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-c8a6c66353b048e0bd9410b9648b22b8 | CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21>>CN(C)CCCn1ncc2ccc(N)cc21 | CN(CCCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C.[Cl-].[NH4+]>>CN(CCCN1N=CC2=CC=C(C=C12)N)C | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][c:10]2[cH:9][n:8][n:7]([CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:16]2[cH:15]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][n:7]1[n:8][cH:9][c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:15][c:16]12 | CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21 | CN(C)CCCn1ncc2ccc(N)cc21 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 15 | MINUTE | A mixture of dimethyl-{3-(6-nitro-indazol-1-yl)-propyl}-amine (0.400 g, 1.61 mmol), iron powder (0.897 g, 16.1 mmol), and ammonium chloride (0.0430 mg, 0.811 mmol) in a 4:1 solution of ethanol/H2O was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cn[nH]c2c1 | Other | [Fe].C(C)O.O | null | 0.25 | CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21>[Fe].C(C)O.O>CN(C)CCCn1ncc2ccc(N)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-931258ae9c17455eb502585125c483a9 | Cl.O=[N+]([O-])c1cccc2[nH]ncc12>>O=[N+]([O-])c1cccc2[nH]nc(Cl)c12 | Cl.[N+](=O)([O-])C1=C2C=NNC2=CC=C1.[OH-].[Na+].[O-]Cl.[Na+]>>ClC1=NNC2=CC=CC(=C12)[N+](=O)[O-] | [ClH:12].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][n:10][cH:11][c:13]12>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][n:10][c:11]([Cl:12])[c:13]12 | Cl.O=[N+]([O-])c1cccc2[nH]ncc12 | O=[N+]([O-])c1cccc2[nH]nc(Cl)c12 | null | null | O | Functional Group Addition | Chlorination | d7565c0d49fd3424f26a8edf0928ad120b0a003a57177c1e3e1e6ba6fde6a68c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc2[nH]ncc2c1 | [ClH;D0;+0:1].[c:2]:[c:3]1:[cH;D2;+0:4]:[#7;a:5]:[#7;a:6]:[c:7]:1:[c:8]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6]:[c:7](:[c:8]):[c:3]:1:[c:2] | null | [] | 0 | CELSIUS | 5 | HOUR | To a mixture of NaOH (0.500 g, 12.5 mmol) in H2O (15.0 mL) was added 4-nitroindazole (0.500 g, 3.07 mmol) after which it was heated until a red solution formed. The solution was immediately placed in an ice-water bath for 15 minutes before NaClO (6.00 mL, 5.25%, 4.50 mmol) was added. The mixture was stirred at 0° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | null | O | 0 | 5 | Cl.O=[N+]([O-])c1cccc2[nH]ncc12>O>O=[N+]([O-])c1cccc2[nH]nc(Cl)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f1ce3ca17d440acba30939cbb5f2814 | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]nc(Cl)c12>>O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1 | ClC1=NNC2=CC=CC(=C12)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCC1>>ClC1=NN(C2=CC=CC(=C12)[N+](=O)[O-])CCN1CCCC1 | Cl[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[c:10]([Cl:11])[n:12][nH:13]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[c:10]([Cl:11])[n:12][n:13]2[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1 | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]nc(Cl)c12 | O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 37f45c65843eb1934d1248942acee56370679d83d9e5e49713f458cd256ddf5b | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 50 | CELSIUS | null | null | A mixture of 3-chloro-4-nitro-1H-indazole (0.550 g, 2.79 mmol) was treated with potassium carbonate (1.20 g 8.70 mmol) in DMF (10 mL) for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (0.710 g, 4.20 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature and filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12.C1CC[NH]C1 | HCl | CN(C)C=O | 50 | null | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]nc(Cl)c12>CN(C)C=O>O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f97ad5d0f3d14ad3bcc2c20530fae0e5 | O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1>>Nc1cccc2c1c(Cl)nn2CCN1CCCC1 | ClC1=NN(C2=CC=CC(=C12)[N+](=O)[O-])CCN1CCCC1.[Cl-].[NH4+]>>ClC1=NN(C2=CC=CC(=C12)N)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[c:8]([Cl:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[c:8]([Cl:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1 | Nc1cccc2c1c(Cl)nn2CCN1CCCC1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | 84 | [{"value": 84.0, "product": "ClC1=NN(C2=CC=CC(=C12)N)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "ClC1=NN(C2=CC=CC(=C12)N)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-Chloro-4-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.40 g, 1.4 mmol), iron powder (0.76 g, 14 mmol), and ammonium chloride (37 mg, 0.68 mmol) in 80% Ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cccc2n[nH]cc12.C1CC[NH]C1 | Other | [Fe].C(C)O | null | 0.25 | O=[N+]([O-])c1cccc2c1c(Cl)nn2CCN1CCCC1>[Fe].C(C)O>Nc1cccc2c1c(Cl)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e118547db8643f1873744afbd99b347 | Nc1cccc2c1c(Cl)nn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Cl)nn2CCN1CCCC1 | ClC1=NN(C2=CC=CC(=C12)N)CCN1CCCC1.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C(=NN(C2=CC=C1)CCN1CCCC1)Cl | [NH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[c:24]1[c:25]([Cl:26])[n:27][n:28]2[CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:1... | Nc1cccc2c1c(Cl)nn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Cl)nn2CCN1CCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | null | [] | null | null | 6 | HOUR | A mixture of 3-chloro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine (300 mg, 1.14 mmol), (4-benzyloxy-phenyl)-acetic acid (302 mg, 1.25 mmol), ethyldimethylpropylcarbodiimide hydrochloride (261 mg g, 1.37 mmol), N-hydroxybenzotriazole (184 mg, 1.37 mmol), N-methyl morpholine (290 mg, 2.72 mmol) in 5 mL of DMF was st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | Nc1cccc2c1c(Cl)nn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Cl)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6bb2a64285e402fb31d762dc9f96674 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1.[Br-]>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Br)nn2CCN1CCCC1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1.[OH-].[Na+].[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C(=NN(C2=CC=C1)CCN1CCCC1)Br | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1)[NH:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[c:24]1[cH:25][n:27][n:28]2[CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.[Br-:26]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11]... | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1.[Br-] | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Br)nn2CCN1CCCC1 | null | null | O.CO | Functional Group Interconversion | Bromination | 25157f9d3af4ae241d48d9986ef2032af184156718cdc4bc554e8a3105505db7 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | [Br-;H0;D0:1].[C:2]-[#7;a:3]1:[#7;a:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5]1:[#7;a:4]:[#7;a:3](-[C:2]):[c:8](:[c:9]):[c:6]:1:[c:7] | null | [] | 0 | CELSIUS | 5 | HOUR | A mixture of 2-[4-(benzyloxy)phenyl]-N-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-yl]acetamide (Example 3, 0.200 g, 0.440 mmol) and NaOH (0.400 g, 10.0 mmol) in H2O (6 mL) was added in methanol (6 mL) was placed in an ice-water bath for 15 minutes before pyridinium tribromide (0.470 g, 1.47 mmol) in MeOH (1.5 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12 | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | null | O.CO | 0 | 5 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1.[Br-]>O.CO>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1c(Br)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3186eb8c24f146f1a18c81ee9a18bf8e | Cl.O=[N+]([O-])c1ccc2[nH]ncc2c1>>O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1 | Cl.[N+](=O)([O-])C=1C=C2C=NNC2=CC1.[OH-].[Na+].[O-]Cl.[Na+]>>ClC1=NNC2=CC=C(C=C12)[N+](=O)[O-] | [ClH:11].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][cH:10][c:12]2[cH:13]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][c:10]([Cl:11])[c:12]2[cH:13]1 | Cl.O=[N+]([O-])c1ccc2[nH]ncc2c1 | O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1 | null | null | O | Functional Group Addition | Chlorination | d7565c0d49fd3424f26a8edf0928ad120b0a003a57177c1e3e1e6ba6fde6a68c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccc2[nH]ncc2c1 | [ClH;D0;+0:1].[c:2]:[c:3]1:[cH;D2;+0:4]:[#7;a:5]:[#7;a:6]:[c:7]:1:[c:8]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6]:[c:7](:[c:8]):[c:3]:1:[c:2] | 92 | [{"value": 92.0, "product": "ClC1=NNC2=CC=C(C=C12)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "ClC1=NNC2=CC=C(C=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | HOUR | A mixture of NaOH (5.00 g, 125 mmol) in H2O (150 mL) was added 5-nitroindazole (5.00 g, 30.7 mmol), and the mixture was heated until a red solution formed. The mixture was cooled in an ice-water bath for 15 minutes, NaClO (60.0 mL, 5.25%, 45.0 mmol) was added and the mixture stirred at 0° C. for 5 hour after which the ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | null | O | 0 | 5 | Cl.O=[N+]([O-])c1ccc2[nH]ncc2c1>O>O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a37e2a2096fd472dbd96dba73ca65231 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1>>O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1 | ClC1=NNC2=CC=C(C=C12)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].ClCCN1CCCC1>>ClC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1 | Cl[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10]([Cl:11])[n:12][nH:13]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10]([Cl:11])[n:12][n:13]2[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1 | O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1c9bfadcc8b17ce33571db0aba6fe4d2adf28d49d529bcf12a641e342e01b0dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 50 | CELSIUS | null | null | A mixture of 3-chloro-5-nitro-1H-indazole (1.5 g, 7.6 mmol) was treated with potassium carbonate (3.1 g, 23 mmol) in DMF (20 mL) for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine (1.9 g, 11 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature, filtered through a plug of sil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 50 | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Cl)c2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1aafaf9b8134916a2f3fa6a6260862d | O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1>>Nc1ccc2c(c1)c(Cl)nn2CCN1CCCC1 | ClC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1.[Cl-].[NH4+]>>ClC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]([Cl:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]([Cl:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1 | Nc1ccc2c(c1)c(Cl)nn2CCN1CCCC1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "ClC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.9, "product": "ClC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-Chloro-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.40 g, 1.4 mmol), iron powder (0.76 g, 14 mmol), and ammonium chloride (37 mg, 0.68 mmol) in 80% ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O | null | 0.25 | O=[N+]([O-])c1ccc2c(c1)c(Cl)nn2CCN1CCCC1>[Fe].C(C)O>Nc1ccc2c(c1)c(Cl)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc15a859aa5645abafbaf42d9c833fd3 | O=[N+]([O-])c1ccc2[nH]ncc2c1.[Br-]>>O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1 | Cl.[N+](=O)([O-])C=1C=C2C=NNC2=CC1.[OH-].[Na+].[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>BrC1=NNC2=CC=C(C=C12)[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][cH:10][c:12]2[cH:13]1.[Br-:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[nH:8][n:9][c:10]([Br:11])[c:12]2[cH:13]1 | O=[N+]([O-])c1ccc2[nH]ncc2c1.[Br-] | O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1 | null | null | O.CO | Functional Group Interconversion | Bromination | c227dfbda497353373bac89bc247ec5b3f58de92ee9133ce1c0d94d6b7643f7c | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2[nH]ncc2c1 | [Br-;H0;D0:1].[c:2]:[c:3]1:[cH;D2;+0:4]:[#7;a:5]:[#7;a:6]:[c:7]:1:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[#7;a:5]:[#7;a:6]:[c:7](:[c:8]):[c:3]:1:[c:2] | 55.1 | [{"value": 55.0, "product": "BrC1=NNC2=CC=C(C=C12)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.1, "product": "BrC1=NNC2=CC=C(C=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A mixture of NaOH (2.0 g) in H2O (60 mL) was added 5-nitroindazole (2.0 g, 12 mmol), and the mixture was heated until a red solution formed. The mixture was placed in an ice-water bath for 15 minutes after which pyridinium tribromide (4.7 g, 15 mmol) in methanol (15 mL) was added. The mixture was stirred at 0° C. for 5... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | null | O.CO | 0 | 0.25 | O=[N+]([O-])c1ccc2[nH]ncc2c1.[Br-]>O.CO>O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5e25737fd3846fd89334f3669445254 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1>>O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1 | BrC1=NNC2=CC=C(C=C12)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].ClCCN1CCCC1>>BrC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1 | Cl[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10]([Br:11])[n:12][nH:13]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[c:10]([Br:11])[n:12][n:13]2[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1 | O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1c9bfadcc8b17ce33571db0aba6fe4d2adf28d49d529bcf12a641e342e01b0dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 133.4 | [{"value": 76.0, "product": "BrC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 133.4, "product": "BrC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 3-bromo-5-nitro-1H-indazole (1.8 g, 7.6 mmol) and potassium carbonate (3.1 g 22 mmol) in DMF (20 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine (0.71 g, 4.2 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature, filtered through a plug of silic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 50 | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]nc(Br)c2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce051226ad6b4516a6a667311b4efcc1 | O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1>>Nc1ccc2c(c1)c(Br)nn2CCN1CCCC1 | BrC1=NN(C2=CC=C(C=C12)[N+](=O)[O-])CCN1CCCC1.[Cl-].[NH4+]>>BrC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]([Br:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]([Br:9])[n:10][n:11]2[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1 | Nc1ccc2c(c1)c(Br)nn2CCN1CCCC1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": "BrC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.3, "product": "BrC1=NN(C2=CC=C(C=C12)N)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-bromo-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.9 g, 5.6 mmol), iron powder (3.1 g, 56 mmol), and ammonium chloride (0.15 g, 2.8 mmol) in 80% ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in trie... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O | null | 0.25 | O=[N+]([O-])c1ccc2c(c1)c(Br)nn2CCN1CCCC1>[Fe].C(C)O>Nc1ccc2c(c1)c(Br)nn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89fd0e5818a94079863ca5d75b90b759 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Cl)n[nH]c2c1>>O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1 | ClC1=NNC2=CC(=CC=C12)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].ClCCN1CCCC1>>ClC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1 | Cl[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Cl:9])[n:10][nH:11][c:19]2[cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Cl:9])[n:10][n:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[c:19]2[cH:20]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Cl)n[nH]c2c1 | O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61b0a224b62ca0b743a21f455645a524e1404d8b5e8bd813e0a3f8c6a5539082 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 66 | [{"value": 66.0, "product": "ClC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "ClC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 3-chloro-6-nitro-1H-indazole (2.4 g, 12 mmol) was treated with potassium carbonate (5.0 g, 36 mmol) in DMF (40 mL) for about 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine (3.1 g, 18 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature and filtered through a plu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2c[nH]nc2c1 | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 50 | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Cl)n[nH]c2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-91125852705c46c2ac65ca624730bb73 | O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1>>Nc1ccc2c(Cl)nn(CCN3CCCC3)c2c1 | ClC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1.[Cl-].[NH4+]>>ClC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[n:8][n:9]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]2[cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[n:8][n:9]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]2[cH:18]1 | O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1 | Nc1ccc2c(Cl)nn(CCN3CCCC3)c2c1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 82.3 | [{"value": 80.0, "product": "ClC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "ClC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-chloro-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (2.3 g, 7.8 mmol), iron powder (3.5 g, 62 mmol), and ammonium chloride (0.21 g, 3.9 mmol) in 80% Ethanol was heated to reflux for 3 hours, cooled to room temperature, and concentrated under reduced pressure. The residue was stirred in triethylamine/e... