]=[C:9]([Br:10])[C:11]2=[N:12]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5]2[cH:6][n:7][cH:8][c:9]([Br:10])[c:11]2[n:12]1 | CCC1CN2C=NC=C(Br)C2=N1 | CCc1cn2cncc(Br)c2n1 | null | [O-2].[O-2].[Mn+4] | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 31d8cb45bfee75d7dc58ada016878d2887065c520615c9f014f8358557a8518a | ec223f8fb0661e09955f4db94fe3afc2006ddb41271eb6ffedd6e26bd39cc60d | c1cc2nccn2cn1 | [Br;D1;H0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[N;H0;D2;+0:4]=[CH;D2;+0:5]-[N;H0;D3;+0:6]2-[CH2;D2;+0:7]-[CH;D3;+0:8](-[C:9]-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12]-1-2>>[Br;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[n;H0;D3;+0:6]2:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9]-[C;D1;H3:10]):[n;H0;D2;+0:11... | 43.7 | [{"value": 43.7, "product": "BrC=1C=2N(C=NC1)C=C(N2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 1 | DAY | 8-Bromo-2-ethyl-2,3-dihydroimidazo[1,2-c]pyrimidine (3.0 g) was dissolved in toluene (60 mL), then activated manganese(IV) dioxide (3.5 g) was added thereto, and the mixture was heated under stirring at 90° C. for 1 day. Manganese(IV) oxide was filtered off through Celite, and the solvent was evaporated. The resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Tertiary amine | Aromatic halide | C1=CC2=NCCN2C=N1 | c1cc2nccn2cn1 | c1cc2nccn2cn1 | null | [O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C | 90 | 24 | CCC1CN2C=NC=C(Br)C2=N1>[O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C>CCc1cn2cncc(Br)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3cca3e00bbc64b42a99f319374361cd1 | CCc1cn2cncc(Br)c2n1.CN(C)C=O>>CCc1nc2c(Br)cncn2c1C=O | BrC=1C=2N(C=NC1)C=C(N2)CC.P(=O)(Cl)(Cl)Cl.CN(C=O)C>>BrC=1C=2N(C=NC1)C(=C(N2)CC)C=O | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Br:7])[cH:8][n:9][cH:10][n:11]2[cH:12]1.CN(C)[CH:13]=[O:14]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([Br:7])[cH:8][n:9][cH:10][n:11]2[c:12]1[CH:13]=[O:14] | CCc1cn2cncc(Br)c2n1.CN(C)C=O | CCc1nc2c(Br)cncn2c1C=O | null | null | null | C-C Coupling | OtherReaction | 8a035d1da1b950c730fa68e247c5a4ba7fa43b3d0c30089a09a34056dd417eea | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1cc2nccn2cn1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:2:[cH;D2;+0:12]:1>>[C:3]-[c:4]1:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:2:[c;H0;D3;+0:12]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | 1 | DAY | 8-Bromo-2-ethylimidazo[1,2-c]pyrimidine (1.0 g) was added to a mixture of phosphorus oxychloride (1.2 mL) and N,N-dimethylformamide (4.4 mL) at room temperature. The mixture was heated under stirring as it was at 80° C. for 1 day. After cooled to room temperature, it was poured slowly on ice. The material was extracted... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1cc2nccn2cn1 | c1cc2nccn2cn1 | c1cc2nccn2cn1 | Other | null | null | 24 | CCc1cn2cncc(Br)c2n1.CN(C)C=O>>CCc1nc2c(Br)cncn2c1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf2dfacaa1cf4bf29ee8cbdd73c6f90d | CC(C)(C)O.CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1C(=O)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1NC(=O)OC(C)(C)C | ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)CC)C(=O)O.C(C)(C)(C)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C(C)N(CC)CC>>ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)CC)NC(OC(C)(C)C)=O | [OH:23][C:24]([CH3:25])([CH3:26])[CH3:27].O[C:21]([c:19]1[c:3]([CH2:2][CH3:1])[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[n:15][cH:16][cH:17][n:18]21)=[O:22].