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-c69003dcc19349faa4e04204fc31f969 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 | FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)(F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:39])[cH:40][n:41]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[c:29]([O:30][CH2:31][C:32]([F:33])([F:34])[F:35])[cH:36]3)[n:37][c:38]12>>[NH2:1][c:2]1[cH:3][cH:4][... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.10) (237 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ec3763c3f1b41aaab2e35be8ddea0fd | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=C(C=C2)C(F)(F)F)OCC(F)(F)F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC(=C(C=C2)C(F)(F)F)OCC(F)(F)F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:38])[cH:39][n:40]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[c:28]([O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[cH:35]3)[n:36][c:37]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C. 14) (228 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aff205c3cbac4afb85940838123e8da2 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:33])[cH:34][n:35]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[c:28]([Cl:29])[cH:30]3)[n:31][c:32]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-chloro-4-trifluoromethyl-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.15) (196 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61ba1dd9c7eb4630ba781c489e5d2d4a | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:34])[cH:35][n:36]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[c:29]([Cl:30])[cH:31]3)[n:32][c:33]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-chloro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.17) (205 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on sili... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5733c9002f2a4b2baaffd568721cdf5a | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=C(C=C2)C(F)(F)F)F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC(=C(C=C2)C(F)(F)F)F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:33])[cH:34][n:35]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[c:28]([F:29])[cH:30]3)[n:31][c:32]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11]... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(3-fluoro-4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.16) (188 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-796893310d614747a64f7a5d0713e4c0 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | FC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>FC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:34])[cH:35][n:36]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[c:29]([F:30])[cH:31]3)[n:32][c:33]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-fluoro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.18) (197 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on sili... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-975b0b3cef1d43cd8050baf6e05626c9 | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl | ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O)C.NC1=NC=C(C(=N)NO)C=C1>>ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C | O=[C:15](O)[c:14]1[cH:13][n:12][n:11]2[c:7]([CH:8]([F:9])[F:10])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:31]([Cl:32])[cH:30][cH:29]3)[n:28][c:27]21.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1)[NH:25][OH:26]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH:8]([F:9])[F:10])[n:11]3[n:12][cH:13][c:1... | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1 | Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-3-methyl-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.13) (169 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (et... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed88b2606df642989c42647fc24eda4f | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | FC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>FC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N | [NH2:1][c:2]1[n:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:34])[cH:35][n:36]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[c:29]([F:30])[cH:31]3)[n:32][c:33]12>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[c... | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12 | Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-fluoro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C. 18) (197 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1cncnc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(F)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd22afe3fd814411a7dd72c145a5f324 | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>ClC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N | [NH2:1][c:2]1[n:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:34])[cH:35][n:36]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[c:29]([Cl:30])[cH:31]3)[n:32][c:33]12>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[... | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12 | Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-chloro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.17) (205 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1cncnc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(Cl)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(Cl)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ba50e7c4ebf4a5e8a70ccc49995ac8f | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 | ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N | [NH2:1][c:2]1[n:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:31])[cH:32][n:33]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[c:26]([Cl:27])[cH:28]3)[n:29][c:30]12>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][n:13]4[c... | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12 | Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.9) (188 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1cncnc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-314a79b6157f4866966400719afeeb44 | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N | [NH2:1][c:2]1[n:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:30])[cH:31][n:32]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[n:28][c:29]12>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][n:13]4[c:14]([C:... | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1cncnc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e97c675d1514d8f9011824683f22681 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([C:33]([F:34])([F:35])[F:36])[cH:31][cH:30]3)[n:29][c:28]21.[NH:17]=[C:18]([c:19]1[cH:20][n:21][c:22]([NH2:23])[n:24][cH:25]1)[NH:26][OH:27]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8]([F:9])([F:1... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cnc(N)nc1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after purification by f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1cncnc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b555dc36331e40e3bcadb4f8357e9e5c | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1Cl | ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)C.NC1=NC=C(C=N1)C(=N)NO>>ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N)C | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([Cl:33])[cH:31][cH:30]3)[n:29][c:28]21.[NH:17]=[C:18]([c:19]1[cH:20][n:21][c:22]([NH2:23])[n:24][cH:25]1)[NH:26][OH:27]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[n:12]3[n:1... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1cnc(N)nc1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.6) (178 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on si... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1cncnc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cnc(N)nc5)no4)c3n2)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b07293521b3e4d54bf190cb3416c0f0a | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)ccn1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=CC(=C1)C(=N)NO>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC(=NC=C2)N | [NH2:1][c:2]1[cH:3][c:4]([C:5]([NH:6][OH:7])=[NH:29])[cH:30][cH:31][n:32]1.O=[C:8](O)[c:9]1[cH:10][n:11][n:12]2[c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[n:27][c:28]12>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][o:7][c:8](-[c:9]3[cH:10][n:11][n:12]4[c:13]([C:14]([... | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)ccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccncc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[NH;D1;+0:17])-[NH;D2;+0:18]-[OH;D1;+0:19]):[c:20]:1>>[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[c;H0;D3;+0:16]2:[n;H0;D2;+0:17]:... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further pu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3dfa4cdd9241454e90ec23f4c742d639 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccnc(N)c1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccnc(N)c5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=CC(=C1)C(=N)NO>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC(=NC=C2)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([C:33]([F:34])([F:35])[F:36])[cH:31][cH:30]3)[n:29][c:28]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][n:22][c:23]([NH2:24])[cH:25]1)[NH:26][OH:27]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8]([F:9])([F:... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccnc(N)c1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccnc(N)c5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccncc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[NH;D1;+0:17])-[NH;D2;+0:18]-[OH;D1;+0:19]):[c:20]:1>>[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[c;H0;D3;+0:16]2:[n;H0;D2;+0:17]:... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccnc(N)c1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccnc(N)c5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-943eca4e9b374abaa48b3e4858d24a84 | CCOC(=O)CC(=O)c1ccncc1.CNC(N)=S>>Cn1c(S)nc(-c2ccncc2)cc1=O | O=C(CC(=O)OCC)C1=CC=NC=C1.CNC(=S)N.C1CCC2=NCCCN2CC1.CS(=O)(=O)O>>SC1=NC(=CC(N1C)=O)C1=CC=NC=C1 | CCO[C:14]([CH2:13][C:6](=O)[c:7]1[cH:8][cH:9][n:10][cH:11][cH:12]1)=[O:15].[CH3:1][NH:2][C:3](=[S:4])[NH2:5]>>[CH3:1][n:2]1[c:3]([SH:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1=[O:15] | CCOC(=O)CC(=O)c1ccncc1.CNC(N)=S | Cn1c(S)nc(-c2ccncc2)cc1=O | null | null | O | Aromatic Heterocycle Formation | OtherReaction | c04b055e21b4031fe26768e0d55d071f6b2babd82702a384a2b10b9819274d93 | 56c959c2c80b99d62790ed298d34d2ee8f8fae36a3429f28bc01961db7dd59db | O=c1cc(-c2ccncc2)nc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1.[C;D1;H3:11]-[NH;D2;+0:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[S;H0;D1;+0:15]>>[C;D1;H3:11]-[n;H0;D3;+0:12]1:[c;H0;D3;+0:1](=[O;D1;H0:2]):[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[c:6]:[c:7]:[#7;a:8... | 72.1 | [{"value": 72.0, "product": "SC1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "SC1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 3-oxo-3-(4-pyridyl)propionate (29.0 g, 150 mmol), N-methyl thiourea (40.6 g, 450 mmol) and 1,8-diazabicyclo[5,4,0]-7-undecene (22.4 ml, 150 mmol) was refluxed for 4 hours and the solution of methanesulfonic acid (14.4 g, 150 mmol) in water (50 ml) was added after cooling by ice-water. The precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Thiourea | Aromatic thiol | null | c1cncnc1 | c1cncnc1.c1ccncc1 | HO- | O | null | null | CCOC(=O)CC(=O)c1ccncc1.CNC(N)=S>O>Cn1c(S)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81c22925f817402c8db318b6e14408b2 | Cn1c(S)nc(-c2ccncc2)cc1=O.O=P(Cl)(Cl)Cl>>Cn1c(Cl)nc(-c2ccncc2)cc1=O | P(=O)(Cl)(Cl)Cl.CN(C=O)C.SC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1 | S[c:3]1[n:2]([CH3:1])[c:14](=[O:15])[cH:13][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[n:5]1.O=P(Cl)(Cl)[Cl:4]>>[CH3:1][n:2]1[c:3]([Cl:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[cH:13][c:14]1=[O:15] | Cn1c(S)nc(-c2ccncc2)cc1=O.O=P(Cl)(Cl)Cl | Cn1c(Cl)nc(-c2ccncc2)cc1=O | null | null | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 2c85b281db58d6bd687109160a9e2955abfaa102a459d1c56e9ab9e9dc07e3b5 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | O=c1cc(-c2ccncc2)nc[nH]1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[#7;a:5](-[C;D1;H3:6]):[c:7]>>[C;D1;H3:6]-[#7;a:5](:[c:7]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:3]:[c:4] | 77.2 | [{"value": 77.0, "product": "ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Phosphorous oxychloride (26.11 g, 170 mmol) was added to dimethyl-formamide (180 ml) and stirred 20 min. 2-Mercapto-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (24.15 g, 110 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 2 hours. Ethyl acetate (630 ml) was added to the ice-cooled solution ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | HCl | C(C)(=O)OCC | null | 0.333333 | Cn1c(S)nc(-c2ccncc2)cc1=O.O=P(Cl)(Cl)Cl>C(C)(=O)OCC>Cn1c(Cl)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b260d5d97bab4bc2add4d337f86dda13 | CCOC(=O)CC(=O)c1ccncn1.CNC(N)=S>>Cn1c(S)nc(-c2ccncn2)cc1=O | CS(=O)(=O)O.O=C(CC(=O)OCC)C1=NC=NC=C1.CNC(=S)N.C1CCC2=NCCCN2CC1>>SC1=NC(=CC(N1C)=O)C1=NC=NC=C1 | CCO[C:14]([CH2:13][C:6](=O)[c:7]1[cH:8][cH:9][n:10][cH:11][n:12]1)=[O:15].[CH3:1][NH:2][C:3](=[S:4])[NH2:5]>>[CH3:1][n:2]1[c:3]([SH:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][n:12]2)[cH:13][c:14]1=[O:15] | CCOC(=O)CC(=O)c1ccncn1.CNC(N)=S | Cn1c(S)nc(-c2ccncn2)cc1=O | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | c04b055e21b4031fe26768e0d55d071f6b2babd82702a384a2b10b9819274d93 | 56c959c2c80b99d62790ed298d34d2ee8f8fae36a3429f28bc01961db7dd59db | O=c1cc(-c2ccncn2)nc[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1.[C;D1;H3:11]-[NH;D2;+0:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[S;H0;D1;+0:15]>>[C;D1;H3:11]-[n;H0;D3;+0:12]1:[c;H0;D3;+0:1](=[O;D1;H0:2]):[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[#7;a:6]:[c:7]:[... | 78 | [{"value": 78.0, "product": "SC1=NC(=CC(N1C)=O)C1=NC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "SC1=NC(=CC(N1C)=O)C1=NC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 3-oxo-3-(4-pyrimidyl)propionate (34.1 g, 176 mmol), N-methyl thiourea (47.5 g, 527 mmol) and 1,8-diazabicyclo[5,4,0]-7-undecene (26.3 ml, 176 mmol) in ethanol (340 ml) was refluxed for 2 hours and the solution of methanesulfonic acid (16.9 g, 176 mmol) in water (70 ml) was added after cooling by ice... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Thiourea | Aromatic thiol | null | c1cncnc1 | c1cncnc1.c1cncnc1 | HO- | O.C(C)O | null | null | CCOC(=O)CC(=O)c1ccncn1.CNC(N)=S>O.C(C)O>Cn1c(S)nc(-c2ccncn2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebba085ddfba44fba0632948aa1012eb | Cn1c(S)nc(-c2ccncn2)cc1=O.O=P(Cl)(Cl)Cl>>Cn1c(Cl)nc(-c2ccncn2)cc1=O | C([O-])([O-])=O.[K+].[K+].SC1=NC(=CC(N1C)=O)C1=NC=NC=C1.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=CC(N1C)=O)C1=NC=NC=C1 | S[c:3]1[n:2]([CH3:1])[c:14](=[O:15])[cH:13][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][n:12]2)[n:5]1.O=P(Cl)(Cl)[Cl:4]>>[CH3:1][n:2]1[c:3]([Cl:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][n:12]2)[cH:13][c:14]1=[O:15] | Cn1c(S)nc(-c2ccncn2)cc1=O.O=P(Cl)(Cl)Cl | Cn1c(Cl)nc(-c2ccncn2)cc1=O | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 2c85b281db58d6bd687109160a9e2955abfaa102a459d1c56e9ab9e9dc07e3b5 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | O=c1cc(-c2ccncn2)nc[nH]1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[#7;a:5](-[C;D1;H3:6]):[c:7]>>[C;D1;H3:6]-[#7;a:5](:[c:7]):[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[#7;a:3]:[c:4] | 27 | [{"value": 27.0, "product": "ClC1=NC(=CC(N1C)=O)C1=NC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.0, "product": "ClC1=NC(=CC(N1C)=O)C1=NC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Phosphorous oxychloride (4.60 g, 30 mmol) was added to dimethyl-formamide (32 ml) and stirred for 20 min at 0° C. 2-Mercapto-3-methyl-6-(4-pyrimidyl)-3H-pyrimidine-4-one (4.40 g, 20 mmol) was added to the solution and stirred 5 min and then stirred at 70° C. for 2 hours. The reaction mixture was poured into ice water, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cncnc1 | HCl | CN(C=O)C | 0 | 0.333333 | Cn1c(S)nc(-c2ccncn2)cc1=O.O=P(Cl)(Cl)Cl>CN(C=O)C>Cn1c(Cl)nc(-c2ccncn2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b94a813eaacb4c7abe63836eb930fc50 | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN>>COc1cc(F)ccc1C1=NCCNC1=O | C(CN)N.FC1=CC(=C(C=C1)C(C(=O)OCC)=O)OC>>FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC | CCO[C:15]([C:10](=O)[c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1)=[O:16].