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O | null | 0.25 | O=[N+]([O-])c1ccc2c(Cl)nn(CCN3CCCC3)c2c1>[Fe].C(C)O>Nc1ccc2c(Cl)nn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2b7d8d1070148d98a5ad00d051f22d2 | O=[N+]([O-])c1ccc2cn[nH]c2c1.[Br-]>>O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1 | Cl.[N+](=O)([O-])C1=CC=C2C=NNC2=C1.[OH-].[Na+].[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>BrC1=NNC2=CC(=CC=C12)[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][n:10][nH:11][c:12]2[cH:13]1.[Br-:9]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][nH:11][c:12]2[cH:13]1 | O=[N+]([O-])c1ccc2cn[nH]c2c1.[Br-] | O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1 | null | null | O.CO | Functional Group Interconversion | Bromination | 35e4f92aa8c0c274f67627ca98b5ec6bde8d1693193a68ce34b02032f7360dd9 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2[nH]ncc2c1 | [Br-;H0;D0:1].[c:2]:[c:3]1:[#7;a:4]:[#7;a:5]:[cH;D2;+0:6]:[c:7]:1:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#7;a:5]:[#7;a:4]:[c:3](:[c:2]):[c:7]:1:[c:8] | null | [] | 0 | CELSIUS | 15 | MINUTE | A mixture of NaOH (2.0 g, 50 mmol) in H2O (60 mL) was added 6-nitroindazole (2.0 g, 12 mmol) and the suspension heated until a red solution formed. The mixture was placed in an ice-water bath for 15 minutes after which pyridinium tribromide (4.7 g, 15 mmol) in MeOH (15 mL) was added. The mixture was stirred at 0° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | null | O.CO | 0 | 0.25 | O=[N+]([O-])c1ccc2cn[nH]c2c1.[Br-]>O.CO>O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d525da7ec79f45ea8aa85457cb1368cd | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1>>O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1 | BrC1=NNC2=CC(=CC=C12)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].ClCCN1CCCC1>>BrC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1 | Cl[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][nH:11][c:19]2[cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][n:11]([CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[c:19]2[cH:20]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1 | O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61b0a224b62ca0b743a21f455645a524e1404d8b5e8bd813e0a3f8c6a5539082 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 64.7 | [{"value": 64.0, "product": "BrC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "BrC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of 3-bromo-6-nitro-1H-indazole (1.0 g, 4.1 mmol) and potassium carbonate (2.9 g 21 mmol) in DMF (20 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine (1.8 g, 10 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature and filtered through a plug of sili... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2c[nH]nc2c1 | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 50 | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc2c(Br)n[nH]c2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82339a0c5f9a4a9eb8ee8a1ec45299e4 | O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1>>Nc1ccc2c(Br)nn(CCN3CCCC3)c2c1 | BrC1=NN(C2=CC(=CC=C12)[N+](=O)[O-])CCN1CCCC1.[Cl-].[NH4+]>>BrC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([Br:7])[n:8][n:9]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]2[cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Br:7])[n:8][n:9]([CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]2[cH:18]1 | O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1 | Nc1ccc2c(Br)nn(CCN3CCCC3)c2c1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 95 | [{"value": 95.0, "product": "BrC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "BrC1=NN(C2=CC(=CC=C12)N)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-bromo-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.90 g, 2.7 mmol), iron powder (1.5 g, 26 mmol), and ammonium chloride (73 mg, 1.3 mmol) in 80% ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in trie... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O | null | 0.25 | O=[N+]([O-])c1ccc2c(Br)nn(CCN3CCCC3)c2c1>[Fe].C(C)O>Nc1ccc2c(Br)nn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4aea544eff374c7797839e5e5d48937d | CC(=O)C(C)=O.Nc1ccc2c(cnn2CCN2CCCC2)c1>>COC(CNc1ccc2c(cnn2CCN2CCCC2)c1)OC | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C1CCOC1.N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.CC(C(=O)C)=O.C1CCOC1>>COC(CNC=1C=C2C=NN(C2=CC1)CCN1CCCC1)OC | CC(=O)[C:3]([CH3:4])=[O:22].[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11][n:12][n:13]2[CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1>>[CH3:1][O:2][CH:3]([CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11][n:12][n:13]2[CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21]1)[O:22][CH3:23] | CC(=O)C(C)=O.Nc1ccc2c(cnn2CCN2CCCC2)c1 | COC(CNc1ccc2c(cnn2CCN2CCCC2)c1)OC | null | null | CC(C)(C)OC | Heteroatom Alkylation and Arylation | OtherReaction | 87896795e963146046544ee0cde49480e26b3c18871424d315206a364e0f56a4 | becaaaecd78523328db920a0fe4df620e3cea197aaac9805e376373b3c66faa1 | c1ccc2c(c1)cnn2CCN1CCCC1 | C-C(=O)-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:8]-[#8:9]-[CH;D3;+0:1](-[CH2;D2;+0:2]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[O;H0;D2;+0:3]-[C;D1;H3:10] | null | [] | null | null | 12 | HOUR | To a solution of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (1.14 g, 0.497 mmol) in 62 mL of dry THF was added 2.04 mL of dimethyl glyoxal in MTBE (45% glyoxal by weight). A slurry of NaBH(OAc)3 (1.66 g, 7.83 mmol) in THF (10 mL) was slowly added via addition funnel over 60 minutes, and the mixture stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | Ether.Ether.Secondary amine | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | null | CC(C)(C)OC | null | 12 | CC(=O)C(C)=O.Nc1ccc2c(cnn2CCN2CCCC2)c1>CC(C)(C)OC>COC(CNc1ccc2c(cnn2CCN2CCCC2)c1)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84c8be1d487f4a98ba71233dc7b69f16 | O=c1n(-c2ccc(Oc3ccccc3)cc2)ccn1-c1ccc2c(cnn2CCN2CCCC2)c1>>O=C1N(c2ccc(Oc3ccccc3)cc2)CCN1c1ccc2c(cnn2CCN2CCCC2)c1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)N1C(N(C=C1)C=1C=C2C=NN(C2=CC1)CCN1CCCC1)=O.[H][H]>>O(C1=CC=CC=C1)C1=CC=C(C=C1)N1C(N(CC1)C=1C=C2C=NN(C2=CC1)CCN1CCCC1)=O | [O:1]=[c:2]1[n:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][cH:16]2)[cH:17][cH:18][n:19]1-[c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25][n:26][n:27]2[CH2:28][CH2:29][N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)[cH:35]1>>[O:1]=[C:2]1[N:3]([c:4]2[cH:5][cH:6][c:7]([O:8][c:9]3[cH:10][cH:11][c... | O=c1n(-c2ccc(Oc3ccccc3)cc2)ccn1-c1ccc2c(cnn2CCN2CCCC2)c1 | O=C1N(c2ccc(Oc3ccccc3)cc2)CCN1c1ccc2c(cnn2CCN2CCCC2)c1 | null | [Pd] | CC(=O)O | Reduction | OtherReaction | 02d4454334aa6aefae7f49d82f12172420ac9a0dc7c46e64c030ab4763c359b1 | 80a720e2607cb3e63102e764b72ebf8ab153bd656e5e1870bdae6ef44ada08f6 | O=C1N(c2ccc(Oc3ccccc3)cc2)CCN1c1ccc2c(cnn2CCN2CCCC2)c1 | [O;D1;H0:1]=[c;H0;D3;+0:2]1:[n;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[c:5]:[c:6]:[c:7]3:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:3:[c:12]:2):[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D3;+0:15]:1-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[N;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[c:5]:[c:6]:[c:7]3:[#7;a:8]:[#7;a:9]:[c:10]:... | null | [] | null | null | 6 | HOUR | 1-(4-phenoxyphenyl)-3-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-yl]-1,3-dihydro-2H-imidazol-2-one (Example 118) (0.100 g, 0.215 mmol) was dissolved in 20 mL of AcOH and 100 mg of Pd/C (10% mol/mol) was added. The mixture was subjected to an atmosphere of hydrogen gas at a pressure of 60 psi in a Parr shaker apparatus, a... | 10.6084/m9.figshare.5104873.v1 | null | null | Urea | c1ncc[nH]1 | C1C[NH]C[NH]1 | C1C[NH]C[NH]1.c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | null | [Pd].CC(=O)O | null | 6 | O=c1n(-c2ccc(Oc3ccccc3)cc2)ccn1-c1ccc2c(cnn2CCN2CCCC2)c1>[Pd].CC(=O)O>O=C1N(c2ccc(Oc3ccccc3)cc2)CCN1c1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9b3ff3d6bf246c4a792e741974357f7 | Nc1ccc(CCCC(=O)O)cc1>>O=C1NC(=O)c2ccccc21 | NC1=CC=C(C=C1)CCCC(=O)O.C(C)N(CC)CC.CN(C)C1=NC=CC=C1.C(C(C)O)O>>C1(C=2C(C(N1)=O)=CC=CC2)=O | C(C[CH2:9][c:8]1[cH:7][cH:6][c:4]([NH2:3])[cH:11][cH:10]1)[C:2](=[O:1])[OH:5]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21 | Nc1ccc(CCCC(=O)O)cc1 | O=C1NC(=O)c2ccccc21 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 9f8eb762b61e31b1c74f37004bc2b68f2e2ba32dacd41072d219be9b2d4c78ea | 969319f6b6b635c4fd197991279ae7a2965391dd6ffca4bfef8c9fe1acfc0d65 | O=C1NC(=O)c2ccccc21 | [NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[CH2;D2;+0:6]-C-C-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]:[cH;D2;+0:11]:1>>[O;D1;H0:8]=[C;H0;D3;+0:7]1-[NH;D2;+0:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:9])-[c;H0;D3;+0:11]2:[c:10]:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:4]:[c;H0;D3;+0:3]:2-1 | null | [] | 140 | CELSIUS | 330 | MINUTE | A suspension of 2.40 g (16.3 mmol) and 2.80 g (15.6 mmol) of 4-(4aminophenyl)butyric acid in 20 mL of propylene glycol, 2.40 mL (1.74 g, 17.3 mmol) of triethylamine and 10 mg (0.08 mmol) of dimethylaminopyridine was heated to 140° C. The mixture became a clear solution after 5 min at 140° C. After stirring for 330 min,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Unsubstituted dicarboximide | c1ccccc1 | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | Other | O | 140 | 5.5 | Nc1ccc(CCCC(=O)O)cc1>O>O=C1NC(=O)c2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58b3cb8204414646ad140d3448e846a9 | NO.Nc1ccc2ncsc2c1.O=CC(Cl)(Cl)Cl>>O=C(C=NO)Nc1ccc2ncsc2c1 | NC1=CC2=C(N=CS2)C=C1.Cl.ON.S(=O)(=O)([O-])[O-].[Na+].[Na+].O=CC(Cl)(Cl)Cl>>S1C=NC2=C1C=C(C=C2)NC(C=NO)=O | [NH2:4][OH:5].[NH2:6][c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][s:13][c:14]2[cH:15]1.Cl[C:2](Cl)(Cl)[CH:3]=[O:1]>>[O:1]=[C:2]([CH:3]=[N:4][OH:5])[NH:6][c:7]1[cH:8][cH:9][c:10]2[n:11][cH:12][s:13][c:14]2[cH:15]1 | NO.Nc1ccc2ncsc2c1.O=CC(Cl)(Cl)Cl | O=C(C=NO)Nc1ccc2ncsc2c1 | null | null | Cl.O.C(C)O | Acylation | OtherReaction | a5f86f1d718ab7ac00a957b033bada788dadb0950aa0d34d7e24a73a42d26116 | d29015920ce18914ddb4669715a8994e1383d81f1a08fa7e118fc3458ea45afa | c1ccc2scnc2c1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[CH;D2;+0:2]=[O;H0;D1;+0:3].[#16;a:4]:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9].[NH2;D1;+0:10]-[O;D1;H1:11]>>[#16;a:4]:[c:5]:[c:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[CH;D2;+0:2]=[N;H0;D2;+0:10]-[O;D1;H1:11]):[c:9] | 94 | [{"value": 94.0, "product": "S1C=NC2=C1C=C(C=C2)NC(C=NO)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a 1-L flask was added a magnetic stir bar, 85 g of sodium sulfate, and 100 mL of water. The mixture was magnetically stirred until all the solids were dissolved. To the resultant aqueous solution was added a solution of 6-aminobenzothiazole (4.96 g, 33.0 mmol) in 50 mL of 1N aqueous hydrochloric acid and 10 mL of et... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Aldehyde.Primary amine.Primary amine | Secondary amide.Oxime | null | null | c1ccc2scnc2c1 | HCl | Cl.O.C(C)O | null | 0.25 | NO.Nc1ccc2ncsc2c1.O=CC(Cl)(Cl)Cl>Cl.O.C(C)O>O=C(C=NO)Nc1ccc2ncsc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-08d169f88caf407d99825c179a1e5d3c | O=C(C=NO)Nc1ccc2ncsc2c1>>O=C1Nc2ccc3ncsc3c2C1=O | S(O)(O)(=O)=O.S(O)(O)(=O)=O.S1C=NC2=C1C=C(C=C2)NC(C=NO)=O>>S1C=NC2=CC=C3NC(C(C3=C12)=O)=O | N(=[CH:13][C:2](=[O:1])[NH:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][s:10][c:11]2[cH:12]1)[OH:14]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]3[n:8][cH:9][s:10][c:11]3[c:12]2[C:13]1=[O:14] | O=C(C=NO)Nc1ccc2ncsc2c1 | O=C1Nc2ccc3ncsc3c2C1=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 76ca54020825c2b52c69b966e96a6ad71d1ab32767482feb664c3cb4ea38d255 | ab4bf08516e66cf6fd8670ac9e8d4ecd074b35f40b66b51c2d0c9c0d98ab1c51 | O=C1Nc2ccc3ncsc3c2C1=O | [O;D1;H0:1]=[C:2](-[#7:3]-[c:4]1:[c:5]:[c:6]:[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2:[cH;D2;+0:12]:1)-[CH;D2;+0:13]=N-[OH;D1;+0:14]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[c:4]2:[c:5]:[c:6]:[c:7]3:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:3:[c;H0;D3;+0:12]:2-[C;H0;D3;+0:13]-1=[O;H0;D1;+0:14] | 46 | [{"value": 46.0, "product": "S1C=NC2=CC=C3NC(C(C3=C12)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a 1-L flask was added a magnetic stir bar, 85 g of sodium sulfate, and 100 mL of water. The mixture was magnetically stirred until all the solids were dissolved. To the resultant aqueous solution was added a solution of 6-aminobenzothiazole (4.96 g, 33.0 mmol) in 50 mL of 1N aqueous hydrochloric acid and 10 mL of et... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Ketone | c1ccc2scnc2c1 | c1nc2ccc3c(c2s1)CCN3 | c1nc2ccc3c(c2s1)CCN3 | Other | O | null | 1 | O=C(C=NO)Nc1ccc2ncsc2c1>O>O=C1Nc2ccc3ncsc3c2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0c12e893fac446f907a14ce49c4c16b | CS(=O)(=O)Nc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO>>CS(=O)(=O)Nc1ccc(N/C=C2\C(=O)Nc3ccccc32)cc1 | OC=C1C(NC2=CC=CC=C12)=O.NC1=CC=C(C=C1)NS(=O)(=O)C>>O=C\1NC2=CC=CC=C2/C1=C/NC1=CC=C(C=C1)NS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:22][cH:23]1.O[CH:11]=[C:12]1[C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10]/[CH:11]=[C:12]2\[C:13](=[O:14])[NH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]32)[cH:22... | CS(=O)(=O)Nc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO | CS(=O)(=O)Nc1ccc(N/C=C2\C(=O)Nc3ccccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2/C1=C/Nc1ccccc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]/[C:2]-1=[CH;D2;+0:1]/[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The title compound was prepared analogous to Example 5 from 3-(hydroxymethylene)-1,3-dihydro-2H-indol-2-one (0.164 g, 1.02 mmol) and N-(4-aminophenyl)-methanesulfonamide [53250-82-1, 0.186 g, 1.0 mmol] to provide a yellow solid (0.249 g). 1H NMR (DMSO) 10.67 (d, 1H); 10.45 (s, 1H); 9.56 (s, 1H); 8.50 (d, 1H); 7.52 (d, ... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | CS(=O)(=O)Nc1ccc(N)cc1.O=C1Nc2ccccc2C1=CO>>CS(=O)(=O)Nc1ccc(N/C=C2\C(=O)Nc3ccccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-99b7a8779cde4571a68bccdeba305e57 | Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2/C1=C/Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1 | OC=C1C(NC2=CC=CC=C12)=O.C=1C=CN=C(C1)NS(=O)(=O)C=2C=CC(=CC2)N>>O=C\1NC2=CC=CC=C2/C1=C/NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1 | [NH2:12][c:13]1[cH:14][cH:15][c:16]([S:17](=[O:18])(=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[cH:27][cH:28]1.O[CH:11]=[C:10]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]21>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2/[C:10]1=[CH:11]/[NH:12][c:13]1[cH:14][cH:15][c:16]([S:17](=[O:18]... | Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1.O=C1Nc2ccccc2C1=CO | O=C1Nc2ccccc2/C1=C/Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2/C1=C/Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]/[C:2]-1=[CH;D2;+0:1]/[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The title compound was prepared analogous to Example 5 from 3-(hydroxymethylene)-1,3-dihydro-2H-indol-2-one and sulfapyridine. Electrospray MS 393 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1ccc2c(c1)CCN2.c1ccccc1.c1ccncc1 | HO- | null | null | null | Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1.O=C1Nc2ccccc2C1=CO>>O=C1Nc2ccccc2/C1=C/Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-346e2a2df06741239ca7c06c272f201f | Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1.O=C1Nc2ccccc2C1=CO>>Cc1nnc(NS(=O)(=O)c2ccc(N/C=C3\C(=O)Nc4ccccc43)cc2)s1 | OC=C1C(NC2=CC=CC=C12)=O.NC1=CC=C(C=C1)S(=O)(=O)NC=1SC(=NN1)C>>CC1=NN=C(S1)NS(=O)(=O)C1=CC=C(C=C1)N\C=C\1/C(NC2=CC=CC=C12)=O | [CH3:1][c:2]1[n:3][n:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][c:13]([NH2:14])[cH:26][cH:27]2)[s:28]1.O[CH:15]=[C:16]1[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]21>>[CH3:1][c:2]1[n:3][n:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][c:13]([NH:14]/[CH:15]=[C:16]3\[C:17](=[O:1... | Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1.O=C1Nc2ccccc2C1=CO | Cc1nnc(NS(=O)(=O)c2ccc(N/C=C3\C(=O)Nc4ccccc43)cc2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | ac661a5987df49e763a2386679221354b73376953f4071e32e52e2d7e8877593 | dc27e5e3871ba014ddcdbe66aa8244518b94cc851f1ff4159b6674656bc3b780 | O=C1Nc2ccccc2/C1=C/Nc1ccc(S(=O)(=O)Nc2nncs2)cc1 | O-[CH;D2;+0:1]=[C:2]1-[c:3]:[c:4]-[#7:5]-[C:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[C:6]1-[#7:5]-[c:4]:[c:3]/[C:2]-1=[CH;D2;+0:1]/[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | The title compound was prepared analogous to Example 5 from 3-(hydroxymethylene)-1,3-dihydro-2H-indol-2-one and 4-amino-N-(5-methyl[1,3,4]thiadiazol-2-yl)-benzenesulfonamide. 1H NMR (DMSO) 13.90 (bs, 1H); 10.84 (d, 1H); 10.58 (s, 1H); 8.62 (d, 1H); 7.81 (d, 2H); 7.60 (d, 1H); 7.55 (d, 2H); 7.12 (m, 1H); 6.95 (m, 1H); 7... | 10.6084/m9.figshare.5104873.v1 | null | Enol.Primary amine | Enamine | null | null | c1nncs1.c1ccccc1.c1ccc2c(c1)CCN2 | HO- | null | null | null | Cc1nnc(NS(=O)(=O)c2ccc(N)cc2)s1.O=C1Nc2ccccc2C1=CO>>Cc1nnc(NS(=O)(=O)c2ccc(N/C=C3\C(=O)Nc4ccccc43)cc2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a54b51f05384a30bd1356871b0a78f2 | COc1ccc(C=O)cc1Br.Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C>>COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C | BrC=1C=C(C=O)C=CC1OC.CC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)B(O)O.C([O-])([O-])=O.[K+].