[N-]=[N+]=[N:20]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14... | CC(C)(C)O.CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1C(=O)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1NC(=O)OC(C)(C)C | null | null | null | Protection | OtherReaction | ff75c28e1d3e252861948e87159e36873498ae0641a66598d10c7093178e37d2 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccc(-c2nccn3ccnc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[#7;a:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[C:12].O=P(-[N;H0;D2;+0:13]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[OH;D1;+0:18]>>[C:12]-[c:11]1:[#7;a:10]:[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[#7;a:4]:2:[c;... | null | [] | null | null | 2 | HOUR | The resulting 8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazine-3-carboxylic acid was dissolved in tert-butyl alcohol (15 mL), then diphenylphosphorylazide (0.69 mL, 3.2 mmol) and triethylamine (0.49 mL, 3.5 mmol) were added thereto, and the mixture was stirred for 2 hours by heating under reflux. After being cooled... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1cn2ccnc2cn1.c1ccccc1.c1ccccc1 | c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | HO- | null | null | 2 | CC(C)(C)O.CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1C(=O)O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CCc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1NC(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47b92d2b3d10436eb9c94b440aa7bc1c | CCCN(C(=O)OC(C)(C)C)c1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12>>CCCNc1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12 | ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)CC)N(C(OC(C)(C)C)=O)CCC.Cl.C(C)(=O)OCC.[OH-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)CC)NCCC | CC(C)(C)OC(=O)[N:4]([CH2:3][CH2:2][CH3:1])[c:5]1[c:6]([CH2:7][CH3:8])[n:9][c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[n:20][cH:21][cH:22][n:23]12>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[c:6]([CH2:7][CH3:8])[n:9][c:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[n:20][cH:2... | CCCN(C(=O)OC(C)(C)C)c1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12 | CCCNc1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nccn3ccnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4]1:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:2:[#7;a:11]:[c:12]:1-[C:13]>>[C:3]-[C:2]-[NH;D2;+0:1]-[c:4]1:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:2:[#7;a:11]:[c:12]:1-[C:13] | null | [] | null | null | 20 | HOUR | tert-Butyl N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-propylcarbamate was dissolved in ethyl acetate (1 mL), then a 4N hydrochloric acid-ethyl acetate solution (1.9 mL, 7.4 mmol) was added thereto at room temperature, and the mixture was stirred at room temperature for 20 hours. Under ice-cooling, a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1cn2ccnc2cn1 | HO- | C(C)(=O)OCC | null | 20 | CCCN(C(=O)OC(C)(C)C)c1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12>C(C)(=O)OCC>CCCNc1c(CC)nc2c(-c3ccc(Cl)cc3Cl)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3dedaa32842468091f1cd400f894547 | CCC(=O)C(Cl)C(=O)OC.Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl>>CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(Cl)cn2c1C(=O)OC | ClC=1N=C(C(=NC1)N)C1=C(C=C(C=C1)Cl)Cl.ClC(C(=O)OC)C(CC)=O>>COC(=O)C1=C(N=C2N1C=C(N=C2C2=C(C=C(C=C2)Cl)Cl)Cl)CC | O=[C:3]([CH2:2][CH3:1])[CH:20](Cl)[C:21](=[O:22])[O:23][CH3:24].