[NH2:11][CH2:12][CH2:13][NH2:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[C:10]1=[N:11][CH2:12][CH2:13][NH:14][C:15]1=[O:16] | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN | COc1cc(F)ccc1C1=NCCNC1=O | null | null | C(C)O | Acylation | OtherReaction | 00bd986bfb0fcd1d6f2e8fce9049849efc71d5fc43b0a15d29645b647aa9a392 | d77bb5590d7a7da62c21e57132eb16f17d004fc6e8f59ceda844445a33958b29 | O=C1NCCN=C1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:10]-[C:9]-[C:8]-[N;H0;D2;+0:7]=[C;H0;D3;+0:3]-1-[c:4](:[c:5]):[c:6] | 79.2 | [{"value": 79.0, "product": "FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethylenediamine (0.60 g, 10.0 mmol) was added to a solution of ethyl 2-(4-fluoro-2-methoxyphenyl)-2-oxoacetate (2.26 g, 10.0 mmol) in ethanol (30 ml) and refluxed 4 hr. After removal of the solvent under reduced pressure, residue was washed with ethanol-diethyl ether to give 5,6-dihydro-3-(4-fluoro-2-methoxyphenyl)pyra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Primary amine | Substituted imine.Secondary amide | null | C1=NCCNC1 | c1ccccc1.C1=NCCNC1 | HO- | C(C)O | null | null | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN>C(C)O>COc1cc(F)ccc1C1=NCCNC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd7ca06cd0184f5092c660972b427ef3 | COc1cc(F)ccc1C1=NCCNC1=O>>COc1cc(F)ccc1C1CNCCN1 | FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>FC1=CC(=C(C=C1)C1NCCNC1)OC | O=[C:11]1[C:10]([c:9]2[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]2)=[N:15][CH2:14][CH2:13][NH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][NH:12][CH2:13][CH2:14][NH:15]1 | COc1cc(F)ccc1C1=NCCNC1=O | COc1cc(F)ccc1C1CNCCN1 | null | null | C(C)OCC | Reduction | OtherReaction | cdb401246d745dfde84770bc7cc3c003c030a11b1a08f556fa161c6008088fe7 | f4d5b1450c342d6f1334e433c03b5b288ecbf4a80f4f65eb4025809a8fa1bd03 | c1ccc(C2CNCCN2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[CH;D3;+0:6]1-[CH2;D2;+0:1]-[#7:2]-[C:3]-[C:4]-[NH;D2;+0:5]-1):[c:9] | 99 | [{"value": 99.0, "product": "FC1=CC(=C(C=C1)C1NCCNC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5,6-Dihydro-3-(4-fluoro-2-methoxyphenyl)pyrazinone was added to the solution of lithium aluminium hydride (0.46 g, 12 mmol) in diethyl ether (25 ml) and refluxed for 6 hr. Water (0.48 ml), 15% sodium hydroxide solution (0.48 ml) and again water (1.21 ml) were added to the ice-cooled solution and the precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine.Secondary amide | Secondary amine | C1=NCCNC1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | Other | C(C)OCC | null | null | COc1cc(F)ccc1C1=NCCNC1=O>C(C)OCC>COc1cc(F)ccc1C1CNCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-148f146bf91d4b0bb471df24340a0852 | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>COc1cc(F)ccc1C1CN(c2nc(-c3ccncc3)cc(=O)n2C)CCN1 | FC1=CC(=C(C=C1)C1NCCNC1)OC.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][NH:12][CH2:27][CH2:28][NH:29]1.Cl[c:13]1[n:14][c:15](-[c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[cH:22][c:23](=[O:24])[n:25]1[CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][N:12]([c:13]2[n:14][c:15](-[c:16]3[cH:17][... | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | COc1cc(F)ccc1C1CN(c2nc(-c3ccncc3)cc(=O)n2C)CCN1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 12e031c56e3265fed397a3e32360d8e1fccdeedb7d10ff4500339614dfe4903f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCNC(c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 62.2 | [{"value": 62.0, "product": "FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Chloro-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (222 mg, 1.0 mmol) was added to an ice-cooled solution of 2-(4-fluoro-2-methoxyphenyl)piperazine (210 mg, 1.0 mmol), triethylamine (0.15 ml, 1.1 mmol) in N,N-dimethylformamide (10 ml) and stirred at that temperature for 1 hr and then at room temperature for 2 hr. Next day... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | C1CNCC[NH]1.c1cncnc1 | c1ccccc1.C1CNCC[NH]1.c1cncnc1.c1ccncc1 | HCl | CN(C=O)C | null | 1 | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>CN(C=O)C>COc1cc(F)ccc1C1CN(c2nc(-c3ccncc3)cc(=O)n2C)CCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2defdc061a3e4af19d2074b117bdb250 | Cl>>Cl.Cl | Cl.FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)OC.C(C)OCC>>Cl.Cl.FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)OC | [ClH:30]>>[ClH:30].[ClH:31] | Cl | Cl.Cl | null | null | O1CCOCC1.ClCCl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 15 | MINUTE | 4N Hydrogen chloride in 1,4-dioxane (0.4 ml) was added to the solution of 2-(2-(4-fluoro-2-methoxyphenyl)piperazin-4-yl)-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (217 mg, 0.6 mmol) in dichloromethane (5 ml) and stirred for 15 min. After addition of diethyl ether, filtration and wash with diethyl ether and dryness gave th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | O1CCOCC1.ClCCl | null | 0.25 | Cl>O1CCOCC1.ClCCl>Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04d9b7cf628749039f767efa7fea906b | COc1ccc(C(=O)CBr)cc1.O>>COc1ccc(C(=O)C=O)cc1 | COC1=CC=C(C(CBr)=O)C=C1.O.O>>COC1=CC=C(C=C1)C(=O)C=O | Br[CH2:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:12][cH:11]1)=[O:8].[OH2:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]=[O:10])[cH:11][cH:12]1 | COc1ccc(C(=O)CBr)cc1.O | COc1ccc(C(=O)C=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e6f195d0eaa3dbf60a64865dd520e91a9420a32204416749e54032cc8ab6f41e | 0dd4cbb38ec6423de2cbac32f3512efe0313fd055cf8857f20d4712b6549de8d | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH2;D0;+0:5]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D2;+0:1]=[O;H0;D1;+0:5] | null | [] | null | null | null | null | Dimethylslufoxide (50 ml) solution of 4-methyoxyphenacylbromide (9.94 g, 43.4 mmol) and water (1.6 ml, 88.8 mmol) were stirred at 50° C. for 2.5 hr. Water was added and the solution was extracted with ethyl acetate 3 times and washed with brine and then dried over sodium sulfate. Removal of the solvent gave 4-methoxyph... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Aldehyde | null | null | c1ccccc1 | HBr | null | null | null | COc1ccc(C(=O)CBr)cc1.O>>COc1ccc(C(=O)C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bb930f324334d69b46eb823f018c576 | COc1ccc(C(=O)C=O)cc1.NCCN>>COc1ccc(C2CNCCN2)cc1 | C(CN)N.[BH4-].[Na+].COC1=CC=C(C=C1)C(=O)C=O>>COC1=CC=C(C=C1)C1NCCNC1 | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][cH:13]1)[CH:8]=O.[NH2:9][CH2:10][CH2:11][NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][NH:9][CH2:10][CH2:11][NH:12]2)[cH:13][cH:14]1 | COc1ccc(C(=O)C=O)cc1.NCCN | COc1ccc(C2CNCCN2)cc1 | null | null | O1CCCC1.CO | Heteroatom Alkylation and Arylation | OtherReaction | 99a2828c3eaad08d3def716f9abc8d657715d71e5744b4123840077b0a9e0844 | de962c7d415480705067419985f082d32cc2486ad026c535b0bd29f2533f2922 | c1ccc(C2CNCCN2)cc1 | O=[CH;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[c:4]:[c:3](-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8]-[C:7]-[NH;D2;+0:6]-1):[c:5] | 45.3 | [{"value": 45.0, "product": "COC1=CC=C(C=C1)C1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.3, "product": "COC1=CC=C(C=C1)C1NCCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | Methanol (5 ml) solution of ethylenediamine (3.74 g, 62.29 mmol) was added to the ice-cooled solution of 4-methoxyphenylglyoxal (8.30 g, 45.5 mmol) in methanol (100 ml) and tetrahydrofuran (50 ml) and stirred for 10 min. After cooling to 0° C., sodium tetrahydroborate (6.14 g, 162.2 mmol) and additional methanol (50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Primary amine.Primary amine | Secondary amine.Secondary amine | null | C1CNCCN1 | c1ccccc1.C1CNCCN1 | Other | O1CCCC1.CO | 0 | 0.166667 | COc1ccc(C(=O)C=O)cc1.NCCN>O1CCCC1.CO>COc1ccc(C2CNCCN2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cc5ded6a9224a0f953c34488890b846 | Cl>>Cl.Cl | Cl.COC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1>>Cl.Cl.COC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [ClH:29]>>[ClH:29].