[K+]>>CC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C=1C=C(C=O)C=CC1OC | Br[c:10]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9]1.OB(O)[c:11]1[cH:12][c:13]2[c:14]([cH:15][c:16]1[CH3:17])[C:18]([CH3:19])([CH3:20])[CH2:21][CH2:22][C:23]2([CH3:24])[CH3:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1-[c:11]1[cH:12][c:13]2[c:14]([cH:15][c:16]1[CH3:17])[C:18]([CH3:19... | COc1ccc(C=O)cc1Br.Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C | COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | b6fa867d6aba2bef80ed68dbf682dd3adb3006465de50d2f754372d7f6e007ef | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)CCCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[C;D1;H3:13]):[c:14]):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 90.1 | [{"value": 90.0, "product": "CC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C=1C=C(C=O)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "CC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C=1C=C(C=O)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-bromo-4-methoxybenzaldehyde (19.0 g, 88.4 mmol), (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl) boronic acid (23.8 g, 97.2 mmol) and potassium carbonate (48.8 g, 353.6 mmol) in 1,2-dimethoxyethane (500 mL) and water (40 mL) was degassed with argon for 60 minutes. Tetrakis(triphenylphosphine) p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC.C(C)(=O)OCC | null | null | COc1ccc(C=O)cc1Br.Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC.C(C)(=O)OCC>COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0c6cd4e3c5d49158be4f08f4d61f8d3 | O=C1CCC(=O)N1Br.O=Cc1ccc(OC(F)(F)F)cc1>>O=Cc1ccc(OC(F)(F)F)c(Br)c1 | BrN1C(CCC1=O)=O.FC(OC1=CC=C(C=O)C=C1)(F)F.C(Cl)Cl.OS(=O)(=O)O>>BrC=1C=C(C=O)C=CC1OC(F)(F)F | O=C1CCC(=O)N1[Br:13].[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[cH:12][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]([F:9])([F:10])[F:11])[c:12]([Br:13])[cH:14]1 | O=C1CCC(=O)N1Br.O=Cc1ccc(OC(F)(F)F)cc1 | O=Cc1ccc(OC(F)(F)F)c(Br)c1 | null | null | C(=O)(C(F)(F)F)O | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]-[C:8]=[O;D1;H0:9]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7]-[C:8]=[O;D1;H0:9] | 62.6 | [{"value": 62.0, "product": "BrC=1C=C(C=O)C=CC1OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "BrC=1C=C(C=O)C=CC1OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a solution of 4-trifluoromethoxybenzaldehyde (215.0 g, 1.13 mol) in a mixture of TFA (300 mL), CH2Cl2 (300 mL) and H2SO4 (150 mL) was added at room temperature N-bromosuccinimide (402.0 g, 2.26 mol) in equal portions over seven hours. The reaction mixture was stirred for four days at room temperature, poured into ic... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(=O)(C(F)(F)F)O | null | 96 | O=C1CCC(=O)N1Br.O=Cc1ccc(OC(F)(F)F)cc1>C(=O)(C(F)(F)F)O>O=Cc1ccc(OC(F)(F)F)c(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ead6c7a55c0f45819004235a7a0643e8 | Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C.O=Cc1ccc(OC(F)(F)F)c(Br)c1>>Cc1cc2c(cc1-c1ccc(C=O)cc1OC(F)(F)F)C(C)(C)CCC2(C)C | C([O-])([O-])=O.[K+].[K+].BrC=1C=C(C=O)C=CC1OC(F)(F)F.CC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)B(O)O.C(C)O>>FC(OC=1C=C(C=O)C=CC1C1=CC=2C(CCC(C2C=C1C)(C)C)(C)C)(F)F | OB(O)[c:7]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([cH:6]1)[C:21]([CH3:22])([CH3:23])[CH2:24][CH2:25][C:26]2([CH3:27])[CH3:28].Br[c:15]1[c:8]([O:16][C:17]([F:18])([F:19])[F:20])[cH:9][cH:10][c:11]([CH:12]=[O:13])[cH:14]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]([CH:12]=[O:13])[cH:14][c:15]1[O:16][... | Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C.O=Cc1ccc(OC(F)(F)F)c(Br)c1 | Cc1cc2c(cc1-c1ccc(C=O)cc1OC(F)(F)F)C(C)(C)CCC2(C)C | 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.C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 7dac6989769981bfec04459edc6c09b6186b097cedd6dde9f0515c1cc3b2b79c | 5a6d5feecbca47ed9520143f4e9a586cd17e903950cdaedb0666222ddfc9f2ae | c1ccc(-c2ccc3c(c2)CCCC3)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[O;H0;D2;+0:9]-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13].O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17](-[C;D1;H3:18]):[c:19]>>[C;D1;H3:18]-[c:17](:[c:19]):[c;H0;D3;+0:14](-[c;H0;D3;+0:8]1:[c:7]:[c:6]:[c:3](-[C:4]=[O;D1;H0:5]):[c:2]... | 76 | [{"value": 76.0, "product": "FC(OC=1C=C(C=O)C=CC1C1=CC=2C(CCC(C2C=C1C)(C)C)(C)C)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-bromo-4-trifluoromethoxybenzaldehyde (10.0 g, 37.2 mmol), (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl) boronic acid (11.0 g, 44.68 mmol, 1.2 eq) in a mixture of toluene (100 mL), ethanol (20 mL) and water (15 mL) was added potassium carbonate (10.28 g, 74.4 mmol, 2 eq). The mixture was d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Boronic acid | Ether | c1ccc2c(c1)CCCC2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCCC2 | c1ccccc1.c1ccc2c(c1)CCCC2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)(=O)OCC | null | null | Cc1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C.O=Cc1ccc(OC(F)(F)F)c(Br)c1>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.C1(=CC=CC=C1)C.C(C)(=O)OCC>Cc1cc2c(cc1-c1ccc(C=O)cc1OC(F)(F)F)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbc2472a465a4e44abf3015595afaaa0 | BrBr.COc1ccccn1>>COc1ccc(Br)cn1 | [OH-].[Na+].COC1=NC=CC=C1.C(C)(=O)[O-].[Na+].BrBr>>BrC=1C=CC(=NC1)OC | Br[Br:7].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:8][n:9]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1 | BrBr.COc1ccccn1 | COc1ccc(Br)cn1 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[c:5]:[c:4]:[c:3]:[#7;a:2]:[c:7]:1 | 51.3 | [{"value": 51.3, "product": "BrC=1C=CC(=NC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of 2-methoxypyridine (10.00 g, 0.09 mol) and sodium acetate (8.27 g, 0.10 mmol) in 30 mL of glacial acetic acid was added a solution of bromine in 20 mL glacial acetic acid while maintaining the reaction temperature below 50° C. After 3 hours, 100 mL of H2O was added and the resulting solution neutraliz... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | O.C(C)(=O)O | null | 3 | BrBr.COc1ccccn1>O.C(C)(=O)O>COc1ccc(Br)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b4a3d696a6b428ba74a62ddda05b982 | COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C.O=C1CSC(=O)N1CCc1ccccn1>>COc1ccc(C=C2SC(=O)N(CCc3ccccn3)C2=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C | COC1=C(C=C(C=O)C=C1)C1=CC=2C(CCC(C2C=C1C)(C)C)(C)C.N1=C(C=CC=C1)CCN1C(SCC1=O)=O>>COC1=C(C=C(C=C2C(N(C(S2)=O)CCC2=NC=CC=C2)=O)C=C1)C1=CC=2C(CCC(C2C=C1C)(C)C)(C)C | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24](-[c:25]2[cH:26][c:27]3[c:28]([cH:29][c:30]2[CH3:31])[C:32]([CH3:33])([CH3:34])[CH2:35][CH2:36][C:37]3([CH3:38])[CH3:39])[cH:23]1.[CH2:8]1[S:9][C:10](=[O:11])[N:12]([CH2:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[C:21]1=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C.O=C1CSC(=O)N1CCc1ccccn1 | COc1ccc(C=C2SC(=O)N(CCc3ccccn3)C2=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C | null | null | null | C-C Coupling | Aldol condensation | 315c5abda6f5c04d5321614cd32fbf107303aab42297b04d1819d58208c94487 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1SC(=Cc2cccc(-c3ccc4c(c3)CCCC4)c2)C(=O)N1CCc1ccccn1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]1-[C:7](=[O;D1;H0:8])-[#16:9]-[CH2;D2;+0:10]-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[C:7](=[O;D1;H0:8])-[#16:9]-[C;H0;D3;+0:10](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]-1=[O;D1;H0:12] | null | [] | null | null | null | null | 5-[4-Methoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzylidene]-3-(2-pyridin-2-yl-ethyl)-thiazolidine-2,4-dione was prepared in a similar manner as described in Example 1 using 4-methoxy-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) benzaldehyde and 3-(2-pyridin-2-yl-ethyl)-thiazol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | c1ccccc1.C1CSC[NH]1.c1ccncc1.c1ccc2c(c1)CCCC2 | HO- | null | null | null | COc1ccc(C=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C.O=C1CSC(=O)N1CCc1ccccn1>>COc1ccc(C=C2SC(=O)N(CCc3ccccn3)C2=O)cc1-c1cc2c(cc1C)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8369fb21e4244d40930a6dee8735a0a3 | CN(C)c1cc2c(cc1C=O)C(C)(C)CCC2(C)C.O=C(O)CN1C(=O)CSC1=S>>CN(C)c1cc2c(cc1-c1ccc3cc(C=C4SC(=S)N(CC(=O)O)C4=O)ccc3c1)C(C)(C)CCC2(C)C | CN(C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C=O)C.S1C(=S)N(C(=O)C1)CC(=O)O>>CN(C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C=1C=C2C=CC(=CC2=CC1)C=C1C(N(C(S1)=S)CC(=O)O)=O)C | O=[CH:10][c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][c:6]2[c:7]([cH:8]1)[C:32]([CH3:33])([CH3:34])[CH2:35][CH2:36][C:37]2([CH3:11])[CH3:12].[CH2:17]1[S:18][C:19](=[S:20])[N:21]([CH2:22][C:23](=[O:24])[OH:25])[C:26]1=[O:27]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]3[cH:14][c:15]... | CN(C)c1cc2c(cc1C=O)C(C)(C)CCC2(C)C.O=C(O)CN1C(=O)CSC1=S | CN(C)c1cc2c(cc1-c1ccc3cc(C=C4SC(=S)N(CC(=O)O)C4=O)ccc3c1)C(C)(C)CCC2(C)C | null | null | null | C-C Coupling | OtherReaction | e8323e93057d9dc5b72df472f79adc1b56d688c7074d60002ae7aab28e700d6b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1NC(=S)SC1=Cc1ccc2cc(-c3ccc4c(c3)CCCC4)ccc2c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](:[c:6]:[c:7]:1-[#7:8])-[C;H0;D4;+0:9](-[CH3;D1;+0:10])(-[CH3;D1;+0:11])-[C:12]-[C:13].[O;D1;H0:14]=[C:15](-[O;D1;H1:16])-[C:17]-[#7:18]1-[C:19](=[S;D1;H0:20])-[#16:21]-[CH2;D2;+0:22]-[C:23]-1=[O;D1;H0:24]>>[#7:8]-[c:7]1:[c:6]:[c:5](:[c:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;... | null | [] | null | null | null | null | {5-[6-(3-Dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-naphthalen-2-yl methylene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic acid was prepared in a similar manner as described in Example 1 using 6-(3-dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-carboxaldehyde and rhodanine acet... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | c1ccc2c(c1)CCCC2.C1CSC[NH]1 | c1ccc2ccccc2c1.C1CSC[NH]1.c1ccc2c(c1)CCCC2 | c1ccc2ccccc2c1.C1CSC[NH]1.c1ccc2c(c1)CCCC2 | null | null | null | null | CN(C)c1cc2c(cc1C=O)C(C)(C)CCC2(C)C.O=C(O)CN1C(=O)CSC1=S>>CN(C)c1cc2c(cc1-c1ccc3cc(C=C4SC(=S)N(CC(=O)O)C4=O)ccc3c1)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f1461830198416ea9317c089d13033f | CCO.O=C(O)c1ccc2cc(O)ccc2c1>>CCOC(=O)c1ccc2cc(O)ccc2c1 | OC=1C=C2C=CC(=CC2=CC1)C(=O)O.C(C)O>>C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]2[cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]2[cH:16]1 | CCO.O=C(O)c1ccc2cc(O)ccc2c1 | CCOC(=O)c1ccc2cc(O)ccc2c1 | null | null | S(O)(O)(=O)=O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccc2ccccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | A solution of 6-hydroxy-2-naphthoic acid (75.9 g, 0.40 mol) in ethanol (1.0 L) and sulfuric acid (5.0 mL) was heated to reflux under an atmosphere of nitrogen. After 16 hours, the volume was removed to approximately half via simple distillation and the resulting solution was diluted with water. The resulting cloudy mix... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2ccccc2c1 | HO- | S(O)(O)(=O)=O | null | 16 | CCO.O=C(O)c1ccc2cc(O)ccc2c1>S(O)(O)(=O)=O>CCOC(=O)c1ccc2cc(O)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b6cb880dfda64425bb78ed2cb9037e1b | CCOC(=O)c1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1>>O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F | C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)OS(=O)(=O)C(F)(F)F.CC(C)C[AlH]CC(C)C>>FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)CO)(F)F | CCO[C:11]([c:10]1[cH:9][c:8]2[cH:7][cH:6][c:5]([O:4][S:2](=[O:1])(=[O:3])[C:17]([F:18])([F:19])[F:20])[cH:16][c:15]2[cH:14][cH:13]1)=[O:12]>>[O:1]=[S:2](=[O:3])([O:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([CH2:11][OH:12])[cH:13][cH:14][c:15]2[cH:16]1)[C:17]([F:18])([F:19])[F:20] | CCOC(=O)c1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1 | O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | Reduction of ester to primary alcohol | cd99347e3144bc4f081bc664a4bc5a11d1e392f7cea47a5adad92bcd498ccf56 | a2b5cf843cfeb048c76ac4cbf0bd8ccab026fcad80259b78e012cdb6ac2f5934 | c1ccc2ccccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 72 | [{"value": 72.0, "product": "FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)CO)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.6, "product": "FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)CO)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a slurry of 6-trifluoromethanesulfonyloxy-naphthalene-2-carboxylic acid ethyl ester (136.50 g, 0.392 mol) in toluene (1.0 L) at −70° C. was added a solution of DIBAL (1.5 M, 5.75 mL, 0.862 mol) dropwise while maintaining an internal temperature below −55° C. The resulting mixture was allowed to stir for 1 hour and s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2ccccc2c1 | HO- | C1(=CC=CC=C1)C | null | 1 | CCOC(=O)c1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1>C1(=CC=CC=C1)C>O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69ef83815cd34e009ed65d285bc956f6 | O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F>>O=Cc1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1 | FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)CO)(F)F.C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl>>FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)C=O)(F)F | [OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([O:9][S:10](=[O:11])(=[O:12])[C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][c:19]2[cH:20]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([O:9][S:10](=[O:11])(=[O:12])[C:13]([F:14])([F:15])[F:16])[cH:17][cH:18][c:19]2[cH:20]1 | O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F | O=Cc1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 94 | [{"value": 94.0, "product": "FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)C=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.8, "product": "FC(S(=O)(=O)OC=1C=C2C=CC(=CC2=CC1)C=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mechanical stirred solution of 6-trifluoromethanesulfonyloxy-naphthalen-2-yl-methanol (70.0 g, 0.228 mol) in CH2Cl2 (600 mL) under an atmosphere of argon was added PCC (54.20 g, 0.25 mol, crushed prior to addition) over a few minutes. After 2 hours the resulting black suspension was poured onto a silica gel column... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2ccccc2c1 | null | C(Cl)Cl | null | null | O=S(=O)(Oc1ccc2cc(CO)ccc2c1)C(F)(F)F>C(Cl)Cl>O=Cc1ccc2cc(OS(=O)(=O)C(F)(F)F)ccc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c298b3b7776043f6998b7e42bc24f8c8 | CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21>>CC1(C)CCC(C)(C)c2cc(N)ccc21 | [N+](=O)([O-])C1=CC=2C(CCC(C2C=C1)(C)C)(C)C.[H][H]>>NC1=CC=2C(CCC(C2C=C1)(C)C)(C)C | O=[N+:12]([O-])[c:11]1[cH:10][c:9]2[c:15]([cH:14][cH:13]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2([CH3:7])[CH3:8]>>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6]([CH3:7])([CH3:8])[c:9]2[cH:10][c:11]([NH2:12])[cH:13][cH:14][c:15]21 | CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21 | CC1(C)CCC(C)(C)c2cc(N)ccc21 | null | [Pd] | ClCCl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)CCCC2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 2-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene (79.0 g, 0.339 mol) in dichloromethane as added 1 g of 10% palladium on carbon and the mixture was hydrogenated at 40–50 psi of hydrogen for 20 hrs. The catalyst was removed by filtration and the organic and the aqueous layers were separated. T... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCCC2 | Other | [Pd].ClCCl | null | null | CC1(C)CCC(C)(C)c2cc([N+](=O)[O-])ccc21>[Pd].ClCCl>CC1(C)CCC(C)(C)c2cc(N)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c3f080bf557442fbfb92d96788e8437 | C=O.CC1(C)CCC(C)(C)c2cc(N)ccc21>>CN(C)c1ccc2c(c1)C(C)(C)CCC2(C)C | C(C)(=O)O.NC1=CC=2C(CCC(C2C=C1)(C)C)(C)C.C=O.C(#N)[BH3-].[Na+]>>CN(C1=CC=2C(CCC(C2C=C1)(C)C)(C)C)C | O=[CH2:3].[NH2:2][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10]([CH3:11])([CH3:12])[CH2:13][CH2:14][C:15]2([CH3:16])[CH3:17] | C=O.CC1(C)CCC(C)(C)c2cc(N)ccc21 | CN(C)c1ccc2c(c1)C(C)(C)CCC2(C)C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccc2c(c1)CCCC2 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[N;H0;D3;+0:2](-[CH3;D1;+0:1])-[c:3](:[c:4]):[c:5] | 70 | [{"value": 70.0, "product": "CN(C1=CC=2C(CCC(C2C=C1)(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (70.10 g, 0.345 mol) and formaldehyde (280 mL, 10 eq) in 2 L of acetonitrile cooled to 0° C. was added sodium cyanoborohydride (65 g, 3 eq.) in portions while maintaining the temperature between 10–20° C. Glacial acetic acid was added to adjust ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccc2c(c1)CCCC2 | null | C(C)#N | null | 2 | C=O.CC1(C)CCC(C)(C)c2cc(N)ccc21>C(C)#N>CN(C)c1ccc2c(c1)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1901d57fac948e9a496e91086c3a4e7 | CC(C)OB(OC(C)C)OC(C)C.CN(C)c1cc2c(cc1Br)C(C)(C)CCC2(C)C>>CN(C)c1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C | B(OC(C)C)(OC(C)C)OC(C)C.BrC1=CC=2C(CCC(C2C=C1N(C)C)(C)C)(C)C.C(CCC)[Li].Cl>>CN(C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)B(O)O)C | CC(C)O[B:10]([O:11]C(C)C)[O:12]C(C)C.Br[c:9]1[c:4]([N:2]([CH3:1])[CH3:3])[cH:5][c:6]2[c:7]([cH:8]1)[C:13]([CH3:14])([CH3:15])[CH2:16][CH2:17][C:18]2([CH3:19])[CH3:20]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[B:10]([OH:11])[OH:12])[C:13]([CH3:14])([CH3:15])[CH2:16][CH2:17][C:18]2([CH3:19])[CH3:20] | CC(C)OB(OC(C)C)OC(C)C.CN(C)c1cc2c(cc1Br)C(C)(C)CCC2(C)C | CN(C)c1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C | null | null | C1CCOC1 | Miscellaneous | Preparation of boronic acids | 44976aedc627652e57cf654966855ab06a9db6d01924d4ea2bf9f8b5ec0f6db6 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc2c(c1)CCCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5]):[c:6].C-C(-C)-O-[B;H0;D3;+0:7](-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[#7:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[B;H0;D3;+0:7](-[OH;D1;+0:8])-[OH;D1;+0:9]):[c:2]:[c:3] | 39 | [{"value": 39.0, "product": "CN(C=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)B(O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To a solution of 2-Bromo-3-dimethylamino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (67.08 g, 0.216 mol) in 300 mL of anhydrous THF at −78° C. was added dropwise at −78° C. a 1.6 molar solution of n-butyl lithium (1.6 M, 203 mL, 1.5 eq.) over a period of 30 minutes. The reaction was stirred for 10 min. at −78° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | HBr | C1CCOC1 | -78 | 0.166667 | CC(C)OB(OC(C)C)OC(C)C.CN(C)c1cc2c(cc1Br)C(C)(C)CCC2(C)C>C1CCOC1>CN(C)c1cc2c(cc1B(O)O)C(C)(C)CCC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecb4f7b1ddfc45b2a209c0bd72c64a72 | CN(C)c1ccc(C=O)cc1.