[NH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[Cl:14])[n:15][c:16]([Cl:17])[cH:18][n:19]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[n:15][c:16]([Cl:17])[cH:18][n:19]2[c:20]1[C:21](=[... | CCC(=O)C(Cl)C(=O)OC.Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl | CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(Cl)cn2c1C(=O)OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 9ef3f8c7d8012f16862df6e6d5d64f5e5c28836502935c9f0f51594189d35521 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1ccc(-c2nccn3ccnc23)cc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8].[Cl;D1;H0:9]-[c:10]1:[#7;a:11]:[c:12](-[c:13]):[c:14](-[NH2;D1;+0:15]):[n;H0;D2;+0:16]:[c:17]:1>>[C;D1;H3:8]-[C:7]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:15]:[c:14]2:[c:12](-[c:13]):[#7;a:11]:[c:10](-[Cl;D1;H0:9]):[c:17]:[n;H0;D3;+0:16]:... | null | [] | 170 | CELSIUS | null | null | 5-Chloro-3-(2,4-dichlorophenyl)-2-pyrazineamine (1.1 g, 4.0 mmol) and methyl 2-chloro-3-oxopentanoate (5.7 mL) were mixed, and the mixture was heated under stirring at 170° C. 3 hours. After being allowed to cool, the reaction mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), and t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1cnccn1 | c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | HCl | null | 170 | null | CCC(=O)C(Cl)C(=O)OC.Nc1ncc(Cl)nc1-c1ccc(Cl)cc1Cl>>CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(Cl)cn2c1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d354e8b3a5f94cb7ac254cd7b9f2205f | CCc1nc2c(Br)nc(C)cn2c1C(=O)OC.OB(O)c1ccc(Cl)cc1Cl>>CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(C)cn2c1C(=O)OC | COC(=O)C1=C(N=C2N1C=C(N=C2Br)C)CC.ClC1=C(C=CC(=C1)Cl)B(O)O>>COC(=O)C1=C(N=C2N1C=C(N=C2C2=C(C=C(C=C2)Cl)Cl)C)CC | Br[c:6]1[c:5]2[n:4][c:3]([CH2:2][CH3:1])[c:20]([C:21](=[O:22])[O:23][CH3:24])[n:19]2[cH:18][c:16]([CH3:17])[n:15]1.OB(O)[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[Cl:14]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[n:15][c:16]([CH3:17])[cH:18][n:19]2[c:20]1[C:21](=... | CCc1nc2c(Br)nc(C)cn2c1C(=O)OC.OB(O)c1ccc(Cl)cc1Cl | CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(C)cn2c1C(=O)OC | null | null | C1(=CC=CC=C1)C.CO | C-C Coupling | Suzuki coupling with boronic acids | f5f68366c974e5c94b4bc855fbfd92fc71b74cb90c46aa9127be16df4ce6917f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nccn3ccnc23)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6](-[C:7](-[#8:8])=[O;D1;H0:9]):[c:10]:[#7;a:11]:[c:12]:2:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[c:10]:[#7;a:11]:[c:12]2:[#7;a:5]:1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:13](:[c:14]:[c:1... | 107.4 | [{"value": 107.4, "product": "COC(=O)C1=C(N=C2N1C=C(N=C2C2=C(C=C(C=C2)Cl)Cl)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Bromo-2-ethyl-6-methylimidazo[1,2-a]pyrazine-3-carboxylic acid methyl ester (0.30 g, 1.0 mmol) was dissolved in a mixed solvent of toluene (5.6 mL) and methanol (1.4 mL). Then 2,4-dichlorobenzeneboronic acid (0.382 g, 2.0 mmol) and tetrakistriphenylphosphine palladium complex (116 mg, 0.1 mmol) were added thereto, an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cn2ccnc2cn1.c1ccccc1 | c1ccccc1.c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | HBr.B | C1(=CC=CC=C1)C.CO | null | null | CCc1nc2c(Br)nc(C)cn2c1C(=O)OC.OB(O)c1ccc(Cl)cc1Cl>C1(=CC=CC=C1)C.CO>CCc1nc2c(-c3ccc(Cl)cc3Cl)nc(C)cn2c1C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3cf04266c89d43188ea72fd741f61495 | Cc1cn2ccnc(-c3ccc(Cl)cc3Cl)c2n1.O=[N+]=O>>Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-] | ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C=C(N2)C.F[B-](F)(F)F.O=[N+]=O.O>>ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)C)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[n:14][cH:15][cH:16][n:17]2[cH:18]1.