[ClH:30] | Cl | Cl.Cl | null | null | ClCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 96 | [{"value": 96.0, "product": "Cl.Cl.COC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4N Hydrogen chloride in ethyl acetate (5 ml) was added to the solution of 2-(2-(4-methoxyphenyl)-piperazine-4-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one (594 mg, 1.6 mmol) in dichloromethane (5 ml) and stirred for 1 hr. Wash with ethyl acetate after removal of the solvent and dryness gave the title compound (683 mg, 96%... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | ClCCl.C(C)(=O)OCC | null | 1 | Cl>ClCCl.C(C)(=O)OCC>Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3289adec1bb49b0b7ded17da9899ca1 | CC(C)(C)OC(=O)N1CCNC(=O)C1c1ccc(Cl)cc1>>CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1 | C(C)(C)(C)OC(=O)N1C(C(NCC1)=O)C1=CC=C(C=C1)Cl.C(C)(=O)O.[BH4-].[Na+]>>C(C)(C)(C)OC(=O)N1C(CNCC1)C1=CC=C(C=C1)Cl | O=[C:12]1[NH:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:13]1[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | CC(C)(C)OC(=O)N1CCNC(=O)C1c1ccc(Cl)cc1 | CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1 | null | null | O1CCOCC1 | Reduction | Reduction of secondary amides to amines | 3ea95105d254d3323d82c191c208d1f768257e4bf908413d908099941762e930 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(C2CNCCN2)cc1 | O=[C;H0;D3;+0:1]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:13]-1-[c:14]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:5]1-[C:4]-[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:13]-1-[c:14] | 69.5 | [{"value": 69.0, "product": "C(C)(C)(C)OC(=O)N1C(CNCC1)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "C(C)(C)(C)OC(=O)N1C(CNCC1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Solution of 4-(tert-butoxycarbonyl)-3-(4-chlorophenyl)-piperazin-2-one (500 mg, 1.6 mmol) and acetic acid (929 μl, 16 mmol) were added to a refluxed solution of sodium borohydride (608 mg, 16 mmol) in 1,4-dioxane (5 ml) and reflux was continued. The reaction was quenched by water and extracted with dichloromethane and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1C[NH]CCN1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccccc1 | Other | O1CCOCC1 | null | null | CC(C)(C)OC(=O)N1CCNC(=O)C1c1ccc(Cl)cc1>O1CCOCC1>CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de30e35dd9cd4166848baa3186d42cd8 | CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | C(C)(C)(C)OC(=O)N1C(CNCC1)C1=CC=C(C=C1)Cl.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N1C(CN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)C1=CC=C(C=C1)Cl | [NH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:15]([c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[CH2:23]1.Cl[c:3]1[n:2]([CH3:1])[c:33](=[O:34])[cH:32][c:25](-[c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[n:24]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][... | CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89a9e7e1366d55004dcd9e6694ddaa661145a78e26c30f61d46c470b984e6100 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCNC(c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 94.3 | [{"value": 93.0, "product": "C(C)(C)(C)OC(=O)N1C(CN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "C(C)(C)(C)OC(=O)N1C(CN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(tert-butoxycarbonyl)-3-(4-chlorophenyl)piperazine (330 mg, 1.1 mmol), 2-chloro-3-methyl-6-(4-pyridyl)pyrimidin-4-one (246 mg, 1.1 mmol) and triethylamine (170 μl, 1.22 mmol) in tetrahydrofuran were refluxed. Usual workup and purification by silica gel column chromatography gave 2-(1-(tert-butoxy-carbon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cncnc1 | c1cncnc1.C1C[NH]CC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1 | null | null | CC(C)(C)OC(=O)N1CCNCC1c1ccc(Cl)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c696d5240cc431587d259cc68331a13 | Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O>>Cn1c(N2CCNC(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | Cl.C(C)(C)(C)OC(=O)N1C(CN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)C1=CC=C(C=C1)Cl>>Cl.ClC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([c:4]2[n:3]([CH3:2])[c:27](=[O:28])[cH:26][c:19](-[c:20]3[cH:21][cH:22][n:23][cH:24][cH:25]3)[n:18]2)[CH2:17][CH:9]1[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[CH3:2][n:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH:9]([c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]3)[CH2:17... | Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | Cn1c(N2CCNC(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1cc(-c2ccncc2)nc(N2CCNC(c3ccccc3)C2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1-[c:7]>>[c:7]-[C:6]1-[C:5]-[#7:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 178.3 | [{"value": 79.0, "product": "Cl.ClC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 178.3, "product": "Cl.ClC1=CC=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4N Hydrogen chloride in ethyl acetate was added to the solution of 2-(1-(tert-butoxycarbonyl)-2-(4-chlorophenyl)-piperazine-4-yl)-3-methyl-6-(4-pyridyl)pyrimidin-4-one (500 mg, 1.0 mmol) in ethyl acetate and stirred. Filtration and successive dryness gave the title compound (373 mg, 79%).
Conditions: See reaction.notes... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | null | Cn1c(N2CCN(C(=O)OC(C)(C)C)C(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O>C(C)(=O)OCC>Cn1c(N2CCNC(c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f69f463b37f64448b84e3814c8772d08 | Brc1cccnc1.O=Cc1ccc(OB(O)O)cc1>>O=Cc1ccc(-c2cccnc2)cc1 | C(=O)C1=CC=C(C=C1)OB(O)O.C([O-])([O-])=O.[Na+].[Na+].C(C)O.BrC=1C=NC=CC1>>N1=CC(=CC=C1)C1=CC=C(C=O)C=C1 | Br[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1.OB(O)O[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:14][cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[cH:13][cH:14]1 | Brc1cccnc1.O=Cc1ccc(OB(O)O)cc1 | O=Cc1ccc(-c2cccnc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e2533727ba49df05c480d8636a7001bec577364d4badd5af5a9fe70fba1ad851 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-O-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | 25.3 | [{"value": 25.0, "product": "N1=CC(=CC=C1)C1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.3, "product": "N1=CC(=CC=C1)C1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrakis(triphenylphosphine)palladium (0.65 g, 0.56 mmol), 4-formylphenylboric acid (2.81 g, 18.7 mmol), 2M aqueous sodium carbonate (18.7 ml, 37.4 mmol) and ethanol were added to the nitrogen-saturated solution of 3-bromopyridine (2.66 g, 16.8 mmol) in toluene and refluxed under nitrogen for 8 hrs. Water was added to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1ccccc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C | null | null | Brc1cccnc1.O=Cc1ccc(OB(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C>O=Cc1ccc(-c2cccnc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a443f0ff195436fbdf1639a06c2e660 | CI.O=Cc1ccc(-c2cccnc2)cc1>>CN1CCC=C(c2ccc(CO)cc2)C1 | [BH4-].[Na+].CI.N1=CC(=CC=C1)C1=CC=C(C=O)C=C1.CI>>OCC1=CC=C(C=C1)C=1CN(CCC1)C | I[CH3:1].[n:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][cH:14]2)[cH:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][cH:14]2)[CH2:15]1 | CI.O=Cc1ccc(-c2cccnc2)cc1 | CN1CCC=C(c2ccc(CO)cc2)C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | ca1fbe2eb8cad657d343ce8428c43ad95b2c1e6e1c1fa4c8aa39961a8191a2b9 | a3581f7a613a227d74f3b0bb5e545b36db14fb12699d780dc0546b4a0bb7524f | C1=C(c2ccccc2)CNCC1 | I-[CH3;D1;+0:1].[O;H0;D1;+0:2]=[CH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8]2:[cH;D2;+0:9]:[n;H0;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1>>[CH3;D1;+0:1]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[C;H0;D3;+0:8](-[c;H0;D3;+0:7]2:[c:6]:[c:5]:[c:4](-[CH2;D2;+0:3]-[OH;D1;+0:2]):[c:15]:[c:... | 72.1 | [{"value": 72.0, "product": "OCC1=CC=C(C=C1)C=1CN(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "OCC1=CC=C(C=C1)C=1CN(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Methyl iodide (0.8 ml, 12.9 mmol) was added to a solution of 4-(3-pyridyl)benzaldehyde (0.78 g, 4.3 mmol) in dichloromethane and stirred 2 days. Additional methyl iodide (0.8 ml, 12.9 mmol) was added and stirred for 3 hr. After removal of the solvent, methanol was added to the residue and ice-cooled. Sodium tetrahydrob... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol.Tertiary amine | c1ccncc1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1 | I- | ClCCl | null | 48 | CI.O=Cc1ccc(-c2cccnc2)cc1>ClCCl>CN1CCC=C(c2ccc(CO)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d3ed45b9ec942bc96557bdad304f18f | CC(=O)OCc1ccc(C2=CCCN(C(=O)OC(C)(C)C)C2)cc1>>CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1 | C(C)(=O)OCC1=CC=C(C=C1)C=1CN(CCC1)C(=O)OC(C)(C)C>>OCC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C | CC(=O)[O:18][CH2:17][c:16]1[cH:15][cH:14][c:13]([C:12]2=[CH:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:21]2)[cH:20][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19][cH:20]2)[CH2:21]1 | CC(=O)OCc1ccc(C2=CCCN(C(=O)OC(C)(C)C)C2)cc1 | CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1 | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | a2ec8d9870f5d1b110f1e1827a9e57345127e35f68eb9d3f5032200c1595139c | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(C2CCCNC2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]1-[C:12]-[C;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])=[CH;D2;+0:17]-[C:18]-[C:19]-1>>[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[#7:11]1-[C:12]-[CH;D3;+0:13](-[c:14](:[c:15]):[c... | 63.7 | [{"value": 62.0, "product": "OCC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.7, "product": "OCC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Palladium on charcoal was added to the solution of 3-(4-acetoxymethylphenyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine (0.71 g, 2.1 mmol) in ethyl acetate and stirred under hydrogen atmosphere. After filtration with celite and removal of the solvent under reduced pressure, methanol and 1N aqueous sodium hydrox... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | C1=CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(=O)OCc1ccc(C2=CCCN(C(=O)OC(C)(C)C)C2)cc1>[Pd].C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-006a6d8fe70a42688554cce043580d69 | C1CCNC1.CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1>>CC(C)(C)OC(=O)N1CCCC(c2ccc(CN3CCCC3)cc2)C1 | C(C)N(CC)CC.CS(=O)(=O)Cl.OCC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C.N1CCCC1>>N1(CCCC1)CC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C | [NH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1.O[CH2:17][c:16]1[cH:15][cH:14][c:13]([CH:12]2[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25]2)[cH:24][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([CH2:17][N:18]3... | C1CCNC1.CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1 | CC(C)(C)OC(=O)N1CCCC(c2ccc(CN3CCCC3)cc2)C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 5b5461e2c999b5ff4ebd02389aabcfa6da1d5461f5b1011870f0b8680e19702d | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1cc(C2CCCNC2)ccc1CN1CCCC1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1):[c:4] | 56.3 | [{"value": 56.0, "product": "N1(CCCC1)CC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "N1(CCCC1)CC1=CC=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7.5 | HOUR | Triethylamine (0.47 g, 3.4 mmol) and methanesulfonyl chloride (0.12 ml, 1.6 mmol) were added to an ice-cooled solution of 3-(4-hydroxymethylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.39 g, 1.34 mmol) in dichloromethane and stirred for 7.5 hr. Pyrrolidine (1.0 ml, 12 mmol) was added to the solution and stirred overnig... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1 | HO- | ClCCl | null | 7.5 | C1CCNC1.CC(C)(C)OC(=O)N1CCCC(c2ccc(CO)cc2)C1>ClCCl>CC(C)(C)OC(=O)N1CCCC(c2ccc(CN3CCCC3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3c0b0bfe2f9418e80b26d8f079d9bbf | Cc1cc(N2CCCC2)ccc1C1CCCN(C(=O)OC(C)(C)C)C1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cn1c(N2CCCC(c3ccc(CN4CCCC4)cc3)C2)nc(-c2ccncc2)cc1=O | Cl.N1(CCCC1)C1=CC(=C(C=C1)C1CN(CCC1)C(=O)OC(C)(C)C)C.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)CN1CCCC1 | CC(C)(C)OC(=O)[N:4]1[CH2:5][CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:19][c:20]2[CH3:13])[CH2:21]1.Cl[c:3]1[n:2]([CH3:1])[c:31](=[O:32])[cH:30][c:23](-[c:24]2[cH:25][cH:26][n:27][cH:28][cH:29]2)[n:22]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH2:7][CH:8]([c:9]3[cH:10][... | Cc1cc(N2CCCC2)ccc1C1CCCN(C(=O)OC(C)(C)C)C1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cn1c(N2CCCC(c3ccc(CN4CCCC4)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1.CC(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | d725ab41a4fd0183219de5fe89a63dd99b54b73567d324e77844e9b95b27a0cd | 664becdce345022b7180315da3be6d6bcc9d100d875d21104c7ae562ed524fb4 | O=c1cc(-c2ccncc2)nc(N2CCCC(c3ccc(CN4CCCC4)cc3)C2)[nH]1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[c;H0;D3;+0:7](-[N;H0;D3;+0:8]2-[C:9]-[C:10]-[C:11]-[C:12]-2):[c:13]:[c;H0;D3;+0:14]:1-[CH3;D1;+0:15])-[C:16]-[C:17].Cl-[c;H0;D3;+0:18](:[#7;a:19]:[c:20]):[#7;a:21](-[C;D1;H3:22]):[c:23]>>[C:17]-[C:16]-[N;H0;D3;+0:1](-[c;H0;D3;+0:18](:[#7;a:19]:[c:20]):... | 84.4 | [{"value": 76.0, "product": "C(\\C=C\\C(=O)O)(=O)O.CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)CN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "C(\\C=C\\C(=O)O)(=O)O.CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)CN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 8 | HOUR | 4N Hydrogen chloride in ethyl acetate was added to 3-(4-(1-pyrrolidinyl)-methylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.26 g, 0.75 mmol) and stirred overnight. After filtration and dryness, triethylamine (0.5 ml, 3.6 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (0.14 g, 0.63 mmol) and tetrahydrofuran were... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Tertiary amine.Boc | Tertiary amine.Tertiary amine | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1cncnc1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccncc1 | HCl | O1CCCC1.CC(=O)C.C(C)(=O)OCC | null | 8 | Cc1cc(N2CCCC2)ccc1C1CCCN(C(=O)OC(C)(C)C)C1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1.CC(=O)C.C(C)(=O)OCC>Cn1c(N2CCCC(c3ccc(CN4CCCC4)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dca0b41a04f43f39ecc56795420884e | O=S(Cl)Cl.O[C@H](CNCc1ccccc1)c1ccc(Cl)cc1>>O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1 | S(=O)(Cl)Cl.C(C1=CC=CC=C1)NC[C@@H](O)C1=CC=C(C=C1)Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)N1S(O[C@H](C1)C1=CC=C(C=C1)Cl)=O | Cl[S:2](Cl)=[O:1].[OH:3][C@@H:4]([c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1)[CH2:12][NH:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[S:2]1[O:3][C@@H:4]([c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[CH2:12][N:13]1[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=S(Cl)Cl.O[C@H](CNCc1ccccc1)c1ccc(Cl)cc1 | O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1 | null | null | ClCCl | Acylation | OtherReaction | 1022b0fd2e889283b9a33d499c05ae577cef391933141cb17575b720a5527289 | 6696b84d86549914126483f310a3cdae7ade48595a34099e6e2bfb6e945a07ed | O=S1O[C@@H](c2ccccc2)CN1Cc1ccccc1 | Cl-[S;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[OH;D1;+0:3]-[C:4](-[c:5])-[C:6]-[NH;D2;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[S;H0;D3;+0:1]1-[O;H0;D2;+0:3]-[C:4](-[c:5])-[C:6]-[N;H0;D3;+0:7]-1-[C:8]-[c:9] | 87.4 | [{"value": 87.4, "product": "C(C1=CC=CC=C1)N1S(O[C@H](C1)C1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "C(C1=CC=CC=C1)N1S(O[C@H](C1)C1=CC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | To a suspension of (S)-2-benzylamino-1-(4-chlorophenyl)ethanol (15.76 g, 60.21 mmol) and triethylamine (33.6 ml, 241 mmol) in dichloromethane (300 ml) was added a solution of thionyl chloride (4.83 ml, 66.2 mmol) in dichloromethane (20 ml) at −78° C. over 20 min. The resulting suspension was stirred at −78° C. for 20 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary amine | Tertiary amine.Sulfinate | null | C1COS[NH]1 | C1COS[NH]1.c1ccccc1.c1ccccc1 | HCl | ClCCl | 0 | 0.333333 | O=S(Cl)Cl.O[C@H](CNCc1ccccc1)c1ccc(Cl)cc1>ClCCl>O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6eb2abc1f944a889777fbf03a22d6e7 | O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1.