[Br-]>>CN(C)c1ccc(C=O)cc1Br | CN(C1=CC=C(C=O)C=C1)C.[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>BrC=1C=C(C=O)C=CC1N(C)C | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][cH:11]1.[Br-:12]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][c:11]1[Br:12] | CN(C)c1ccc(C=O)cc1.[Br-] | CN(C)c1ccc(C=O)cc1Br | null | null | ClCCl | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | [#7:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]-[C:7]=[O;D1;H0:8].[Br-;H0;D0:9]>>[#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[Br;H0;D1;+0:9]):[c:5]:[c:6]-[C:7]=[O;D1;H0:8] | 92 | [{"value": 92.0, "product": "BrC=1C=C(C=O)C=CC1N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "BrC=1C=C(C=O)C=CC1N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-(dimethylamino)-benzaldehyde (10.0 g, 67.03 mmol) in dichloromethane (250 mL) was added pyridinium tribromide (21.4 g, 67.03 mmol). The reaction mixture was stirred at room temperature overnight. The solution was washed successively with water and brine, dried over anhydrous magnesium sulfate, filter... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | ClCCl | null | 8 | CN(C)c1ccc(C=O)cc1.[Br-]>ClCCl>CN(C)c1ccc(C=O)cc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b00ee9768ad48a898dd923a0cb62874 | CN1C(=O)CSC1=O.Cc1cc2c(cc1-c1cc(C=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C>>Cc1cc2c(cc1-c1cc(C=C3SC(=O)N(C)C3=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C | C1(=CC=CC=C1)C.N1CCCCC1.CN1C(CC(C2=CC(=C(C=C12)C=1C=C(C=O)C=CC1OC(F)(F)F)C)(C)C)=O.CN1C(SCC1=O)=O>>CN1C(SC(C1=O)=CC1=CC(=C(C=C1)OC(F)(F)F)C1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C)=O | [CH2:12]1[S:13][C:14](=[O:15])[N:16]([CH3:17])[C:18]1=[O:19].O=[CH:11][c:10]1[cH:9][c:8](-[c:7]2[c:2]([CH3:1])[cH:3][c:4]3[c:5]([cH:6]2)[N:28]([CH3:29])[C:30](=[O:31])[CH2:32][C:33]3([CH3:34])[CH3:35])[c:22]([O:23][C:24]([F:25])([F:26])[F:27])[cH:21][cH:20]1>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1-[c:8]1[cH:9][c:1... | CN1C(=O)CSC1=O.Cc1cc2c(cc1-c1cc(C=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C | Cc1cc2c(cc1-c1cc(C=C3SC(=O)N(C)C3=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C | null | null | C(C)(=O)O.C(C)(=O)OCC | C-C Coupling | Aldol condensation | 315c5abda6f5c04d5321614cd32fbf107303aab42297b04d1819d58208c94487 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1CCc2ccc(-c3cccc(C=C4SC(=O)NC4=O)c3)cc2N1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7:6]1-[C:7](=[O;D1;H0:8])-[#16:9]-[CH2;D2;+0:10]-[C:11]-1=[O;D1;H0:12]>>[C;D1;H3:5]-[#7:6]1-[C:7](=[O;D1;H0:8])-[#16:9]-[C;H0;D3;+0:10](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]-1=[O;D1;H0:12] | null | [] | null | null | null | null | A mixture of toluene (80 mL), piperidine (380 μL), acetic acid (380 μL), 3-(1,4,4,6-Tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-trifluoromethoxy-benzaldehyde (7.5 g, 19.16 mmol) and a 3-alkyl—thiazolidine-2,4-dione such as 3-Methyl-thiazolidine-2,4-dione (19.16 mmol) is heated at reflux overnight. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1CSC[NH]1 | C1CSC[NH]1 | c1ccccc1.C1CSC[NH]1.c1ccc2c(c1)CCC[NH]2 | HO- | C(C)(=O)O.C(C)(=O)OCC | null | null | CN1C(=O)CSC1=O.Cc1cc2c(cc1-c1cc(C=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C>C(C)(=O)O.C(C)(=O)OCC>Cc1cc2c(cc1-c1cc(C=C3SC(=O)N(C)C3=O)ccc1OC(F)(F)F)N(C)C(=O)CC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b65c66c2fa4497087cd2562941f4a17 | CI.Cc1cc2c(cc1Br)NC(=O)CC2(C)C>>Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C | O.BrC1=C(C=C2C(CC(NC2=C1)=O)(C)C)C.[OH-].[K+].CI>>BrC1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C | I[CH3:10].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[NH:9][C:11](=[O:12])[CH2:13][C:14]2([CH3:15])[CH3:16]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[N:9]([CH3:10])[C:11](=[O:12])[CH2:13][C:14]2([CH3:15])[CH3:16] | CI.Cc1cc2c(cc1Br)NC(=O)CC2(C)C | Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 28e9bbae9e351621b70430e528cb53ce2fca2ea13e7a82f3ed5f3b0a20d55e94 | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1CCc2ccccc2N1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:2]-[C:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[c:6](:[c:7]):[c:8] | 101.3 | [{"value": 99.0, "product": "BrC1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.3, "product": "BrC1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | A mixture of powdered KOH (14.06 g, 0.250 mol) in DMSO (150 mL) was stirred at 0° C. for 10 min. 7-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one (33.59 g, 0.125 mol) was added cautiously, followed immediately by the addition of methyl iodide (39 mL, 0.625 mol). The reaction mixture was kept at 0° C. for 30 min t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HI | CS(=O)C | 0 | 0.166667 | CI.Cc1cc2c(cc1Br)NC(=O)CC2(C)C>CS(=O)C>Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbf0f186371046a78ad1fca5bc79a0a1 | CC(C)=CC(=O)Nc1ccc(C)c(Br)c1>>Cc1cc2c(cc1Br)NC(=O)CC2(C)C | BrC=1C=C(C=CC1C)NC(C=C(C)C)=O.[Cl-].[Al+3].[Cl-].[Cl-]>>BrC1=C(C=C2C(CC(NC2=C1)=O)(C)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:9][C:10](=[O:11])[CH:12]=[C:13]([CH3:14])[CH3:15])[cH:6][c:7]1[Br:8]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[NH:9][C:10](=[O:11])[CH2:12][C:13]2([CH3:14])[CH3:15] | CC(C)=CC(=O)Nc1ccc(C)c(Br)c1 | Cc1cc2c(cc1Br)NC(=O)CC2(C)C | null | null | null | C-C Coupling | OtherReaction | aea010e81c6715af41577808b3395b1a500e0b61256ebfb3a34fc3616fdf9072 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1CCc2ccccc2N1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[c:8](:[c:9]):[c;H0;D3;+0:10]-1:[c:11]:[c:12] | 65.7 | [{"value": 65.7, "product": "BrC1=C(C=C2C(CC(NC2=C1)=O)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-methyl-but-2-enoic acid (3-bromo-4-methyl-phenyl)-amide (70.0 g, 261 mmol) at 90° C. was added portion wise, under argon, with vigorous stirring aluminum chloride (52.3 g, 391 mmol) over 1.5 hr. The reaction mixture was stirred for 2 hours at 110–120° C. The reaction mixture was cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | null | null | null | 2 | CC(C)=CC(=O)Nc1ccc(C)c(Br)c1>>Cc1cc2c(cc1Br)NC(=O)CC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e4616a7bf65640f491ce4b54c4225ed0 | CC(C)=CC(=O)Cl.Cc1ccc(N)cc1Br>>CC(C)=CC(=O)Nc1ccc(C)c(Br)c1 | BrC=1C=C(N)C=CC1C.[OH-].[Na+].CC(=CC(=O)Cl)C>>BrC=1C=C(C=CC1C)NC(C=C(C)C)=O | Cl[C:5]([CH:4]=[C:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([Br:14])[cH:15]1>>[CH3:1][C:2]([CH3:3])=[CH:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([Br:14])[cH:15]1 | CC(C)=CC(=O)Cl.Cc1ccc(N)cc1Br | CC(C)=CC(=O)Nc1ccc(C)c(Br)c1 | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4](-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])=[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 97 | [{"value": 97.0, "product": "BrC=1C=C(C=CC1C)NC(C=C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "BrC=1C=C(C=CC1C)NC(C=C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a biphasic mixture of 3-bromo-4-methylaniline (50 g, 0.269 mol), 10% NaOH (270 mL) and dichloromethane (160 mL) was added dropwise over a period of 2 hours 3,3-dimethylacryloyl chloride (36 mL, 0.322 mol) in dichloromethane (95 mL). The solution was stirred at room temperature for 48 hours then diluted with water (1... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | ClCCl.O | null | 48 | CC(C)=CC(=O)Cl.Cc1ccc(N)cc1Br>ClCCl.O>CC(C)=CC(=O)Nc1ccc(C)c(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c72610874ea448b4a4768ec392bc794b | Cc1ccc([N+](=O)[O-])cc1Br>>Cc1ccc(N)cc1Br | C([O-])([O-])=O.[K+].[K+].BrC1=C(C=CC(=C1)[N+](=O)[O-])C.C(C)O.O.O.[Sn](Cl)Cl>>BrC=1C=C(N)C=CC1C | O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8]([Br:9])[cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:7][c:8]1[Br:9] | Cc1ccc([N+](=O)[O-])cc1Br | Cc1ccc(N)cc1Br | null | null | C(C)OC(C)=O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "BrC=1C=C(N)C=CC1C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-bromo-4-nitrotoluene (50 g, 0.231 mol in ethylacetate (330 mL) and Ethanol (150 mL) was added Tin(II)chloride dihydrate (208 g, 0.924 mol) portionwise. The reaction mixture was stirred at room temperature overnight. The solution was then treated with potassium carbonate until pH=7 and filtered over c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)OC(C)=O | null | 8 | Cc1ccc([N+](=O)[O-])cc1Br>C(C)OC(C)=O>Cc1ccc(N)cc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77caa91568234d24a077c16a3f1fb4fb | Cc1cc2c(cc1Br)NC(=O)CC2(C)C>>Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C | O.BrC1=C(C=C2C(CC(NC2=C1)=O)(C)C)C.[OH-].[K+].C(C)I>>BrC1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C | [CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[NH:9][C:11](=[O:12])[CH2:13][C:14]2([CH3:15])[CH3:16]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[N:9]([CH3:10])[C:11](=[O:12])[CH2:13][C:14]2([CH3:15])[CH3:16] | Cc1cc2c(cc1Br)NC(=O)CC2(C)C | Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C | null | null | CS(=O)C | Miscellaneous | OtherReaction | dfbdcbb9d33b82807e03a0fdd7314a553d6e1569f469cd8b72d4636c9de45108 | 7fae2ddae661851fbaf2a59d877a8345033038358ec191ec2c5e2351a33f569b | O=C1CCc2ccccc2N1 | [C:1]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:8])-[c:5](:[c:6]):[c:7] | 104.5 | [{"value": 104.5, "product": "BrC1=C(C=C2C(CC(N(C2=C1)C)=O)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | A mixture of powdered potassium hydroxide (3.35 g, 59.67 mmol) in DMSO (40 mL) was stirred at 0° C. for 10 min. 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one (Example 1e) (8.0 g, 29.83 mmol) was added cautiously, followed immediately by the addition of ethyl iodide (12 mL, 149.17 mmol). The reaction mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | Other | CS(=O)C | 0 | 0.166667 | Cc1cc2c(cc1Br)NC(=O)CC2(C)C>CS(=O)C>Cc1cc2c(cc1Br)N(C)C(=O)CC2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-976c401de5844f6db056c8abc7fdf8dc | BrBr.Cc1ccc2c(c1)n(C)c(=O)c(=O)n2C>>Cc1cc2c(cc1Br)n(C)c(=O)c(=O)n2C | [OH-].[Na+].O.CN1C(C(N(C2=CC(=CC=C12)C)C)=O)=O.BrBr>>BrC=1C=C2N(C(C(N(C2=CC1C)C)=O)=O)C | Br[Br:8].[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[n:9]([CH3:10])[c:11](=[O:12])[c:13](=[O:14])[n:15]2[CH3:16]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[n:9]([CH3:10])[c:11](=[O:12])[c:13](=[O:14])[n:15]2[CH3:16] | BrBr.Cc1ccc2c(c1)n(C)c(=O)c(=O)n2C | Cc1cc2c(cc1Br)n(C)c(=O)c(=O)n2C | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 82e70b0f760eee9ea654cea51b2b5192206b0037c5d0fce055e76049ea3dc1eb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1[nH]c2ccccc2[nH]c1=O | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[#7;a:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]2:[c:8]:[c:9](-[C;D1;H3:10]):[cH;D2;+0:11]:[c:12]:[c:13]:1:2>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:11]1:[c:12]:[c:13]2:[#7;a:3](-[C;D1;H3:2]):[c:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1-[C;D1;H3:10] | 99.3 | [{"value": 99.3, "product": "BrC=1C=C2N(C(C(N(C2=CC1C)C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 8 | HOUR | To a solution of 1,4,6-trimethyl-1,4-dihydro-quinoxaline-2,3-dione (0.66 g, 3.2 mmol) in acetic acid (40 mL) was added bromine (0.52 g, 3.2 mmol) and the solution stirred at 50° C. overnight. The reaction mixture was cooled to room temperature and poured into water. The solution was neutralized with aqueous NaOH to Ph=... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HBr | C(C)(=O)O | 50 | 8 | BrBr.Cc1ccc2c(c1)n(C)c(=O)c(=O)n2C>C(C)(=O)O>Cc1cc2c(cc1Br)n(C)c(=O)c(=O)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47389a4cedf14c17a95ffc3eefc86c4e | COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1>>Cc1cc2c(cc1O)N(Cc1ccccc1)C(=O)C2(C)C | C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)OC)C)(C)C)=O.B(Br)(Br)Br>>C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)O)C)(C)C)=O | C[O:8][c:7]1[c:2]([CH3:1])[cH:3][c:4]2[c:5]([cH:6]1)[N:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[C:19]2([CH3:20])[CH3:21]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[OH:8])[N:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[C:19]2([CH3:20])[CH3:21] | COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1 | Cc1cc2c(cc1O)N(Cc1ccccc1)C(=O)C2(C)C | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1Cc2ccccc2N1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)O)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 8 | HOUR | To a solution of 1-benzyl-6-methoxy-3,3,5-trimethyl-1,3-dihydro-indol-2-one (1.52 g, 5.15 mmol) in anhydrous dichloromethane (50 mL) was added slowly, under argon at −78° C., BBr3 (0.87 mL, 9.27 mmol). The reaction was warmed up to −20° C. and stirred overnight at room temperature. Water and the layer separated. The aq... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]2 | Other | ClCCl | -20 | 8 | COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1>ClCCl>Cc1cc2c(cc1O)N(Cc1ccccc1)C(=O)C2(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fbc489b022444d9881717fee9d6c961a | COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C>>COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1 | [Cl-].[NH4+].C(C1=CC=CC=C1)N(C(C(C)C)=O)C1=C(C=C(C(=C1)OC)C)Br.CC(C)([O-])C.[Na+]>>C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)OC)C)(C)C)=O | Br[c:6]1[c:5]([N:15]([C:13]([CH:10]([CH3:11])[CH3:12])=[O:14])[CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:4][c:3]([O:2][CH3:1])[c:8]([CH3:9])[cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH3:9])[C:10]([CH3:11])([CH3:12])[C:13](=[O:14])[N:15]2[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C | COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 | O1CCOCC1 | Functional Group Interconversion | OtherReaction | df1aa182059fb9257c102fb9f33a1d3c689b7330b48d169f061515a6fc482e69 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1Cc2ccccc2N1Cc1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7:5](-[C:6])-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C;D1;H3:10])-[C;D1;H3:11]):[c:12]>>[C:6]-[#7:5]1-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]-1:[c:12] | 57 | [{"value": 57.0, "product": "C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)OC)C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C(C1=CC=CC=C1)N1C(C(C2=CC(=C(C=C12)OC)C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-benzyl-N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (4.35 g, 11.56 mmol) in 1,4-dioxane (115 mL) was added sodium tert-butoxide (1.66 g, 17.34 mmol). The mixture was degassed under argon for 30 minutes, then palladium (II) acetate (130 mg, 0.58 mmol) and tricyclohexylphosphine (162 mg, 0.58 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2.c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.O1CCOCC1 | null | null | COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.O1CCOCC1>COc1cc2c(cc1C)C(C)(C)C(=O)N2Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-702e68e33e77400490e5eec9993d467b | BrCc1ccccc1.COc1cc(NC(=O)C(C)C)c(Br)cc1C>>COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C | O.BrC1=C(C=C(C(=C1)C)OC)NC(C(C)C)=O.[OH-].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N(C(C(C)C)=O)C1=C(C=C(C(=C1)OC)C)Br | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:14](=[O:15])[CH:16]([CH3:17])[CH3:18])[c:19]([Br:20])[cH:21][c:22]1[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14](=[O:15])[CH:16]([CH3:17])[CH3:18])[c:19]([Br:20])[cH:21][c:22... | BrCc1ccccc1.COc1cc(NC(=O)C(C)C)c(Br)cc1C | COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:9](:[c:10]):[c:11] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)N(C(C(C)C)=O)C1=C(C=C(C(=C1)OC)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "C(C1=CC=CC=C1)N(C(C(C)C)=O)C1=C(C=C(C(=C1)OC)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A mixture of powdered KOH (1.3 g, 23.13 mmol) in DMSO (25 mL) was stirred at 0° C. for 5 minutes. N-(2-bromo-5-methoxy-4-methyl-phenyl)-isobutyramide (3.30 g, 11.56 mmol) was added cautiously followed immediately by the addition of benzylbromide (2.75 mL, 23.13 mmol) and the reaction stirred at room temperature for 48 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1.c1ccccc1 | HBr | CS(=O)C | 0 | 0.083333 | BrCc1ccccc1.COc1cc(NC(=O)C(C)C)c(Br)cc1C>CS(=O)C>COc1cc(N(Cc2ccccc2)C(=O)C(C)C)c(Br)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bce456ac6a614e5089098c99135f35ff | CC(C)C(=O)Cl.COc1cc(N)c(Br)cc1C>>COc1cc(NC(=O)C(C)C)c(Br)cc1C | BrC1=C(N)C=C(C(=C1)C)OC.[OH-].[K+].C(C(C)C)(=O)Cl>>BrC1=C(C=C(C(=C1)C)OC)NC(C(C)C)=O | Cl[C:7](=[O:8])[CH:9]([CH3:10])[CH3:11].