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-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb25c0044288436ca48716586983b5a5 | Nc1ccc(-c2cc(=S)ss2)cc1.O=C(O)c1ccccc1O>>O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O | C(C=1C(O)=CC=CC1)(=O)O.[OH-].[K+].C([O-])([O-])=O.[Na+].[Na+].NC1=CC=C(C=C1)C1=CC(SS1)=S.[OH-].[K+].C(C=1C(O)=CC=CC1)(=O)O.N(=O)[O-].[Na+]>>OC1=C(C(=O)O)C=C(C=C1)N=NC1=CC=C(C=C1)C=1SSC(C1)=S | [NH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15](=[S:16])[s:17][s:18]2)[cH:19][cH:20]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:21][cH:22][c:23]1[OH:24]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([N:7]=[N:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][c:15](=[S:16])[s:17][s:18]3)[cH:19][cH:20]2)[cH:21][cH:22][c:23]1[OH... | Nc1ccc(-c2cc(=S)ss2)cc1.O=C(O)c1ccccc1O | O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O | null | null | Cl.O | Functional Group Addition | OtherReaction | 4dfa1e0075917e3f76a2c771d85af2eb7328e8c1dacc2fef053ab9d7871727bb | 369e32a405523c63be3b198dc14b1fa8567bb17806d598f8dc85ecca177f9307 | S=c1cc(-c2ccc(N=Nc3ccccc3)cc2)ss1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:5]=[C:6](-[O;D1;H1:7])-[c:8]:[c:9]:[c;H0;D3;+0:10](-[#7:13]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11]:[c:12] | 85 | [{"value": 85.0, "product": "OC1=C(C(=O)O)C=C(C=C1)N=NC1=CC=C(C=C1)C=1SSC(C1)=S", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 5-(4-Amino-phenyl)-[1,2]dithiole-3-thione (3, 0.56 mmol) was dissolved in a mixture of 5 mL of concentrated HCl and 2.5 mL of water and diazotized with a solution of sodium nitrite (0.56 mmol). In the meantime salicylic acid (0.56 mmol), potassium hydroxide (1.12 mmol) and sodium carbonate are dissolved in water. The d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccss1 | Other | Cl.O | 50 | null | Nc1ccc(-c2cc(=S)ss2)cc1.O=C(O)c1ccccc1O>Cl.O>O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abfbf49e1c654e2ab6e68346eddbb4a2 | Nc1ccc(C(=O)O)c(O)c1.S=c1cc(-c2ccccc2)ss1>>O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O | NC1=CC(=C(C(=O)O)C=C1)O.C1(=CC=CC=C1)C1=CC(SS1)=S.CN(C=O)C.N(=O)[O-].[Na+]>>OC1=C(C(=O)O)C=C(C=C1)N=NC1=CC=C(C=C1)C=1SSC(C1)=S | [O:1]=[C:2]([OH:3])[c:4]1[cH:22][cH:21][c:6]([NH2:7])[cH:5][c:23]1[OH:24].[cH:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][c:15](=[S:16])[s:17][s:18]2)[cH:19][cH:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([N:7]=[N:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][c:15](=[S:16])[s:17][s:18]3)[cH:19][cH:20]2)[cH:21][cH:22][c:23]1[... | Nc1ccc(C(=O)O)c(O)c1.S=c1cc(-c2ccccc2)ss1 | O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O | null | null | Cl.O | Functional Group Addition | OtherReaction | e7ead6de41e9f51b1a48facdbf3982a7c26bbfff6dfd25854111885b035e4954 | 4d68627ef5356ad3bd626f290e6fbe884afdaa64f5fd45b0d12d5932350b0cef | S=c1cc(-c2ccc(N=Nc3ccccc3)cc2)ss1 | [NH2;D1;+0:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c;H0;D3;+0:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1.[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]>>[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[c;H0;D3;+0:5]1:[cH;D2;+0:11]:[c:2](-[N;H0;D2;+0:1]=[#7:17]-[c;H0;D3;+0:14](:[c:13]:[c:12]):[c:15]:[c:16]):[c:... | 65 | [{"value": 65.0, "product": "OC1=C(C(=O)O)C=C(C=C1)N=NC1=CC=C(C=C1)C=1SSC(C1)=S", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 4-Amino-2-hydroxy-benzoic acid (1, 1 mmol) was dissolved in a mixture of 10 mL of concentrated HCl and 5 mL of water and diazotized with a solution of sodium nitrite (1 mmol). The diazo suspension is added in portions to a solution of 5-phenyl-[1,2]dithiole-3-thione (1 mmol) in dimethylformamide. After 2 days the react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Diazene.Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccss1 | Other | Cl.O | 50 | null | Nc1ccc(C(=O)O)c(O)c1.S=c1cc(-c2ccccc2)ss1>Cl.O>O=C(O)c1cc(N=Nc2ccc(-c3cc(=S)ss3)cc2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91f794e2c45f4da0aa5f8a5161f797bb | CC(C)(C)OC(=O)Nc1ccc(OC(C)(C)C)c(C(=O)O)c1.NC(=S)c1ccc(O)cc1>>NC(=S)c1ccc(OC(=O)c2cc(N)ccc2O)cc1 | C(C)(C)(C)OC(=O)NC=1C=CC(=C(C(=O)O)C1)OC(C)(C)C.OC1=CC=CC=2NN=NC21.C1CCC(CC1)N=C=NC2CCCCC2.OC1=CC=C(C(=S)N)C=C1>>C(N)(=S)C1=CC=C(C=C1)OC(C1=C(C=CC(=C1)N)O)=O | CC(C)(C)OC(=O)[NH:14][c:13]1[cH:12][c:11]([C:9](O)=[O:10])[c:17]([O:18]C(C)(C)C)[cH:16][cH:15]1.[NH2:1][C:2](=[S:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:19][cH:20]1>>[NH2:1][C:2](=[S:3])[c:4]1[cH:5][cH:6][c:7]([O:8][C:9](=[O:10])[c:11]2[cH:12][c:13]([NH2:14])[cH:15][cH:16][c:17]2[OH:18])[cH:19][cH:20]1 | CC(C)(C)OC(=O)Nc1ccc(OC(C)(C)C)c(C(=O)O)c1.NC(=S)c1ccc(O)cc1 | NC(=S)c1ccc(OC(=O)c2cc(N)ccc2O)cc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | OtherReaction | f4589b4bc8c9727986ce3aceef4713c98172984db51d6e267147b7b7d0564cbe | 49f518314a1fcbb823dd2624ce8448d8812751c992b9b3e1cf3ca207031f38ed | O=C(Oc1ccccc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](-O)=[O;D1;H0:6]):[c:7](-[O;H0;D2;+0:8]-C(-C)(-C)-C):[c:9]:[c:10]:1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]):[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:1 | 48 | [{"value": 48.0, "product": "C(N)(=S)C1=CC=C(C=C1)OC(C1=C(C=CC(=C1)N)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To the solution of 4- or 5-tert-butoxycarbonylamino-2-hydroxy-benzoic acid (2) (3.0 mmol) in 50 mL of dimethylformamide, hydroxybenzotriazole (3.3 mmol) and DCC (3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture, 4-hydroxy-thiobenzamide (3.0 mmol) was added and stirred mechanically for 3 h at... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Aromatic alcohol.Boc | Ester.Aromatic alcohol.Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | 0 | 1 | CC(C)(C)OC(=O)Nc1ccc(OC(C)(C)C)c(C(=O)O)c1.NC(=S)c1ccc(O)cc1>CN(C=O)C.C(C)(=O)OCC>NC(=S)c1ccc(OC(=O)c2cc(N)ccc2O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a5283155c7343ffbe19bb6f560a263a | CC(=O)NC(CS)C(=O)O.CC(C)(C)OC(=O)c1cc(N)ccc1OC(C)(C)C>>CC(=O)NC(CS)C(=O)Nc1ccc(O)c(C(=O)O)c1 | C(C)(=O)NC(C(=O)O)CS.OC1=CC=CC=2NN=NC21.C1CCC(CC1)N=C=NC2CCCCC2.C(C)(C)(C)OC(C1=C(C=CC(=C1)N)OC(C)(C)C)=O>>C(C)(=O)NC(C(=O)NC=1C=CC(=C(C(=O)O)C1)O)CS | O[C:8]([CH:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][SH:7])=[O:9].CC(C)(C)[O:15][c:14]1[cH:13][cH:12][c:11]([NH2:10])[cH:20][c:16]1[C:17](=[O:18])[O:19]C(C)(C)C>>[CH3:1][C:2](=[O:3])[NH:4][CH:5]([CH2:6][SH:7])[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([OH:15])[c:16]([C:17](=[O:18])[OH:19])[cH:20]1 | CC(=O)NC(CS)C(=O)O.CC(C)(C)OC(=O)c1cc(N)ccc1OC(C)(C)C | CC(=O)NC(CS)C(=O)Nc1ccc(O)c(C(=O)O)c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Protection | OtherReaction | 2d6959908aa84683df5dc8de7ac887f3e55a72d4f9adcbadd631267543db97ce | 237afe4a9c2606229b5cc3555a7e43d412c3d6637ed55efe8606fa424e63619a | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C(-C)(-C)-C.O-[C;H0;D3;+0:12](=[O;D1;H0:13])-[C:14](-[C:15])-[#7:16]-[C:17](-[C;D1;H3:18])=[O;D1;H0:19]>>[C:15]-[C:14](-[#7:16]-[C:17](-[C;D1;H3:18])=[O;D1;H0:19])-[C;H0;D3;+0:12](=[O;D1;H0:13])-[NH;D2... | 78 | [{"value": 78.0, "product": "C(C)(=O)NC(C(=O)NC=1C=CC(=C(C(=O)O)C1)O)CS", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To the solution of 2-acetylamino-3-mercapto-propionic acid (3.0 mmol) in 50 mL of dimethylformamide, hydroxybenzotriazole (3.3 mmol) and DCC (3.3 mmol) were added with stirring at 0°C. for 1 h. To the reaction mixture, 4 or 5-amino-2-tert-butoxy-benzoic acid tert-butyl ester (3) (3.0 mmol) was added and stirred mechani... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Ether.Primary amine.Boc | Carboxylic acid.Secondary amide.Aromatic alcohol | null | null | c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | 0 | 1 | CC(=O)NC(CS)C(=O)O.CC(C)(C)OC(=O)c1cc(N)ccc1OC(C)(C)C>CN(C=O)C.C(C)(=O)OCC>CC(=O)NC(CS)C(=O)Nc1ccc(O)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01f836b342f54dd0904850f3d1fe6486 | CC(=O)c1ccc(O)cc1O.CC=C(C)CBr>>CC(=O)c1ccc(O)c(CCC(C)C)c1O | OC1=C(C=CC(=C1)O)C(C)=O.BrCC(=CC)C>>OC1=C(C=CC(=C1CCC(C)C)O)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][c:15]1[OH:16].Br[CH2:14][C:12](=[CH:11][CH3:10])[CH3:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[c:15]1[OH:16] | CC(=O)c1ccc(O)cc1O.CC=C(C)CBr | CC(=O)c1ccc(O)c(CCC(C)C)c1O | null | [Pd] | [OH-].[K+].CO.CO | C-C Coupling | OtherReaction | abd82b32c15853d5913cc8f5d51923ff8cee2c9e5cfc2628ece51b84576c3f2d | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[CH3;D1;+0:5].[C;D1;H3:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[O;D1;H1:11]):[cH;D2;+0:12]:[c:13](-[O;D1;H1:14]):[c:15]>>[C;D1;H3:3]-[CH;D3;+0:2](-[CH3;D1;+0:1])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c;H0;D3;+0:12](:[c:10](-[O;D1;H1:11]):[c:9]-[C:7](-[C;D1;H3:6])=[O;D1;H0:... | null | [] | null | null | null | null | 2′,4′-Dihydroxyacetophenone (manufactured by Wako Pure Chemical Industries, Ltd.) was treated with 1-bromo-2-methyl-2-butene (manufactured by Aldrich) in 2 M KOH/methanol solution under ice-cooling, and thereafter the treated solution was hydrogenated in methanol, in the presence of palladium black (manufactured by Nak... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [Pd].[OH-].[K+].CO.CO | null | null | CC(=O)c1ccc(O)cc1O.CC=C(C)CBr>[Pd].[OH-].[K+].CO.CO>CC(=O)c1ccc(O)c(CCC(C)C)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39fd2f48840549549438a935e50fa32c | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(F)cc1>>O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1 | FC=1C=C(C=C(C1F)F)[N+](=O)[O-].FC1=CC=C(C=C1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>>FC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1 | F[c:8]1[c:6]([F:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][c:17]1[F:18].[OH:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[c:17]([F:18])[cH:19]1 | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(F)cc1 | O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:5](-[F;D1;H0:6]):[c:7] | 105 | [{"value": 105.0, "product": "FC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3,4,5-trifluoronitrobenzene (20.0 g, 113 mmol, commercially available from AsymChem of Durham, N.C.), dry DMF (100 ml), 4-fluorophenol (13.9 g, 124 mmol), and Cs2CO3 (56 g, 172 mmol) was stirred under N2 at 60-70° C. for 1-2 hrs. After cooling to room temperature, the reaction mixture was partitioned betwe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C)C=O | null | null | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(F)cc1>CN(C)C=O>O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-166ff02425a24a15954489f12f0c1398 | O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1>>Nc1cc(F)c(Oc2ccc(F)cc2)c(F)c1 | FC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1>>FC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]([F:16])[cH:17]1>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]([F:16])[cH:17]1 | O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1 | Nc1cc(F)c(Oc2ccc(F)cc2)c(F)c1 | null | [Pd] | CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "FC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "FC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 4-(4-fluorophenoxy)-3,5-difluoronitrobenzene (30.4 g, 113 mmol), EtOAc (300 ml), 10% Pd/C (2.6 g) was stirred under an atmosphere of H2 at room temperature and pressure for approximately 6 hrs. The reaction mixture was filtered through Celite and concentrated in vacuo to give 4-(4-fluorophenoxy)-3,5-difluo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].CCOC(=O)C | null | 6 | O=[N+]([O-])c1cc(F)c(Oc2ccc(F)cc2)c(F)c1>[Pd].CCOC(=O)C>Nc1cc(F)c(Oc2ccc(F)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24921d02d2734e22a3feb6de0f0c5b92 | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(Cl)cc1>>O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 | FC=1C=C(C=C(C1F)F)[N+](=O)[O-].ClC1=CC=C(C=C1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>>ClC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1 | F[c:8]1[c:6]([F:7])[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][c:17]1[F:18].[OH:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([O:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[c:17]([F:18])[cH:19]1 | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(Cl)cc1 | O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:5](-[F;D1;H0:6]):[c:7] | 106.9 | [{"value": 106.0, "product": "ClC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.9, "product": "ClC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of 3,4,5-trifluoronitrobenzene (6.6 g, 37 mmol), dry DMF (30 ml), 4-chlorophenol (5.26 g, 41 mmol), and Cs2CO3 (18.8 g, 58 mmol) was stirred under N2 at 60-70 C for 1-2 hrs. After cooling to room temperature, the reaction mixture was partitioned between H2O and EtOAc. The phases were separated and the aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CN(C)C=O | null | 1.5 | O=[N+]([O-])c1cc(F)c(F)c(F)c1.Oc1ccc(Cl)cc1>CN(C)C=O>O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72623480a76c452b8b0b4b8ebae28266 | O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1>>Nc1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 | ClC1=CC=C(OC2=C(C=C(C=C2F)[N+](=O)[O-])F)C=C1.C1(=CC=CC=C1)C.C(C)(=O)[O-].[NH4+]>>ClC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15]([F:16])[cH:17]1>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([O:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[c:15]([F:16])[cH:17]1 | O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 | Nc1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 | null | [Fe] | O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 114.2 | [{"value": 113.0, "product": "ClC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 114.2, "product": "ClC1=CC=C(OC2=C(C=C(N)C=C2F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A mixture of 4-(4-chlorophenoxy)-3,5-difluoronitrobenzene (10.6 g, 37 mmol), toluene (150 ml), H2O (150 ml), iron powder (6.9 g, 124 mmol), and ammonium acetate (9.3 g, 120 mmol) was heated to reflux with stirring for 2-3 hrs. After cooling to room temperature, the reaction mixture was filtered through Celite with thor... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Fe].O | null | 2.5 | O=[N+]([O-])c1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1>[Fe].O>Nc1cc(F)c(Oc2ccc(Cl)cc2)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a93a042afc094e30a288bfc84bfe67eb | O.O=S(Cl)Cl.[N-]=[N+]=C1C=C(F)C(F)=C(F)C1>>O=S(=O)(Cl)c1cc(F)c(F)c(F)c1 | O=S(Cl)Cl.O.FC=1CC(C=C(C1F)F)=[N+]=[N-]>>FC=1C=C(C=C(C1F)F)S(=O)(=O)Cl | [OH2:3].Cl[S:2](=[O:1])[Cl:4].[N-]=[N+]=[C:5]1[CH:6]=[C:7]([F:8])[C:9]([F:10])=[C:11]([F:12])[CH2:13]1>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([F:10])[c:11]([F:12])[cH:13]1 | O.O=S(Cl)Cl.[N-]=[N+]=C1C=C(F)C(F)=C(F)C1 | O=S(=O)(Cl)c1cc(F)c(F)c(F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 98c1736d1ebbd7cfa5142deb7e1a7addfd815789737234badb4285197722694e | 7695a23fa9acae08e540c42f1f8e7e2d5ada49d34fd5c5779ebf42049c26c52c | c1ccccc1 | Cl-[S;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3].[F;D1;H0:4]-[C;H0;D3;+0:5]1=[C;H0;D3;+0:6](-[F;D1;H0:7])-[CH2;D2;+0:8]-[C;H0;D3;+0:9](=[N+]=[N-])-[CH;D2;+0:10]=[C;H0;D3;+0:11]-1-[F;D1;H0:12].[OH2;D0;+0:13]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:13])-[c;H0;D3;+0:9]1:[cH;D2;+0:8]:[c;H0;D3;+0:6](-[F;D1;H0:7]... | 83 | [{"value": 83.0, "product": "FC=1C=C(C=C(C1F)F)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 5 | MINUTE | The flask containing the SOCl2/H2O solution is cooled again to −10° C. and a catalytic amount of Cu(I)Cl (˜50 mg) was added. The solution turns dark green in color. The flask was fitted with a 500 mL addition funnel (previously chilled to 0° C.) and the 3,4,5-trifluorodiazobenzene solution was quickly transferred to th... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Alkenyl halide.Diazo | Aromatic halide.Aromatic halide.Aromatic halide.Sulfonyl halide | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | HCl | null | -10 | 0.083333 | O.O=S(Cl)Cl.[N-]=[N+]=C1C=C(F)C(F)=C(F)C1>>O=S(=O)(Cl)c1cc(F)c(F)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c678e63368ab4cf7bc500a3f9f2690e3 | C=O.CNC.c1cnc2[nH]ccc2c1>>CN(C)Cc1c[nH]c2ncccc12 | N1C=CC=2C1=NC=CC2.Cl.CNC.C=O.O.Cl>>CN(CC1=CNC2=NC=CC=C21)C | O=[CH2:4].[CH3:1][NH:2][CH3:3].[cH:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12 | C=O.CNC.c1cnc2[nH]ccc2c1 | CN(C)Cc1c[nH]c2ncccc12 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 729711dde8e4bb3512a9568794c75eebc8e37945891e0605b6795a0e1a750d62 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1cnc2[nH]ccc2c1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[c:5]:[#7;a:6]:[c:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c:7](:[#7;a:6]:[c:5]):[c:11]:1:[c:12] | 67.4 | [{"value": 67.4, "product": "CN(CC1=CNC2=NC=CC=C21)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "CN(CC1=CNC2=NC=CC=C21)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | Into a 3-neck round bottom flask was added Isopropyl alcohol (320.0 mL) followed by the addition of 1H-pyrrolo[2,3-b]pyridine 1 (7.10 g, 60.1 mmol), dimethylamine hydrochloride (5.4 g, 0.066 mol), and formaldehyde (2.0 g, 0.066 mol). The reaction mixture was stirred at room temperature for 12 hours, and then refluxed f... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HO- | C(C)(C)O | null | 12 | C=O.CNC.c1cnc2[nH]ccc2c1>C(C)(C)O>CN(C)Cc1c[nH]c2ncccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c27948d78e94570bbd4bab7da14537d | O=C(Cl)c1ccc(Cl)nc1.c1cnc2[nH]ccc2c1>>O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12 | CO.ClC1=CC=C(C=N1)C(=O)Cl.N1C=CC=2C1=NC=CC2.[Cl-].[Cl-].[Cl-].[Al+3]>>ClC1=CC=C(C=N1)C(=O)C1=CNC2=NC=CC=C21 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1.