[N-]=[N+]=[N-]>>[N-]=[N+]=N[C@@H](CNCc1ccccc1)c1ccc(Cl)cc1 | C(C1=CC=CC=C1)N1S(O[C@H](C1)C1=CC=C(C=C1)Cl)=O.[N-]=[N+]=[N-].[Na+]>>C(C1=CC=CC=C1)NC[C@@H](C1=CC=C(C=C1)Cl)N=[N+]=[N-] | O=S1O[C@@H:4]([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:5][N:6]1[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][C@@H:4]([CH2:5][NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1.[N-]=[N+]=[N-] | [N-]=[N+]=N[C@@H](CNCc1ccccc1)c1ccc(Cl)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f97c74e4d28ad2248e700afce42330df49eaba62aa843c455de5e3e6b886aa61 | 291bb4152657ff595172285eee78e7ae29c88cad717c5e59068096af46251444 | c1ccc(CCNCc2ccccc2)cc1 | O=S1-O-[C@@H;D3;+0:1](-[c:2](:[c:3]):[c:4])-[C:5]-[N;H0;D3;+0:6]-1-[C:7]-[c:8].[N-;H0;D1:9]=[#7;+:10]=[N;-;D1;H0:11]>>[N;-;D1;H0:11]=[#7;+:10]=[N;H0;D2;+0:9]-[C@@H;D3;+0:1](-[C:5]-[NH;D2;+0:6]-[C:7]-[c:8])-[c:2](:[c:3]):[c:4] | 84.2 | [{"value": 83.8, "product": "C(C1=CC=CC=C1)NC[C@@H](C1=CC=C(C=C1)Cl)N=[N+]=[N-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "C(C1=CC=CC=C1)NC[C@@H](C1=CC=C(C=C1)Cl)N=[N+]=[N-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2RS,5S)-3-benzyl-5-(4-chlorophenyl)-1,2,3-oxathiazolidine 2-oxide (16.2 g, 52.6 mmol) and sodium azide (17.11 g, 263.2 mmol) in N,N-dimethylformamide (100 ml) was heated at 70° C. for 24 hours. The reaction mixture was partitioned between ether and water, and the organic layer was washed with water and b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Sulfinate | Azide.Secondary amine | C1COS[NH]1 | null | c1ccccc1.c1ccccc1 | Other | CN(C=O)C | null | null | O=S1O[C@@H](c2ccc(Cl)cc2)CN1Cc1ccccc1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=N[C@@H](CNCc1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1de0259a8a84327b9e2f24dc67382a6 | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)C[C@H]1c1ccc(Cl)cc1.CC(Cl)OC(=O)Cl>>Cl.Cl.Clc1ccc([C@@H]2CNCCN2)cc1 | C(C1=CC=CC=C1)N1C[C@H](N(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)Cl.ClC(=O)OC(C)Cl>>Cl.Cl.ClC1=CC=C(C=C1)[C@H]1NCCNC1 | CC(C)(C)OC(=O)[N:13]1[C@H:8]([c:7]2[cH:6][cH:5][c:4]([Cl:3])[cH:15][cH:14]2)[CH2:9][N:10](Cc2ccccc2)[CH2:11][CH2:12]1.CC(OC(=O)[Cl:2])[Cl:1]>>[ClH:1].[ClH:2].[Cl:3][c:4]1[cH:5][cH:6][c:7]([C@@H:8]2[CH2:9][NH:10][CH2:11][CH2:12][NH:13]2)[cH:14][cH:15]1 | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)C[C@H]1c1ccc(Cl)cc1.CC(Cl)OC(=O)Cl | Cl.Cl.Clc1ccc([C@@H]2CNCCN2)cc1 | null | null | ClCCCl | Miscellaneous | OtherReaction | 89cd83581a5439a20bbaabef74686371eeff8ef5764adacfc5aa868c5c8adfb2 | dd9a8ca002668a303c0d2a46c0c52d2c7964341fa1886fb5b6d9629fd15fadd5 | c1ccc([C@@H]2CNCCN2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4](-C-c2:c:c:c:c:c:2)-[C:5]-[C:6]-1-[c:7].C-C(-[Cl;H0;D1;+0:8])-O-C(=O)-[Cl;H0;D1;+0:9]>>[ClH;D0;+0:8].[ClH;D0;+0:9].[c:7]-[C:6]1-[C:5]-[NH;D2;+0:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | null | null | To a solution of (R)-1-benzyl-4-(tert-butoxycarbonyl)-3-(4-chlorophenyl)piperazine (11.6 g, 30.1 mmol) in 1,2-dichloroethane (80 ml) was added 1-chloroethyl chloroformate (4.91 ml, 45.1 mmol) at room temperature. Upon disappearance of the starting material, the reaction mixture was concentrated under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Carbamic ester.Ether.Ether.Tertiary amine.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1.c1ccccc1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | HO- | ClCCCl | null | null | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)C[C@H]1c1ccc(Cl)cc1.CC(Cl)OC(=O)Cl>ClCCCl>Cl.Cl.Clc1ccc([C@@H]2CNCCN2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5a684e1cab24b28bfa1c9f6becec9f7 | Clc1ccc([C@@H]2CNCCN2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cn1c(N2CCN[C@H](c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | ClC1=NC(NC=C1)=O.C(C)N(CC)CC.Cl.Cl.ClC1=CC=C(C=C1)[C@H]1NCCNC1.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>ClC1=CC=C(C=C1)[C@H]1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [NH:4]1[CH2:5][CH2:6][NH:7][C@H:8]([c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[CH2:16]1.Cl[c:3]1[n:2]([CH3:1])[c:26](=[O:27])[cH:25][c:18](-[c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[n:17]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][NH:7][C@H:8]([c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[CH2:16]2)[n:17]... | Clc1ccc([C@@H]2CNCCN2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cn1c(N2CCN[C@H](c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@H](c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 77.4 | [{"value": 77.4, "product": "ClC1=CC=C(C=C1)[C@H]1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "ClC1=CC=C(C=C1)[C@H]1NCCN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of (R)-2-(4-chlorophenyl)piperazine dihydrochloride (1.09 g, 4.05 mmol) in tetrahydrofuran (24 ml) was added triethylamine (2.82 ml, 20.3 mmol). After stirring for 15 min at room temperature, 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (748 mg, 3.38 mmol) was added portionwise. Upon disappearance... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1 | null | 0.25 | Clc1ccc([C@@H]2CNCCN2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>Cn1c(N2CCN[C@H](c3ccc(Cl)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3214dec4a244d639a6af1e5525a6813 | CCOC(=O)C(=O)OCC.COc1cc(F)ccc1Br>>CCOC(=O)C(=O)c1ccc(F)cc1OC | C(C(=O)OCC)(=O)OCC.Cl.BrC1=C(C=C(C=C1)F)OC.[Mg].BrCCBr>>FC1=CC(=C(C=C1)C(C(=O)OCC)=O)OC | CCO[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7].Br[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]1[O:15][CH3:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]1[O:15][CH3:16] | CCOC(=O)C(=O)OCC.COc1cc(F)ccc1Br | CCOC(=O)C(=O)c1ccc(F)cc1OC | null | null | O1CCCC1.O.C(C)OCC | C-C Coupling | Ester and halide to ketone | d844864d847e2bd5ea6d4b5b2fb00effd3f7cb7f2d2eae4a16a38b62104a1db8 | dd03ca4e617545414fae7e22c410ecd4f78e4fd10d5a86bce7e36a4a1d0f1e9d | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#8:5]):[c:6].C-C-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:2]:[c:3] | 59.3 | [{"value": 59.0, "product": "FC1=CC(=C(C=C1)C(C(=O)OCC)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "FC1=CC(=C(C=C1)C(C(=O)OCC)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | A solution of 2-bromo-5-fluoroanisole (11.8 g, 57.6 mmol) in tetrahydrofuran (60 ml) was dropped into the magnesium (1.40 g, 57.6 mmol) in refluxed tetrahydrofuran (32 ml) containing small amount of 1,2-dibromoethane and refluxed for 15 min. After addition of tetrahydrofuran (50 ml), the solution was cooled to −78° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1.O.C(C)OCC | -78 | 0.5 | CCOC(=O)C(=O)OCC.COc1cc(F)ccc1Br>O1CCCC1.O.C(C)OCC>CCOC(=O)C(=O)c1ccc(F)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f63a0773934e44e2b521cfb5edb6cf45 | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN>>COc1cc(F)ccc1C1=NCCNC1=O | C(CN)N.FC1=CC(=C(C=C1)C(C(=O)OCC)=O)OC>>FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC | CCO[C:15]([C:10](=O)[c:9]1[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1)=[O:16].[NH2:11][CH2:12][CH2:13][NH2:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[C:10]1=[N:11][CH2:12][CH2:13][NH:14][C:15]1=[O:16] | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN | COc1cc(F)ccc1C1=NCCNC1=O | null | null | C(C)O | Acylation | OtherReaction | 00bd986bfb0fcd1d6f2e8fce9049849efc71d5fc43b0a15d29645b647aa9a392 | d77bb5590d7a7da62c21e57132eb16f17d004fc6e8f59ceda844445a33958b29 | O=C1NCCN=C1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[C:9]-[NH2;D1;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:10]-[C:9]-[C:8]-[N;H0;D2;+0:7]=[C;H0;D3;+0:3]-1-[c:4](:[c:5]):[c:6] | 79.2 | [{"value": 79.0, "product": "FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethylenediamine (0.60 g, 10.0 mmol) was added to a solution of ethyl 2-(4-fluoro-2-methoxyphenyl)-2-oxoacetate (2.26 g, 10.0 mmol) in ethanol (30 ml) and refluxed 4 hr; After removal of the solvent under reduced pressure, residue was washed with ethanol-diethyl ether to give 5,6-dihydro-3-(4-fluoro-2-methoxyphenyl)pyra... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Primary amine | Substituted imine.Secondary amide | null | C1=NCCNC1 | c1ccccc1.C1=NCCNC1 | HO- | C(C)O | null | null | CCOC(=O)C(=O)c1ccc(F)cc1OC.NCCN>C(C)O>COc1cc(F)ccc1C1=NCCNC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea66092116594ad1b3ec7c6eb5d87e87 | COc1cc(F)ccc1C1=NCCNC1=O>>COc1cc(F)ccc1C1CNCCN1 | FC1=CC(=C(C=C1)C=1C(NCCN1)=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>FC1=CC(=C(C=C1)C1NCCNC1)OC | O=[C:11]1[C:10]([c:9]2[c:3]([O:2][CH3:1])[cH:4][c:5]([F:6])[cH:7][cH:8]2)=[N:15][CH2:14][CH2:13][NH:12]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][NH:12][CH2:13][CH2:14][NH:15]1 | COc1cc(F)ccc1C1=NCCNC1=O | COc1cc(F)ccc1C1CNCCN1 | null | null | C(C)OCC | Reduction | OtherReaction | cdb401246d745dfde84770bc7cc3c003c030a11b1a08f556fa161c6008088fe7 | f4d5b1450c342d6f1334e433c03b5b288ecbf4a80f4f65eb4025809a8fa1bd03 | c1ccc(C2CNCCN2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3]-[C:4]-[N;H0;D2;+0:5]=[C;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[CH;D3;+0:6]1-[CH2;D2;+0:1]-[#7:2]-[C:3]-[C:4]-[NH;D2;+0:5]-1):[c:9] | 99 | [{"value": 99.0, "product": "FC1=CC(=C(C=C1)C1NCCNC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5,6-Dihydro-3-(4-fluoro-2-methoxyphenyl)pyrazinone was added to the solution of lithium aluminium hydride (0.46 g, 12 mmol) in diethyl ether (25 ml) and refluxed for 6 hr. Water (0.48 ml), 15% sodium hydroxide solution (0.48 ml) and again water (1.21 ml) were added to the ice-cooled solution and the precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine.Secondary amide | Secondary amine | C1=NCCNC1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | Other | C(C)OCC | null | null | COc1cc(F)ccc1C1=NCCNC1=O>C(C)OCC>COc1cc(F)ccc1C1CNCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-441686eb1364445383a1c7aab5741191 | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncn2)cc1=O>>COc1cc(F)ccc1C1CN(c2nc(-c3ccncn3)cc(=O)n2C)CCN1 | FC1=CC(=C(C=C1)C1NCCNC1)OC.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=NC=NC=C1>>FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=NC=NC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][NH:12][CH2:27][CH2:28][NH:29]1.Cl[c:13]1[n:14][c:15](-[c:16]2[cH:17][cH:18][n:19][cH:20][n:21]2)[cH:22][c:23](=[O:24])[n:25]1[CH3:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]1[CH2:11][N:12]([c:13]2[n:14][c:15](-[c:16]3[cH:17][c... | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncn2)cc1=O | COc1cc(F)ccc1C1CN(c2nc(-c3ccncn3)cc(=O)n2C)CCN1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 12e031c56e3265fed397a3e32360d8e1fccdeedb7d10ff4500339614dfe4903f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncn2)nc(N2CCNC(c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 66 | [{"value": 66.0, "product": "FC1=CC(=C(C=C1)C1NCCN(C1)C1=NC(=CC(N1C)=O)C1=NC=NC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 2-Chloro-3-methyl-6-(4-pyrimidyl)-pyrimidin-4-one (223 mg, 1:0 mmol) was added to an ice-cooled solution of 2-(4-fluoro-2-methoxyphenyl)piperazine (210 mg, 1.0 mmol), triethylamine (0.15 ml, 1.1 mmol) in N,N-dimethylformamide (10 ml) and stirred at that temperature for 0.5 hr and then at room temperature for 3 hours. R... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | C1CNCC[NH]1.c1cncnc1 | c1ccccc1.C1CNCC[NH]1.c1cncnc1.c1cncnc1 | HCl | CN(C=O)C | null | 0.5 | COc1cc(F)ccc1C1CNCCN1.Cn1c(Cl)nc(-c2ccncn2)cc1=O>CN(C=O)C>COc1cc(F)ccc1C1CN(c2nc(-c3ccncn3)cc(=O)n2C)CCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1633c9ffe56c4fc4b75471ceff8591df | CS(C)=O.O=C(CBr)c1ccc(Cl)cc1>>O=CC(=O)c1ccc(Cl)cc1 | CS(=O)C.ClC1=CC=C(C(CBr)=O)C=C1>>ClC1=CC=C(C=C1)C(=O)C=O | CS(C)=[O:1].Br[CH2:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[O:1]=[CH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1 | CS(C)=O.O=C(CBr)c1ccc(Cl)cc1 | O=CC(=O)c1ccc(Cl)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 30e31f7c52850f256ba2bbca994259286fade061bb844a302399cf92f770ac34 | 5daa5f99c89a6674dd453f175d77d2b71103e29228a56e75708dd50c7985125a | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-S(-C)=[O;H0;D1;+0:5]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D2;+0:1]=[O;H0;D1;+0:5] | 50 | [{"value": 50.0, "product": "ClC1=CC=C(C=C1)C(=O)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethyl sulfoxide (60 ml) solution of 4-chlorophenacylbromide (11.11 g, 65.9 mmol) and water (1.7 ml) were stirred. The solution was extracted with ethyl acetate 3 times and washed with water twice and brine and then dried over sodium sulfate. After removal of the solvent, the residue was washed with hexane-ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Sulfoxide | Aldehyde | null | null | c1ccccc1 | HBr | O | null | null | CS(C)=O.O=C(CBr)c1ccc(Cl)cc1>O>O=CC(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2588ad8fe3934c25819aac4bbb482aa5 | CS(C)=O.O.O=C(CBr)c1ccc(Cl)cc1>>O=C(c1ccc(Cl)cc1)C(O)O | O.ClC1=CC=C(C=C1)C(CBr)=O.O.Br.CS(=O)C>>ClC1=CC=C(C=C1)C(C(O)O)=O | CS(C)=[O:12].[OH2:11].Br[CH2:10][C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[CH:10]([OH:11])[OH:12] | CS(C)=O.O.O=C(CBr)c1ccc(Cl)cc1 | O=C(c1ccc(Cl)cc1)C(O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df24e23b0a4f351701efee2d07f0d6d8593313630a6f8f0438637274c7aef392 | be2570c8f3c09e705d3edf621bfac8d976c0ab1f5e2eafbc4da2e57fed5ef70b | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-S(-C)=[O;H0;D1;+0:5].[OH2;D0;+0:6]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D3;+0:1](-[OH;D1;+0:6])-[OH;D1;+0:5] | 70 | [{"value": 70.0, "product": "ClC1=CC=C(C=C1)C(C(O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4′-chloro-2-bromoacetophenone (25.0 g, 107 mmol), water (1.92 mL, 107 mmol) and 47% hydrobromic acid (0.20 mL) in dimethylsulfoxide (160 mL) was stirred at 80° C. for 5 h. After the reaction mixture was poured into water, the precipitate was filtered, washed with diethylether and dried, affording 4′-chlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Sulfoxide | Ketone.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1 | HBr | null | null | null | CS(C)=O.O.O=C(CBr)c1ccc(Cl)cc1>>O=C(c1ccc(Cl)cc1)C(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ad92844a8fe4dc194db8be14063770b | CC1(C)CN(C(=O)OC(C)(C)C)CC(c2ccc(Cl)cc2)N1>>CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl | Cl.C(C)(=O)OCC.ClC1=CC=C(C=C1)C1NC(CN(C1)C(=O)OC(C)(C)C)(C)C>>Cl.Cl.ClC1=CC=C(C=C1)C1NC(CNC1)(C)C | CC(C)(C)OC(=O)[N:5]1[CH2:4][C:2]([CH3:1])([CH3:3])[NH:15][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[CH2:6]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[NH:15]1.[ClH:17] | CC1(C)CN(C(=O)OC(C)(C)C)CC(c2ccc(Cl)cc2)N1 | CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl | null | null | null | Miscellaneous | Boc amine deprotection | 5bce0046779ff0f9ed2eabe37580051145cbfd588614dcf2a6c4f0aed71992de | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | c1ccc(C2CNCCN2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 95 | [{"value": 95.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)C1NC(CNC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 4 M Hydrogen chloride in ethyl acetate (5.0 mL, 20.0 mmol) was added to a solution of 2-(4-chlorophenyl)-4-t-butoxycarbonyl-6,6-dimethyl-piperazine (1.69 g, 5.2 mmol). After 12 h, removing the solvent, filtrating and washing the precipitate with ethyl acetate gave 2-(4-chlorophenyl)-6,6-dimethyl-piperazine dihydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CCN1 | C1CNCCN1 | C1CNCCN1.c1ccccc1 | HO- | null | null | 12 | CC1(C)CN(C(=O)OC(C)(C)C)CC(c2ccc(Cl)cc2)N1>>CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b6569ce1e9846a4b5c75f5aa63335d8 | CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cl.Cn1c(N2CC(c3ccc(Cl)cc3)NC(C)(C)C2)nc(-c2ccncc2)cc1=O | Cl.ClC1=CC=C(C=C1)C1NC(CNC1)(C)C.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1.C(C)N(CC)CC.Cl.C(C)(=O)OCC>>Cl.Cl.ClC1=CC=C(C=C1)C1NC(CN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)(C)C | [NH:6]1[CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[NH:16][C:17]([CH3:18])([CH3:19])[CH2:20]1.[ClH:2].Cl[c:5]1[n:4]([CH3:3])[c:30](=[O:31])[cH:29][c:22](-[c:23]2[cH:24][cH:25][n:26][cH:27][cH:28]2)[n:21]1>>[ClH:2].