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:12]([Br:13])[cH:14][c:15]1[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][C:7](=[O:8])[CH:9]([CH3:10])[CH3:11])[c:12]([Br:13])[cH:14][c:15]1[CH3:16] | CC(C)C(=O)Cl.COc1cc(N)c(Br)cc1C | COc1cc(NC(=O)C(C)C)c(Br)cc1C | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99.3 | [{"value": 99.0, "product": "BrC1=C(C=C(C(=C1)C)OC)NC(C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "BrC1=C(C=C(C(=C1)C)OC)NC(C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a biphasic mixture of 2-bromo-5-methoxy-4-methyl-aniline (5.6 g, 25.96 mmol), 10% KOH (27 mL) and dichloromethane (30 mL), was added dropwise isobutyryl chloride (3 mL, 28.55 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 48 hrs. The layers were separated. The aqueous laye... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | ClCCl | null | 48 | CC(C)C(=O)Cl.COc1cc(N)c(Br)cc1C>ClCCl>COc1cc(NC(=O)C(C)C)c(Br)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ae525a6995242d69c3583ae30f02c03 | COc1cc(N)ccc1C.[Br-]>>COc1cc(N)c(Br)cc1C | C(=O)(O)[O-].[Na+].COC=1C=C(N)C=CC1C.[Br-].[Br-].[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC.C(CCC)[N+](CCCC)(CCCC)CCCC>>BrC1=C(N)C=C(C(=C1)C)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:9][c:10]1[CH3:11].[Br-:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([Br:8])[cH:9][c:10]1[CH3:11] | COc1cc(N)ccc1C.[Br-] | COc1cc(N)c(Br)cc1C | null | null | ClCCl | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | [Br-;H0;D0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 85.6 | [{"value": 85.0, "product": "BrC1=C(N)C=C(C(=C1)C)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "BrC1=C(N)C=C(C(=C1)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 3-methoxy-4-methyl-aniline (8.19 g, 59.71 mmol) in dichloromethane (200 mL), was added tetrabutylammonium tribromide (28.79 g, 59.71 mmol) and the reaction mixture was stirred at room temperature for 2.5 hrs. Aqueous NaHCO3 was added and the layers separated. The aqueous layer was further extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | ClCCl | null | 2.5 | COc1cc(N)ccc1C.[Br-]>ClCCl>COc1cc(N)c(Br)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c885315dcbe54d788919632571ee7f87 | COc1cc([N+](=O)[O-])ccc1C>>COc1cc(N)ccc1C | CC1=C(C=C(C=C1)[N+](=O)[O-])OC.O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>>COC=1C=C(N)C=CC1C | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:9]([CH3:10])[cH:8][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:8][c:9]1[CH3:10] | COc1cc([N+](=O)[O-])ccc1C | COc1cc(N)ccc1C | null | null | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 86 | [{"value": 86.0, "product": "COC=1C=C(N)C=CC1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "COC=1C=C(N)C=CC1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-methyl-5-nitroanisole (11.56 g, 69.2 mmol) in a mixture of ethyl acetate (200 mL) and ethanol (70 mL) was added portionwise tin (II) chloride dihydrate (109 g, 0.483 mol) and the mixture was stirred at room temperature overnight. The reaction mixture was basified with aq. K2CO3 and filtered over celi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)(=O)OCC.C(C)O | null | 8 | COc1cc([N+](=O)[O-])ccc1C>C(C)(=O)OCC.C(C)O>COc1cc(N)ccc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5bf0860457b4e248df486a68c484723 | CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2.CC(C)OB(OC(C)C)OC(C)C>>CC(C)Cc1cc(B(O)O)c2c(c1)C(C)(C)CO2 | Cl.[Li]CCCC.BrC1=CC(=CC=2C(COC21)(C)C)CC(C)C.C(C)(C)OB(OC(C)C)OC(C)C>>C(C(C)C)C=1C=C(C2=C(C(CO2)(C)C)C1)B(O)O | Br[c:7]1[cH:6][c:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[cH:13][c:12]2[c:11]1[O:18][CH2:17][C:14]2([CH3:15])[CH3:16].CC(C)O[B:8]([O:9]C(C)C)[O:10]C(C)C>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][c:7]([B:8]([OH:9])[OH:10])[c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])([CH3:16])[CH2:17][O:18]2 | CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2.CC(C)OB(OC(C)C)OC(C)C | CC(C)Cc1cc(B(O)O)c2c(c1)C(C)(C)CO2 | null | null | C(C)(=O)OCC.C1CCOC1 | Miscellaneous | Preparation of boronic acids | 112c72bbe77af87a2ef270f9ef3e900f83a6ad272e2a1ee47eb37bf96c79880a | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc2c(c1)CCO2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[#8:6]-[C:7].C-C(-C)-O-[B;H0;D3;+0:8](-[O;H0;D2;+0:9]-C(-C)-C)-[O;H0;D2;+0:10]-C(-C)-C>>[C:7]-[#8:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[B;H0;D3;+0:8](-[OH;D1;+0:9])-[OH;D1;+0:10]):[c:2]:[c:3] | 49.6 | [{"value": 46.0, "product": "C(C(C)C)C=1C=C(C2=C(C(CO2)(C)C)C1)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "C(C(C)C)C=1C=C(C2=C(C(CO2)(C)C)C1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 5 | MINUTE | To a mixture of 7-bromo-5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (9.9 g, 34.96 mmol) in THF (50 mL) cooled to −78° C. under an atmosphere of argon was added n-BuLi (25.17 mL, 2.5 M, 62.93 mmol) dropwise. The reaction mixture was stirred for 5 minutes and triisopropylborate (24.2 mL, 104.87 mmol) was added dropwis... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HBr | C(C)(=O)OCC.C1CCOC1 | -78 | 0.083333 | CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2.CC(C)OB(OC(C)C)OC(C)C>C(C)(=O)OCC.C1CCOC1>CC(C)Cc1cc(B(O)O)c2c(c1)C(C)(C)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89cfa1cd693841edb6b03ec011fb8e03 | CC(C)Cc1ccc2c(c1)C(C)(C)CO2.[Br-]>>CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2 | C(C(C)C)C=1C=CC2=C(C(CO2)(C)C)C1.[Br-].[Br-].[Br-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>BrC1=CC(=CC=2C(COC21)(C)C)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:9]2[c:10]([cH:11]1)[C:12]([CH3:13])([CH3:14])[CH2:15][O:16]2.[Br-:8]>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][c:7]([Br:8])[c:9]2[c:10]([cH:11]1)[C:12]([CH3:13])([CH3:14])[CH2:15][O:16]2 | CC(C)Cc1ccc2c(c1)C(C)(C)CO2.[Br-] | CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2 | null | null | ClCCl | Functional Group Interconversion | Bromination | 8a5899f39c577ae2f5dbb7e89484f9814910050aa00e810b5c8bafb1acd06dbc | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)CCO2 | [Br-;H0;D0:1].[C:2]-[#8:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](:[c:5])-[#8:3]-[C:2] | 68.5 | [{"value": 68.0, "product": "BrC1=CC(=CC=2C(COC21)(C)C)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "BrC1=CC(=CC=2C(COC21)(C)C)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (1.59 g, 7.78 mmol) in dichloromethane (40 mL) was added pyridinium tribromide (2.49 g, 7.78 mmol) and the reaction mixture stirred at room temperature overnight. The solution was washed with water and brine, dried (Mg2SO4), filtered and evaporated. The re... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | null | ClCCl | null | 8 | CC(C)Cc1ccc2c(c1)C(C)(C)CO2.[Br-]>ClCCl>CC(C)Cc1cc(Br)c2c(c1)C(C)(C)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-901ce828923d41e8b5486673c213dff6 | CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2>>CC(C)Cc1ccc2c(c1)C(C)(C)CO2 | O.FC(C(=O)O)(F)F.CC1(COC2=C1C=C(C=C2)C(C(C)C)O)C.C(C)[SiH](CC)CC>>C(C(C)C)C=1C=CC2=C(C(CO2)(C)C)C1 | O[CH:4]([CH:2]([CH3:1])[CH3:3])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11]([CH3:12])([CH3:13])[CH2:14][O:15]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11]([CH3:12])([CH3:13])[CH2:14][O:15]2 | CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2 | CC(C)Cc1ccc2c(c1)C(C)(C)CO2 | null | null | ClCCl | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc2c(c1)CCO2 | O-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | 87.7 | [{"value": 87.0, "product": "C(C(C)C)C=1C=CC2=C(C(CO2)(C)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "C(C(C)C)C=1C=CC2=C(C(CO2)(C)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | To a cold solution (0° C.) of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (1.97 g, 8.93 mmol) in dry dichloromethane (40 mL) was added triethylsilane (2.85 mL, 17.86 mmol). After 10 minutes, trifluoroacetic acid was the reaction mixture stirred at 0° C. for 30 minutes. Water was poured into the re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccc2c(c1)CCO2 | Other | ClCCl | 0 | 0.166667 | CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2>ClCCl>CC(C)Cc1ccc2c(c1)C(C)(C)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ced0d5f185d429ab03b60c0c8ee990d | CC(C)C=O.CC1(C)COc2ccc(Br)cc21>>CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2 | [Cl-].[NH4+].C(C(C)C)=O.BrC=1C=CC2=C(C(CO2)(C)C)C1.[Li]CCCC>>CC1(COC2=C1C=C(C=C2)C(C(C)C)O)C | [CH3:1][CH:2]([CH3:3])[CH:4]=[O:5].Br[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12]([CH3:13])([CH3:14])[CH2:15][O:16]2>>[CH3:1][CH:2]([CH3:3])[CH:4]([OH:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12]([CH3:13])([CH3:14])[CH2:15][O:16]2 | CC(C)C=O.CC1(C)COc2ccc(Br)cc21 | CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | a56606a78163c88dc4bf48a7c5ab26b38cb3fda591dd4b56afdf051b12beb5dd | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc2c(c1)CCO2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[CH;D2;+0:9]=[O;H0;D1;+0:10]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[CH;D3;+0:9](-[OH;D1;+0:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 106.7 | [{"value": 100.0, "product": "CC1(COC2=C1C=C(C=C2)C(C(C)C)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.7, "product": "CC1(COC2=C1C=C(C=C2)C(C(C)C)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (2.03 g, 8.93 mmol) in dry THF (10 mL) at −78° C., under argon, was added dropwise n-BuLi (1.6 M in hexane, 13.4 mmol, 8.38 mL). The mixture was stirred for 5 minutes then isobutyraldehyde (1.22 mL, 8.38 mmol) was added and the mixture was slowly warmed up to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | Br- | C1CCOC1 | null | 0.083333 | CC(C)C=O.CC1(C)COc2ccc(Br)cc21>C1CCOC1>CC(C)C(O)c1ccc2c(c1)C(C)(C)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a5800cb92e94a7ab363a3619bc4b26c | COc1ccc(Br)cc1C(C)(C)CCl>>CC1(C)COc2ccc(Br)cc21 | BrC1=CC(=C(C=C1)OC)C(CCl)(C)C.Cl.N1=CC=CC=C1.N1=CC=CC2=CC=CC=C12>>BrC=1C=CC2=C(C(CO2)(C)C)C1 | C[O:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]1[C:2]([CH3:1])([CH3:3])[CH2:4]Cl>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]21 | COc1ccc(Br)cc1C(C)(C)CCl | CC1(C)COc2ccc(Br)cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 17eeb4763d9302b5045a1417df199ffda8f8cc9d73817017e66cab6c94957c5a | 969a4609e178674696657c590a647839ca01abd1f90b8f0c9e475b1d6507651b | c1ccc2c(c1)CCO2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[CH2;D2;+0:8]-Cl>>[C;D1;H3:6]-[C:5]1(-[C;D1;H3:7])-[CH2;D2;+0:8]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-1 | 98 | [{"value": 98.0, "product": "BrC=1C=CC2=C(C(CO2)(C)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "BrC=1C=CC2=C(C(CO2)(C)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-bromo-2-(2-chloro-1,1-dimethyl-ethyl)-1-methoxy-benzene (65 g, 0.234 mol), pyridine hydrochloride (121.8 g, 1.054 mol) and quinoline (110.67 mL, 0.936 mol) was refluxed at 164° C.–167° C. under argon for 5 hrs. After cooling to room temperature the reaction mixture was treated with ice-cold 6N HCl and ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | null | c1ccc2c(c1)CCO2 | c1ccc2c(c1)CCO2 | HCl | null | null | null | COc1ccc(Br)cc1C(C)(C)CCl>>CC1(C)COc2ccc(Br)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6143f107a610417eb57f1701b3304807 | C=C(C)CCl.COc1ccc(Br)cc1>>COc1ccc(Br)cc1C(C)(C)CCl | S(O)(O)(=O)=O.BrC1=CC=C(C=C1)OC.O.ClCC(=C)C>>BrC1=CC(=C(C=C1)OC)C(CCl)(C)C | [C:10]([CH3:11])(=[CH2:12])[CH2:13][Cl:14].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[C:10]([CH3:11])([CH3:12])[CH2:13][Cl:14] | C=C(C)CCl.COc1ccc(Br)cc1 | COc1ccc(Br)cc1C(C)(C)CCl | null | null | ClCCl | C-C Coupling | Friedel-Crafts alkylation | f6021e53f57d07d48a856391b21137517c9bd669381174a55381b6219a6afd68 | 48297e5b607b4624d5b08506879ba8f9dd47fb272c10888542fa01ef83829ef2 | c1ccccc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[C;D1;H3:7]-[C;H0;D3;+0:8](=[CH2;D1;+0:9])-[C:10]-[Cl;D1;H0:11]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D4;+0:8](-[C;D1;H3:7])(-[CH3;D1;+0:9])-[C:10]-[Cl;D1;H0:11]):[c:5]:[c:6] | null | [] | null | null | null | null | Sulfuric acid (2 mL, 0.033 mol) was added dropwise under argon to 4-bromoanisole (14.6 mL, 0.117 mol). The mixture was warmed to 40–43° C. (warm water bath) and 3-chloro-2-methyl propene was added dropwise in 4 equal portions over 2 hrs. After 2 hrs at 40–43° C. the solution was diluted with dichloromethane and washed ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | ClCCl | null | null | C=C(C)CCl.COc1ccc(Br)cc1>ClCCl>COc1ccc(Br)cc1C(C)(C)CCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9e5ce56ff19449393d82f4c2ca17317 | CN(C)C(=O)c1cc(Br)c2c(c1)C(C)(C)CO2.O=Cc1ccc(OC(F)(F)F)c(Br)c1>>CN(C)C(=O)c1cc(-c2cc(C=O)ccc2OC(F)(F)F)c2c(c1)C(C)(C)CO2 | C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.[B]1OC(C(O1)(C)C)(C)C.BrC=1C=C(C=O)C=CC1OC(F)(F)F.C(C)N(CC)CC.CN(C(=O)C=1C=C(C2=C(C(CO2)(C)C)C1)Br)C>>CN(C(=O)C=1C=C(C2=C(C(CO2)(C)C)C1)C1=C(C=CC(=C1)C=O)OC(F)(F)F)C | Br[c:8]1[cH:7][c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[cH:24][c:23]2[c:22]1[O:29][CH2:28][C:25]2([CH3:26])[CH3:27].Br[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][cH:15][c:16]1[O:17][C:18]([F:19])([F:20])[F:21]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][c:11]([CH:12]=[O:13])[cH:14][cH:15][c:16]2[... | CN(C)C(=O)c1cc(Br)c2c(c1)C(C)(C)CO2.O=Cc1ccc(OC(F)(F)F)c(Br)c1 | CN(C)C(=O)c1cc(-c2cc(C=O)ccc2OC(F)(F)F)c2c(c1)C(C)(C)CO2 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | O1CCOCC1.O.C(C)(=O)OCC | C-C Coupling | Negishi | cb7e770ee1be461bb20a647f5f502c8c42a3886a14e9e2a7bc53a51bdf846d0a | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2cccc3c2OCC3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](:[c:8])-[#8:9]-[C:10].Br-[c;H0;D3;+0:11](:[c:12]:[c:13]-[C:14]=[O;D1;H0:15]):[c:16](-[#8:17]):[c:18]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]-[C:14]=[O;D1;H0:15]):[c:16](-[#8:17]):[c:18]):[c:7](:[c:8])-[#8:9]-... | 50 | [{"value": 50.0, "product": "CN(C(=O)C=1C=C(C2=C(C(CO2)(C)C)C1)C1=C(C=CC(=C1)C=O)OC(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "CN(C(=O)C=1C=C(C2=C(C(CO2)(C)C)C1)C1=C(C=CC(=C1)C=O)OC(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid dimethylamide (437 mg, 1.46 mmol) in dioxane (4 mL), were added under argon, triethylamine (0.82 mL, 5.86 mmol), Pd(OAc)2 (16 mg, 0.07 mmol), 2-(dicyclohexylphosphino)biphenyl (103 mg, 0.29 mmol) and pinacolborane (0.64 mL, 4.40 mmol) dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccc2c(c1)CCO2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCO2 | c1ccccc1.c1ccc2c(c1)CCO2 | Br- | CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1.O.C(C)(=O)OCC | 80 | null | CN(C)C(=O)c1cc(Br)c2c(c1)C(C)(C)CO2.O=Cc1ccc(OC(F)(F)F)c(Br)c1>CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1.O.C(C)(=O)OCC>CN(C)C(=O)c1cc(-c2cc(C=O)ccc2OC(F)(F)F)c2c(c1)C(C)(C)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc5fd901768f4887b9c9ef8595d7ca2c | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1>>COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | C(=O)(N1C=NC=C1)N1C=NC=C1.COC(=O)C=1SC(=CC1)C(=O)O.C(C)(C)(C)OC(NC1=C(C=CC=C1)N)=O>>COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O | [NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25].O[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:26]1)=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[NH:18][C:19](=[O:20]... | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1 | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]-[C:7](-[#8:8])=[O;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]:[#16;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:4] | 80.2 | [{"value": 80.2, "product": "COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Under an argon atmosphere 21.0 g (129 mmol) carbonyldiimidazol was added to a solution of 24.1 g (129 mmol) thiophene-2,5-dicarboxylic acid monomethyl ester in 600 ml THF. After 2 h at rt 26.9 g (129 mmol) (2-amino-phenyl)-carbamic acid tert-butyl ester were added and the reaction mixture was stirred for further 4 h at... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)Nc1ccccc1N.COC(=O)c1ccc(C(=O)O)s1>C1CCOC1>COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe083d7fc1964a5597f6c4073c73ab34 | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1>>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 | COC(=O)C=1SC(=CC1)C(NC1=C(C=CC=C1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O | C[O:24][C:22]([c:21]1[cH:20][cH:19][c:18]([C:16]([NH:15][c:14]2[c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:10][cH:11][cH:12][cH:13]2)=[O:17])[s:25]1)=[O:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:... | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 | null | null | O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)c1cccs1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a suspension of 18.5 g (50 mmol) 5-(2-tert-Butoxycarbonylamino-phenyl-carbamoyl)-thiophene-2-carboxylic acid methyl ester in 500 ml MeOH was added within 20 minutes a solution of 5.6 g (100 mmol) potassium hydroxide in 100 ml water. The reaction mixture was stirred at room temperature for 2 d. The MeOH was evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1 | Other | O.CO | null | 48 | COC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1>O.CO>CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2cea9a32b0044a881f3c9217467f865 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N>>CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | CC(CCC)N.C(C)(C)(C)OC(=O)NC1=C(C=CC=C1)NC(=O)C1=CC=C(S1)C(=O)O.