[N+:19](=[O:20])=[O:21]>>[CH3:1][c:2]1[n:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[n:14][cH:15][cH:16][n:17]2[c:18]1[N+:19](=[O:20])[O-:21] | Cc1cn2ccnc(-c3ccc(Cl)cc3Cl)c2n1.O=[N+]=O | Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-] | null | null | C(C)#N | Functional Group Addition | OtherReaction | 57eebfeb389d6a773d16b3708a163218e309f50f4d5b0ce8352432d25e433fec | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccc(-c2nccn3ccnc23)cc1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:[cH;D2;+0:10]:1.[O;D1;H0:11]=[N+;H0;D2:12]=[O;H0;D1;+0:13]>>[C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:[c;H0;D3;+0:10]:1-[N+;H0;D3:12](-[O-;H0;D1:13])=[O;D1;H0:11] | 1,323.8 | [{"value": 1323.8, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 8-(2,4-Dichlorophenyl)-2-methylimidazo[1,2-a]pyrazine (0.10 g, 0.36 mmol) was dissolved in acetonitrile (0.36 mL), then nitronium tetrafluoroborate (72 mg, 0.54 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour under nitrogen atmosphere. Water was added to the reaction mixture, and it ... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1cn2ccnc2cn1 | c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | null | C(C)#N | null | 1 | Cc1cn2ccnc(-c3ccc(Cl)cc3Cl)c2n1.O=[N+]=O>C(C)#N>Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e461046a28c4037887e2fccf29aeadc | Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-]>>Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1N | ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)C)[N+](=O)[O-].C(C)(=O)O>>ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)C)N | O=[N+:19]([O-])[c:18]1[c:2]([CH3:1])[n:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[n:14][cH:15][cH:16][n:17]21>>[CH3:1][c:2]1[n:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[n:14][cH:15][cH:16][n:17]2[c:18]1[NH2:19] | Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-] | Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1N | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2nccn3ccnc23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[#7;a:9]:[c:10]:1-[C;D1;H3:11]>>[C;D1;H3:11]-[c:10]1:[#7;a:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]:[c:4]:[#7;a:3]:2:[c:2]:1-[NH2;D1;+0:1] | 35.4 | [{"value": 35.4, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=2N(C=CN1)C(=C(N2)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 8-(2,4-Dichlorophenyl)-2-methyl-3-nitroimidazo[1,2-a]pyrazine (25 mg, 0.077 mmol) was dissolved in ethanol (0.36 mL), then acetic acid (0.5 mL) and iron powders (22 mg) were added thereto, and the mixture was stirred for 1 hour by heating under reflux. After the reaction mixture was allowed to cool, the solvent was eva... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cn2ccnc2cn1 | Other | [Fe].C(C)O | null | 1 | Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1[N+](=O)[O-]>[Fe].C(C)O>Cc1nc2c(-c3ccc(Cl)cc3Cl)nccn2c1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d298d32255543de800e4507a8f82d71 | CCCC(=O)c1c(CC)nc2c(Cl)nccn12.COc1cc(C)cc(C)c1B(O)O>>CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | ClC=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)=O.CC1=CC(=C(C(=C1)C)B(O)O)OC.