[cH:10]1[cH:11][nH:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[n:8][cH:9]1)[c:10]1[cH:11][nH:12][c:13]2[n:14][cH:15][cH:16][cH:17][c:18]12 | O=C(Cl)c1ccc(Cl)nc1.c1cnc2[nH]ccc2c1 | O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 1bac1dd3ebf1eec66abc5940fc68d0b3d89999c986d197b8a60e9b2fcd4b0fbd | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1cccnc1)c1c[nH]c2ncccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[c:8]:[#7;a:9]:[c:10]1:[#7;a:11]:[c:12]:[cH;D2;+0:13]:[c:14]:1:[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])-[c;H0;D3;+0:13]1:[c:12]:[#7;a:11]:[c:10](:[#7;a:9]:[c:8]):[c:14]:1:[c:15] | 89.1 | [{"value": 88.6, "product": "ClC1=CC=C(C=N1)C(=O)C1=CNC2=NC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.1, "product": "ClC1=CC=C(C=N1)C(=O)C1=CNC2=NC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 70 | MINUTE | Into a round bottom flask was added aluminum trichloride (16.0 g, 0.12 mol) and methylene chloride (100.0 mL) under an atmosphere of nitrogen. Into the reaction mixture, was added 1H-Pyrrolo[2,3-b]pyridine 1 (3.2 g, 0.027 mol) in methylene dichloride (20.0 mL). The reaction was stirred at room temperature for 70.0 minu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccncc1.c1cnc2[nH]ccc2c1 | HCl | C(Cl)Cl | null | 1.166667 | O=C(Cl)c1ccc(Cl)nc1.c1cnc2[nH]ccc2c1>C(Cl)Cl>O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-057dd52497a24d4aa9f9f21f8ab5eec8 | CC(C)[Si](C(C)C)(C(C)C)n1cc(Cc2ccc(NCc3ccccc3)nc2)c2cccnc21>>c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | C(C1=CC=CC=C1)NC1=NC=C(C=C1)CC1=CN(C2=NC=CC=C21)[Si](C(C)C)(C(C)C)C(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)NC1=NC=C(C=C1)CC1=CNC2=NC=CC=C21 | CC(C)[Si](C(C)C)(C(C)C)[n:14]1[cH:13][c:12]([CH2:11][c:10]2[cH:9][cH:8][c:7]([NH:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:24][cH:23]3)[n:22][cH:21]2)[c:20]2[c:15]1[n:16][cH:17][cH:18][cH:19]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][c:12]3[cH:13][nH:14][c:15]4[n:16][cH:17][cH:18][cH:19][c:20... | CC(C)[Si](C(C)C)(C(C)C)n1cc(Cc2ccc(NCc3ccccc3)nc2)c2cccnc21 | c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | null | null | O | Deprotection | OtherReaction | 4aaf27f2186a543cc5d627575c5db0d3bfdf22297cd9a7e3e12afecfd9535da5 | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[#7;a:6]:[c:7]>>[c:7]:[#7;a:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 82.4 | [{"value": 82.4, "product": "C(C1=CC=CC=C1)NC1=NC=C(C=C1)CC1=CNC2=NC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C(C1=CC=CC=C1)NC1=NC=C(C=C1)CC1=CNC2=NC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 30 | MINUTE | Into a round bottom flask was added compound 10 (400.0 mg, 0.85 mmol), tetrahydrofuran (20.0 mL) and tetra-n-butylammonium fluoride (240 mg, 0.93 mmol). The reaction mixture was stirred at 20 Celsius for 30 min. TLC indicated no starting material. The reaction mixture was poured into water, extracted with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1c[nH]c2ncccc12 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1ccncc1.c1cnc2[nH]ccc2c1 | Other | O | 20 | 0.5 | CC(C)[Si](C(C)C)(C(C)C)n1cc(Cc2ccc(NCc3ccccc3)nc2)c2cccnc21>O>c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d56fba1fdda94189818e0af4c5401e1b | NCc1ccc(C(F)(F)F)cc1.O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12>>O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | ClC1=CC=C(C=N1)C(=O)C1=CNC2=NC=CC=C21.FC(C1=CC=C(CN)C=C1)(F)F.O1CCCC1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C>>N1C=C(C=2C1=NC=CC2)C(=O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F | [NH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]1.Cl[c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[c:21]2[cH:22][nH:23][c:24]3[n:25][cH:26][cH:27][cH:28][c:29]23)[cH:20][n:19]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH... | NCc1ccc(C(F)(F)F)cc1.O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12 | O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1ccc(NCc2ccccc2)nc1)c1c[nH]c2ncccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[c:4]:[c:5] | 18.5 | [{"value": 18.5, "product": "N1C=C(C=2C1=NC=CC2)C(=O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.0, "product": "N1C=C(C=2C1=NC=CC2)C(=O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 8 | HOUR | Into a pressure flask was added compound 7 (3.5 g, 0.014 mol) and 4-(trifluoromethyl)benzylamine (9.0 g, 0.051 mol) and tetrahydrofuran (30.0 mL, 0.37 mol) and palladium acetate (200.0 mg, 0.890 mmol) and 2-(di-t-butylphosphino)biphenyl (200.0 mg, 0.67 mmol). The reaction mixture was stirred at 180 Celsius overnight, p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1cnc2[nH]ccc2c1 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O | 180 | 8 | NCc1ccc(C(F)(F)F)cc1.O=C(c1ccc(Cl)nc1)c1c[nH]c2ncccc12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O>O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4230cc2c101e473cbcbd83d6b520d4c1 | O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12>>OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | N1C=C(C=2C1=NC=CC2)C(=O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F.[BH4-].[Na+].O>>N1C=C(C=2C1=NC=CC2)C(O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[n:19][cH:20]1)[c:21]1[cH:22][nH:23][c:24]2[n:25][cH:26][cH:27][cH:28][c:29]12>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18... | O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | null | null | CN(C=O)C.C(C)O | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | [#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5](-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]):[c:13]:1>>[#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5](-[CH;D3;+0:6](-[OH;D1;+0:7])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]):[c:13]:1 | 30 | [{"value": 30.0, "product": "N1C=C(C=2C1=NC=CC2)C(O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "N1C=C(C=2C1=NC=CC2)C(O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into a round bottom flask was added compound 13 (210.0 mg, 0.53 mmol) and sodium tetrahydroborate (80.0 mg, 2.11 mmol) and dissolved in N,N-dimethylformamide (5.0 mL) and ethanol (20.0 mL). The reaction was stirred at room temperature overnight, poured into water, and the product was extracted with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccncc1.c1ccccc1.c1cnc2[nH]ccc2c1 | null | CN(C=O)C.C(C)O | null | 8 | O=C(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12>CN(C=O)C.C(C)O>OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f6417165d0346b58668bea51b35c166 | OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12>>FC(F)(F)c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | C([O-])(O)=O.[Na+].N1C=C(C=2C1=NC=CC2)C(O)C=2C=NC(=CC2)NCC2=CC=C(C=C2)C(F)(F)F.FC(C(=O)O)(F)F.C(C)[SiH](CC)CC>>N1C=C(C=2C1=NC=CC2)CC=2C=CC(=NC2)NCC2=CC=C(C=C2)C(F)(F)F | O[CH:15]([c:14]1[cH:13][cH:12][c:11]([NH:10][CH2:9][c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:28][cH:27]2)[n:26][cH:25]1)[c:16]1[cH:17][nH:18][c:19]2[n:20][cH:21][cH:22][cH:23][c:24]12>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][c:11]2[cH:12][cH:13][c:14]([CH2:15][c:16]3[cH:17][nH:18][c:19... | OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12 | FC(F)(F)c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | null | null | null | Reduction | OtherReaction | 3c5af32aa639db2ebe4d9851942e9468e1838e06ae5b2c1669bca1d5e0922c33 | 46f8a11b80b06e754a5a34198d843342612a5e7ede950bda52ce3a500cedba0b | c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[c:7]1:[c:8]:[#7;a:9]:[c:10](:[#7;a:11]):[c:12]:1>>[#7;a:11]:[c:10]1:[#7;a:9]:[c:8]:[c:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):[c:12]:1 | 62.8 | [{"value": 62.8, "product": "N1C=C(C=2C1=NC=CC2)CC=2C=CC(=NC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.8, "product": "N1C=C(C=2C1=NC=CC2)CC=2C=CC(=NC2)NCC2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Into a round bottom flask was added compound 14 (200.0 mg, 0.50 mmol) and trifluoroacetic acid (5.0 mL, 0.065 mol) and triethylsilane (3.0 mL, 0.019 mol). The reaction was stirred at room temperature for 30 min, poured into aqueous sodium bicarbonate, and the product was extracted with ethyl acetate. The organic layer ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | null | null | c1ccccc1.c1ccncc1.c1cnc2[nH]ccc2c1 | Other | null | null | 0.5 | OC(c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1)c1c[nH]c2ncccc12>>FC(F)(F)c1ccc(CNc2ccc(Cc3c[nH]c4ncccc34)cn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60798bafc8d2443e83492772e0af6030 | CCOC(C)(OCC)OCC.N#CCC#N>>CCOC(C)=C(C#N)C#N | C(C)(OCC)(OCC)OCC.C(CC#N)#N>>C(C)OC(C)=C(C#N)C#N | CCO[C:4](OCC)([O:3][CH2:2][CH3:1])[CH3:5].[CH2:6]([C:7]#[N:8])[C:9]#[N:10]>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])=[C:6]([C:7]#[N:8])[C:9]#[N:10] | CCOC(C)(OCC)OCC.N#CCC#N | CCOC(C)=C(C#N)C#N | null | C(C)(=O)O | C(C)O | C-C Coupling | OtherReaction | 9d0000e86d6f33b615f7919c1f0221440b9043cbb7b3d0af049d5d091c34f404 | fd4a9f4582a23be02b9aaad230da234fe33873302a3bdf8caf1a8217cd2fc678 | null | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-[#8:3]-[C:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])-[C:6]#[N;D1;H0:5] | 91.4 | [{"value": 91.0, "product": "C(C)OC(C)=C(C#N)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.4, "product": "C(C)OC(C)=C(C#N)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | Triethyl orthoacetate (97 g, 0.6 mol), malononitrile (33 g, 0.5 mol) and glacial acetic acid (1.5 g) were placed in a 1 L flask equipped with a stirrer, thermometer and a Vigreux column (20×1 in.) on top of which a distillation condenser was placed. The reaction mixture was heated and ethyl alcohol began to distill whe... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Ether | null | null | null | HO- | C(C)(=O)O.C(C)O | null | 0.666667 | CCOC(C)(OCC)OCC.N#CCC#N>C(C)(=O)O.C(C)O>CCOC(C)=C(C#N)C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-959a3d40ae2148beae62f7d18c8db73d | CCO/C(C)=C(\C#N)C(N)=S.N>>C/C(N)=C(/C#N)C(N)=S | C(#N)/C(/C(N)=S)=C(/C)\OCC.N>>N/C(=C(/C(N)=S)\C#N)/C | CCO/[C:2]([CH3:1])=[C:4](\[C:5]#[N:6])[C:7]([NH2:8])=[S:9].[NH3:3]>>[CH3:1]/[C:2]([NH2:3])=[C:4](/[C:5]#[N:6])[C:7]([NH2:8])=[S:9] | CCO/C(C)=C(\C#N)C(N)=S.N | C/C(N)=C(/C#N)C(N)=S | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5132028908218d0a570eb2b2ac493e42e1a216124294e5ff728b2eb927eef034 | f4d71ded74a56725823fcbb2ae78f980194bc0045e19b1491967e395a5e29d8c | null | C-C-O/[C;H0;D3;+0:1](-[C;D1;H3:2])=[C:3](\[C:4]#[N;D1;H0:5])-[C:6](-[N;D1;H2:7])=[S;D1;H0:8].[NH3;D0;+0:9]>>[C;D1;H3:2]/[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[C:3](/[C:4]#[N;D1;H0:5])-[C:6](-[N;D1;H2:7])=[S;D1;H0:8] | 63 | [{"value": 63.0, "product": "N/C(=C(/C(N)=S)\\C#N)/C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (2E)-2-Cyano-3-ethoxybut-2-enethioamide (method 2) (19.2 g, 0.136 mol) was dissolved in a saturated solution of ammonia in methanol (500 mL) and stirred at r.t. overnight. The reaction mixture was concentrated and the residue was dissolved in hot water (600 mL) and the undissoved solid was filtered and dried to recover... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Enamine | null | null | null | HO- | CO | null | 8 | CCO/C(C)=C(\C#N)C(N)=S.N>CO>C/C(N)=C(/C#N)C(N)=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0f1da479c8b47ec961c75f0b1292d85 | C/C(N)=C(/C#N)C(N)=S>>Cc1nsc(N)c1C#N | N/C(=C(/C(N)=S)\C#N)/C.OO>>NC1=C(C(=NS1)C)C#N | [CH3:1]/[C:2]([NH2:3])=[C:7](\[C:5](=[S:4])[NH2:6])[C:8]#[N:9]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:7]1[C:8]#[N:9] | C/C(N)=C(/C#N)C(N)=S | Cc1nsc(N)c1C#N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 53973ab0cc444428b63bf8e333f084965288c268c6e3344b0072e9468e2d332e | df818a125b449aa80d1964ad752d90e7bc820054c3a49c48866fa5bae4094f85 | c1cnsc1 | [C;D1;H3:1]/[C;H0;D3;+0:2](-[NH2;D1;+0:3])=[C;H0;D3;+0:4](/[C:5]#[N;D1;H0:6])-[C;H0;D3;+0:7](-[N;D1;H2:8])=[S;H0;D1;+0:9]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[s;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[c;H0;D3;+0:4]:1-[C:5]#[N;D1;H0:6] | 80.3 | [{"value": 80.0, "product": "NC1=C(C(=NS1)C)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "NC1=C(C(=NS1)C)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a stirred solution of (2E)-3-amino-2-cyanobut-2-enethioamide (method 3) (6.83 g, 48.4 mmol) in methanol (300 mL) was added dropwise 13.6 mL (124 mmoL) of 30% hydrogen peroxide. The mixture was stirred at 60° C. for 4 h and evaporated to 60 mL in a rotary evaporator and cooled in an ice-bath. The crystallized product... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Thioamide | null | null | c1cnsc1 | c1cnsc1 | null | CO | 60 | 4 | C/C(N)=C(/C#N)C(N)=S>CO>Cc1nsc(N)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-359c7aa4a0d249c2b93218dff21924ea | CCCC(=O)Cl.Cc1nsc(N)c1C#N>>CCCC(=O)Nc1snc(C)c1C#N | C(CCC)(=O)Cl.NC1=C(C(=NS1)C)C#N.CCN(CC)CC>>C(#N)C=1C(=NSC1NC(CCC)=O)C | Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[s:8][n:9][c:10]([CH3:11])[c:12]1[C:13]#[N:14]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[s:8][n:9][c:10]([CH3:11])[c:12]1[C:13]#[N:14] | CCCC(=O)Cl.Cc1nsc(N)c1C#N | CCCC(=O)Nc1snc(C)c1C#N | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cnsc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1 | 95 | [{"value": 95.0, "product": "C(#N)C=1C(=NSC1NC(CCC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.7, "product": "C(#N)C=1C(=NSC1NC(CCC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (5.31 g, 38.2 mmol) in DCM (200 mL) at 0° C., NEt3 (5 g, 50 mmol) was added followed by the dropwise addition of a solution of the butyryl chloride (4.88 g, 45.8 mmol) in DCM (50 mL). After the completion of the addition the reaction mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnsc1 | HCl | C(Cl)Cl | null | 8 | CCCC(=O)Cl.Cc1nsc(N)c1C#N>C(Cl)Cl>CCCC(=O)Nc1snc(C)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9cc2fe68a73465a8617c117e76ea606 | CCCC(=O)Nc1snc(C)c1C#N.OO>>CCCC(=O)Nc1snc(C)c1C(N)=O | C(#N)C=1C(=NSC1NC(CCC)=O)C.OO>>C(CCC)(=O)NC1=C(C(=NS1)C)C(=O)N | [CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[s:8][n:9][c:10]([CH3:11])[c:12]1[C:13]#[N:14].O[OH:15]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[s:8][n:9][c:10]([CH3:11])[c:12]1[C:13]([NH2:14])=[O:15] | CCCC(=O)Nc1snc(C)c1C#N.OO | CCCC(=O)Nc1snc(C)c1C(N)=O | null | null | [NH4+].[OH-] | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | c1cnsc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;H0;D1;+0:1] | 72 | [{"value": 72.0, "product": "C(CCC)(=O)NC1=C(C(=NS1)C)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | To a solution of N-(4-cyano-3-methyl-isothiazol-5-yl)-butyramide (method 5) (4.18 g, 20 mmol) in 30% aqueous NH4OH (250 mL), was added dropwise 100 mL of hydrogen peroxide at r.t. After the completion of the addition the reaction mixture was stirred at 60° C. overnight after which the TLC showed the complete disappeara... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | c1cnsc1 | Other | [NH4+].[OH-] | 60 | 8 | CCCC(=O)Nc1snc(C)c1C#N.OO>[NH4+].[OH-]>CCCC(=O)Nc1snc(C)c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe28396beac44d89a69e369124bb1b5a | CCCC(=O)Nc1snc(C)c1C(N)=O>>CCCc1nc2snc(C)c2c(=O)[nH]1 | C(CCC)(=O)NC1=C(C(=NS1)C)C(=O)N>>CC1=NSC=2N=C(NC(C21)=O)CCC | O=[C:4]([CH2:3][CH2:2][CH3:1])[NH:5][c:6]1[s:7][n:8][c:9]([CH3:10])[c:11]1[C:12](=[O:13])[NH2:14]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[nH:14]1 | CCCC(=O)Nc1snc(C)c1C(N)=O | CCCc1nc2snc(C)c2c(=O)[nH]1 | null | null | N | Aromatic Heterocycle Formation | OtherReaction | 949006d8c772b36f999683041f038f05b089c287074275bc26b8515cb4d0af67 | 9d5aef0cada2072f52eb60b6996e8c9e376baa92104aa4e87786338b6493e605 | O=c1[nH]cnc2sncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:2:[c;H0;D3;+0:11](=[O;D1;H0:13]):[nH;D2;+0:12]:1 | 46.1 | [{"value": 34.0, "product": "CC1=NSC=2N=C(NC(C21)=O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "CC1=NSC=2N=C(NC(C21)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 5-Butyrylamino-3-methyl-isothiazole-4-carboxylic acid amide (method 6) (1.9 g, 8.3 mmol) was suspended in 75 mL of 30% NH3 and then was heated to 140° C. for 4 h in a pressure reactor. The mixture was cooled and neutralized to pH 8. The precipitated 3-methyl-6-propyl-5H-isothiazolo[5,4-d]pyrimidin-4-one was filtered of... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | null | c1cnsc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | HO- | N | 140 | null | CCCC(=O)Nc1snc(C)c1C(N)=O>N>CCCc1nc2snc(C)c2c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd89b6b9fdb140fd9b306123a3818cc8 | BrCc1ccccc1.CCCc1nc2snc(C)c2c(=O)[nH]1>>CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1 | C(C1=CC=CC=C1)Br.CC1=NSC=2N=C(NC(C21)=O)CCC.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CCC | Br[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | BrCc1ccccc1.CCCc1nc2snc(C)c2c(=O)[nH]1 | CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 489c04ab50559560a149376d4f33f86b7dd628ef17c4a055bc399e6f8281e8e6 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 32 | [{"value": 32.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-methyl-6-propyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 7) (800 mg, 3.8 mmol) in 20 mL of anhydrous DMF was added 1.38 g (10 mmol) of anhydrous 10 K2CO3 followed by benzyl bromide (655 mg, 3.8 mmol) and the mixture was stirred at room temperature overnight. The TLC of the reaction mixture showed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1 | HBr | CN(C)C=O | null | 8 | BrCc1ccccc1.CCCc1nc2snc(C)c2c(=O)[nH]1>CN(C)C=O>CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ed2462266734bb4ae4329e9ba4b1ad9 | BrBr.CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1>>CCC(Br)c1nc2snc(C)c2c(=O)n1Cc1ccccc1 | C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CCC.C(C)(=O)[O-].[Na+].BrBr.CCOC(=O)C>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(CC)Br | Br[Br:4].[CH3:1][CH2:2][CH2:3][c:5]1[n:6][c:7]2[s:8][n:9][c:10]([CH3:11])[c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[n:6][c:7]2[s:8][n:9][c:10]([CH3:11])[c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | BrBr.CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1 | CCC(Br)c1nc2snc(C)c2c(=O)n1Cc1ccccc1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH2;D2;+0:7]-[C:8]-[C;D1;H3:9]):[#7;a:10](-[C:11]):[c:12]>>[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH;D3;+0:7](-[Br;H0;D1;+0:1])-[C:8]-[C;D1;H3:9]):[#7;a:10](-[C:11]):[c:12] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(CC)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(CC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-benzyl-3-methyl-6-propyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 8) (369 mg, 1.23 mmol) and sodium acetate (1 g) in acetic acid (5 mL) at 100° C., a solution of the bromine (318 mg, 2 mmol) in acetic acid (10 mL) was added dropwise over a period of 20 minutes. The reaction mixture was cooled aft... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ncc2cnsc2n1.c1ccccc1 | HBr | C(C)(=O)O | null | null | BrBr.CCCc1nc2snc(C)c2c(=O)n1Cc1ccccc1>C(C)(=O)O>CCC(Br)c1nc2snc(C)c2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f2ed5386ee84f7fa2589af8693fda08 | CCC(NCCCNC(=O)OC(C)(C)C)c1nc2snc(C)c2c(=O)n1Cc1ccccc1.Cc1ccc(C(=O)Cl)cc1>>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1 | C(C)(C)(C)OC(NCCCNC(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O.C(C)N(CC)CC.C1(=CC=C(C=C1)C(=O)Cl)C>>C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O | [CH3:1][CH2:2][CH:3]([c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33].Cl[C:34](=[O:35])[c:36]1[cH:37][cH:38][c:39]([CH3:40])[cH:41][cH:42]1>>[CH3:1][CH2... | CCC(NCCCNC(=O)OC(C)(C)C)c1nc2snc(C)c2c(=O)n1Cc1ccccc1.Cc1ccc(C(=O)Cl)cc1 | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NCc1nc2sncc2c(=O)n1Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]):[#7;a:13]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[#7;a:13] | null | [] | null | null | 30 | MINUTE | To a solution of {3-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propyl}-carbamic acid tert-butyl ester (method 10) (0.1 g, 0.21 mmol) and triethylamine (0.303 g, 3 mmol) in DCM (20 mL) at r.t. was added dropwise a solution of p-toluoyl chloride (0.1 g, 0.6 mmol) in DCM (10 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ncc2cnsc2n1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | CCC(NCCCNC(=O)OC(C)(C)C)c1nc2snc(C)c2c(=O)n1Cc1ccccc1.Cc1ccc(C(=O)Cl)cc1>C(Cl)Cl>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1e918d29d5a473da79e52707134315a | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1.Cl>>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1.[Cl-] | C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O.Cl>>[Cl-].NCCCN(C(C1=CC=C(C=C1)C)=O)C(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2 | CC(C)(C)OC(=O)[NH:26][CH2:25][CH2:24][CH2:23][N:22]([CH:3]([CH2:2][CH3:1])[c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:27](=[O:28])[c:29]1[cH:30][cH:31][c:32]([CH3:33])[cH:34][cH:35]1.[ClH:36]>>[CH3:1][CH2:2][CH:3]([c:4]1[n:5][c:6]2[s:7][n... | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1.Cl | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1.[Cl-] | null | null | CCOCC | Miscellaneous | OtherReaction | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | O=C(NCc1nc2sncc2c(=O)n1Cc1ccccc1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[ClH;D0;+0:4]>>[C:3]-[C:2]-[NH2;D1;+0:1].[Cl-;H0;D0:4] | 87 | [{"value": 87.0, "product": "[Cl-].NCCCN(C(C1=CC=C(C=C1)C)=O)C(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | (+) {3-[[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester (method 12) (0.117 g, 0.19 mmol) was dissolved in 2M HCl in ether and the mixture was stirred at r.t. for 20 h. The precipitated product was filtered off and washed with... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ncc2cnsc2n1.c1ccccc1.c1ccccc1 | HO- | CCOCC | null | 20 | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(=O)OC(C)(C)C)C(=O)c1ccc(C)cc1.Cl>CCOCC>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1.[Cl-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74d6595daca041fd97c7ce6f78c91b53 | CC(C)=O.CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1>>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(C)C)C(=O)c1ccc(C)cc1 | Cl.NCCCN(C(C1=CC=C(C=C1)C)=O)C(CC)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2.CC(=O)C.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(CC)N(C(C2=CC=C(C=C2)C)=O)CCCNC(C)C | O=[C:27]([CH3:28])[CH3:29].[CH3:1][CH2:2][CH:3]([c:4]1[n:5][c:6]2[s:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[N:22]([CH2:23][CH2:24][CH2:25][NH2:26])[C:30](=[O:31])[c:32]1[cH:33][cH:34][c:35]([CH3:36])[cH:37][cH:38]1>>[CH3:1][CH2:2][CH:3]([c:4]1[n:5][c:6]2[s... | CC(C)=O.CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1 | CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(C)C)C(=O)c1ccc(C)cc1 | null | C(C)(=O)O | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=C(NCc1nc2sncc2c(=O)n1Cc1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | 2 | HOUR | To a solution of N-(3-amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-benzamide hydrogen chloride (method 13g) (1.24 g, 2.54 mmol), in the presence of molecular sieves (2 g,) was added acetone (1 mL) and the mixture was stirred at room temperature for 2 h. Anal... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ncc2cnsc2n1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | 2 | CC(C)=O.CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCN)C(=O)c1ccc(C)cc1>C(C)(=O)O>CCC(c1nc2snc(C)c2c(=O)n1Cc1ccccc1)N(CCCNC(C)C)C(=O)c1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63f611e8c256424799d887f9799d5c73 | Cc1noc(N)c1C(N)=O>>CCCC(=O)Nc1onc(C)c1C(N)=O | NC1=C(C(=NO1)C)C(=O)N>>C(CCC)(=O)NC1=C(C(=NO1)C)C(=O)N | [CH3:1][c:10]1[n:9][o:8][c:7]([NH2:6])[c:12]1[C:13](=[O:5])[NH2:14]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[o:8][n:9][c:10]([CH3:11])[c:12]1[C:13]([NH2:14])=[O:15] | Cc1noc(N)c1C(N)=O | CCCC(=O)Nc1onc(C)c1C(N)=O | null | null | C(CCC)(=O)OC(CCC)=O.CCCCCC | Functional Group Addition | OtherReaction | 451df6fb9d8140ba56f5e518a3998fac145811ecbd984d4b0df9f2c9c1699191 | fb9048c83eb6edf8a08f7fd84a29a515b5632fb12ddeea96d9d12cb515d984fe | c1cnoc1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[#8;a:4]:[c:5](-[NH2;D1;+0:6]):[c:7]:1-[C;H0;D3;+0:8](-[N;D1;H2:9])=[O;H0;D1;+0:10]>>[C;D1;H3:11]-[c;H0;D3;+0:2]1:[#7;a:3]:[#8;a:4]:[c:5](-[NH;D2;+0:6]-[C:12](=[O;H0;D1;+0:10])-[C:13]-[C:14]-[CH3;D1;+0:1]):[c:7]:1-[C;H0;D3;+0:8](-[N;D1;H2:9])=[O;D1;H0:15] | 173.6 | [{"value": 173.6, "product": "C(CCC)(=O)NC1=C(C(=NO1)C)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 0.75 | HOUR | A mixture of 5-amino-3-methyl-isoxazole-4-carboxylic acid amide (2 g, 14.18 mmol) in 10 ml of butyric anhydride was stirred at 150° C. for 0.5-1 h. The brown solution was diluted with hexane (100 ml) and cooled to room temperature. The solid crushed out from the mixture was filtered and washed with hexane, dried in vac... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Primary amide.Secondary amide | c1cnoc1 | c1cnoc1 | c1cnoc1 | Other | C(CCC)(=O)OC(CCC)=O.CCCCCC | 150 | 0.75 | Cc1noc(N)c1C(N)=O>C(CCC)(=O)OC(CCC)=O.CCCCCC>CCCC(=O)Nc1onc(C)c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdd43cc6aeab4044b0a5cab0f123088d | BrCc1ccccc1.CCCc1nc2onc(C)c2c(=O)[nH]1>>CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1 | CC1=NOC=2N=C(NC(C21)=O)CCC.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)CCC | Br[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[o:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[o:7][n:8][c:9]([CH3:10])[c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | BrCc1ccccc1.CCCc1nc2onc(C)c2c(=O)[nH]1 | CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e0a1975c2a88d5fc896ad5f7370942057d696c2cd3db1fcacb958490ae4465f4 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2cnoc2ncn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#8;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#8;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 68 | [{"value": 68.0, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A suspension of 3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one (method 17) (1.698 g, 8.8 mmol), benzylbromide (1.5 g, 8.8 mmol), potassium carbonate (2.43 g, 17.6 mmol) in 10 ml DMF was stirred at room temperature overnight. The mixture was diluted with water, extracted with EtOAc (50 ml×3), the combined organic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2cnoc2n1 | c1ncc2cnoc2n1 | c1ncc2cnoc2n1.c1ccccc1 | HBr | O.CN(C)C=O | null | 8 | BrCc1ccccc1.CCCc1nc2onc(C)c2c(=O)[nH]1>O.CN(C)C=O>CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efd2875fdf074953aba16d39ec090ed9 | BrBr.CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1>>CCC(Br)c1nc2onc(C)c2c(=O)n1Cc1ccccc1 | BrBr.C([O-])([O-])=O.[K+].[K+].C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)CCC.C(C)(=O)[O-].[Na+].BrBr>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)C(CC)Br | Br[Br:4].[CH3:1][CH2:2][CH2:3][c:5]1[n:6][c:7]2[o:8][n:9][c:10]([CH3:11])[c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[n:6][c:7]2[o:8][n:9][c:10]([CH3:11])[c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | BrBr.CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1 | CCC(Br)c1nc2onc(C)c2c(=O)n1Cc1ccccc1 | null | null | O.C(C)(=O)O | Functional Group Interconversion | Bromination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=c1c2cnoc2ncn1Cc1ccccc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[#8;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH2;D2;+0:7]-[C:8]-[C;D1;H3:9]):[#7;a:10](-[C:11]):[c:12]>>[#7;a:2]:[#8;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH;D3;+0:7](-[Br;H0;D1;+0:1])-[C:8]-[C;D1;H3:9]):[#7;a:10](-[C:11]):[c:12] | 61.6 | [{"value": 61.6, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NO2)C)C(CC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 24 | HOUR | A solution of 5-benzyl-3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one (method 18) (3.167 g, 11.2 mmol) and sodium acetate (4.59 g, 56 mmol, 5 eq) in glacial acetic acid (26 ml) was treated with a preformed bromine solution (0.7 ml bromine in 10 ml of glacial acetic acid) (8.64 ml, 22.4 mmol, 2 eq). The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ncc2cnoc2n1.c1ccccc1 | HBr | O.C(C)(=O)O | 100 | 24 | BrBr.CCCc1nc2onc(C)c2c(=O)n1Cc1ccccc1>O.C(C)(=O)O>CCC(Br)c1nc2onc(C)c2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a6784ca2b954ddfa9449e001f3e6e0b | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N>>Cc1nsc(NC(=O)CC(C)C)c1C#N | NC1=C(C(=NS1)C)C#N.C(CC(C)C)(=O)Cl>>C(#N)C=1C(=NSC1NC(CC(C)C)=O)C | Cl[C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12].[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:13]1[C:14]#[N:15]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH:6][C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12])[c:13]1[C:14]#[N:15] | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N | Cc1nsc(NC(=O)CC(C)C)c1C#N | null | null | N1=CC=CC=C1.C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cnsc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1 | 79 | [{"value": 79.0, "product": "C(#N)C=1C(=NSC1NC(CC(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "C(#N)C=1C(=NSC1NC(CC(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (6.38 g, 45.9 mmol) in pyridine (20 mL) at 0° C., isovaleryl chloride (6.65 g, 55 mmol) was added dropwise. After the completion of the addition the reaction mixture was allowed to warm to r.t. and stirred overnight. The TLC and the MS showed the co... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnsc1 | HCl | N1=CC=CC=C1.C(Cl)(Cl)Cl | null | 8 | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N>N1=CC=CC=C1.C(Cl)(Cl)Cl>Cc1nsc(NC(=O)CC(C)C)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dcce0b8578ac45eab9f0f98071258bd7 | Cc1nsc(NC(=O)CC(C)C)c1C#N.OO>>Cc1nsc(NC(=O)CC(C)C)c1C(N)=O | C(#N)C=1C(=NSC1NC(CC(C)C)=O)C.OO>>CC1=NSC(=C1C(=O)N)NC(CC(C)C)=O | [CH3:1][c:2]1[n:3][s:4][c:5]([NH:6][C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12])[c:13]1[C:14]#[N:15].O[OH:16]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH:6][C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12])[c:13]1[C:14]([NH2:15])=[O:16] | Cc1nsc(NC(=O)CC(C)C)c1C#N.OO | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O | null | null | [NH4+].[OH-] | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | c1cnsc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;H0;D1;+0:1] | 71 | [{"value": 71.0, "product": "CC1=NSC(=C1C(=O)N)NC(CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | To a solution of N-(4-cyano-3-methyl-isothiazol-5-yl)-3-methyl-butyramide (method 24) (8 g, 35.8 mmol) in 30% aqueous NH4OH (200 mL), was added dropwise 100 mL of hydrogen peroxide at r.t. After the completion of the addition the reaction mixture was stirred at 60° C. overnight after which the TLC showed the complete d... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | c1cnsc1 | Other | [NH4+].[OH-] | 60 | 8 | Cc1nsc(NC(=O)CC(C)C)c1C#N.OO>[NH4+].[OH-]>Cc1nsc(NC(=O)CC(C)C)c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-415a6ebd4492432b8814bf1a6a72c014 | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O>>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | CC1=NSC(=C1C(=O)N)NC(CC(C)C)=O>>C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O | O=[C:7]([NH:6][c:5]1[s:4][n:3][c:2]([CH3:1])[c:15]1[C:13]([NH2:12])=[O:14])[CH2:8][CH:9]([CH3:10])[CH3:11]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:13](=[O:14])[c:15]12 | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O | Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | null | null | N | Aromatic Heterocycle Formation | OtherReaction | 949006d8c772b36f999683041f038f05b089c287074275bc26b8515cb4d0af67 | 9d5aef0cada2072f52eb60b6996e8c9e376baa92104aa4e87786338b6493e605 | O=c1[nH]cnc2sncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:2:[c;H0;D3;+0:11](=[O;D1;H0:13]):[nH;D2;+0:12]:1 | 39.4 | [{"value": 38.0, "product": "C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.4, "product": "C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 3-Methyl-5-(3-methyl-butyrylamino)-isothiazole-4-carboxylic acid amide (method 25) (6 g, 25 mmol) was suspended in 150 mL of 30% NH3 and then was heated to 140° C. for 5 h in a pressure reactor. The mixture was cooled and neutralized to pH 7. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined org... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | null | c1cnsc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | HO- | N | 140 | null | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O>N>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d91ae4131f8e4d948384a8edae960114 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12>>Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | C(C1=CC=CC=C1)Br.C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CC(C)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:20](=[O:21])[c:22]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[n:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20](=[O:21])[c:22]12 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 489c04ab50559560a149376d4f33f86b7dd628ef17c4a055bc399e6f8281e8e6 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 26) (1.31 g, 5.8 mmol) in 20 mL of anhydrous DMF was added 1.38 g (10 mmol) of anhydrous K2CO3 followed by benzyl bromide (1.18 g, 6.9 mmol) and the mixture was stirred at room temperature overnight. The TLC of the reaction mixture showed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1 | HBr | CN(C)C=O | null | 8 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12>CN(C)C=O>Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ed0a09c568c4885981bccebe03e4687 | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 | C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CC(C)C.C(C)(=O)[O-].[Na+].BrBr.CCOC(=O)C>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br | Br[Br:9].[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[O:22])[c:23]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([Br:9])[CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[O:22])... | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]):[#7;a:11](-[C:12]):[c:13]>>[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH;D3;+0:7](-[Br;H0;D1;+0:1])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]):[#7;a:11](-[C:12]):[c:13] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-benzyl-6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 27) (1.3 g, 4.2 mmol) and sodium acetate (2 g) in acetic acid (10 mL) at 100° C., a solution of the bromine (1.32 g, 8.4 mmol) in acetic acid (10 mL) was added dropwise over a period of 20 minutes. The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ncc2cnsc2n1.c1ccccc1 | HBr | C(C)(=O)O | null | 0.5 | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12>C(C)(=O)O>Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee92dc7998df47eca5eb8a8415a53341 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-]>>Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | [Br-].C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2 | Br[CH:8]([c:7]1[n:6][c:5]2[s:4][n:3][c:2]([CH3:1])[c:25]2[c:23](=[O:24])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:12]([CH3:13])[CH3:14].[N-:9]=[N+:10]=[N-:11]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([N:9]=[N+:10]=[N-:11])[CH:12]([CH3:13])[CH3:14])[n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][... | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-] | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 6463ff1d29bf5113d76baa7212c34a105b5cabf370ebc2d8763f73a63584c2da | 5dc52e0dd157494eb8237d0e03fb32787b3b51b4d3f04e5bbbe4fdfe5a135995 | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:5](:[#7;a:6]:[c:7]:[#16;a:8]:[#7;a:9]):[#7;a:10](-[C:11]):[c:12].[N-;H0;D1:13]=[#7;+:14]=[N;-;D1;H0:15]>>[#7;a:9]:[#16;a:8]:[c:7]:[#7;a:6]:[c:5](-[CH;D3;+0:1](-[N;H0;D2;+0:13]=[#7;+:14]=[N;-;D1;H0:15])-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[#7;a:10](-[C:11]):[c:12] | 94 | [{"value": 94.0, "product": "N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-benzyl-6-(1-bromo-2-methyl-propyl)-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 28) (0.6 g, 1.52 mmol) in anhydrous DMF (20 mL), sodium azide (0.65 g, 10 mmol) was added and the mixture was stirred at room temperature for 1 hour. The TLC of the RM showed the complete disappearance of the sta... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Azide | null | null | c1ncc2cnsc2n1.c1ccccc1 | Br- | CN(C)C=O | null | 1 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-]>CN(C)C=O>Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3cec36b897f4f80a2ba67d2862cffbe | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2>>NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2 | [N-]=[N+]=[N:9][CH:8]([c:7]1[n:6][c:5]2[s:4][n:3][c:2]([CH3:1])[c:23]2[c:21](=[O:22])[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH:10]([CH3:11])[CH3:12]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH2:9])[CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[... | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=c1c2cnsc2ncn1Cc1ccccc1 | [#7;a:1]:[c:2](-[C:3](-[C:4])-[N;H0;D2;+0:5]=[N+]=[N-]):[#7;a:6]>>[#7;a:1]:[c:2](-[C:3](-[C:4])-[NH2;D1;+0:5]):[#7;a:6] | null | [] | null | null | null | null | To a solution of 6-(1-azido-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyramidin-4-one (method 29) (0.5 g, 1.41 mmol) in methanol (20 mL) was added 5% Pd/C (20% by wt.) and the resulting mixture was stirred at r.t. in an atmosphere of H2 and the progress of the reaction was monitored by MS. After the disap... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ncc2cnsc2n1.c1ccccc1 | Other | [Pd].CO | null | null | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>[Pd].CO>Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f987da265dd4e879f128a121cab73a6 | BrCCC1OCCO1.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12 | NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2.BrCCC1OCCO1>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)NCCC2OCCO2 | Br[CH2:10][CH2:11][CH:12]1[O:13][CH2:14][CH2:15][O:16]1.[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH2:9])[CH:17]([CH3:18])[CH3:19])[n:20]([CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:28](=[O:29])[c:30]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH:9][CH2:10][CH2:11][CH:12]3[O:13][CH2:14][CH2:15]... | BrCCC1OCCO1.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=c1c2cnsc2nc(CNCCC2OCCO2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3](-[#8:4])-[#8:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH2;D1;+0:10]):[#7;a:11]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[CH2;D2;+0:1]-[C:2]-[C:3](-[#8:4])-[#8:5]):[#7;a:11] | 95.6 | [{"value": 95.6, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)NCCC2OCCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 6-(1-amino-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 30) (1.6 g, 4.88 mmol) in anhydrous DMF (20 mL), 2-(2-bromo-ethyl)-[1,3]dioxolane (0.88 g, 4.88 mmol) was added and the resulting solution was heated at 70° C. for 2 h. The reaction mixture was cooled, diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ncc2cnsc2n1.C1COCO1.c1ccccc1 | HBr | O.CN(C)C=O | 70 | null | BrCCC1OCCO1.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12>O.CN(C)C=O>Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25242c552b7c4e45be8644cc2ac88d77 | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | C(C)(C)(C)OC(NCCCNC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O.C1(=CC=C(C=C1)C(=O)Cl)C>>C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O | Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:43][cH:42]1)=[O:7].[NH:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([c:21]1[n:22][c:23]2[s:24][n:25][c:26]([CH3:27])[c:28]2[c:29](=[O:30])[n:31]1[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[CH:39]([CH3:40])[CH3:41]>>... | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | null | null | N1=CC=CC=C1.C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NCc1nc2sncc2c(=O)n1Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]):[#7;a:13]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[#7;a:13] | null | [] | null | null | 2 | DAY | To a solution of the crude {3-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester (method 31) in pyridine (10 mL) at r.t., a solution of the p-toluoyl chloride (0.616 g, 4 mmol) in DCM (10 mL) was added dropwise and the resulting solutio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ncc2cnsc2n1.c1ccccc1 | HCl | N1=CC=CC=C1.C(Cl)Cl | null | 48 | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>N1=CC=CC=C1.C(Cl)Cl>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f8306cfc3fd4915a6ed4a52ebd8f881 | Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12.O.[N-]=[N+]=[N-]>>Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)NCCC2OCCO2.[N-]=[N+]=[N-].[Na+].O>>N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2 | C(CC1OCCO1)N[CH:8]([c:7]1[n:6][c:5]2s[n:3][c:2]([CH3:1])[c:25]2[c:23](=[O:24])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:12]([CH3:13])[CH3:14].[OH2:4].[N-:9]=[N+:10]=[N-:11]>>[CH3:1][c:2]1[n:3][o:4][c:5]2[n:6][c:7]([CH:8]([N:9]=[N+:10]=[N-:11])[CH:12]([CH3:13])[CH3:14])[n:15]([CH2:16][c:17]3[cH:18][... | Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12.O.[N-]=[N+]=[N-] | Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | f69cda4bba70054f8666ea6627d6b4e759987d043a8a6195e1360f88ea426f8d | 3c77b00162143582a3f0164369533237f9320d6d62e453e25486ff46e36eeb43 | O=c1c2cnoc2ncn1Cc1ccccc1 | [C:1]-[#7;a:2]1:[c:3](=[O;D1;H0:4]):[c:5]2:[c:6](-[C;D1;H3:7]):[n;H0;D2;+0:8]:s:[c;H0;D3;+0:9]:2:[#7;a:10]:[c:11]:1-[CH;D3;+0:12](-N-C-C-C1-O-C-C-O-1)-[C:13](-[C;D1;H3:14])-[C;D1;H3:15].[N-;H0;D1:16]=[#7;+:17]=[N;-;D1;H0:18].[OH2;D0;+0:19]>>[C:1]-[#7;a:2]1:[c:3](=[O;D1;H0:4]):[c:5]2:[c:6](-[C;D1;H3:7]):[n;H0;D2;+0:8]:[... | null | [] | 60 | CELSIUS | 1 | HOUR | A suspension of 5-benzyl-6-(1-bromo-2-methyl-propyl)-3-methyl-5H-isoxazolo[5,4-d]pyramidin-4-one (method 44) (100 mg, 0.266 mmol) and sodium azide (34.5 mg, 0.53 mmol) in DMF (2 ml) was stirred at 60° C. for 1 h. Water (5 ml) was added to the mixture and then extracted with EtOAc (3×20 ml). The combined organic phases ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amine | Azide | C1COCO1.c1ncc2cnsc2n1 | c1ncc2cnoc2n1 | c1ncc2cnoc2n1.c1ccccc1 | Other | CN(C)C=O | 60 | 1 | Cc1nsc2nc(C(NCCC3OCCO3)C(C)C)n(Cc3ccccc3)c(=O)c12.O.[N-]=[N+]=[N-]>CN(C)C=O>Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-73ed0a4d46be4f99a4aa48ca69ccae37 | Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1noc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | O.N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O>>NC(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2 | [N-]=[N+]=[N:9][CH:8]([c:7]1[n:6][c:5]2[o:4][n:3][c:2]([CH3:1])[c:23]2[c:21](=[O:22])[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH:10]([CH3:11])[CH3:12]>>[CH3:1][c:2]1[n:3][o:4][c:5]2[n:6][c:7]([CH:8]([NH2:9])[CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[... | Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1noc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=c1c2cnoc2ncn1Cc1ccccc1 | [#7;a:1]:[c:2](-[C:3](-[C:4])-[N;H0;D2;+0:5]=[N+]=[N-]):[#7;a:6]>>[#7;a:1]:[c:2](-[C:3](-[C:4])-[NH2;D1;+0:5]):[#7;a:6] | 68 | [{"value": 68.0, "product": "NC(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.2, "product": "NC(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 5 | HOUR | A mixture of 6-(1-azido-2-methyl-propyl)-5-benzyl-3-methyl-5H-isoxazolo[5,4-d]pyrimidin-4-one (method 45) (40 mg, 1.118 mmol), triphenylphosphine (62 mg, 0.237 mmol) and water (4 μl) in THF was stirred at 60° C. for 5 hours. Excess amount of water (30 μl) was added to the mixture and stirred at 60° C. for another 10 ho... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ncc2cnoc2n1.c1ccccc1 | Other | C1CCOC1 | 60 | 5 | Cc1noc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>C1CCOC1>Cc1noc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-272b205fc5b044419958ff01abad37a8 | Cc1ccc(C(=O)Cl)cc1.Cc1noc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | C(C)N(CC)CC.C(C)(C)(C)OC(NCCCNC(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2)=O.C1(=CC=C(C=C1)C(=O)Cl)C>>C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2)=O | Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:43][cH:42]1)=[O:7].[NH:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([c:21]1[n:22][c:23]2[o:24][n:25][c:26]([CH3:27])[c:28]2[c:29](=[O:30])[n:31]1[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[CH:39]([CH3:40])[CH3:41]>>... | Cc1ccc(C(=O)Cl)cc1.Cc1noc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NCc1nc2oncc2c(=O)n1Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]):[#7;a:13]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[#7;a:13] | 92 | [{"value": 92.0, "product": "C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | 2 | DAY | A solution of {3-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester (method 47) (100 mg, 0.213 mmol) in DCM (4 ml) was added p-toluoyl chloride (66 mg, 0.426 mmol) followed by triethylamine (65 mg, 0.639 mmol). The mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ncc2cnoc2n1.c1ccccc1 | HCl | C(Cl)Cl | 35 | 48 | Cc1ccc(C(=O)Cl)cc1.Cc1noc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>C(Cl)Cl>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-239c1fdacc4546d59960acf2916b05d9 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1>>Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1.Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2)=O.Cl>>NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2.Cl.NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)ON=C2C)=O)CC2=CC=CC=C2 | [CH3:1][C:2]([O:53][C:42]([NH:12][CH2:45][CH2:46][CH2:9][N:8]([C:6]([c:5]1[cH:4][cH:3][c:38]([CH3:37])[cH:72][cH:35]1)=[O:7])[CH:13]([c:14]1[n:15][c:16]2[o:17][n:18][c:19]([CH3:20])[c:21]2[c:22](=[O:23])[n:24]1[CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[CH:32]([CH3:33])[CH3:34])=[O:43])([CH3:66])[CH3:71]>>[CH3... | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1.Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | Hydrogenolysis of amides/imides/carbamates | bc1dc48e296874df6c1c89defbd9eda1ae57b80a51acd54c12768411d609e565 | 045af7475309100db10da2bb514795044fde65573933b6705b6119ac22dc425f | O=C(NCc1nc2oncc2c(=O)n1Cc1ccccc1)c1ccccc1.O=C(NCc1nc2oncc2c(=O)n1Cc1ccccc1)c1ccccc1 | [C:1]-[#7:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[CH3;D1;+0:12])-[CH3;D1;+0:13])-[C:14](=[O;D1;H0:15])-[c:16]1:[c:17]:[cH;D2;+0:18]:[c;H0;D3;+0:19](-[C;D1;H3:20]):[cH;D2;+0:21]:[cH;D2;+0:22]:1>>[#7;a:23]:[c:24]1:[c:25]:[c:26... | null | [] | null | null | null | null | A solution of {3-[[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-2-methyl-propyl]-(4-methyl-benzoyl)-amino]-propyl}-carbamic acid tert-butyl ester (method 48) (0.058 g, 0.1 mmol) in 3 ml of 4 M HCl in dioxane was stirred at room temperature for 2 hr. The solvent was distilled off by vacuo, the ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Tertiary amide.Primary amine.Primary amine | c1ccccc1 | c1ccccc1.c1ccccc1.c1ncc2cnoc2n1.c1ccccc1 | c1ccccc1.c1ncc2cnoc2n1.c1ccccc1.c1ccccc1.c1ncc2cnoc2n1.c1ccccc1 | Other | O1CCOCC1 | null | null | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1>O1CCOCC1>Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1.Cc1ccc(C(=O)N(CCCN)C(c2nc3onc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-727584dd7ec24f73a180017f95f08213 | CCOC(=O)C(C=S)=C(C)N>>CCOC(=O)c1csnc1C | C(C)OC(C(=C(C)N)C=S)=O.ClC1=CC(=CC=C1)C(=O)OO>>C(C)OC(=O)C=1C(=NSC1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH:7]=[S:8])=[C:10]([NH2:9])[CH3:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][s:8][n:9][c:10]1[CH3:11] | CCOC(=O)C(C=S)=C(C)N | CCOC(=O)c1csnc1C | null | null | CCOCC.C(C)O | Aromatic Heterocycle Formation | OtherReaction | cbfe844c86d12b325c976583963f58c71fcd7dff8396a8fc490f21155142c53b | 3ebb2c140ea2b2324e5f01ef7711e5dce466dc00bf3ced4f040548cc270eb4a6 | c1cnsc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](-[CH;D2;+0:6]=[S;H0;D1;+0:7])=[C;H0;D3;+0:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[s;H0;D2;+0:7]:[n;H0;D2;+0:10]:[c;H0;D3;+0:8]:1-[C;D1;H3:9] | null | [] | null | null | null | null | To a solution of 3-amino-2-thioformyl-but-2-enoic acid ethyl ester (method 52) (25.6 g, 147 mmol) in ethanol (300 mL), was added m-chloroperbenzoic acid (33.3 g, 77%, 149 mmol) in ethanol (200 mL) dropwise with stirring at room temperature. After the completion of the addition the reaction mixture was heated at 75° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester | Ester | null | c1cnsc1 | c1cnsc1 | null | CCOCC.C(C)O | null | null | CCOC(=O)C(C=S)=C(C)N>CCOCC.C(C)O>CCOC(=O)c1csnc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c63aa08483ae457c896a51b59577395c | CCOC(=O)c1csnc1C>>Cc1nscc1C(=O)O | C(C)OC(=O)C=1C(=NSC1)C.C1CCOC1.Cl>>CC1=NSC=C1C(=O)O | CC[O:9][C:7]([c:6]1[c:2]([CH3:1])[n:3][s:4][cH:5]1)=[O:8]>>[CH3:1][c:2]1[n:3][s:4][cH:5][c:6]1[C:7](=[O:8])[OH:9] | CCOC(=O)c1csnc1C | Cc1nscc1C(=O)O | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cnsc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[#16;a:7]:[c:8]:1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[#7;a:6]:[#16;a:7]:[c:8]:1 | null | [] | null | null | 16 | HOUR | To a solution of 3-methyl-isothiazole-4-carboxylic acid ethyl ester (method 53) (23.3 g, 136 mmol) in THF (200 mL) aqueous NaOH (6.5 g, 162 mmol, in 100 ml of water) was added and the mixture was stirred at room temperature for 16 h. The TLC of the reaction mixture showed the complete disappearance of the starting mate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnsc1 | Other | null | null | 16 | CCOC(=O)c1csnc1C>>Cc1nscc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31c4b79aa6ad465ca0f7eded1be3fab2 | Cc1nscc1NC(=O)OC(C)(C)C.O=C=O>>Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C | C(=O)=O.C(C)(C)(C)OC(NC=1C(=NSC1)C)=O.[Li+].CC(C)[N-]C(C)C>>C(C)(C)(C)OC(=O)NC=1C(=NSC1C(=O)O)C | [CH3:1][c:2]1[n:3][s:4][cH:5][c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17].[C:6](=[O:7])=[O:8]>>[CH3:1][c:2]1[n:3][s:4][c:5]([C:6](=[O:7])[OH:8])[c:9]1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17] | Cc1nscc1NC(=O)OC(C)(C)C.O=C=O | Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C | null | null | C1CCOC1 | Acylation | OtherReaction | e408f453a685b3d5cc4d656aa36f3a0ee5c294639e560b50d74fa3e5887262bf | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1cnsc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9]1:[cH;D2;+0:10]:[#16;a:11]:[#7;a:12]:[c:13]:1-[C;D1;H3:14].[O;D1;H0:15]=[C;H0;D2;+0:16]=[O;H0;D1;+0:17]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9]1:[c:13](-[C;D1;H3:14]):[#7;a:12]:[#16;a:11]:... | null | [] | null | null | 3 | HOUR | To a solution of (3-methyl-isothiazol-4-yl)-carbamic acid tert-butyl ester (method 55) (21.4 g, 100 mmol) in anhydrous THF (200 mL) at -78° C., LDA (139 mL, 1.8 M solution, 250 mmol) was added dropwise over a period of 1 h. The reaction mixture was stirred at that temperature for a further 3 h after which powdered dry ... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1cnsc1 | c1cnsc1 | c1cnsc1 | null | C1CCOC1 | null | 3 | Cc1nscc1NC(=O)OC(C)(C)C.O=C=O>C1CCOC1>Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7dc112e99194e489a6f48d4466c973a | Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C>>Cc1nsc(C(=O)O)c1N | C(C)(C)(C)OC(=O)NC=1C(=NSC1C(=O)O)C.O1CCOCC1>>NC=1C(=NSC1C(=O)O)C | CC(C)(C)OC(=O)[NH:10][c:9]1[c:2]([CH3:1])[n:3][s:4][c:5]1[C:6](=[O:7])[OH:8]>>[CH3:1][c:2]1[n:3][s:4][c:5]([C:6](=[O:7])[OH:8])[c:9]1[NH2:10] | Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C | Cc1nsc(C(=O)O)c1N | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cnsc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#16;a:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C;D1;H3:4]-[c:3]1:[#7;a:5]:[#16;a:6]:[c:7](-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | 8 | HOUR | 4-tert-Butoxycarbonylamino-3-methyl-isothiazole-5-carboxylic acid (method 56) (11 g, 45 mmol) was dissolved in 50 mL of 4M solution of HCl in 1,4-dioxane (200 mmol) and the resulting solution was stirred at room temperature overnight. The TLC showed the complete disappearance of the starting acid. The reaction was conc... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cnsc1 | HO- | Cl | null | 8 | Cc1nsc(C(=O)O)c1NC(=O)OC(C)(C)C>Cl>Cc1nsc(C(=O)O)c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b91ab75ac094a7e9ecc0cda3af0ec4a | CCCC(=O)Cl.Cc1nsc(C(=O)O)c1N>>CCCc1nc2c(C)nsc2c(=O)o1 | NC=1C(=NSC1C(=O)O)C.C(CCC)(=O)Cl.Cl>>CC1=NSC2=C1N=C(OC2=O)CCC | O=[C:4](Cl)[CH2:3][CH2:2][CH3:1].[NH2:5][c:6]1[c:7]([CH3:8])[n:9][s:10][c:11]1[C:12](=[O:13])[OH:14]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([CH3:8])[n:9][s:10][c:11]2[c:12](=[O:13])[o:14]1 | CCCC(=O)Cl.Cc1nsc(C(=O)O)c1N | CCCc1nc2c(C)nsc2c(=O)o1 | null | null | N1=CC=CC=C1.C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 902426b4a088e8343aba1423cc20d4a47a5cd397344dc05ed2244c46cf688361 | bd3eed28c8485f0d5a54b9572c189e3c1ddb148eaacd326cd875cdab2e64ffc8 | O=c1ocnc2cnsc12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[#16;a:7]:[c:8](-[C;H0;D3;+0:9](=[O;D1;H0:10])-[OH;D1;+0:11]):[c:12]:1-[NH2;D1;+0:13]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:8](:[#16;a:7]:[#7;a:6]:[c:5]:2-[C;D1;H3:4]):[c;H0;D3;+0:9](=[O;D1;H0:10]):[o;H0;D2;+0:11]:1 | null | [] | null | null | 8 | HOUR | To a solution of 4-amino-3-methyl-isothiazole-5-carboxylic acid (method 57) (2.91 g, 15 mmol) in pyridine (20 mL) at 0° C., was added dropwise a solution of butyryl chloride (3.18 g, 30 mmol) in chloroform (30 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. Chloroform (200 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Primary amine | null | c1cnsc1 | c1nc2c[nH]sc2co1 | c1nc2c[nH]sc2co1 | HCl | N1=CC=CC=C1.C(Cl)(Cl)Cl | null | 8 | CCCC(=O)Cl.Cc1nsc(C(=O)O)c1N>N1=CC=CC=C1.C(Cl)(Cl)Cl>CCCc1nc2c(C)nsc2c(=O)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ff559a3b35b48078af70975912cd821 | CCCc1nc2c(C)nsc2c(=O)o1.NCc1ccccc1>>CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1 | CC1=NSC2=C1N=C(OC2=O)CCC.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)SN=C2C)CCC | o1[c:4]([CH2:3][CH2:2][CH3:1])[n:5][c:6]2[c:7]([CH3:8])[n:9][s:10][c:11]2[c:12]1=[O:13].[NH2:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([CH3:8])[n:9][s:10][c:11]2[c:12](=[O:13])[n:14]1[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CCCc1nc2c(C)nsc2c(=O)o1.NCc1ccccc1 | CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1 | null | null | Cl | Miscellaneous | OtherReaction | 975417f11e5c9dec4372f5fce1716395b75449a73ad73960e0ceff3588a6ab5f | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1c2sncc2ncn1Cc1ccccc1 | [C:1]-[C:2]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#16;a:8]:[c:9]:2:[c;H0;D3;+0:10](=[O;D1;H0:11]):o:1.[NH2;D1;+0:12]-[C:13]-[c:14]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[#16;a:8]:[c:9]:2:[c;H0;D3;+0:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]:1-[C:13]-[c:14] | null | [] | 200 | CELSIUS | null | null | 3-Methyl-5-propyl-isothiazolo[4,5-d][1,3]oxazin-7-one (method 58) (200 mg, 1.02 mmol) was taken in a 10 mL microwavable pyrex tube and benzyl amine (1 g, 9.34 mmol) was added to it. The resulting mixture was heated in a microwave synthesizer (CEM's Discoverer) at 200° C. for 20 min. The MS of the reaction mixture showe... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nc2c[nH]sc2co1 | c1ncc2sncc2n1 | c1ncc2sncc2n1.c1ccccc1 | HO- | Cl | 200 | null | CCCc1nc2c(C)nsc2c(=O)o1.NCc1ccccc1>Cl>CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b91fbfc67a7046248cef5aad38afdbce | BrBr.CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1>>CCC(Br)c1nc2c(C)nsc2c(=O)n1Cc1ccccc1 | CCOC(=O)C.C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)SN=C2C)CCC.C(C)(=O)[O-].