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(C)(C)(C)OC(NC1=C(C=CC=C1)NC(=O)C=1SC(=CC1)C(NC(CCC)C)=O)=O | O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[s:30]1.[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[NH2:6]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[NH:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[N... | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N | CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6]-[C:7](-[#7:8])=[O;D1;H0:9].[C:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[c:6]:[#16;a:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:11](-[C:10])-[C;D1;H3:12]):[c:4] | null | [] | 45 | CELSIUS | 1 | HOUR | To a solution of 4.4 g (12.1 mmol) 5-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid in 80 ml THF were added 2.2 g (13.6 mmol) carbonyldiimidazol. The reaction mixture was stirred at 45° C. for 1 h and then cooled to rt. After addition of 1.05 g (12 mmol) 2-pentylamine the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | C1CCOC1 | 45 | 1 | CC(C)(C)OC(=O)Nc1ccccc1NC(=O)c1ccc(C(=O)O)s1.CCCC(C)N>C1CCOC1>CCCC(C)NC(=O)c1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d54340666b7148d9a6bdec48400dbcf4 | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1>>COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | COC(=O)C=1C=CC(=NC1)C(=O)[O-].[K+].S(=O)(Cl)Cl.C(C)(C)N(CCN)C(C)C.C(C)N(CC)CC>>COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O | [NH2:11][CH2:12][CH2:13][N:14]([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20].[O-][C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:22][n:21]1)=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][CH2:12][CH2:13][N:14]([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:19])[CH3:20])[n:21][c... | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1 | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | null | null | ClC(C)Cl.C(Cl)Cl.CN(C)C=O | Acylation | OtherReaction | 01b411aa709aa72475efefee2037796aeb41c60940ddba8e15aefc45a95317a8 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | c1ccncc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O-]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[#7;a:8]:[c:9] | 74 | [{"value": 74.0, "product": "COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A suspension of 1.1 g (5 mmol) potassium 5-methoxycarbonyl-pyridine-2-carboxylate, 0.9 ml (12 mmol) thionyl chloride and 0.1 ml DMF in 5 ml dichloroethane was heated at reflux for 2 h. To the reaction mixture 5 ml CH2Cl2 were added and the solvent was evaporated. This procedure was repeated three times. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | ClC(C)Cl.C(Cl)Cl.CN(C)C=O | null | 12 | CC(C)N(CCN)C(C)C.COC(=O)c1ccc(C(=O)[O-])nc1>ClC(C)Cl.C(Cl)Cl.CN(C)C=O>COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-32090cdb0df14200be7298a12d733dd7 | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1>>CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C | COC(C1=CN=C(C=C1)C(NCCN(C(C)C)C(C)C)=O)=O.[OH-].[Na+]>>C(C)(C)N(CCNC(=O)C1=NC=C(C(=O)O)C=C1)C(C)C | C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:19]([CH3:20])[CH3:21])=[O:9])[n:18][cH:17]1)=[O:15]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][n:18]1)[CH:19]([CH3:20])[CH3:21] | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1 | CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.9 | [{"value": 88.9, "product": "C(C)(C)N(CCNC(=O)C1=NC=C(C(=O)O)C=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1100 mg (3.6 mmol) 6-(2-diisopropylamino-ethylcarbamoyl)-nicotinic acid methyl ester in 10 ml THF and 3.0 ml MeOH was added 3.6 ml of an 2N aqueous NaOH solution. After 4 h at rt the solvent was evaporated. The residue was acidified with 1N HCl, filtered off and washed with water to give 936 mg (3.2 mm... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | CO.C1CCOC1 | null | null | COC(=O)c1ccc(C(=O)NCCN(C(C)C)C(C)C)nc1>CO.C1CCOC1>CC(C)N(CCNC(=O)c1ccc(C(=O)O)cn1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c68c8c1c71e8490ca4bfbc32fb5643b0 | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1 | ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1.C1CCOC1.NC1=C(C=C(C(=O)OC)C=C1)S(=O)(=O)C.[H-].[Na+].[H-].[Na+]>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[s:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][c... | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1 | null | null | CN(C)C=O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 44.7 | [{"value": 44.7, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into a mixed solvent of 20 mL of THF and 3 mL of DMF was dissolved 985 mg of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 170 mg of sodium hydride (oily, 60%) at 0° C. After 20 minutes of stirring at the same temperature, 1.28 g of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0°... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | CN(C)C=O | null | 1 | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>CN(C)C=O>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a152e2c19d984a5485caa2e2058b994e | COC(=O)c1cc(S(C)(=O)=O)c(N)cc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>COC(=O)c1cc(S(C)(=O)=O)c(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1C | ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1.[H-].[Na+].ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1.C1CCOC1.NC1=CC(=C(C(=O)OC)C=C1S(=O)(=O)C)C.[H-].[Na+]>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=CC(=C(C(=O)OC)C=C2S(=O)(=O)C)C)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([NH2:13])[cH:28][c:29]1[CH3:30].Cl[S:14](=[O:15])(=[O:16])[c:17]1[s:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][c:25]2[c:26]1[CH3:27]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([NH:13][S:14](=[O:15... | COC(=O)c1cc(S(C)(=O)=O)c(N)cc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | COC(=O)c1cc(S(C)(=O)=O)c(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1C | null | null | CN(C)C=O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 45.2 | [{"value": 45.2, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=CC(=C(C(=O)OC)C=C2S(=O)(=O)C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into 10 mL of THF was dissolved 135 mg of methyl 4-amino-5-methanesulfonyl-2-methylbenzoate, followed by addition of 22 mg of sodium hydride (oily, 60%) at room temperature. After 20 minutes of stirring at the same temperature, 130 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed b... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | CN(C)C=O | null | 1 | COC(=O)c1cc(S(C)(=O)=O)c(N)cc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>CN(C)C=O>COC(=O)c1cc(S(C)(=O)=O)c(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-46eef5de2b1e4935b5dd697656646385 | COC(=O)c1ccc(N)c(C(=O)OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(C(=O)OC)c1 | [H-].[Na+].NC1=C(C=C(C(=O)OC)C=C1)C(=O)OC.[H-].[Na+].ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:24]([C:25](=[O:26])[O:27][CH3:28])[cH:29]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[s:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][cH:1... | COC(=O)c1ccc(N)c(C(=O)OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(C(=O)OC)c1 | null | null | C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]>>[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7]):[c:14] | 29.5 | [{"value": 29.5, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Into 8 mL of THF was dissolved 115 mg of dimethyl 4-aminoisophthalate, followed by addition of 22 mg of sodium hydride (oily, 60%). After 20 minutes of stirring at room temperature, 130 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at the same temperature, followed by 30 minutes of stirring at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | C1CCOC1 | null | 0.333333 | COC(=O)c1ccc(N)c(C(=O)OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>C1CCOC1>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(C(=O)OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ae174be5f614c5994a1b87d3f53b153 | COC(=O)c1ccc(N)c(OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(OC)c1 | NC1=C(C=C(C(=O)OC)C=C1)OC.ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:24]([O:25][CH3:26])[cH:27]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[s:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][cH:17][c:18]([Cl:19... | COC(=O)c1ccc(N)c(OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(OC)c1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 48.4 | [{"value": 48.4, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | Into 4 mL of pyridine were dissolved 120 mg of methyl 4-amino-3-methoxybenzoate and 150 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene, followed by 14 hours of stirring at room temperature. After confirmation of disappearance of the starting material, the reaction was terminated by adding water at 0° C., fol... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | N1=CC=CC=C1 | null | 14 | COC(=O)c1ccc(N)c(OC)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>N1=CC=CC=C1>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d655178a714a49b1b6bcea7037858048 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1>>Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(Cl)cc12 | [H-].C(C(C)C)[Al+]CC(C)C.ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)CO)S(=O)(=O)C)C=C1 | CO[C:12]([c:11]1[cH:10][cH:9][c:8]([NH:7][S:4]([c:3]2[c:2]([CH3:1])[c:27]3[c:21]([s:20]2)[cH:22][cH:23][c:24]([Cl:25])[cH:26]3)(=[O:5])=[O:6])[c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:14]1)=[O:13]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]2[S:16]([CH3:17])(=... | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1 | Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(Cl)cc12 | null | null | C1(=CC=CC=C1)C | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 80.1 | [{"value": 80.1, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)CO)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | Into 10 mL of toluene was dissolved 305 mg of Compound 1, and the solution was cooled to −78° C., followed by addition of 2.2 mL of 1.01 mol/L toluene solution of diisobutylaluminum hydride. After 20 minutes of stirring at the same temperature, the mixture was gradually warmed to 0° C. and stirred for 1 hour. After the... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2sccc2c1 | Other | C1(=CC=CC=C1)C | -78 | 0.333333 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1>C1(=CC=CC=C1)C>Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(Cl)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7b088af0aa04e6893ff19a8160fc6c1 | CCOC(=O)c1ccc(N)cc1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>CCOC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1 | NC1=CC=C(C(=O)OCC)C=C1.ClC1=CC2=C(SC(=C2C)S(=O)(=O)Cl)C=C1.Cl>>ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=CC=C(C(=O)OCC)C=C2)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:25][cH:26]1.Cl[S:11](=[O:12])(=[O:13])[c:14]1[s:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]2[c:23]1[CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]2[s:15][c:16]3[cH:17][cH:18][c:19]([Cl:2... | CCOC(=O)c1ccc(N)cc1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | CCOC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 53.7 | [{"value": 53.7, "product": "ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=CC=C(C(=O)OCC)C=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Into 3 mL of pyridine was dissolved 60 mg of ethyl 4-aminobenzoate, and 123 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 2 hours of stirring at room temperature. After confirmation of disappearance of the starting material, 2 mol/L hydrochloric acid was added, followed by ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | N1=CC=CC=C1 | null | 2 | CCOC(=O)c1ccc(N)cc1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>N1=CC=CC=C1>CCOC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45831d6810984499afc47944b982521b | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1 | [H-].[Na+].NC1=C(C=C(C(=O)OC)C=C1)S(=O)(=O)C.ClS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[s:14][c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]2[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][cH... | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1 | null | null | C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 89.7 | [{"value": 89.7, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Into 300 mL of THF was dissolved 14.0 g of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 6.10 g of sodium hydride (oily, 60%) at 0° C. After 40 minutes of stirring at the same temperature, 16.0 g of 2-chlorosulfonyl-5-fluoro-3-methylbenzo[b]thiophene was added at 0° C., followed by 3 hours of stirri... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | C1CCOC1 | null | 3 | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12>C1CCOC1>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b427e01b17ac4285894a0f804cc42901 | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1ccc2sc(S(=O)(=O)Cl)c(C)c2c1>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(C)cc3c2C)c(S(C)(=O)=O)c1 | [H-].[Na+].NC1=C(C=C(C(=O)OC)C=C1)S(=O)(=O)C.ClS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)C)C>>CC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29]1.Cl[S:10](=[O:11])(=[O:12])[c:13]1[s:14][c:15]2[cH:16][cH:17][c:18]([CH3:19])[cH:20][c:21]2[c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][... | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1ccc2sc(S(=O)(=O)Cl)c(C)c2c1 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(C)cc3c2C)c(S(C)(=O)=O)c1 | null | null | C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 50 | [{"value": 50.0, "product": "CC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Into 8.0 mL of THF was dissolved 183 mg of methyl 4-amino-3-methanesulfonylbenzoate, followed by addition of 96 mg of sodium hydride (oily, 60%) at 0° C. After 20 minutes of stirring at the same temperature, 250 mg of 2-chlorosulfonyl-5-methyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 6 hours of stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2sccc2c1 | HCl | C1CCOC1 | null | 6 | COC(=O)c1ccc(N)c(S(C)(=O)=O)c1.Cc1ccc2sc(S(=O)(=O)Cl)c(C)c2c1>C1CCOC1>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(C)cc3c2C)c(S(C)(=O)=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfaf5cab0b8e4e7188a11fb0523060d5 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1>>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccccc3c2C)c(S(C)(=O)=O)c1 | CO.ClC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1>>CC=1C2=C(SC1S(=O)(=O)NC1=C(C=C(C(=O)OC)C=C1)S(=O)(=O)C)C=CC=C2 | Cl[c:18]1[cH:17][cH:16][c:15]2[s:14][c:13]([S:10]([NH:9][c:8]3[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:28][c:23]3[S:24]([CH3:25])(=[O:26])=[O:27])(=[O:11])=[O:12])[c:21]([CH3:22])[c:20]2[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][cH:17][cH:... | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccccc3c2C)c(S(C)(=O)=O)c1 | null | [Pd] | O1CCOCC1 | Functional Group Interconversion | Aromatic dehalogenation | ab6c258853a046ce112a28199ff0524dc13007f2a0961d19b739094801efd0b3 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[c:7]:1>>[#16;a:5]:[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:7]:[c:6]:1 | 22.9 | [{"value": 22.9, "product": "CC=1C2=C(SC1S(=O)(=O)NC1=C(C=C(C(=O)OC)C=C1)S(=O)(=O)C)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Into a mixed solvent of 30 mL of methanol and 30 mL of dioxane was dissolved 640 mg of 5% palladium/carbon, followed by 10 minutes of stirring under a hydrogen atmosphere. Under an argon atmosphere, 330 mg of Compound 1 was added, followed by 3 days of stirring under a hydrogen atmosphere at 5 atm. After confirmation o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | Other | [Pd].O1CCOCC1 | null | 0.166667 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(Cl)cc3c2C)c(S(C)(=O)=O)c1>[Pd].O1CCOCC1>COC(=O)c1ccc(NS(=O)(=O)c2sc3ccccc3c2C)c(S(C)(=O)=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9df67f8241b94f8eab40a4e21dcad1f1 | COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1>>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)co3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | CO.FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)OC)S(=O)(=O)C)C=C1.[OH-].[Na+]>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)O)S(=O)(=O)C)C=C1 | C[O:17][C:15]([c:14]1[n:13][c:12](-[c:11]2[cH:10][cH:9][c:8]([NH:7][S:4]([c:3]3[c:2]([CH3:1])[c:33]4[c:27]([s:26]3)[cH:28][cH:29][c:30]([F:31])[cH:32]4)(=[O:5])=[O:6])[c:21]([S:22]([CH3:23])(=[O:24])=[O:25])[cH:20]2)[o:19][cH:18]1)=[O:16]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3... | COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1 | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)co3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(Nc1ccc(-c2ncco2)cc1)c1cc2ccccc2s1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#8;a:7]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#8;a:7] | 75.7 | [{"value": 75.7, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)O)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Into 150 mL of methanol was dissolved 7.85 g of Compound 23, and 15 mL of 10% aqueous sodium hydroxide solution and 15 mL of water were added thereto at room temperature, followed by 15 minutes of stirring. The precipitated crystals were dissolved by adding 90 mL of water, and the solution was stirred at the same tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cocn1.c1ccc2sccc2c1 | Other | O | null | 0.25 | COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1>O>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)co3)cc2S(C)(=O)=O)sc2ccc(F)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89c4ff77a58446e3918a1698969d9ac0 | CO.COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1.C[O-]>>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.