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>>C(C)C=1N=C2N(C=CN=C2C2=C(C=C(C=C2C)C)OC)C1C(CCC)=O | Cl[c:12]1[c:11]2[n:10][c:7]([CH2:8][CH3:9])[c:6]([C:4]([CH2:3][CH2:2][CH3:1])=[O:5])[n:26]2[cH:25][cH:24][n:23]1.OB(O)[c:13]1[c:14]([CH3:15])[cH:16][c:17]([CH3:18])[cH:19][c:20]1[O:21][CH3:22]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[c:6]1[c:7]([CH2:8][CH3:9])[n:10][c:11]2[c:12](-[c:13]3[c:14]([CH3:15])[cH:16][c:17]([CH3:18... | CCCC(=O)c1c(CC)nc2c(Cl)nccn12.COc1cc(C)cc(C)c1B(O)O | CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | null | null | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | f5f68366c974e5c94b4bc855fbfd92fc71b74cb90c46aa9127be16df4ce6917f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nccn3ccnc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:1:[#7;a:7]:[c:8]:[c:9]:2-[C:10]=[O;D1;H0:11].O-B(-O)-[c;H0;D3;+0:12](:[c:13](-[C;D1;H3:14]):[c:15]):[c:16](-[#8:17]):[c:18]>>[#8:17]-[c:16](:[c:18]):[c;H0;D3;+0:12](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:1:[#7;a:7]:[c:8]:[c:9]:2-[C:10]=[O;D1;H0:11])... | 77.5 | [{"value": 77.5, "product": "C(C)C=1N=C2N(C=CN=C2C2=C(C=C(C=C2C)C)OC)C1C(CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(8-Chloro-2-ethylimidazo[1,2-a]pyrazin-3-yl)-1-butanone (226 mg, 0.90 mmol) and 4,6-dimethyl-2-methoxybenzeneboronic acid (198 mg, 1.1 mmol) were dissolved in a mixed solvent of 1,2-dimethoxyethane (4.5 mL) and water (0.75 mL). Barium hydroxide octahydrate (347 mg, 1.1 mmol) and tetrakis(triphenylphosphine)palladium ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cn2ccnc2cn1.c1ccccc1 | c1ccccc1.c1cn2ccnc2cn1 | c1ccccc1.c1cn2ccnc2cn1 | HCl.B | O.COCCOC | null | null | CCCC(=O)c1c(CC)nc2c(Cl)nccn12.COc1cc(C)cc(C)c1B(O)O>O.COCCOC>CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-192e1a40a6384d7292b3d4f44ff27a9d | CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12.CC[CH2][Mg][Br]>>CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | C(C)C=1N=C2N(C=CN=C2C2=C(C=C(C=C2C)C)OC)C1C(CCC)=O.C(CC)[Mg]Br.[Cl-].[NH4+]>>C(C)C=1N=C2N(C=CN=C2C2=C(C=C(C=C2C)C)OC)C1C(CCC)(CCC)O | [C:4](=[O:5])([CH2:6][CH2:7][CH3:8])[c:9]1[c:10]([CH2:11][CH3:12])[n:13][c:14]2[c:15](-[c:16]3[c:17]([CH3:18])[cH:19][c:20]([CH3:21])[cH:22][c:23]3[O:24][CH3:25])[n:26][cH:27][cH:28][n:29]12.[Br][Mg][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][C:4]([OH:5])([CH2:6][CH2:7][CH3:8])[c:9]1[c:10]([CH2:11][CH3:12])[n:13][c:14... | CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12.CC[CH2][Mg][Br] | CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | null | null | O1CCCC1 | C-C Coupling | Grignard from ketone to alcohol | 4737491c367e985251b8e6236de937de0f5f777bcb09b5971359565d81ed217a | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | c1ccc(-c2nccn3ccnc23)cc1 | [Br]-[Mg]-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[c:5]1:[#7;a:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:2:[c:13]:1-[C;H0;D3;+0:14](=[O;H0;D1;+0:15])-[C:16]-[C:17]>>[C:4]-[c:5]1:[#7;a:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:2:[c:13]:1-[C;H0;D4;+0:14](-[OH;D1;+0:15])(-[C:16]-[C:17])-[CH2;D2;+0:1]-[C:2]-[C;... | null | [] | null | null | 2 | HOUR | The resulting 1-[2-ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-1-butanone (220 mg, 0.63 mmol) was dissolved in tetrahydrofuran (2 mL), then a 0.90M propylmagnesium bromide solution in tetrahydrofuran (3.6 mL, 3.2 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | null | null | c1ccccc1.c1cn2ccnc2cn1 | Br-.Mg | O1CCCC1 | null | 2 | CCCC(=O)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12.CC[CH2][Mg][Br]>O1CCCC1>CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-193aa487bb724d47ad2b1c9bf3bf0bf9 | CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12>>CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | C([O-])(O)=O.