[Na+].BrBr.BrBr>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)SN=C2C)C(CC)Br | Br[Br:4].[CH3:1][CH2:2][CH2:3][c:5]1[n:6][c:7]2[c:8]([CH3:9])[n:10][s:11][c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][CH:3]([Br:4])[c:5]1[n:6][c:7]2[c:8]([CH3:9])[n:10][s:11][c:12]2[c:13](=[O:14])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | BrBr.CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1 | CCC(Br)c1nc2c(C)nsc2c(=O)n1Cc1ccccc1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=c1c2sncc2ncn1Cc1ccccc1 | Br-[Br;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[c:5]2:[#16;a:6]:[#7;a:7]:[c:8]:[c:9]:2:[#7;a:10]:[c:11]:1-[CH2;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[Br;H0;D1;+0:1]-[CH;D3;+0:12](-[C:13]-[C;D1;H3:14])-[c:11]1:[#7;a:10]:[c:9]2:[c:8]:[#7;a:7]:[#16;a:6]:[c:5]:2:[c:4]:[#7;a:3]:1-[C:2] | null | [] | null | null | null | null | To a solution of 6-benzyl-3-methyl-5-propyl-6H-isothiazolo[4,5-d]pyrimidin-7-one (method 59) (208 mg, 0.69 mmol) and sodium acetate (0.5 g, 5 mmol) in acetic acid (10 mL) at 100° C., a solution of the bromine (0.232 g, 1.46 mmol) in acetic acid (20 mL) was added dropwise [The next drop of Bromine was added only after t... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ncc2sncc2n1.c1ccccc1 | HBr | C(C)(=O)O | null | null | BrBr.CCCc1nc2c(C)nsc2c(=O)n1Cc1ccccc1>C(C)(=O)O>CCC(Br)c1nc2c(C)nsc2c(=O)n1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9695923ea33e43519c2b89140c8818ca | CCOC(C)(OCC)OCC.N#CCC#N>>CCOC(C)=C(C#N)C#N | C(C)(OCC)(OCC)OCC.C(CC#N)#N.C(C)(=O)O>>C(C)OC(C)=C(C#N)C#N | CCO[C:4](OCC)([O:3][CH2:2][CH3:1])[CH3:5].[CH2:6]([C:7]#[N:8])[C:9]#[N:10]>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])=[C:6]([C:7]#[N:8])[C:9]#[N:10] | CCOC(C)(OCC)OCC.N#CCC#N | CCOC(C)=C(C#N)C#N | null | null | C(C)O | C-C Coupling | OtherReaction | 9d0000e86d6f33b615f7919c1f0221440b9043cbb7b3d0af049d5d091c34f404 | fd4a9f4582a23be02b9aaad230da234fe33873302a3bdf8caf1a8217cd2fc678 | null | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-[#8:3]-[C:4].[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])-[C:6]#[N;D1;H0:5] | 94.5 | [{"value": 94.0, "product": "C(C)OC(C)=C(C#N)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "C(C)OC(C)=C(C#N)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Triethyl orthoacetate (1.6 L, 9 mol), malononitrile (500 g, 7.57 mol) and glacial acetic acid (25 ml) were placed in a 5 l RB flask equipped with a stirrer, thermometer and a Vigreux column (20×1 in.) on top of which a distillation condenser was placed. The reaction mixture was heated and ethyl alcohol began to distil ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether | Ether | null | null | null | HO- | C(C)O | null | 3 | CCOC(C)(OCC)OCC.N#CCC#N>C(C)O>CCOC(C)=C(C#N)C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05d72e07370d4e7799255439f0253d79 | CCO/C(C)=C(\C#N)C(N)=S.N>>C/C(N)=C(/C#N)C(N)=S | C(#N)/C(/C(N)=S)=C(/C)\OCC.N>>N/C(=C(/C(N)=S)\C#N)/C | CCO/[C:2]([CH3:1])=[C:4](\[C:5]#[N:6])[C:7]([NH2:8])=[S:9].[NH3:3]>>[CH3:1]/[C:2]([NH2:3])=[C:4](/[C:5]#[N:6])[C:7]([NH2:8])=[S:9] | CCO/C(C)=C(\C#N)C(N)=S.N | C/C(N)=C(/C#N)C(N)=S | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5132028908218d0a570eb2b2ac493e42e1a216124294e5ff728b2eb927eef034 | f4d71ded74a56725823fcbb2ae78f980194bc0045e19b1491967e395a5e29d8c | null | C-C-O/[C;H0;D3;+0:1](-[C;D1;H3:2])=[C:3](\[C:4]#[N;D1;H0:5])-[C:6](-[N;D1;H2:7])=[S;D1;H0:8].[NH3;D0;+0:9]>>[C;D1;H3:2]/[C;H0;D3;+0:1](-[NH2;D1;+0:9])=[C:3](/[C:4]#[N;D1;H0:5])-[C:6](-[N;D1;H2:7])=[S;D1;H0:8] | 89 | [{"value": 89.0, "product": "N/C(=C(/C(N)=S)\\C#N)/C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (2E)-2-Cyano-3-ethoxybut-2-enethioamide (method 2) (150 g, 0.88 mol) was dissolved in 7M solution of ammonia in methanol (2.9 L) and stirred at r.t. overnight. The reaction mixture was concentrated and the residue was crystallized from hot water (1. L) to provide (2E)-3-amino-2-cyanobut-2-enethioamide (111.6 g, 89%) as... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Enamine | null | null | null | HO- | CO | null | 8 | CCO/C(C)=C(\C#N)C(N)=S.N>CO>C/C(N)=C(/C#N)C(N)=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8387002c57c4f798a8f130b75631399 | C/C(N)=C(/C#N)C(N)=S>>Cc1nsc(N)c1C#N | N/C(=C(/C(N)=S)\C#N)/C.OO>>NC1=C(C(=NS1)C)C#N | [CH3:1]/[C:2]([NH2:3])=[C:7](\[C:5](=[S:4])[NH2:6])[C:8]#[N:9]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:7]1[C:8]#[N:9] | C/C(N)=C(/C#N)C(N)=S | Cc1nsc(N)c1C#N | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 53973ab0cc444428b63bf8e333f084965288c268c6e3344b0072e9468e2d332e | df818a125b449aa80d1964ad752d90e7bc820054c3a49c48866fa5bae4094f85 | c1cnsc1 | [C;D1;H3:1]/[C;H0;D3;+0:2](-[NH2;D1;+0:3])=[C;H0;D3;+0:4](/[C:5]#[N;D1;H0:6])-[C;H0;D3;+0:7](-[N;D1;H2:8])=[S;H0;D1;+0:9]>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[s;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[c;H0;D3;+0:4]:1-[C:5]#[N;D1;H0:6] | 97.3 | [{"value": 96.0, "product": "NC1=C(C(=NS1)C)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "NC1=C(C(=NS1)C)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a stirred solution of (2E)-3-amino-2-cyanobut-2-enethioamide (method 3) (111 g, 0.78 mol) in methanol (2 L) was added dropwise 200 ml of 35% hydrogen peroxide over a period of 30 min. After the completion of the addition the mixture was stirred at 60° C. for 3 h after which the TLC showed the completion of the react... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Thioamide | null | null | c1cnsc1 | c1cnsc1 | null | CO | 60 | 3 | C/C(N)=C(/C#N)C(N)=S>CO>Cc1nsc(N)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c892cb4f85d94013a7c726f78c32171d | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N>>Cc1nsc(NC(=O)CC(C)C)c1C#N | NC1=C(C(=NS1)C)C#N.C(CC(C)C)(=O)Cl>>C(#N)C=1C(=NSC1NC(CC(C)C)=O)C | Cl[C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12].[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:13]1[C:14]#[N:15]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH:6][C:7](=[O:8])[CH2:9][CH:10]([CH3:11])[CH3:12])[c:13]1[C:14]#[N:15] | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N | Cc1nsc(NC(=O)CC(C)C)c1C#N | null | null | N1=CC=CC=C1.C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cnsc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[#7;a:8]:[c:9]:[c:10]:1 | 88.2 | [{"value": 88.0, "product": "C(#N)C=1C(=NSC1NC(CC(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "C(#N)C=1C(=NSC1NC(CC(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (105.6 g, 0.76 mol) in pyridine (250 ml) at 0° C., isovaleryl chloride (100 g, 0.83 mol) in chloroform (300 ml) was added dropwise. After the completion of the addition the reaction mixture was allowed to warm to r.t. and stirred overnight. The TLC ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnsc1 | HCl | N1=CC=CC=C1.C(Cl)(Cl)Cl | null | 8 | CC(C)CC(=O)Cl.Cc1nsc(N)c1C#N>N1=CC=CC=C1.C(Cl)(Cl)Cl>Cc1nsc(NC(=O)CC(C)C)c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1ca5c8115cc43c8aacefbb9bbb0407f | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O>>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | CC1=NSC(=C1C(=O)N)NC(CC(C)C)=O.Cl>>C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O | O=[C:7]([NH:6][c:5]1[s:4][n:3][c:2]([CH3:1])[c:15]1[C:13]([NH2:12])=[O:14])[CH2:8][CH:9]([CH3:10])[CH3:11]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:13](=[O:14])[c:15]12 | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O | Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | null | null | N | Aromatic Heterocycle Formation | OtherReaction | 949006d8c772b36f999683041f038f05b089c287074275bc26b8515cb4d0af67 | 9d5aef0cada2072f52eb60b6996e8c9e376baa92104aa4e87786338b6493e605 | O=c1[nH]cnc2sncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[#16;a:6]:[#7;a:7]:[c:8](-[C;D1;H3:9]):[c:10]:2:[c;H0;D3;+0:11](=[O;D1;H0:13]):[nH;D2;+0:12]:1 | 26 | [{"value": 26.0, "product": "C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.9, "product": "C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | The 3-methyl-5-(3-methyl-butyrylamino)-isothiazole-4-carboxylic acid amide (method 25) (45.8 g, 190 mmol) was suspended in 700 ml of 30% NH3 and then was heated to 140° C. for 5 h in a pressure reactor. The mixture was poured into a 4 L beaker and cooled in an ice bath. To the cold solution con HCl (560 ml) was added d... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | null | c1cnsc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | HO- | N | 140 | null | Cc1nsc(NC(=O)CC(C)C)c1C(N)=O>N>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e08fb2cf7f6d41a0a3fa572f3e25be05 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12>>Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | C(C1=CC=CC=C1)Br.C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CC(C)C | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:20](=[O:21])[c:22]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[n:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20](=[O:21])[c:22]12 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 489c04ab50559560a149376d4f33f86b7dd628ef17c4a055bc399e6f8281e8e6 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8]2:[#16;a:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 8 | HOUR | To a solution of the 6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 26) (11 g, 49 mmol) in 60 ml of anhydrous DMF at 0° C., was added 13.8 g (100 mmol) of anhydrous K2CO3 followed by benzyl bromide (9.3 g, 54 mmol) and the mixture was stirred at 0-20° C. overnight. The TLC of the reaction mixture show... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1.c1ccccc1 | HBr | CN(C)C=O | 10 | 8 | BrCc1ccccc1.Cc1nsc2nc(CC(C)C)[nH]c(=O)c12>CN(C)C=O>Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6605a993f30949919462471c05ae8a0c | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 | C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)CC(C)C.C(C)(=O)[O-].[Na+].BrBr.CCOC(=O)C>>C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br | Br[Br:9].[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[O:22])[c:23]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([Br:9])[CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[O:22])... | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | fb976bf1eab8c62577a847af299a41a3ccb21dd6033b1d12da0fc75ebe4f95a0 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH2;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]):[#7;a:11](-[C:12]):[c:13]>>[#7;a:2]:[#16;a:3]:[c:4]:[#7;a:5]:[c:6](-[CH;D3;+0:7](-[Br;H0;D1;+0:1])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10]):[#7;a:11](-[C:12]):[c:13] | 100.2 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.2, "product": "C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-benzyl-6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 27) (5.81 g, 18.5 mmol) and sodium acetate (10 g) in acetic acid (100 ml) at 100° C., a solution of the bromine (6 g, 38 mmol) in acetic acid (60 ml) was added dropwise over a period of 20 minutes. The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | null | null | c1ncc2cnsc2n1.c1ccccc1 | HBr | C(C)(=O)O | null | 0.5 | BrBr.Cc1nsc2nc(CC(C)C)n(Cc3ccccc3)c(=O)c12>C(C)(=O)O>Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3f8d3d6443a45bd8329349f7662a4e5 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-]>>Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | [Br-].C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C(=NS2)C)C(C(C)C)Br.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2 | Br[CH:8]([c:7]1[n:6][c:5]2[s:4][n:3][c:2]([CH3:1])[c:25]2[c:23](=[O:24])[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH:12]([CH3:13])[CH3:14].[N-:9]=[N+:10]=[N-:11]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([N:9]=[N+:10]=[N-:11])[CH:12]([CH3:13])[CH3:14])[n:15]([CH2:16][c:17]3[cH:18][cH:19][cH:20][... | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-] | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 6463ff1d29bf5113d76baa7212c34a105b5cabf370ebc2d8763f73a63584c2da | 5dc52e0dd157494eb8237d0e03fb32787b3b51b4d3f04e5bbbe4fdfe5a135995 | O=c1c2cnsc2ncn1Cc1ccccc1 | Br-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:5](:[#7;a:6]:[c:7]:[#16;a:8]:[#7;a:9]):[#7;a:10](-[C:11]):[c:12].[N-;H0;D1:13]=[#7;+:14]=[N;-;D1;H0:15]>>[#7;a:9]:[#16;a:8]:[c:7]:[#7;a:6]:[c:5](-[CH;D3;+0:1](-[N;H0;D2;+0:13]=[#7;+:14]=[N;-;D1;H0:15])-[C:2](-[C;D1;H3:3])-[C;D1;H3:4]):[#7;a:10](-[C:11]):[c:12] | 94 | [{"value": 94.0, "product": "N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-benzyl-6-(1-bromo-2-methyl-propyl)-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 28) (7.27 g, 18.5 mmol) in anhydrous DMF (60 ml), sodium azide (2.33 g, 37 mmol) was added and the mixture was stirred at room temperature for 2 hour. The TLC of the RM showed the complete disappearance of the st... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | Azide | null | null | c1ncc2cnsc2n1.c1ccccc1 | Br- | CN(C)C=O | null | 2 | Cc1nsc2nc(C(Br)C(C)C)n(Cc3ccccc3)c(=O)c12.[N-]=[N+]=[N-]>CN(C)C=O>Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-148c9e5d6a564c5abd1dfa5e526de3ab | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | N(=[N+]=[N-])C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2>>NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2 | [N-]=[N+]=[N:9][CH:8]([c:7]1[n:6][c:5]2[s:4][n:3][c:2]([CH3:1])[c:23]2[c:21](=[O:22])[n:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH:10]([CH3:11])[CH3:12]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH2:9])[CH:10]([CH3:11])[CH3:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21](=[... | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | [Pd] | CO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=c1c2cnsc2ncn1Cc1ccccc1 | [#7;a:1]:[c:2](-[C:3](-[C:4])-[N;H0;D2;+0:5]=[N+]=[N-]):[#7;a:6]>>[#7;a:1]:[c:2](-[C:3](-[C:4])-[NH2;D1;+0:5]):[#7;a:6] | 86 | [{"value": 86.0, "product": "NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(1-azido-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 29) (6.8 g, 19.2 mmol) in methanol (400 ml) was added 5% Pd/C (1 g, 20% by wt.) and the resulting mixture was stirred at r.t. in an atmosphere of H2 and the progress of the reaction was monitored by MS. After the... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ncc2cnsc2n1.c1ccccc1 | Other | [Pd].CO | null | null | Cc1nsc2nc(C(N=[N+]=[N-])C(C)C)n(Cc3ccccc3)c(=O)c12>[Pd].CO>Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f372935c6bc4a57ae60e08e9fb13d0a | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | C1(=CC=C(C=C1)C(=O)Cl)C.C(C)(C)(C)OC(NCCCNC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O.C(C)(C)N(CC)C(C)C>>C(C)(C)(C)OC(NCCCN(C(C1=CC=C(C=C1)C)=O)C(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O | Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:43][cH:42]1)=[O:7].[NH:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([c:21]1[n:22][c:23]2[s:24][n:25][c:26]([CH3:27])[c:28]2[c:29](=[O:30])[n:31]1[CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[CH:39]([CH3:40])[CH3:41]>>... | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NCc1nc2sncc2c(=O)n1Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]):[#7;a:13]>>[#7;a:6]:[c:7](-[C:8](-[C:9])-[N;H0;D3;+0:10](-[C:11]-[C:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[#7;a:13] | null | [] | 60 | CELSIUS | null | null | To a solution of {3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester obtained from method 31 alternative procedure above in chloroform (300 ml), diisopropylethylamine (6 g, 46.5 mmol) was added and the reaction mixture was heated to 6... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ncc2cnsc2n1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | 60 | null | Cc1ccc(C(=O)Cl)cc1.Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12>C(Cl)(Cl)Cl>Cc1ccc(C(=O)N(CCCNC(=O)OC(C)(C)C)C(c2nc3snc(C)c3c(=O)n2Cc2ccccc2)C(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0887a0e8931430f991311bcea63e31a | Cc1nsc(N)c1C#N.O=S(=O)(O)O>>Cc1nsc(N)c1C(N)=O | S(O)(O)(=O)=O.NC1=C(C(=NS1)C)C#N.N>>NC1=C(C(=NS1)C)C(=O)N | [CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:7]1[C:8]#[N:9].O=S(=O)(O)[OH:10]>>[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:7]1[C:8]([NH2:9])=[O:10] | Cc1nsc(N)c1C#N.O=S(=O)(O)O | Cc1nsc(N)c1C(N)=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1cnsc1 | O-S(=O)(=O)-[OH;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1-[C;H0;D2;+0:9]#[N;H0;D1;+0:10]>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[#16;a:5]:[c:6](-[N;D1;H2:7]):[c:8]:1-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[O;H0;D1;+0:1] | 80 | [{"value": 80.0, "product": "NC1=C(C(=NS1)C)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To a chilled solution of sulfuric acid (7.2 volumes, 12.9 equivs) was charged 5-amino-3-methylisothiazole-4-carbonitrile (method 4) (1.0 equiv). The temperature was maintained below 55° C. The reaction mixture was heated to 70° C. and held for 1 hour until TLC showed disappearance of starting material. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1cnsc1 | Other | null | 70 | 1 | Cc1nsc(N)c1C#N.O=S(=O)(O)O>>Cc1nsc(N)c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb0c0b8467484fba9b96596c5fbc15c7 | CC(C)CC=O.Cc1nsc(N)c1C(N)=O>>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | NC1=C(C(=NS1)C)C(=O)N.C1(=CC=C(C=C1)S(=O)(=O)O)C.CN(C)C=O.C(CC(C)C)=O>>C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O | O=[CH:7][CH2:8][CH:9]([CH3:10])[CH3:11].[CH3:1][c:2]1[n:3][s:4][c:5]([NH2:6])[c:15]1[C:13]([NH2:12])=[O:14]>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[nH:12][c:13](=[O:14])[c:15]12 | CC(C)CC=O.Cc1nsc(N)c1C(N)=O | Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | b0154a065c2391b669abb329e4685304f1ad2daab4a434ccc2a7821863226bec | ceb7d2be5fd3c53280bb210c67f3169c7e42474e161e9a018274901b7db7d3cf | O=c1[nH]cnc2sncc12 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[#16;a:7]:[c:8](-[NH2;D1;+0:9]):[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;D1;H0:13]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:9]:[c:8]2:[#16;a:7]:[#7;a:6]:[c:5](-[C;D1;H3:4]):[c:10]:2:[c;H0;D3;+0:11](=[O;D1;H0:13]):[nH;D2;+0:12]:1 | 89 | [{"value": 89.0, "product": "C(C(C)C)C=1NC(C2=C(N1)SN=C2C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 7 | HOUR | To a 2 L flask equipped with Dean Stark was charged 5-amino-3-methylisothiazole-4-carboxamide (method 63) (1 equiv), p-toluene sulphonic acid (0.049 equiv), DMF (9.75 volumes). The reaction was stirred until a solution was obtained and isovaleraldehyde (1.10 equiv) and toluene (4.9 volumes) were added. The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amide.Primary amine | null | c1cnsc1 | c1ncc2cnsc2n1 | c1ncc2cnsc2n1 | HO- | C1(=CC=CC=C1)C | 130 | 7 | CC(C)CC=O.Cc1nsc(N)c1C(N)=O>C1(=CC=CC=C1)C>Cc1nsc2nc(CC(C)C)[nH]c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91f07718005a4de5bb5eea1aa9bfbba0 | CCOC(CCNC(=O)OC(C)(C)C)OCC.