[Na+] | CO.FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)OC)S(=O)(=O)C)C=C1.C[O-].[Na+]>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)[O-])S(=O)(=O)C)C=C1.[Na+].[Na+].FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)[O-])S(=O)(=O)C)C=C1 | [CH3:36][OH:50].[CH3:1][c:2]1[c:3]([S:4](=[O:5])([NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3[n:13][c:14]([C:15](=[O:16])[O:17][CH3:34])[cH:18][o:19]3)[cH:20][c:21]2[S:22]([CH3:23])(=[O:24])=[O:25])=[O:58])[s:26][c:27]2[cH:28][cH:29][c:30]([F:31])[cH:32][c:33]12.[O-:52][CH3:65]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:... | CO.COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1.C[O-] | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.[Na+] | null | null | CCOCC | Aromatic Heterocycle Formation | OtherReaction | 26022037f8d7c84b958e14966f0bcd76e966ebf215529d8ad30dc9f8d5064d07 | cd1d61d325f3072edfb3fd370ba9e4b1a70ae92ebeaf5ee47d1c354d420de8de | O=S(=O)(Nc1ccc(-c2ncco2)cc1)c1cc2ccccc2s1.O=S(=O)(Nc1ccc(-c2ncco2)cc1)c1cc2ccccc2s1 | [#7;a:1]:[c:2](-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:6]):[c:7]:[#8;a:8].[O;D1;H0:9]=[S;H0;D4;+0:10](=[O;H0;D1;+0:11])(-[#7:12]-[c:13])-[c:14](:[c:15]):[#16;a:16]:[c:17].[CH3;D1;+0:18]-[O-;H0;D1:19].[CH3;D1;+0:20]-[OH;D1;+0:21]>>[#7;a:1]:[c:2](-[C:3](-[O-;H0;D1:5])=[O;D1;H0:4]):[c:7]:[#8;a:8].[O;D1;H0:9]=[S;H0;... | 101.9 | [{"value": 101.9, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)[O-])S(=O)(=O)C)C=C1.[Na+].[Na+].FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2OC=C(N2)C(=O)[O-])S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into 30 mL of methanol was dissolved 290 mg of Compound 23, followed by addition of 77 mg of sodium methoxide. After 8 hours of stirring at room temperature, ether was added and the precipitated crystals were collected by filtration and washed with ether to obtain 300 mg of the title compound as colorless powder.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ester.Methanol | Sulfonamide.Sulfonamide.Aromatic halide.Sulfone | null | c1ccccc1.c1cocn1.c1ccc2sccc2c1 | c1ccccc1.c1cocn1.c1ccc2sccc2c1.c1ccccc1.c1cocn1.c1ccc2sccc2c1 | null | CCOCC | null | 8 | CO.COC(=O)c1coc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1.C[O-]>CCOCC>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)[O-])co3)cc2S(C)(=O)=O)sc2ccc(F)cc12.[Na+] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-506f97002f0944aab9bd2fc61fbd9358 | COc1sc(-c2ccc(N)c(S(C)(=O)=O)c2)nc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12>>COc1sc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)nc1C | Cl.ClS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C.[H-].[Na+].CS(=O)(=O)C1=C(N)C=CC(=C1)C=1SC(=C(N1)C)OC>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC(=C(N2)C)OC)S(=O)(=O)C)C=C1 | [CH3:1][O:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:25]([S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2)[n:31][c:32]1[CH3:33].Cl[S:11](=[O:12])(=[O:13])[c:14]1[s:15][c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]2[c:23]1[CH3:24]>>[CH3:1][O:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][S:11](=[O:12])(=[O:... | COc1sc(-c2ccc(N)c(S(C)(=O)=O)c2)nc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12 | COc1sc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)nc1C | null | null | CC(=O)N(C)C.C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccc(-c2nccs2)cc1)c1cc2ccccc2s1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:4](:[c:5]):[#16;a:6]:[c:7] | 70.5 | [{"value": 70.5, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC(=C(N2)C)OC)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -25 | CELSIUS | 10 | MINUTE | Under an argon atmosphere, 41 mg of 2-methanesulfonyl-4-(5-methoxy-4-methylthiazol-2-yl)aniline was dissolved into a mixed solution of 3 mL of THF and 3 mL of dimethylacetamide. The solution was cooled to −25° C. and 15 mg of sodium hydride (oily, 60%) was added thereto, followed by 10 minutes of stirring at the same t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cscn1.c1ccccc1.c1ccc2sccc2c1 | HCl | CC(=O)N(C)C.C1CCOC1 | -25 | 0.166667 | COc1sc(-c2ccc(N)c(S(C)(=O)=O)c2)nc1C.Cc1c(S(=O)(=O)Cl)sc2ccc(F)cc12>CC(=O)N(C)C.C1CCOC1>COc1sc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)nc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9673436fbafd4e999edf685887af37da | CC(=O)CNC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>Cc1cnc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)s1 | FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)NCC(C)=O)C=C2)S(=O)(=O)C)C=C1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC(=CN2)C)S(=O)(=O)C)C=C1 | O=[C:2]([CH3:1])[CH2:3][NH:4][C:5](=O)[c:6]1[cH:7][cH:8][c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]2[s:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]3[c:23]2[CH3:24])[c:25]([S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]1.S=P12SP3(=S)SP(=S)(S1)[S:31]P(=S)(S2)S3>>[CH3:1][c:2]1[cH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH:... | CC(=O)CNC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | Cc1cnc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)s1 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | a308741a740680bec166bc8e57be6165194b01af60efe4a9b838a9dd9812f89a | fc147a74b43bd8ea0c955e2e68acca90d32ef33bb23f18686fa46c093607a24f | O=S(=O)(Nc1ccc(-c2nccs2)cc1)c1cc2ccccc2s1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].S=P12-S-P3(=S)-S-P(=S)(-S-1)-[S;H0;D2;+0:11]-P(=S)(-S-2)-S-3>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[s;H0;D2;+0:11]:1 | 77 | [{"value": 77.0, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC(=CN2)C)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | Into 5 mL of 1,4-dioxane solution of 150 mg of 4-(5-fluoro-3-methylbenzo[b]thiophene-2-yl)sulfonamido-3-methanesulfonyl-N-(2-oxopropyl)benzamide was added 135 mg of diphosphorus pentasulfide, followed by 4.5 hours of heating under refluxing. The reaction was terminated by adding water to the reaction mixture and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide.Monosulfide | null | S1P2SP3SP1SP(S2)S3 | c1cscn1 | c1cscn1.c1ccccc1.c1ccc2sccc2c1 | Other | O1CCOCC1 | null | 4.5 | CC(=O)CNC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>O1CCOCC1>Cc1cnc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d1b90adae4349a2acadac9aa9c5d382 | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CO)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12.O=S(Cl)Cl>>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | S(=O)(Cl)Cl.C(Cl)(Cl)Cl.FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)CO)S(=O)(=O)C)C=C1.S(=O)(Cl)Cl>>ClCC=1N=C(SC1)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C | O[CH2:15][c:14]1[n:13][c:12](-[c:11]2[cH:10][cH:9][c:8]([NH:7][S:4]([c:3]3[c:2]([CH3:1])[c:32]4[c:26]([s:25]3)[cH:27][cH:28][c:29]([F:30])[cH:31]4)(=[O:5])=[O:6])[c:20]([S:21]([CH3:22])(=[O:23])=[O:24])[cH:19]2)[s:18][cH:17]1.O=S(Cl)[Cl:16]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12... | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CO)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12.O=S(Cl)Cl | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | null | C(C)N(CC)CC | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=S(=O)(Nc1ccc(-c2nccs2)cc1)c1cc2ccccc2s1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#16;a:6]:[c:7]:1 | null | [] | null | null | 21 | HOUR | Into 20 mL of chloroform was suspended 159 mg of Compound 63, and 47 μL of thionyl chloride was added at 0° C., followed by 21 hours of stirring at room temperature. Further, 1 mL of thionyl chloride was added, followed by 1 hour of heating under refluxing. After 2 mL of triethylamine was added at 0° C. and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1.c1cscn1.c1ccc2sccc2c1 | HCl | C(C)N(CC)CC | null | 21 | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CO)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12.O=S(Cl)Cl>C(C)N(CC)CC>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41efe53e0c8b4b2eb8ad50e1253946aa | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12>>Cc1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1 | ClCC=1N=C(SC1)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C.[I-].[Na+].[I-].[Na+]>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)C)S(=O)(=O)C)C=C1 | Cl[CH2:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]3[s:15][c:16]4[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]4[c:23]3[CH3:24])[c:25]([S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2)[n:31]1>>[CH3:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH:10][S:11](=[O:12])(=[O:13])[c:14]3[s:... | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | Cc1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1 | null | null | CC(=O)C | Functional Group Interconversion | Dehalogenation | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=S(=O)(Nc1ccc(-c2nccs2)cc1)c1cc2ccccc2s1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1>>[CH3;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1 | 48.5 | [{"value": 48.5, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)C)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Into 10 mL of acetone was dissolved 64 mg of Compound 64, and 180 mg of sodium iodide was added, followed by 24 hours of heating under refluxing. Further, 180 mg of sodium iodide was added and the mixture was heated under refluxing for 19 hours. The solvent was removed by evaporation under reduced pressure and the resi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1cscn1.c1ccccc1.c1ccc2sccc2c1 | Other | CC(=O)C | null | 24 | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(CCl)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12>CC(=O)C>Cc1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f731784ee373406e9c581e111ac0c2f4 | COC(=O)c1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1>>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)C(=O)OC)S(=O)(=O)C)C=C1.[OH-].[Na+]>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)C(=O)O)S(=O)(=O)C)C=C1 | C[O:17][C:15]([c:14]1[n:13][c:12](-[c:11]2[cH:10][cH:9][c:8]([NH:7][S:4]([c:3]3[c:2]([CH3:1])[c:33]4[c:27]([s:26]3)[cH:28][cH:29][c:30]([F:31])[cH:32]4)(=[O:5])=[O:6])[c:21]([S:22]([CH3:23])(=[O:24])=[O:25])[cH:20]2)[s:19][cH:18]1)=[O:16]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11](-[c:12]3... | COC(=O)c1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1 | Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=S(=O)(Nc1ccc(-c2nccs2)cc1)c1cc2ccccc2s1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#16;a:7]>>[#16;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | 80.3 | [{"value": 80.3, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2SC=C(N2)C(=O)O)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Into 45 mL of methanol was dissolved 954 mg of Compound 69, and 4.0 mL of 1 mol/L sodium hydroxide was added thereto. After 20 minutes of stirring under heating and refluxing, the solvent was removed by evaporation under reduced pressure, and the resulting residue was extracted with ether-water (1/1). To the aqueous la... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cscn1.c1ccc2sccc2c1 | Other | CO | null | 0.333333 | COC(=O)c1csc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)n1>CO>Cc1c(S(=O)(=O)Nc2ccc(-c3nc(C(=O)O)cs3)cc2S(C)(=O)=O)sc2ccc(F)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e4aa71acf48406f8e6045f64380a89b | CC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.[Br-]>>Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12 | C(C)(=O)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C.[Br-].[Br-].[Br-].C(C1=CC=CC=C1)[N+](C)(C)C.C(C1=CC=CC=C1)[N+](C)(C)C.C(C1=CC=CC=C1)[N+](C)(C)C>>BrCC(=O)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C | [CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[CH3:14])[cH:16][c:17]2[S:18]([CH3:19])(=[O:20])=[O:21])[s:22][c:23]2[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]12.[Br-:15]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[CH2:14][Br:15])[cH:16]... | CC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.[Br-] | Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | [Br-;H0;D0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 137.5 | [{"value": 137.5, "product": "BrCC(=O)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Into 4.0 mL of chloroform was dissolved 200 mg of Compound 19, and 194 mg of benzyltrimethylammonium tribromide was added, followed by 1 hour of stirring at room temperature. The reaction was terminated by adding water to the reaction solution and then the solvent was once removed by evaporation. The residue was adjust... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1.c1ccc2sccc2c1 | null | C(Cl)(Cl)Cl | null | 1 | CC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1.[Br-]>C(Cl)(Cl)Cl>Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b7c1db2cb9ec4c41b044969a894ab304 | CC(N)=S.Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12>>Cc1nc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)cs1 | BrCC(=O)C1=CC(=C(C=C1)NS(=O)(=O)C1=C(C2=C(S1)C=CC(=C2)F)C)S(=O)(=O)C.O1CCOCC1.C(O)([O-])=O.[Na+].C(C)(=S)N>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2N=C(SC2)C)S(=O)(=O)C)C=C1 | [CH3:1][C:2]([NH2:3])=[S:31].O=[C:4]([c:5]1[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]2[s:14][c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]3[c:22]2[CH3:23])[c:24]([S:25]([CH3:26])(=[O:27])=[O:28])[cH:29]1)[CH2:30]Br>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([NH:9][S:10](=[O:11])(=[O:12])[c:13]3[s:1... | CC(N)=S.Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12 | Cc1nc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)cs1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | O=S(=O)(Nc1ccc(-c2cscn2)cc1)c1cc2ccccc2s1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C;D1;H3:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[s;H0;D2;+0:11]:1 | 42.6 | [{"value": 42.6, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)C=2N=C(SC2)C)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Into 4.0 mL of chloroform was dissolved 200 mg of Compound 19, and 194 mg of benzyltrimethylammonium tribromide was added, followed by 1 hour of stirring at room temperature. The reaction was terminated by adding water to the reaction solution and then the solvent was once removed by evaporation. The residue was adjust... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1.c1ccccc1.c1ccc2sccc2c1 | HBr | C(C)O | null | 2 | CC(N)=S.Cc1c(S(=O)(=O)Nc2ccc(C(=O)CBr)cc2S(C)(=O)=O)sc2ccc(F)cc12>C(C)O>Cc1nc(-c2ccc(NS(=O)(=O)c3sc4ccc(F)cc4c3C)c(S(C)(=O)=O)c2)cs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff5388fdf5e343ff9a10e18ce76848f7 | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1>>Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(F)cc12 | C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[K+].C1(=CC=CC=C1)C.FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C(=O)OC)C=C2)S(=O)(=O)C)C=C1.C1(=CC=CC=C1)C.[H-].C(C(C)C)[Al+]CC(C)C>>FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)CO)S(=O)(=O)C)C=C1 | CO[C:12]([c:11]1[cH:10][cH:9][c:8]([NH:7][S:4]([c:3]2[c:2]([CH3:1])[c:27]3[c:21]([s:20]2)[cH:22][cH:23][c:24]([F:25])[cH:26]3)(=[O:5])=[O:6])[c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:14]1)=[O:13]>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[NH:7][c:8]2[cH:9][cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]2[S:16]([CH3:17])(=[... | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1 | Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(F)cc12 | null | null | O.C(C)(=O)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=S(=O)(Nc1ccccc1)c1cc2ccccc2s1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 70.7 | [{"value": 70.7, "product": "FC1=CC2=C(SC(=C2C)S(=O)(=O)NC2=C(C=C(C=C2)CO)S(=O)(=O)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | null | null | Into 120 mL of toluene was dissolved 2.08 g of Compound 17. After cooling to −30° C., 22.5 mL of 1.01 mol/L toluene solution of diisobutylaluminum hydride was added thereto. After 5 hours of stirring at the same temperature, water was added to the reaction solution to terminate the reaction and then the mixture was dil... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2sccc2c1 | Other | O.C(C)(=O)OCC | -30 | null | COC(=O)c1ccc(NS(=O)(=O)c2sc3ccc(F)cc3c2C)c(S(C)(=O)=O)c1>O.C(C)(=O)OCC>Cc1c(S(=O)(=O)Nc2ccc(CO)cc2S(C)(=O)=O)sc2ccc(F)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-556fc30c333c40f3bdcee69717499612 | CCOC(C(=O)OC)P(=O)(OCC)OCC.O=Cc1ccc(OCCCl)cc1>>CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC | [H-].