[Na+].C(C)C=1N=C2N(C=CN=C2C2=C(C=C(C=C2C)C)OC)C1C(CCC)(CCC)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>COC1=C(C(=CC(=C1)C)C)C=1C=2N(C=CN1)C(=C(N2)CC)\C(=C/CC)\CCC | O[C:4]([CH2:3][CH2:2][CH3:1])([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16]([CH3:17])[cH:18][c:19]([CH3:20])[cH:21][c:22]3[O:23][CH3:24])[n:25][cH:26][cH:27][n:28]12>>[CH3:1][CH2:2]/[CH:3]=[C:4](/[CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16... | CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 2552af78a9ee7fee2cf4bc86811ade6ce7c2595ea6de1b1217b4ecd33d9a5077 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | c1ccc(-c2nccn3ccnc23)cc1 | O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[CH2;D2;+0:4]-[C:5]-[C;D1;H3:6])-[c:7]1:[#7;a:8]2:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:2:[#7;a:14]:[c:15]:1-[C:16]>>[C:16]-[c:15]1:[#7;a:14]:[c:13]2:[c:12]:[#7;a:11]:[c:10]:[c:9]:[#7;a:8]:2:[c:7]:1/[C;H0;D3;+0:1](-[C:2]-[C:3])=[CH;D2;+0:4]\[C:5]-[C;D1;H3:6] | 101.4 | [{"value": 101.4, "product": "COC1=C(C(=CC(=C1)C)C)C=1C=2N(C=CN1)C(=C(N2)CC)\\C(=C/CC)\\CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-[2-Ethyl-8-(2-methoxy-4,6-dimethylphenyl)imidazo[1,2-a]pyrazin-3-yl]-4-heptanol (115 mg, 0.29 mmol) and triethylamine (0.48 mL, 3.5 mmol) were dissolved in methylene chloride (3 mL), then methanesulfonyl chloride (0.13 mL, 1.7 mmol) was added thereto under ice-cooling, and the mixture was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | null | null | c1ccccc1.c1cn2ccnc2cn1 | HO- | C(Cl)Cl | null | 1 | CCCC(O)(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12>C(Cl)Cl>CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fc9f175b03846b1aa0f510d61c8cec7 | CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12>>CCCC(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | COC1=C(C(=CC(=C1)C)C)C=1C=2N(C=CN1)C(=C(N2)CC)\C(=C/CC)\CCC>>COC1=C(C(=CC(=C1)C)C)C=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)CCC | [CH3:1][CH2:2]/[CH:3]=[C:4](/[CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16]([CH3:17])[cH:18][c:19]([CH3:20])[cH:21][c:22]3[O:23][CH3:24])[n:25][cH:26][cH:27][n:28]12>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([CH2:10][CH3:11])[n:12][c:13]2[c:14](-[c:15]3[c:16](... | CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | CCCC(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 | null | [C].[Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(-c2nccn3ccnc23)cc1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:[c:10]:1/[C;H0;D3;+0:11](-[C:12]-[C:13])=[CH;D2;+0:14]\[C:15]-[C;D1;H3:16]>>[C:1]-[c:2]1:[#7;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:2:[c:10]:1-[CH;D3;+0:11](-[C:12]-[C:13])-[CH2;D2;+0:14]-[C:15]-[C;D1;H3:16] | 54.9 | [{"value": 54.9, "product": "COC1=C(C(=CC(=C1)C)C)C=1C=2N(C=CN1)C(=C(N2)CC)C(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 4 | HOUR | 2-[2-Ethyl-3-[(Z)-1-propyl-1-butenyl]imidazo[1,2-a]pyrazin-8-yl]-3,5-dimethylphenyl methyl ether (41 mg, 0.12 mmol) was dissolved in ethanol (1.5 mL), then 10% palladium-carbon (50% hydrous product; 120 mg) was added thereto, and the mixture was heated under stirring at 45° C. for 4 hours at a normal pressure under hyd... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cn2ccnc2cn1 | null | [C].[Pd].C(C)O | 45 | 4 | CC/C=C(/CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12>[C].[Pd].C(C)O>CCCC(CCC)c1c(CC)nc2c(-c3c(C)cc(C)cc3OC)nccn12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0e9e6b47a37641d8819dfc59e60223ca | CC(=O)CC(C#N)c1ccc(C)cc1C.NN>>Cc1ccc(-c2cc(C)nnc2N)c(C)c1 | C(C)(=O)O.O.NN.CC1=C(C=CC(=C1)C)C(CC(C)=O)C#N>>CC1=C(C=CC(=C1)C)C1=C(N=NC(=C1)C)N | O=[C:8]([CH2:7][CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:16][c:14]1[CH3:15])[C:12]#[N:13])[CH3:9].[NH2:10][NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH3:9])[n:10][n:11][c:12]2[NH2:13])[c:14]([CH3:15])[cH:16]1 | CC(=O)CC(C#N)c1ccc(C)cc1C.NN | Cc1ccc(-c2cc(C)nnc2N)c(C)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 6f197e66869b240851a231d1f25cb4d9d2823d9fa9f4c5d7adfd582c66000e3d | a78e9303472e036bbc8878e5b3222e30e9aba072d6de158deb64f510e46fb597 | c1ccc(-c2ccnnc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[CH;D3;+0:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12].[NH2;D1;+0:13]-[NH2;D1;+0:14]>>[C;D1;H3:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:13]:[n;H0;D2;+0:14]:[c;H0;... | null | [] | null | null | null | null | Acetic acid (5 mL) and hydrazine monohydrate (2.52 g, 0.05 mol) were added to a solution of 1-(2,4-dimethylphenyl)-3-oxobutyl cyanide (10.13 g, 0.05 mol) in ethanol (100 mL), and the mixture was heated under reflux for 8 hours. The reaction mixture was evaporated as it was. Water was added thereto, and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Nitrile | Primary amine | null | c1ccnnc1 | c1ccccc1.c1ccnnc1 | HO- | C(C)O | null | null | CC(=O)CC(C#N)c1ccc(C)cc1C.NN>C(C)O>Cc1ccc(-c2cc(C)nnc2N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4cf939a5affd4488b7559b3acba5ae40 | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2cc(C)nnc2N)c(C)c1>>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC | ClC(C(=O)OC)C(CC)=O.CC1=C(C=CC(=C1)C)C1=C(N=NC(=C1)C)N.O>>COC(=O)C1=C(N=C2N1N=C(C=C2C2=C(C=C(C=C2)C)C)C)CC | O=[C:3]([CH2:2][CH3:1])[CH:20](Cl)[C:21](=[O:22])[O:23][CH3:24].[NH2:4][c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]2[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([CH3:11])[cH:12][c:13]3[CH3:14])[cH:15][c:16]([CH3:17])[n:18][n:19]2[c:20]1[C:... | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2cc(C)nnc2N)c(C)c1 | CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | e9a3a6063b8692570315ac7f7821b744f54b8f587cd5476dacd07314c341cb27 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1ccc(-c2ccnn3ccnc23)cc1 | Cl-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5])-[C;H0;D3;+0:6](=O)-[C:7]-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[#7;a:13]:[c:14]>>[C;D1;H3:8]-[C:7]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:9]:[c:10](:[c:11]):[n;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5] | null | [] | 140 | CELSIUS | null | null | Methyl 2-chloro-3-oxopentanoate (7 mL) was added to a solution of the resulting 4-(2,4-dimethylphenyl)-6-methyl-3-pyridazinamine in N,N-dimethylformamide (60 mL), and the mixture was heated at 140° C. for 6 hours. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with an aque... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1ccnnc1 | c1cnn2ccnc2c1 | c1ccccc1.c1cnn2ccnc2c1 | HCl | CN(C=O)C | 140 | null | CCC(=O)C(Cl)C(=O)OC.Cc1ccc(-c2cc(C)nnc2N)c(C)c1>CN(C=O)C>CCc1nc2c(-c3ccc(C)cc3C)cc(C)nn2c1C(=O)OC |
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