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12>>Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 | C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)OC(CCN)OCC.C(C)(C)(C)OC(=O)OC(=O)OC(C)(C)C.C(C)OC(CCNC(OC(C)(C)C)=O)OCC.C(C)(=O)O[BH3-].[Na+].NC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2>>C(C)(C)(C)OC(NCCCNC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O | CCO[CH:10](OCC)[CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH2:9])[CH:21]([CH3:22])[CH3:23])[n:24]([CH2:25][c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[c:32](=[O:33])[c:34]12>>[CH3:1][c:2]1[n:3][s:4][c:5]2[n:6][c:7]([CH:8]([NH:9][CH2:10]... | CCOC(CCNC(=O)OC(C)(C)C)OCC.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12 | Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 | null | null | O.C(C)(=O)O.C1(=CC=CC=C1)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 195459a3df13b9f6a3ac9e95fa34f12215bcc175daa16d824f73efce6c4f3922 | c773bdbff86697879727fed205b521624504ab38dc50d7c1d7232a521281a6bb | O=c1c2cnsc2ncn1Cc1ccccc1 | C-C-O-[CH;D3;+0:1](-O-C-C)-[C:2]-[C:3].[#7;a:4]:[c:5](-[C:6](-[C:7])-[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:4]:[c:5](-[C:6](-[C:7])-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[#7;a:9] | 92 | [{"value": 92.0, "product": "C(C)(C)(C)OC(NCCCNC(C(C)C)C=1N(C(C2=C(N1)SN=C2C)=O)CC2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 0.5 | HOUR | To (3,3-diethoxypropyl)amine (1.00 equiv) in THF (2 volumes) was charged di-t-butyldicarbonate (1.05 equiv) in THF (3 volumes). The reaction was heated to 45° C. and held for ½ h. Analysis showed the disappearance of starting material, and the resulting solution was heated to 65° C. p-Toluene sulphonic acid (0.1 equiv)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | Secondary amine | null | null | c1ncc2cnsc2n1.c1ccccc1 | HO- | O.C(C)(=O)O.C1(=CC=CC=C1)C.C1CCOC1 | 45 | 0.5 | CCOC(CCNC(=O)OC(C)(C)C)OCC.Cc1nsc2nc(C(N)C(C)C)n(Cc3ccccc3)c(=O)c12>O.C(C)(=O)O.C1(=CC=CC=C1)C.C1CCOC1>Cc1nsc2nc(C(NCCCNC(=O)OC(C)(C)C)C(C)C)n(Cc3ccccc3)c(=O)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b0e308a0b52401a804fb50ad54449c9 | CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-]>>CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-] | CN(C)C1=CC=C(C=C1)C(=C2C=CC(=[N+](C)C)C=C2)C3=CC=CC=C3.[Cl-].C1CN(CCN1CCS(=O)(=O)O)CCS(=O)(=O)O.[OH-].[K+].P(O)(=O)(OP(=O)(O)OP(=O)(O)O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)O.[Mg+2].[Cl-].[Cl-].CN(C)C1=CC=C(C=C1)C(=C2C=CC(=[N+](C)C)C=C2)C3=CC=CC=C3.[Cl-].CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]... | CN(C)c1ccc(C(c2ccccc2)=[C:21]2[CH:20]=CC(=[N+](C)C)[CH:23]=[CH:22]2)cc1.c1cc[cH:19][c:18]([C:8]([c:7]2[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:25][cH:24]2)=[C:9]2[CH:10]=[CH:11][C:12](=[N+:13]([CH3:14])[CH3:15])[CH:16]=[CH:17]2)c1.[NH4+:27].[O-:29][Mo:30](=[O:31])([O-:32])=[O:33]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][c... | CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-] | CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-] | null | null | Cl.O.C(C(C)[*:2])[*:1] | Miscellaneous | OtherReaction | 23f6f20aaffaeed01450d5c182dd2c56dfbb11e4b7774b9e78eab872051ce3c0 | e0e88c13ed23bc13580ea72b7622523bab16ba5707a3942cafb26e1a1fd53aa9 | [N+]=C1C=CC(=C(c2ccccc2)c2ccccc2)C=C1 | C-N(-C)-c1:c:c:c(-C(=[C;H0;D3;+0:1]2-[CH;D2;+0:2]=C-C(=[N+](-C)-C)-[CH;D2;+0:3]=[CH;D2;+0:4]-2)-c2:c:c:c:c:c:2):c:c:1.[C:5]=[C:6]-[C:7](=[C:8](-[c:9])-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:c:c:c:c:1)-[C:12]=[C:13].[O-;H0;D1:14]-[Mo;H0;D4;+0:15](-[O;-;D1;H0:16])(=[O;D1;H0:17])=[O;H0;D1;+0:18]>>[C:5]=[C:6]-[C:7](=[C:8](-[c:9])-... | null | [] | null | null | 20 | MINUTE | Enzymatic activity of the Eg5 motor and effects of inhibitors was measured using a malachite green assay, which measures phosphate liberated from ATP, and has been used previously to measure the activity of kinesin motors (Hackney and Jiang, 2001). Enzyme was recombinant HsEg5 motor domain (amino acids 1-369-8His) and ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccccc1.c1ccccc1.C1=CCC=CC1.c1ccccc1 | c1ccccc1 | c1ccccc1.C1=CCC=CC1.c1ccccc1 | Other | Cl.O.C(C(C)[*:2])[*:1] | null | 0.333333 | CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-]>Cl.O.C(C(C)[*:2])[*:1]>CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.[NH4+].[O]=[Mo](=[O])([O-])[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47b79b56e0894c9aa8116ee58ca7f4d3 | C=Cc1ccccc1>>C=Cc1ccccc1 | P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-].C=CC1=CC=CC=C1.C(C=C)#N.CC(C)(C#N)N=NC(C)(C)C#N>>C=CC#N.C=CC1=CC=CC=C1 | [CH2:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=Cc1ccccc1 | C=Cc1ccccc1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | 71 parts of styrene, 29 parts of acrylonitrile, 120 parts of deionized water and 0.17 parts of azobisisobutylonitrile (AIBN) were mixed. To the blend, 0.5 parts of tricalciumphosphate and 0.4 parts of t-dodecyl mercaptan chain transfer agent were added. The resultant solution was suspension polymerized at 75° C. for 5 ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O | null | null | C=Cc1ccccc1>O>C=Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8afee5cf262241de8d877b4321071517 | C#Cc1cccc(N)c1.CCOP(=O)(CCBr)OCC>>C#Cc1cccc(NCCP(=O)(OCC)OCC)c1 | C(#C)C=1C=C(N)C=CC1.BrCCP(OCC)(OCC)=O.C([O-])([O-])=O.[K+].[K+]>>C(#C)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O | [CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:19]1.Br[CH2:9][CH2:10][P:11](=[O:12])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18]>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][CH2:9][CH2:10][P:11](=[O:12])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[cH:19]1 | C#Cc1cccc(N)c1.CCOP(=O)(CCBr)OCC | C#Cc1cccc(NCCP(=O)(OCC)OCC)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#15:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#15:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 7.2 | [{"value": 7.2, "product": "C(#C)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Ethynyl aniline (2.36 g, 22.1 mmol), diethyl 2-bromoethylphosphonate (5.41 g, 22.1 mmol) and potassium carbonate (3.1 gm, 22.1 mmol) were heated at 90° C. in anhydrous acetonitrile (40 mL) for 26 h. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HBr | C(C)#N | null | null | C#Cc1cccc(N)c1.CCOP(=O)(CCBr)OCC>C(C)#N>C#Cc1cccc(NCCP(=O)(OCC)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f1d4e2fd773458f8602059d2230dd49 | C#Cc1cccc(NCCP(=O)(OCC)OCC)c1.ON=C(Cl)c1c(Cl)cccc1Cl>>CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC | ClC1=C(C(=NO)Cl)C(=CC=C1)Cl.C(#C)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O.C(C)N(CC)CC>>ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]#[CH:15])[cH:27]1)[O:28][CH2:29][CH3:30].Cl[C:16]([c:17]1[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]1[Cl:24])=[N:25][OH:26]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][c:13](-[c:14]2[cH:15][... | C#Cc1cccc(NCCP(=O)(OCC)OCC)c1.ON=C(Cl)c1c(Cl)cccc1Cl | CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 0acd4387903ecef3644ca983a4d97270f147df71c89a735cfcdfe351f79b20db | c396d0116405f0fb9e31fa23799a4838037a90cc446bdd74768e7dde19fceca1 | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[OH;D1;+0:3])-[c;H0;D3;+0:4](:[c:5](-[Cl;D1;H0:6]):[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10].[CH;D1;+0:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[Cl;D1;H0:6]-[c:5](:[c:7]):[c;H0;D3;+0:4](-[c;H0;D3;+0:1]1:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[... | 89.2 | [{"value": 89.2, "product": "ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,6-Dichloro-N-hydroxybenzimidoyl chloride (370 mg, 1.6 mmol) and diethyl 2-(3-ethynylphenylamino)ethylphosphonate (450 mg, 1.6 mmol) were dissolved in anhydrous tetrahydrofuran (40 mL) and triethylamine (0.30 mL, 1.6 mmol). The mixture was then heated at reflux for 5 h. The reaction was cooled to room temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkyne.Oxime | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | HCl | O1CCCC1 | null | null | C#Cc1cccc(NCCP(=O)(OCC)OCC)c1.ON=C(Cl)c1c(Cl)cccc1Cl>O1CCCC1>CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3c5b0ff62ce4d4fa218b3393f7980d0 | CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC.O=C(Cl)C(Cl)Cl>>CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC | ClC(C(=O)Cl)Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NCCP(OCC)(OCC)=O.C(C)N(CC)CC>>ClC(C(=O)N(C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCP(OCC)(OCC)=O)Cl | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][NH:8][c:14]1[cH:15][cH:16][cH:17][c:18](-[c:19]2[cH:20][c:21](-[c:22]3[c:23]([Cl:24])[cH:25][cH:26][cH:27][c:28]3[Cl:29])[n:30][o:31]2)[cH:32]1)[O:33][CH2:34][CH3:35].Cl[C:9](=[O:10])[CH:11]([Cl:12])[Cl:13]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][CH2:7][N:8]([C:9](=[O:1... | CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC.O=C(Cl)C(Cl)Cl | CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC | null | null | ClCCl.C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 8 | HOUR | Diethyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylphosphonate (660 mg, 1.4 mmol) was dissolved in anhydrous methylene chloride (10 mL) with triethylamine (0.28 mL, 1.7 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (161 μL, 1.7 mmol) in anhydrous... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | HCl | ClCCl.C(Cl)Cl | null | 8 | CCOP(=O)(CCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC.O=C(Cl)C(Cl)Cl>ClCCl.C(Cl)Cl>CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f52de335c6ce4011aaf0caf825dbf36c | CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC>>O=C(C(Cl)Cl)N(CCP(=O)(O)O)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)N(C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCP(OCC)(OCC)=O)Cl.Br[Si](C)(C)C>>ClC(C(=O)N(C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCP(O)(O)=O)Cl | CC[O:11][P:9]([CH2:8][CH2:7][N:6]([C:2](=[O:1])[CH:3]([Cl:4])[Cl:5])[c:13]1[cH:14][cH:15][cH:16][c:17](-[c:18]2[cH:19][c:20](-[c:21]3[c:22]([Cl:23])[cH:24][cH:25][cH:26][c:27]3[Cl:28])[n:29][o:30]2)[cH:31]1)(=[O:10])[O:12]CC>>[O:1]=[C:2]([CH:3]([Cl:4])[Cl:5])[N:6]([CH2:7][CH2:8][P:9](=[O:10])([OH:11])[OH:12])[c:13]1[cH... | CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC | O=C(C(Cl)Cl)N(CCP(=O)(O)O)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | C(Cl)Cl | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | null | [] | null | null | 4 | HOUR | Diethyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylphosphonate (Cpd. No. 1, 50 mg, 0.09 mmol) was dissolved in anhydrous methylene chloride (1 mL). Bromotrimethylsilane (750 μL, 5.7 mmol) was added and the mixture was stirred for 4 h whereupon the LC-MS confirmed the starting materi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | Other | C(Cl)Cl | null | 4 | CCOP(=O)(CCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1)OCC>C(Cl)Cl>O=C(C(Cl)Cl)N(CCP(=O)(O)O)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-095da1055b1b4e4e842ad764ab26ce5b | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CNOC>>CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C | C(#N)P(OCC)(OCC)=O.C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)O.Cl.CNOC.C(C)N(CC)CC>>CON(C([C@@H](C(C)C)NC(OC(C)(C)C)=O)=O)C | O[C:5](=[O:6])[C@@H:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH3:17])[CH3:18].[CH3:1][O:2][NH:3][CH3:4]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[C@H:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:16]([CH3:17])[CH3:18] | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CNOC | CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C;D1;H3:13]-[#8:14]-[NH;D2;+0:15]-[C;D1;H3:16]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:15](-... | null | [] | null | null | 12 | HOUR | N-Boc-L-valine (3.72 g, 17.2 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.84 g, 18.86 mmol) were dissolved in anhydrous methylene chloride (50 mL) under nitrogen. Triethylamine (2.09 g, 20.64 mmol) was added to the mixture, followed by dropwise addition of diethyl cyanophosphonate (3.09 g, 18.92 mmol). The resu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | null | HO- | C(Cl)Cl | null | 12 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CNOC>C(Cl)Cl>CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f103eeb2d91449ebbbaf3a89ad18b677 | CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C>>C=CC(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C | CO.C(=C)[Mg]Br.CON(C([C@@H](C(C)C)NC(OC(C)(C)C)=O)=O)C.C(C)(=O)OC(C)=O>>CC(C)[C@H](C(C=C)=O)NC(OC(C)(C)C)=O | CON(C)[C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16]>>[CH2:1]=[CH:2][C:3](=[O:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16] | CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C | C=CC(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 8cb1f70db25cd2e49aa8c02b721d3a6ba1ee5d1c92b808df123961da515206be | 83001898a9706edc6aefcd7a24faac7c8cfe173e0a37aec6c15c15ef6e2aa60e | null | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:13]=[C;D1;H2:14] | 64.1 | [{"value": 64.1, "product": "CC(C)[C@H](C(C=C)=O)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Vinylmagnesium bromide (1M soln in THF, 34.6 mL, 34.6 mmol) was added to a solution of (R)-tert-butyl 1-(methoxy(methyl)amino)-3-methyl-1-oxobutan-2-ylcarbamate (4.5 g, 17.30 mmol) in anhydrous tetrahydrofuran (50 mL) under nitrogen at −78° C., dropwise, over 20 min. The reaction was slowly warmed to 0° C. and then sti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone.Vinyl | null | null | null | HO- | O1CCCC1 | 0 | 0.333333 | CON(C)C(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C>O1CCCC1>C=CC(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f354f5c808144c182616a7296bf1a62 | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>>CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)Cl)Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)NCCC(C(C(C)C)NC(OC(C)(C)C)=O)=O.C(C)N(CC)CC>>ClC(C(=O)N(C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCC(C(C(C)C)NC(OC(C)(C)C)=O)=O)Cl | [CH3:1][CH:2]([CH3:3])[CH:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[CH2:15][CH2:16][NH:17][c:23]1[cH:24][cH:25][n:26][c:27](-[c:28]2[cH:29][c:30](-[c:31]3[c:32]([Cl:33])[cH:34][cH:35][cH:36][c:37]3[Cl:38])[n:39][o:40]2)[cH:41]1.Cl[C:18](=[O:19])[CH:20]([Cl:21])[Cl:22]>>[CH3:1][CH:2]([... | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[O;D1;H0:6]=[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C:9]-[C:8]-[C:7]=[O;D1;H0:6])-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1 | 34.6 | [{"value": 34.6, "product": "ClC(C(=O)N(C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCC(C(C(C)C)NC(OC(C)(C)C)=O)=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | tert-Butyl 6-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)-2-methyl-4-oxohexan-3-ylcarbamate (445 mg, 0.83 mmol) was dissolved in methylene chloride (10 mL) with triethylamine (140 μL, 1.0 mmol). The solution was cooled on an ice-water bath and then a solution of dichloroacetyl chloride (100 μL, 1.0 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HCl | C(Cl)Cl | null | 8 | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>C(Cl)Cl>CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e815ee4cdbf4333954884d6a3a5fa5d | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | FC(C(=O)O)(F)F.ClC(C(=O)N(C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCC(C(C(C)C)NC(OC(C)(C)C)=O)=O)Cl>>NC(C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O)C(C)C | CC(C)(C)OC(=O)[NH:5][CH:4]([CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[CH2:8][CH2:9][N:10]([C:11](=[O:12])[CH:13]([Cl:14])[Cl:15])[c:16]1[cH:17][cH:18][n:19][c:20](-[c:21]2[cH:22][c:23](-[c:24]3[c:25]([Cl:26])[cH:27][cH:28][cH:29][c:30]3[Cl:31])[n:32][o:33]2)[cH:34]1>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[C:6](=[O:7])[CH2:8][... | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](-[C:5])=[O;D1;H0:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](-[C:5])=[O;D1;H0:6] | null | [] | 0 | CELSIUS | 2 | HOUR | Trifluoroacetic acid (1 mL) was added to a solution of tert-butyl 6-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-2-methyl-4-oxohexan-3-ylcarbamate (185 mg, 0.29 mmol) in methylene chloride (2 mL) at 0° C. The resulting mixture was allowed to stir at 0° C. for 2 hours, then concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HO- | C(Cl)Cl | 0 | 2 | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>C(Cl)Cl>CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa467d45ccf34f83b406c64b885cea87 | CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | C(C)(C)N(CC)C(C)C.C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)O.NC(C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O)C(C)C>>ClC(C(=O)N(C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCC(C(C(C)C)NC(OC(C)(C)C)=O)=O)Cl | N[CH:4]([CH:2]([CH3:1])[CH3:3])[C:13](=[O:14])[CH2:15][CH2:16][N:17]([C:18](=[O:19])[CH:20]([Cl:21])[Cl:22])[c:23]1[cH:24][cH:25][n:26][c:27](-[c:28]2[cH:29][c:30](-[c:31]3[c:32]([Cl:33])[cH:34][cH:35][cH:36][c:37]3[Cl:38])[n:39][o:40]2)[cH:41]1.CC(C)[C@@H](C(=O)O)[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:1... | CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Boc amine protection of primary amine | c782b414f98ec475726103942e307a4d4d8f0a394197d95cd4a4510d35a113ef | 508f15e32ce499ac5c8c2e3c89248ef7296b3b84d4eb7736b40faf3adec24330 | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | C-C(-C)-[C@@H](-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-C(-O)=O.N-[CH;D3;+0:9](-[C:10](-[C:11])=[O;D1;H0:12])-[C:13](-[C;D1;H3:14])-[C;D1;H3:15]>>[C:11]-[C:10](=[O;D1;H0:12])-[CH;D3;+0:9](-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8... | null | [] | null | null | 5 | HOUR | Pybop (164 mg, 0.32 mmol), diisopropylethylamine (50 mg, 0.39 mmol) and N-boc-L-valine (69 mg, 0.32 mmol) were added to a solution of N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide (Cpd. No. 3, lot 2, 75 mg, 0.11 mmol) in methylene chloride (5 mL) at 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ketone.Primary amine | Carbamic ester.Ketone | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HO- | C(Cl)Cl | null | 5 | CC(C)C(N)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O>C(Cl)Cl>CC(C)C(NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09cec3fa6f11486db674177703dc5958 | CON(C)C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C>>C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)N(C)OC.C(=C)[Mg]Br>>C(C)(C)(C)OC(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(C=C)=O | CON(C)[C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH2:1]=[CH:2][C:3](=[O:4])[C@H:5]([CH2:6][CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3... | CON(C)C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C | null | null | O1CCCC1.C1CCOC1 | Functional Group Interconversion | OtherReaction | 8cb1f70db25cd2e49aa8c02b721d3a6ba1ee5d1c92b808df123961da515206be | 83001898a9706edc6aefcd7a24faac7c8cfe173e0a37aec6c15c15ef6e2aa60e | null | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:13]=[C;D1;H2:14] | null | [] | -70 | CELSIUS | 30 | MINUTE | (S)-tert-Butyl 4-(tert-butoxycarbonylamino)-5-(methoxy(methyl)amino)-5-oxopentanoate (4.12 g, 12.2 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to −70° C. under nitrogen. Vinylmagnesium bromide (37 mL, 1.0 M soln in THF, 3.0 eq) was added dropwise. The reaction stirred for 30 min at −70° C. and ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone.Vinyl | null | null | null | HO- | O1CCCC1.C1CCOC1 | -70 | 0.5 | CON(C)C(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C>O1CCCC1.C1CCOC1>C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec3e3b0c7a8244189344af93d1df6ba5 | C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | C(C)(C)(C)OC(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(C=C)=O.Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)N.C(C)(C)N(CC)C(C)C>>C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCNC1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[CH:21]=[CH2:22].[NH2:23][c:24]1[cH:25][cH:26][n:27][c:28](-[c:29]2[cH:30][c:31](-[c:32]3[c:33]([Cl:34])[cH:35][cH:36][cH:37][c:38]3[Cl:39])[n:40][o:41]2)[cH:42]1>>[CH3:1]... | C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl.C(C)#N | Heteroatom Alkylation and Arylation | aza-Michael addition primary | ea977b64b99803a268ce3d52d5145acd9fbeecc6012c6963c6cfcd78daea06d1 | 91f6f443bfd8db4ff8a0d492b874e4ea7b49bc9f54d6bfc18045426972890acc | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | [C:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | 43.7 | [{"value": 43.7, "product": "C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCNC1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 89 | CELSIUS | null | null | (S)-tert-butyl 4-(tert-butoxycarbonylamino)-5-oxohept-6-enoate (0.94 g) and 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine hydrochloride salt (0.40 g) were dissolved in acetonitrile (4 mL). Diisopropylethylamine (0.52 mL) was added and the mixture wad heated at 89° C. for 25 h. The mixture was cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Vinyl | Ketone.Secondary amine | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | null | ClCCl.C(C)#N | 89 | null | C=CC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>ClCCl.C(C)#N>CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9152ddfe9d37466d9f0d1af79330defc | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>>CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)Cl)Cl.C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCNC1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][C@@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C:19](=[O:20])[CH2:21][CH2:22][NH:23][c:29]1[cH:30][cH:31][n:32][c:33](-[c:34]2[cH:35][c:36](-[c:37]3[c:38]([Cl:39])[cH:40][cH:41][cH:42][c:43]3[Cl:44])[n:45][o:46]2)[cH:47]1.Cl[C:24](... | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[O;D1;H0:6]=[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[C:9]-[C:8]-[C:7]=[O;D1;H0:6])-[c:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15]:[c:16]:1 | 50.2 | [{"value": 50.2, "product": "C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (R)-tert-butyl 4-(tert-butoxycarbonylamino)-7-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)-5-oxoheptanoate (280 mg, 0.45 mmol) was dissolved in anhydrous dichloromethane with triethylamine (126 μL, 0.90 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>ClCCl>CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8880890ba3a7468a93ddd53c721d32ae | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>N[C@H](CCC(=O)O)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | C(C)(C)(C)OC(=O)N[C@H](CCC(=O)OC(C)(C)C)C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.N[C@H](CCC(=O)O)C(CCN(C(C(Cl)Cl)=O)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)=O | CC(C)(C)OC(=O)[NH:1][C@H:2]([CH2:3][CH2:4][C:5](=[O:6])[O:7]C(C)(C)C)[C:8](=[O:9])[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]([Cl:16])[Cl:17])[c:18]1[cH:19][cH:20][n:21][c:22](-[c:23]2[cH:24][c:25](-[c:26]3[c:27]([Cl:28])[cH:29][cH:30][cH:31][c:32]3[Cl:33])[n:34][o:35]2)[cH:36]1>>[NH2:1][C@H:2]([CH2:3][CH2:4][C:5](=[... | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | N[C@H](CCC(=O)O)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Reduction | OtherReaction | a9c34b673cad0c9c6a25393bce36078a9c87373914ad0b7d479edb4e8fabdb81 | 916867313deb4914774d4338093c724679e8e044ecc93ea05b264a9284c43163 | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C(-C)(-C)-C)-[C:8](-[C:9])=[O;D1;H0:10]>>[C:9]-[C:8](=[O;D1;H0:10])-[C:2](-[NH2;D1;+0:1])-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | null | null | null | null | (R)-tert-Butyl 4-(tert-butoxycarbonylamino)-7-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-5-oxoheptanoate (165 mg) was dissolved in anhydrous dichloromethane (2 mL) and cooled in an ice-bath under nitrogen. Then trifluoroacetic acid (2 mL) was added. After 4.5 h at 4° C. the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc.Boc | Carboxylic acid.Primary amine | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)CC[C@@H](NC(=O)OC(C)(C)C)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>ClCCl>N[C@H](CCC(=O)O)C(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67ba2c47208b41cfba83c3a8e0553269 | C=O.CC(C)O.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | C=O.[H][H].[H-].[Na+].C(C)(C)O.Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)N>>ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)NCOC(C)C | O=[CH2:5].[CH3:1][CH:2]([CH3:3])[OH:4].[NH2:6][c:7]1[cH:8][cH:9][n:10][c:11](-[c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[Cl:22])[n:23][o:24]2)[cH:25]1>>[CH3:1][CH:2]([CH3:3])[O:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][n:10][c:11](-[c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][... | C=O.CC(C)O.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | bbc980cf503d9ddbe24975dd37ca9d5171d8f4b8c4b85d663cb501b7a28cc609 | 8545c78f4dc30a5eecebea3d75d649374c31a98628bac6688a66c533bfe25f63 | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])-[OH;D1;+0:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | null | [] | null | null | 5 | HOUR | Sodium hydride (120 mg, 2.9 mmol) was added slowly to isopropyl alcohol (15 mL) at 0° C. Once the evolution of hydrogen ceased 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine hydrochloride (200 mg, 0.58 mmol) and paraformaldehyde (147 mg, 1.64 mmol) added. The resulting mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary alcohol.Primary amine | Ether.Secondary amine | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HO- | O | null | 5 | C=O.CC(C)O.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>O>CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f98f37c0f544b6aa3af9b7554f1742b | CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>>CC(C)OCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)Cl)Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)NCOC(C)C.C(C)N(CC)CC>>ClC(C(=O)N(COC(C)C)C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)Cl | [CH3:1][CH:2]([CH3:3])[O:4][CH2:5][NH:6][c:12]1[cH:13][cH:14][n:15][c:16](-[c:17]2[cH:18][c:19](-[c:20]3[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]3[Cl:27])[n:28][o:29]2)[cH:30]1.Cl[C:7](=[O:8])[CH:9]([Cl:10])[Cl:11]>>[CH3:1][CH:2]([CH3:3])[O:4][CH2:5][N:6]([C:7](=[O:8])[CH:9]([Cl:10])[Cl:11])[c:12]1[cH:13][cH:14][n:15]... | CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl | CC(C)OCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[#8:6]-[C:7]-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[#8:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | null | [] | null | null | 8 | HOUR | 2-(3-(2,6-Dichlorophenyl)isoxazol-5-yl)-N-(isopropoxymethyl)pyridin-4-amine (269 mg, 0.58 mmol) was dissolved in anhydrous dichloromethane with triethylamine (100 μL, 0.70 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (70 μL, 0.70 mmol) was added dropwise. After... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)OCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>ClCCl>CC(C)OCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0edcbd0b3fc40dfa3369abff8964eed | C#Cc1cccc(N)c1.CC(C)(C)OC(=O)NCC(=O)O>>C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1 | C(C)(C)N(CC)C(C)C.C(#C)C=1C=C(N)C=CC1.C(=O)(OC(C)(C)C)NCC(=O)O.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=C5)N=N4.F[P-](F)(F)(F)(F)F>>C(#C)C=1C=C(C=CC1)NC(CNC(OC(C)(C)C)=O)=O | [CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:20]1.O[C:9](=[O:10])[CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[CH2:11][NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1 | C#Cc1cccc(N)c1.CC(C)(C)OC(=O)NCC(=O)O | C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | null | [] | null | null | 10 | HOUR | 3-Ethynylaniline (1.0 g, 8.54 mmol), N-Boc glycine (2.7 g, 15.41 mmol) and PyBOP (8.1 g, 15.41 mmol) were combined in dichloromethane (25 mL). Diisopropylethylamine (3.3 g, 25.61 mmol) was added to the solution and the mixture was allowed to stir at room temperature under argon for 10 h. The reaction mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 10 | C#Cc1cccc(N)c1.CC(C)(C)OC(=O)NCC(=O)O>ClCCl>C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff60e3aa8a074314b81765d581055ed8 | C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1.ON=C(Cl)c1c(Cl)cccc1Cl>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | C(#C)C=1C=C(C=CC1)NC(CNC(OC(C)(C)C)=O)=O.C(C)N(CC)CC.ClC1=C(C(=NO)Cl)C(=CC=C1)Cl>>ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NC(CNC(OC(C)(C)C)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[CH:19])[cH:31]1.Cl[C:20]([c:21]1[c:22]([Cl:23])[cH:24][cH:25][cH:26][c:27]1[Cl:28])=[N:29][OH:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:1... | C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1.ON=C(Cl)c1c(Cl)cccc1Cl | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | O1CCCC1.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 0acd4387903ecef3644ca983a4d97270f147df71c89a735cfcdfe351f79b20db | c396d0116405f0fb9e31fa23799a4838037a90cc446bdd74768e7dde19fceca1 | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[N;H0;D2;+0:2]-[OH;D1;+0:3])-[c;H0;D3;+0:4](:[c:5](-[Cl;D1;H0:6]):[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10].[CH;D1;+0:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[Cl;D1;H0:6]-[c:5](:[c:7]):[c;H0;D3;+0:4](-[c;H0;D3;+0:1]1:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[... | null | [] | null | null | 15 | MINUTE | tert-Butyl 2-(3-ethynylphenylamino)-2-oxoethylcarbamate (1.6 g, 5.83 mmol) was dissolved in anhydrous tetrahydrofuran (25 mL) and treated with triethylamine (0.82 g, 8.1 mmol) and then 2,6-dichloro-N-hydroxybenzimidoyl chloride (1.4 g, 6.3 mmol). After stirring 15 min at room temperature the mixture was heated at reflu... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkyne.Oxime | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | HCl | O1CCCC1.C(C)(=O)OCC | null | 0.25 | C#Cc1cccc(NC(=O)CNC(=O)OC(C)(C)C)c1.ON=C(Cl)c1c(Cl)cccc1Cl>O1CCCC1.C(C)(=O)OCC>CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43f83f8c6bec4f0fa47db2bdd986dc0c | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NC(CNC(OC(C)(C)C)=O)=O.B.O1CCCC1>>ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NCCNC(OC(C)(C)C)=O | O=[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][c:19](-[c:20]3[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]3[Cl:27])[n:28][o:29]2)[cH:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:1... | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | null | [] | 0 | CELSIUS | null | null | tert-Butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)-2-oxoethylcarbamate (500 mg, 1.08 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to 0° C. Borane-tetrahydrofuran complex (1M soln in THF, 10.8 mL, 10.8 mmol) was added dropwise to the cool solution. The reaction mixture was allowed t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | Other | O1CCCC1 | 0 | null | CC(C)(C)OC(=O)NCC(=O)Nc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>O1CCCC1>CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17d7fafd1516472bab6b2d77e50431b9 | CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>>CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)Cl)Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C=1C=C(C=CC1)NCCNC(OC(C)(C)C)=O.C(C)N(CC)CC>>ClC(C(=O)N(C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCNC(OC(C)(C)C)=O)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][c:17]1[cH:18][cH:19][cH:20][c:21](-[c:22]2[cH:23][c:24](-[c:25]3[c:26]([Cl:27])[cH:28][cH:29][cH:30][c:31]3[Cl:32])[n:33][o:34]2)[cH:35]1.Cl[C:12](=[O:13])[CH:14]([Cl:15])[Cl:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C... | CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl | CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5])-[c:9](:[c:10]):[c:11] | null | [] | null | null | 8 | HOUR | tert-Butyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylcarbamate (230 mg, 0.51 mmol) was dissolved in anhydrous dichloromethane with triethylamine (120 μL, 0.82 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (120 mg, 0.82 mmol) was added dropwise. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)(C)OC(=O)NCCNc1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>ClCCl>CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad392387124d414bb3c5f5899dd40bc6 | CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)N(C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCNC(OC(C)(C)C)=O)Cl.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.NCCN(C(C(Cl)Cl)=O)C1=CC(=CC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][N:4]([C:5](=[O:6])[CH:7]([Cl:8])[Cl:9])[c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[cH:16][c:17](-[c:18]3[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]3[Cl:25])[n:26][o:27]2)[cH:28]1>>[NH2:1][CH2:2][CH2:3][N:4]([C:5](=[O:6])[CH:7]([Cl:8])[Cl:9])[c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[c... | CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cc(-c3ccccc3)on2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | tert-butyl 2-(2,2-dichloro-N-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenyl)acetamido)ethylcarbamate (100 mg, 0.18 mmol) was dissolved in anhydrous dichloromethane (3 mL) and cooled in an ice-bath under nitrogen. Then trifluoroacetic acid (3 mL) was added. After 3 h at 4° C. the mixture was concentrated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>ClCCl>NCCN(C(=O)C(Cl)Cl)c1cccc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6684edb1a38245708d9efba7575d7177 | CC(C)O.O=C(Cl)OCCl>>CC(C)OC(=O)OCCl | ClCOC(=O)Cl.C(C)(C)O.N1=CC=CC=C1>>C(OCCl)(OC(C)C)=O | [CH3:1][CH:2]([CH3:3])[OH:4].Cl[C:5](=[O:6])[O:7][CH2:8][Cl:9]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[O:7][CH2:8][Cl:9] | CC(C)O.O=C(Cl)OCCl | CC(C)OC(=O)OCCl | null | null | CCOCC | Acylation | Schotten-Baumann to ester | 16a18aa130cea39a3a662ee8b6057b54f71a5546be78b0c40ff9ad2c1213d664 | 75f277925c316017cfa5d00758bde92cc568ffecb2651aae6fab24b6daa74c11 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[OH;D1;+0:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of chloroformic acid chloromethyl ester (6.23 mL, 70.0 mmol) and isopropyl alcohol (4.4 g, 73.0 mmol) in anhydrous ether (150 mL) was added dropwise to a solution of pyridine (5.7 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then 3 h at room temperature. The reaction mixture was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Carbonic Ester | null | null | null | HCl | CCOCC | 0 | 1 | CC(C)O.O=C(Cl)OCCl>CCOCC>CC(C)OC(=O)OCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4743145e64694620a48b0d24d78ebb40 | CC(C)=O.CC(C)OC(=O)OCCl.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | [I-].[Na+].C(OCCl)(OC(C)C)=O.CC(=O)C.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)N>>ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)NCCC(=O)OC(C)C | CC(=O)[CH3:7].Cl[CH2:8]O[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[O:6].[NH2:9][c:10]1[cH:11][cH:12][n:13][c:14](-[c:15]2[cH:16][c:17](-[c:18]3[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]3[Cl:25])[n:26][o:27]2)[cH:28]1>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][CH2:8][NH:9][c:10]1[cH:11][cH:12][n:13][c:14](-[c:15]2[cH:16]... | CC(C)=O.CC(C)OC(=O)OCCl.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | null | C-C Coupling | OtherReaction | 595777a27a002253d0e4a7ffe5c400f6c6a10392de172a26cc97b586dad6e6e9 | 83dbb7bc843708e162bf6cc8456a0aa7d4806d42069e9fd67fe51bf2918a2427 | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | C-C(=O)-[CH3;D1;+0:1].Cl-[CH2;D2;+0:2]-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[C:6]-[#8:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[NH;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1 | null | [] | null | null | 2.5 | HOUR | Sodium iodide (1.4 g, 9.3 mmol) was added to a solution of chloromethyl isopropyl carbonate (750 mg, 4.8 mmol) in acetone (5 mL). The resulting mixture was stirred at room temperature for 2.5 h, followed by addition of 2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-amine (500 mg, 1.6 mmol). The reaction mixture was t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester.Ketone.Primary amine | Ester.Secondary amine | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HCl | null | null | 2.5 | CC(C)=O.CC(C)OC(=O)OCCl.Nc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1>>CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-517a6a3359654cc69758b385cdba65dd | CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>>CC(C)OC(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | ClC(C(=O)Cl)Cl.ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1)C1=NC=CC(=C1)NCCC(=O)OC(C)C.C(C)N(CC)CC>>ClC(C(=O)N(C1=CC(=NC=C1)C1=CC(=NO1)C1=C(C=CC=C1Cl)Cl)CCC(=O)OC(C)C)Cl | [CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][CH2:8][NH:9][c:15]1[cH:16][cH:17][n:18][c:19](-[c:20]2[cH:21][c:22](-[c:23]3[c:24]([Cl:25])[cH:26][cH:27][cH:28][c:29]3[Cl:30])[n:31][o:32]2)[cH:33]1.Cl[C:10](=[O:11])[CH:12]([Cl:13])[Cl:14]>>[CH3:1][CH:2]([CH3:3])[O:4][C:5](=[O:6])[CH2:7][CH2:8][N:9]([C:10](=[O:11])[CH:1... | CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl | CC(C)OC(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2cc(-c3ccccn3)on2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[NH;D2;+0:11]-[c:12]1:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])-[Cl;D1;H0:5])-[c:12]1:[c:13]:[c:14]:[#7;a:15... | null | [] | null | null | 8 | HOUR | Isopropyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)propanoate (520 mg, 1.23 mmol) was dissolved in anhydrous dichloromethane (25 mL) with triethylamine (270 mg, 2.7 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (320 mg, 2.17 mmol) was added dr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1cnoc1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)OC(=O)CCNc1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1.O=C(Cl)C(Cl)Cl>ClCCl>CC(C)OC(=O)CCN(C(=O)C(Cl)Cl)c1ccnc(-c2cc(-c3c(Cl)cccc3Cl)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38d8a6fb12e24687aa04fbca0a63597e | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O>>FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 | C1(=C(C=CC=C1)N)N.FC(C(C(=O)O)(F)F)(C(=O)O)F>>N1=C(NC2=C1C=CC=C2)C(C(F)(F)C=2NC1=C(N2)C=CC=C1)(F)F | [NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[NH2:12].O=[C:16](O)[C:2]([F:1])([F:3])[C:18]([F:14])([F:15])[C:23](=O)O>>[F:1][C:2]([F:3])([c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1)[C:13]([F:14])([F:15])[c:16]1[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[nH:24]1 | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O | FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d8bb4423619e5b6e1a1183ec72b61c8c6bd81d8c419173f3499a36a0ba67607d | 6affff663b9fd2961056497c561c38101c041d6e07e5e9d7618df47ef448e4e4 | c1ccc2[nH]c(CCc3nc4ccccc4[nH]3)nc2c1 | O-[C;H0;D3;+0:1](=O)-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:5](-[F;H0;D1;+0:6])(-[F;H0;D1;+0:7])-[C;H0;D3;+0:8](-O)=O.[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[F;D1;H0:3]-[C;H0;D4;+0:2](-[F;D1;H0:4])(-[c:15]1:[n;H0;D2;+0:13]:[c:12](:[c:14]):[c:10](:[c:11]):[nH;D2;+0:9]:1)-[C:16](-[F... | null | [] | 160 | CELSIUS | 7 | HOUR | In a 250 mL 35/25 ball joint flask, 1,2-phenylenediamine (5.92 g, 54.7 mmol) was combined with tetrafluorosuccinic acid (5.2 g, 27.36 mmol). Polyphosphoric acid (83 g) was added directly to the solid mixture. The flask was fitted with an air-driven mechanical stirring shaft and heated to 160° C. under a nitrogen purge ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | c1ccccc1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1 | null | null | 160 | 7 | Nc1ccccc1N.O=C(O)C(F)(F)C(F)(F)C(=O)O>>FC(F)(c1nc2ccccc2[nH]1)C(F)(F)c1nc2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c26e4473b77647adb7f608be14a477d3 | BrBr.CCC(=O)c1ccccc1F>>CC(Br)C(=O)c1ccccc1F | FC1=C(C=CC=C1)C(CC)=O.BrBr>>BrC(C(=O)C1=C(C=CC=C1)F)C | Br[Br:3].[CH3:1][CH2:2][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[F:12]>>[CH3:1][CH:2]([Br:3])[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[F:12] | BrBr.CCC(=O)c1ccccc1F | CC(Br)C(=O)c1ccccc1F | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | c4e4001f7df68217305f4e3df4c72011ad7e2bce5a268f8554ebe23f061baf28 | fe149a07f370bdd2ea40b2dff4f3462711fb34a60b8733c443efdeb5ab4d5c53 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[Br;H0;D1;+0:1]-[CH;D3;+0:3](-[C;D1;H3:2])-[C:4](=[O;D1;H0:5])-[c:6] | 97 | [{"value": 97.0, "product": "BrC(C(=O)C1=C(C=CC=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2′-fluoropropiophenone (25.0 g) in acetic acid (250 mL) was slowly added bromine (8.4 mL). The mixture was stirred at room temperature for 3 hr, and concentrated under reduced pressure. Water (200 mL) was added to the residue, and the mixture was extracted with diisopropyl ether. The extract was washed... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary halide | null | null | c1ccccc1 | HBr | C(C)(=O)O | null | 3 | BrBr.CCC(=O)c1ccccc1F>C(C)(=O)O>CC(Br)C(=O)c1ccccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e2000a6279840fa93a48a66fd6f56ad | CCOC(=O)CC#N.O=C(CBr)c1ccccc1>>CCOC(=O)C(C#N)CC(=O)c1ccccc1 | C([O-])([O-])=O.[K+].[K+].C(#N)CC(=O)OCC.C(C(=O)C1=CC=CC=C1)Br>>C(#N)C(C(=O)OCC)CC(C1=CC=CC=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]#[N:8].Br[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7]#[N:8])[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CCOC(=O)CC#N.O=C(CBr)c1ccccc1 | CCOC(=O)C(C#N)CC(=O)c1ccccc1 | null | null | CC(=O)C | C-C Coupling | OtherReaction | 8f6d4b304f760571a184e9fdd40a1eea1ac2caef68076ef062be84edd531cf09 | 4c05eab7fc11daae7c29afd57dcd00ee6caafc643a857cb0c2660dc4a28e52eb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]#[N;D1;H0:11])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 90 | [{"value": 90.0, "product": "C(#N)C(C(=O)OCC)CC(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 42.5 | CELSIUS | 45 | MINUTE | Potassium carbonate (13.82 g) was added to ethyl cyanoacetate (37 mL), and the mixture was stirred at 40-45° C. for 45 min. A solution (100 mL) of phenacyl bromide (10.0 g) in acetone was added dropwise over 30 min. After completion of the dropwise addition, and the mixture was stirred at room temperature for 18 hr. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HBr | CC(=O)C | 42.5 | 0.75 | CCOC(=O)CC#N.O=C(CBr)c1ccccc1>CC(=O)C>CCOC(=O)C(C#N)CC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55d2701fff0c494399c26885e226c1e0 | CC(Br)C(=O)c1ccccc1F.COC(=O)CC#N>>COC(=O)C(C#N)C(C)C(=O)c1ccccc1F | C(#N)CC(=O)OC.C(C)(C)N(CC)C(C)C.BrC(C(=O)C1=C(C=CC=C1)F)C>>C(#N)C(C(=O)OC)C(C(=O)C1=C(C=CC=C1)F)C | Br[CH:8]([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18].[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]#[N:7]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([C:6]#[N:7])[CH:8]([CH3:9])[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18] | CC(Br)C(=O)c1ccccc1F.COC(=O)CC#N | COC(=O)C(C#N)C(C)C(=O)c1ccccc1F | null | null | O1CCCC1 | C-C Coupling | OtherReaction | c8821ef96099d637ba6242fffeac2fc1dacfe0e0b13897f7aebe27ef1eb37366 | b7431acf00a39af4551ecb3587d274d2869bf98fcb947f300f78983dddd0f26e | c1ccccc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12]>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11]#[N;D1;H0:12])-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[c:5] | 80 | [{"value": 80.0, "product": "C(#N)C(C(=O)OC)C(C(=O)C1=C(C=CC=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 20 | HOUR | To a solution of methyl cyanoacetate (15.5 mL) and diisopropylethylamine (64 mL) in tetrahydrofuran (110 mL) was added a solution of 2-bromo-1-(2-fluorophenyl)propan-1-one (36.8 g) in tetrahydrofuran (160 mL), and the mixture was stirred at 70° C. for 20 hr. The reaction mixture was allowed to cool to room temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HBr | O1CCCC1 | 70 | 20 | CC(Br)C(=O)c1ccccc1F.COC(=O)CC#N>O1CCCC1>COC(=O)C(C#N)C(C)C(=O)c1ccccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e33a9ba343394335877606309aa8e11d | CCOC(=O)CC#N.O=C(CBr)c1ccccc1F>>CCOC(=O)C(C#N)CC(=O)c1ccccc1F | BrCC(=O)C1=C(C=CC=C1)F.O.C([O-])([O-])=O.[K+].[K+].C(#N)CC(=O)OCC>>C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]#[N:8].Br[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7]#[N:8])[CH2:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[F:18] | CCOC(=O)CC#N.O=C(CBr)c1ccccc1F | CCOC(=O)C(C#N)CC(=O)c1ccccc1F | null | null | CC(=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 8f6d4b304f760571a184e9fdd40a1eea1ac2caef68076ef062be84edd531cf09 | 4c05eab7fc11daae7c29afd57dcd00ee6caafc643a857cb0c2660dc4a28e52eb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]#[N;D1;H0:11])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 100 | [{"value": 100.0, "product": "C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 1 | HOUR | To a solution of 2′-fluoroacetophenone (28.6 g) in ethyl acetate (400 mL) was added copper (II) bromide (92.6 g), and the mixture was heated under reflux for 4 hr. The reaction mixture was allowed to cool to room temperature and the insoluble material was filtered off. The filtrate was concentrated under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HBr | CC(=O)C.C(C)(=O)OCC | 45 | 1 | CCOC(=O)CC#N.O=C(CBr)c1ccccc1F>CC(=O)C.C(C)(=O)OCC>CCOC(=O)C(C#N)CC(=O)c1ccccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e2bcfebb34145d58aa45fbb1eb71025 | BrBr.CC(=O)c1ccccc1C(F)(F)F>>O=C(CBr)c1ccccc1C(F)(F)F | BrBr.FC(C1=C(C=CC=C1)C(C)=O)(F)F.O>>BrCC(=O)C1=C(C=CC=C1)C(F)(F)F | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14] | BrBr.CC(=O)c1ccccc1C(F)(F)F | O=C(CBr)c1ccccc1C(F)(F)F | null | null | C(Cl)(Cl)Cl.C(C)OCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[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] | null | [] | 25 | CELSIUS | 1 | HOUR | 2′-(Trifluoromethyl)acetophenone (10.0 g) was dissolved in chloroform (30 mL) and diethyl ether (30 mL), a solution of bromine (8.50 g) in chloroform (20 mL) was added dropwise while maintaining the reaction temperature at not higher than 25° C. After the dropwise addition, the mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)Cl.C(C)OCC | 25 | 1 | BrBr.CC(=O)c1ccccc1C(F)(F)F>C(Cl)(Cl)Cl.C(C)OCC>O=C(CBr)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-322f74b94b034236b52a29697c4a25af | CCOC(=O)C(C#N)CC(=O)c1ccccc1.Cl>>CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl | C(#N)C(C(=O)OCC)CC(C1=CC=CC=C1)=O.Cl>>ClC=1NC(=CC1C(=O)OCC)C1=CC=CC=C1 | O=[C:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:16]#[N:15])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[ClH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[nH:15][c:16]1[Cl:17] | CCOC(=O)C(C#N)CC(=O)c1ccccc1.Cl | CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | ee999686a7991e07d7c287a446be67936cb0259cc7da34bde8489e32aa619966 | 463beee1c06ff6990c2e1332d51dae761cf1d15bf3cb1e31ff2630a30ad5b435 | c1ccc(-c2ccc[nH]2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[ClH;D0;+0:15]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[nH;D2;+0:5]:[c;H0;D3;... | 79 | [{"value": 79.0, "product": "ClC=1NC(=CC1C(=O)OCC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "ClC=1NC(=CC1C(=O)OCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution (60 mL) of ethyl 2-cyano-4-oxo-4-phenylbutanoate (5.0 g) in tetrahydrofuran was blown in hydrogen chloride (28 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Then, nitrogen was blown in to remove excess hydrogen chloride. The reaction mixture was concentrated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Aromatic halide.Ester | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | O1CCCC1 | null | 3 | CCOC(=O)C(C#N)CC(=O)c1ccccc1.Cl>O1CCCC1>CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7497cdae865947da87330c33767b9096 | CCOC(=O)C(C#N)CC(=O)c1ccccc1F.Cl>>CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl | C(#N)C(C(=O)OCC)CC(=O)C1=C(C=CC=C1)F.C(C)(=O)OCC.Cl>>ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1)F | O=[C:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:17]#[N:16])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[F:15].[ClH:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[nH:16][c:17]1[Cl:18] | CCOC(=O)C(C#N)CC(=O)c1ccccc1F.Cl | CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee999686a7991e07d7c287a446be67936cb0259cc7da34bde8489e32aa619966 | 463beee1c06ff6990c2e1332d51dae761cf1d15bf3cb1e31ff2630a30ad5b435 | c1ccc(-c2ccc[nH]2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[CH;D3;+0:3](-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[F;D1;H0:14]):[c:15].[ClH;D0;+0:16]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[F;D1;H0:14]):... | 53 | [{"value": 53.0, "product": "ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate (19.3 g) and 4 mol/L hydrogen chloride-ethyl acetate solution (100 mL) was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-et... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Aromatic halide.Ester | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | null | null | 18 | CCOC(=O)C(C#N)CC(=O)c1ccccc1F.Cl>>CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d05759a24fef4e8c80aabc4eaaafe1f1 | COC(=O)C(C#N)C(C)C(=O)c1ccccc1F.Cl>>COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C | O.C(#N)C(C(=O)OC)C(C(=O)C1=C(C=CC=C1)F)C.C(C)(=O)OCC.Cl>>ClC=1NC(=C(C1C(=O)OC)C)C1=C(C=CC=C1)F | O=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[F:16])[CH:17]([CH:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]#[N:8])[CH3:18].[ClH:7]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[c:17]1[CH3:18] | COC(=O)C(C#N)C(C)C(=O)c1ccccc1F.Cl | COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | ee999686a7991e07d7c287a446be67936cb0259cc7da34bde8489e32aa619966 | 463beee1c06ff6990c2e1332d51dae761cf1d15bf3cb1e31ff2630a30ad5b435 | c1ccc(-c2ccc[nH]2)cc1 | O=[C;H0;D3;+0:1](-[CH;D3;+0:2](-[C;D1;H3:3])-[CH;D3;+0:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[F;D1;H0:15]):[c:16].[ClH;D0;+0:17]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:4](-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c;H0;D3;+0:5](-[Cl;H0;D1;+... | 58 | [{"value": 58.0, "product": "ClC=1NC(=C(C1C(=O)OC)C)C1=C(C=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of methyl 2-cyano-4-(2-fluorophenyl)-3-methyl-4-oxobutanoate (31.0 g) in ethyl acetate (30 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (150 mL), and the mixture was stirred at room temperature for 2 days. Water (200 mL) was added to the reaction mixture, and the mixture was extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Aromatic halide.Ester | null | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | C(C)(=O)OCC | null | 48 | COC(=O)C(C#N)C(C)C(=O)c1ccccc1F.Cl>C(C)(=O)OCC>COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6217e8c0b5ec4c3b8b1fdf1c2a31eaeb | CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl>>CCOC(=O)c1c[nH]c(-c2ccccc2)c1 | ClC=1NC(=CC1C(=O)OCC)C1=CC=CC=C1>>C1(=CC=CC=C1)C1=CC(=CN1)C(=O)OCC | Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:16][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[nH:8]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl | CCOC(=O)c1c[nH]c(-c2ccccc2)c1 | null | [C].[Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccc[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 62 | [{"value": 62.0, "product": "C1(=CC=CC=C1)C1=CC(=CN1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "C1(=CC=CC=C1)C1=CC(=CN1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution (50 mL) of ethyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate (8.5 g) in ethanol was added 10% palladium carbon (50% containing water, 0.5 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 24 hr. The reaction mixture was filtered, and the filtrate was concentrated under red... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | [C].[Pd].C(C)O | null | 24 | CCOC(=O)c1cc(-c2ccccc2)[nH]c1Cl>[C].[Pd].C(C)O>CCOC(=O)c1c[nH]c(-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e435de1f55f40cfbf7d760009513f65 | CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl>>CCOC(=O)c1c[nH]c(-c2ccccc2F)c1 | ClC=1NC(=CC1C(=O)OCC)C1=C(C=CC=C1)F>>FC1=C(C=CC=C1)C1=CC(=CN1)C(=O)OCC | Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[nH:8]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][nH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[F:16])[cH:17]1 | CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl | CCOC(=O)c1c[nH]c(-c2ccccc2F)c1 | null | [C].[Pd] | C(C)O | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccc[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 18.3 | [{"value": 18.0, "product": "FC1=C(C=CC=C1)C1=CC(=CN1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.3, "product": "FC1=C(C=CC=C1)C1=CC(=CN1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | To a solution (80 mL) of ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (8.6 g) in ethanol was added 10% palladium carbon (50% containing water, 0.86 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 36 hr. The reaction mixture was filtered, and the filtrate was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | [C].[Pd].C(C)O | null | 36 | CCOC(=O)c1cc(-c2ccccc2F)[nH]c1Cl>[C].[Pd].C(C)O>CCOC(=O)c1c[nH]c(-c2ccccc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04366fbca85f43829a12fc304e12f120 | COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C>>COC(=O)c1c[nH]c(-c2ccccc2F)c1C | ClC=1NC(=C(C1C(=O)OC)C)C1=C(C=CC=C1)F>>FC1=C(C=CC=C1)C1=C(C(=CN1)C(=O)OC)C | Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:16]([CH3:17])[c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[nH:7]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][nH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[c:16]1[CH3:17] | COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C | COC(=O)c1c[nH]c(-c2ccccc2F)c1C | null | [C].[Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | 0ec084506a1195e403239281a55b47251adfd459417d17893b063b33c6f08040 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-c2ccc[nH]2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[#8:8]-[C;D1;H3:9]>>[C;D1;H3:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[cH;D2;+0:1]:1 | 76 | [{"value": 76.0, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1)C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1)C(=O)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of methyl 2-chloro-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylate (10.2 g) in methanol (200 mL) was added 10% palladium carbon (50% containing water, 1.28 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 20 hr. The reaction mixture was filtered, and the filtrate wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | Other | [C].[Pd].CO | null | 20 | COC(=O)c1c(Cl)[nH]c(-c2ccccc2F)c1C>[C].[Pd].CO>COC(=O)c1c[nH]c(-c2ccccc2F)c1C |
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