[Na+].C(C)OC(C(=O)OC)P(=O)(OCC)OCC.ClCCOC1=CC=C(C=O)C=C1>>ClCCOC1=CC=C(C=C1)C=C(C(=O)OC)OCC | CCOP(=O)(OCC)[CH:4]([O:3][CH2:2][CH3:1])[C:16](=[O:17])[O:18][CH3:19].O=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH3:19] | CCOC(C(=O)OC)P(=O)(OCC)OCC.O=Cc1ccc(OCCCl)cc1 | CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 8652fada27b05b79779ff34a157bb972c7cd6d780fd24e805781fdaca3689897 | ad62a0adadbf9069bf98289a96ce8b021437ecd0412624495fbcba2ade6d16f3 | c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH;D3;+0:1](-[#8:2]-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[#8:2]-[C;H0;D3;+0:1](=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | 1 | HOUR | To 150 ml of freshly distilled tetrahydrofuran, placed in a bath of ice-cold water at 0° C., under argon, add sodium hydride (0.0473 mol) and then methyl 2-ethoxy-2-diethylphosphonoacetate (0.0394 mol) while maintaining the temperature at 0° C. After stirring for 1 hour, add 4-(2-chloroethoxy)benzaldehyde (0.0394 mol) ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ether | Ester.Ether | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 1 | CCOC(C(=O)OC)P(=O)(OCC)OCC.O=Cc1ccc(OCCCl)cc1>O1CCCC1>CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b19f6cc62aa46e2873a435775cda091 | CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC>>CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC | ClCCOC1=CC=C(C=C1)C=C(C(=O)OC)OCC>>ClCCOC1=CC=C(C=C1)CC(C(=O)OC)OCC | [CH3:1][CH2:2][O:3][C:4](=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH3:19]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH3:19] | CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC | null | [Pd] | O1CCCC1 | Reduction | Hydrogenation (double to single) | d0e0332973c77aabb8c3717dddd351d2250737d1acb0f694289dece8c206d06e | fc479563bf5f932f09579579b5e31753bf159d03a224d56dc67a29b9e37b0ad6 | c1ccccc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:1]-[#8:2]-[CH;D3;+0:3](-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 1 | DAY | To 100 ml of tetrahydrofuran add the compound obtained in Step A (0.0175 mol) and then palladium-on-carbon (0.2 g). Stir at ambient temperature under hydrogen for 1 day. Filter off the palladium-on-carbon and then evaporate the filtrate. The oily product is purified on a column of silica gel using the eluant mixture: p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Ether | null | null | c1ccccc1 | null | [Pd].O1CCCC1 | null | 24 | CCOC(=Cc1ccc(OCCCl)cc1)C(=O)OC>[Pd].O1CCCC1>CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-18b711fee87f4c259f9e62bbac53b196 | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N=CS2=O)C=C1.C([O-])([O-])=O.[K+].[K+].ClCCOC1=CC=C(C=C1)CC(C(=O)OC)OCC>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1 | Cl[CH2:12][CH2:11][O:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:33](=[O:34])[O:35][CH3:36])[cH:32][cH:31]1.[N:13]1=[CH:14][S:16](=[O:15])[c:17]2[cH:18][c:19]([C:20](=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][c:30]21>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([... | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2 | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 42c83f048334b1ed148ed7afdbd743f45dba21a36b3061112c38545e7e60436d | 3dcb031a7507da808ae5e1b8f13ca2c4f0152648164857a941ec9d83076e2a56 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;H0;D1;+0:4]=[S;H0;D3;+0:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[s;H0;D2;+0:5]:[c;H0;D3;+0:6]:1=[O;H0;D1;+0:4] | null | [] | 100 | CELSIUS | null | null | To 20 ml of dimethylformamide add potassium carbonate (0.01044 mol) and then 6-benzoylbenzothiazolinone (0.00453 mol). Heat at 100° C. for 1 hour. Add the compound obtained in Step B (0.00348 mol) and heat at 150° C. for 16 hours. Evaporate off the dimethylformamide. Take up the residue in 50 ml of water and then extra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C=O)C | 100 | null | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>CN(C=O)C>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e9e46de2e79a488992aeb4f0734723aa | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1.Cl.CON.N1=CC=CC=C1>>C(C)OC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | O=[C:20]([c:19]1[cH:18][c:17]2[s:16][c:14](=[O:15])[n:13]([CH2:12][CH2:11][O:10][c:9]3[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:35](=[O:36])[O:37][CH3:38])[cH:34][cH:33]3)[c:32]2[cH:31][cH:30]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.[NH2:21][O:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6]1[cH:7]... | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | To 30 ml of methanol add the compound obtained in Step C (0.00198 mol), O-methyl-hydroxylamine hydrochloride (0.00594 mol) and pyridine (0.00594 mol). Heat at reflux for 3 hours. Evaporate to dryness. Add 100 ml of hydrochloric acid (1N) and then extract with 50 ml of dichloromethane twice. The organic phase is dried o... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | CO | null | null | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON>CO>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8813f2ad16624e089fe1a0bc73d73751 | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N=CS2=O)C=C1.C([O-])([O-])=O.[K+].[K+].ClCCOC1=CC=C(C=C1)CC(C(=O)OC)OCC>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1 | Cl[CH2:12][CH2:11][O:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:33](=[O:34])[O:35][CH3:36])[cH:32][cH:31]1.[N:13]1=[CH:14][S:16](=[O:15])[c:17]2[cH:18][c:19]([C:20](=[O:21])[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][c:30]21>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6]1[cH:7][cH:8][c:9]([... | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2 | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 42c83f048334b1ed148ed7afdbd743f45dba21a36b3061112c38545e7e60436d | 3dcb031a7507da808ae5e1b8f13ca2c4f0152648164857a941ec9d83076e2a56 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;H0;D1;+0:4]=[S;H0;D3;+0:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[s;H0;D2;+0:5]:[c;H0;D3;+0:6]:1=[O;H0;D1;+0:4] | null | [] | 100 | CELSIUS | null | null | To 20 ml of dimethylformamide add potassium carbonate (0.01044 mol) and then 6-benzoylbenzothiazolinone (0.00453 mol). Heat at 100° C. for 1 hour. Add the compound obtained in Step B of Example 1 (0.00348 mol) and heat at 150° C. for 16 hours. Evaporate off the dimethylformamide. Take up the residue in 50 ml of water a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C=O)C | 100 | null | CCOC(Cc1ccc(OCCCl)cc1)C(=O)OC.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>CN(C=O)C>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8787f5a444a64b81aa74c1046a7e90d1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC(C)(C)C)C=C1.CON>>C(C)(C)(C)OC(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[C:38](=[O:39])[O:40][CH3:41])[cH:42][cH:43]1.[CH3:1][O:2][NH2:3]>>[CH3:... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step C, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9097aceecf54623a7ba7ac7d11124e7 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C>>COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC(C)(C)C)C=C1.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O | CC(C)(C)OC(=O)[NH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][n:15]2[c:16](=[O:17])[s:18][c:19]3[cH:20][c:21]([C:22](=[O:23])[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31][c:32]23)[cH:33][cH:34]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH2:6])[CH2:7][c:8]1[cH:9][cH:1... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | 4 | HOUR | 4 g of the compound obtained in Step C of Example 10 are dissolved in 200 ml of dichloromethane and the temperature is lowered to 0° C. 12.47 ml of trifluoroacetic acid are then added and the reaction mixture is stirred at ambient temperature for 4 hours.
Conditions: See reaction.notes.procedure_details.
Workup: is low... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | ClCCl | null | 4 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C>ClCCl>COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d27a926032c4fd3b521a094bbec068f | CCCCOC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>>CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.ClC(=O)OCCCC>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OCCCC)C=C1 | Cl[C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7].[NH2:8][CH:9]([CH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][CH2:17][n:18]2[c:19](=[O:20])[s:21][c:22]3[cH:23][c:24]([C:25](=[O:26])[c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[cH:33][cH:34][c:35]23)[cH:36][cH:37]1)[C:38](=[O:39])[O:40][CH3:41]>>[CH3:1][CH2:2][CH2:3]... | CCCCOC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | C(C)(=O)OCC | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | 700 mg of the compound obtained in Step A are dissolved in 10 ml of ethyl acetate; 0.494 ml of triethylamine is then added and the temperature is lowered to 0° C. 0.229 ml of butyl chloroformate is added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | CCCCOC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>C(C)(=O)OCC>CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72dcbc5d7d0641808f1523b51fa60c26 | CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON>>CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OCCCC)C=C1.CON>>C(CCC)OC(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | O=[C:25]([c:24]1[cH:23][c:22]2[s:21][c:19](=[O:20])[n:18]([CH2:17][CH2:16][O:15][c:14]3[cH:13][cH:12][c:11]([CH2:10][CH:9]([NH:8][C:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[C:40](=[O:41])[O:42][CH3:43])[cH:39][cH:38]3)[c:37]2[cH:36][cH:35]1)[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[NH2:26][O:27][CH3:28]>>[CH3:1]... | CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON | CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step B, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.CON>>CCCCOC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13992fe0befe48999b1f2b27de427aba | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Oc1ccccc1>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1 | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.ClC(=O)OC1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC2=CC=CC=C2)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH2:34].Cl[C:35](=[O:36])[O:37][c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1>>[CH3:1][O:... | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Oc1ccccc1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1 | null | null | C(C)(=O)OCC | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCCc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | 1.5 g of the compound obtained in Step A of Example 12 are dissolved in 20 ml of ethyl acetate; 1.06 ml of triethylamine are then added and the temperature is lowered to 0° C. 0.637 ml of phenyl chloroformate is then added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Oc1ccccc1>C(C)(=O)OCC>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c72ed27bd59f40559ae816b565ea20b1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Oc2ccccc2)C(=O)OC)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC2=CC=CC=C2)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC2=CC=CC=C2)C=C1)C1=CC=CC=C1 | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([NH:30][C:31](=[O:32])[O:33][c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[C:40](=[O:41])[O:42][CH3:43])[cH:44][cH:45]1.[CH3:1][O:2][NH2:... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Oc2ccccc2)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CCNC(=O)Oc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Oc1ccccc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Oc2ccccc2)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-36a2284b3914451da4caa41aaa3484ca | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)OCc1ccccc1>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OCc1ccccc1 | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.ClC(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OCC2=CC=CC=C2)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH2:34].Cl[C:35](=[O:36])[O:37][CH2:38][c:39]1[cH:40][cH:41][cH:42][cH:43][cH:44]1>>[C... | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)OCc1ccccc1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OCc1ccccc1 | null | null | C(C)(=O)OCC | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(NCCc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | 1.5 g of the compound obtained in Step A of Example 12 are dissolved in 20 ml of ethyl acetate; 1.06 ml of triethylamine are then added and the temperature is lowered to 0° C. 0.725 ml of benzyl chloroformate are added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)OCc1ccccc1>C(C)(=O)OCC>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d82f864ac1fb47c593bfbc678401124d | CC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O | Cl[C:35]([CH3:36])=[O:37].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH2:34]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8]... | CC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]>>[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10] | null | [] | null | null | 8 | HOUR | 500 mg of the compound obtained in Step A of Example 12 are dissolved in 10 ml of ethyl acetate; 0.353 ml of triethylamine is then added and the temperature is lowered to 0° C. 0.121 ml of acetyl chloride is added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | CC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>C(C)(=O)OCC>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc6f7c8c4ba2404bbed671328fca3321 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(C)=O)C(=O)OC)cc1 | C(C)(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.CON>>C(C)(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([NH:30][C:31]([CH3:32])=[O:33])[C:34](=[O:35])[O:36][CH3:37])[cH:38][cH:39]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3]=[C:4]([c:5]1[cH:6][... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(C)=O)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(C)=O.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(C)=O)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5d99a487dd824cc1886a6c201ec4a455 | CCCC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>>CCCC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.C(CCC)(=O)Cl>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(CCC)=O)C=C1 | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH:7]([CH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][n:16]2[c:17](=[O:18])[s:19][c:20]3[cH:21][c:22]([C:23](=[O:24])[c:25]4[cH:26][cH:27][cH:28][cH:29][cH:30]4)[cH:31][cH:32][c:33]23)[cH:34][cH:35]1)[C:36](=[O:37])[O:38][CH3:39]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[... | CCCC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | CCCC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](-[C:5])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | 500 mg of the compound obtained in Step A of Example 12 are dissolved in 10 ml of ethyl acetate; 0.353 ml of triethylamine is then added and the temperature is lowered to 0° C. 0.177 ml of butyryl chloride is added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | CCCC(=O)Cl.COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1>C(C)(=O)OCC>CCCC(=O)NC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8c38dab124e4d2190af98e5b41f45d6 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)c1ccccc1>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)c1ccccc1 | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH2:34].Cl[C:35](=[O:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1>>[CH3:1][O:2][C:3... | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)c1ccccc1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)c1ccccc1 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | 8 | HOUR | 500 mg of the compound obtained in Step A of Example 12 are dissolved in 10 ml of ethyl acetate; 0.353 ml of triethylamine is then added and the temperature is lowered to 0° C. 0.197 ml of benzoyl chloride is added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)c1ccccc1>C(C)(=O)OCC>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ffab1b33acd54a0e919e87ad681cd354 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Cc1ccccc1>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1 | FC(C(=O)O)(F)F.NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=O)=O.C(C)N(CC)CC.C1(=CC=CC=C1)CC(=O)Cl>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(CC2=CC=CC=C2)=O)C=C1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH2:34].Cl[C:35](=[O:36])[CH2:37][c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1>>[CH3:1][... | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Cc1ccccc1 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1 | null | null | C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)NCCc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4])-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11] | null | [] | null | null | 8 | HOUR | 500 mg of the compound obtained in Step A of Example 12 are dissolved in 10 ml of ethyl acetate; 0.353 ml of triethylamine is then added and the temperature is lowered to 0° C. 0.226 ml of phenylacetyl chloride is added and the mixture is allowed to return to ambient temperature and is stirred overnight.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 8 | COC(=O)C(N)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.O=C(Cl)Cc1ccccc1>C(C)(=O)OCC>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5bb22604b46646c795135d0fe0712371 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Cc2ccccc2)C(=O)OC)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(CC2=CC=CC=C2)=O)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(CC2=CC=CC=C2)=O)C=C1)C1=CC=CC=C1 | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([NH:30][C:31](=[O:32])[CH2:33][c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[C:40](=[O:41])[O:42][CH3:43])[cH:44][cH:45]1.[CH3:1][O:2][NH... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Cc2ccccc2)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CCNC(=O)Cc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)Cc1ccccc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)Cc2ccccc2)C(=O)OC)cc1 |
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