[CH3:3][n:4]1[c:5]([N:6]2[CH2:7][CH:8]([c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:... | CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cl.Cn1c(N2CC(c3ccc(Cl)cc3)NC(C)(C)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCNC(c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 187.2 | [{"value": 97.0, "product": "Cl.Cl.ClC1=CC=C(C=C1)C1NC(CN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 187.2, "product": "Cl.Cl.ClC1=CC=C(C=C1)C1NC(CN(C1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(4-chlorophenyl)-6,6-dimethyl-piperazine hydrochloride (155 mg, 0.52 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (111 mg, 0.50 mmol) and triethylamine (0.42 mL, 2.50 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 6 h. The whole was evaporated in vacuo and the residue was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1 | null | null | CC1(C)CNCC(c2ccc(Cl)cc2)N1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>Cl.Cn1c(N2CC(c3ccc(Cl)cc3)NC(C)(C)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d30735954690405681598bb28dc295f4 | Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cn1cnc(-c2ccncc2)cc1=O | O.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1.C(C)(C)N(CC)C(C)C>>CN1C=NC(=CC1=O)C1=CC=NC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:13](=[O:14])[cH:12][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[n:4]1>>[CH3:1][n:2]1[cH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][n:9][cH:10][cH:11]2)[cH:12][c:13]1=[O:14] | Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cn1cnc(-c2ccncc2)cc1=O | null | null | CN(C=O)C | Functional Group Interconversion | Aromatic dehalogenation | 76895d15d2d466b89a30aacc2ef4edbb246f8c7b092db05f2443e4acbf4f85b3 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=c1cc(-c2ccncc2)nc[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[cH;D2;+0:1]:[#7;a:2]:[c:3] | 160.5 | [{"value": 54.0, "product": "CN1C=NC(=CC1=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 160.5, "product": "CN1C=NC(=CC1=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2S-(4-bromophenyl)-4-benzyloxycarbonyl-piperazine (788 mg, 2.10 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (444 mg, 2.00 mmol) and diisopropylethylamine (0.70 mL, 4.00 mmol) in dimethylformamide (20 mL) was stirred at 80° C. for 3 h. The reaction mixture was poured into water and the whole wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1 | Other | CN(C=O)C | null | null | Cn1c(Cl)nc(-c2ccncc2)cc1=O>CN(C=O)C>Cn1cnc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a2856f551e44886a69872cb3f08fc44 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.O[C@@H]1CCNC1>>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1 | BrC1=CC=C(C=C1)[C@@H]1N(CCN(C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.N1C[C@@H](CC1)O.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)O | Br[c:23]1[cH:22][cH:21][c:20]([C@@H:19]2[N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:32]2)[cH:31][cH:30]1.[NH:24]1[CH2:25][CH2:26][C@@H:27]([OH:28])[CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.O[C@@H]1CCNC1 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(C)(C)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCCC2)ccc1[C@H]1CNCCN1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:4]:[c:5] | 54.6 | [{"value": 54.5, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.6, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A suspension of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl) piperazine (1.33 g, 3.00 mmol), (R)-3-pyrrolidinol (520 mg, 4.20 mmol), palladium acetate (27 mg, 0.12 mmol), 2-(di-t-butylphosphino)biphenyl (72 mg, 0.24 mmol), and sodium t-butoxide (808 mg, 8.41 mmol) in tert-butanol (20 mL) was heated at 90° C. for 3.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNC1 | c1ccccc1.C1CC[NH]C1 | C1C[NH]CC[NH]1.c1ccccc1.C1CC[NH]C1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O.C(C)(=O)OCC | 90 | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.O[C@@H]1CCNC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36f5f20f38a24420a5fc702d6f4d925d | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1 | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)OS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[C@@H:19]([c:20]2[cH:21][cH:22][c:23]([N:24]3[CH2:25][CH2:26][C@@H:27]([OH:28])[CH2:33]3)[cH:34][cH:35]2)[CH2:36]1.Cl[S:29]([CH3:30])(=[O:31])=[O:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | c1cc(N2CCCC2)ccc1[C@H]1CNCCN1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7:5]-[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9] | 101.7 | [{"value": 101.7, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)OS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-((R)-3-hydroxy pyrrolidino)phenyl)piperazine (733 mg, 1.64 mmol) and triethylamine (0.34 mL, 2.46 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (0.152 mL, 1.97 mmol) at 0° C. After stirring for 20 min, the reaction mixture was partitioned between ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1C[NH]CC[NH]1.c1ccccc1.C1CC[NH]C1 | HCl | ClCCl | null | 0.333333 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](O)C3)cc2)C1.CS(=O)(=O)Cl>ClCCl>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f79941e7f1e45968fcc77f4f8f261b8 | C1CCNC1.CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1>>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1 | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@@H](CC1)OS(=O)(=O)C.N1CCCC1>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@H](CC1)N1CCCC1 | [NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1.CS(=O)(=O)O[C@@H:27]1[CH2:26][CH2:25][N:24]([c:23]2[cH:22][cH:21][c:20]([C@@H:19]3[N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36]3)[cH:35][cH:34]2)[CH2:33]1>>[CH3:1][C:2]([CH3:3])([CH3... | C1CCNC1.CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Alkylation of amines | 546e49a456acdd2d5bf1b8e274d2996a815f8544a23dc3789c48220d8bd3ae96 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | C-S(=O)(=O)-O-[C@@H;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5])-[C:6]-1.[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[c:5]-[#7:4]1-[C:3]-[C:2]-[C@H;D3;+0:1](-[N;H0;D3;+0:11]2-[C:7]-[C:8]-[C:9]-[C:10]-2)-[C:6]-1 | 58.3 | [{"value": 58.0, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@H](CC1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@H](CC1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | 90 | CELSIUS | null | null | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-((R)-3-methansulfonyloxy-pyrrolidino)phenyl)piperazine (877 mg, 1.64 mmol) in toluene (10 mL) was added pyrrolidine (0.64 mL, 8.19 mmol), and the resulting solution was heated at 90° C. for 8 h. After checking consumption of the starting material with TLC, the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CCNC1.C1CC[NH]C1 | C1CC[NH]C1.C1CC[NH]C1 | C1C[NH]CC[NH]1.c1ccccc1.C1CC[NH]C1.C1CC[NH]C1 | MsOH.HO- | C1(=CC=CC=C1)C | 90 | null | C1CCNC1.CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@@H](OS(C)(=O)=O)C3)cc2)C1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-272d8969cbd642f9a3d2a4c56e57bbf6 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1>>Cl.Cl.Cl.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N1C[C@H](CC1)N1CCCC1.Cl>>Cl.Cl.Cl.Cl.N1(CCCC1)[C@@H]1CN(CC1)C1=CC=C(C=C1)[C@@H]1NCCNC1 | CC(C)(C)OC(=O)[N:23]1[CH2:22][C@H:21]([c:20]2[cH:5][cH:6][c:7]([N:8]3[CH2:9][CH2:10][C@H:11]([N:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)[CH2:17]3)[cH:18][cH:19]2)[N:26](C(=O)OC(C)(C)C)[CH2:25][CH2:24]1>>[ClH:2].[ClH:3].[ClH:4].[cH:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][C@H:11]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1 | Cl.Cl.Cl.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | null | null | ClCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 08ac0381a99ce87510db4bc15073b49b2abc743214633aaa7c6faa36177fdebd | 3c4f51b1c1f508215f616109a3309695a74a7c119e69c8c1a7e8536489a089af | c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[c:4])-[N;H0;D3;+0:5](-C(=O)-O-C(-C)(-C)-C)-[C:6]-[C:7]-1>>[c:4]-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-[NH;D2;+0:5]-1 | 87 | [{"value": 87.0, "product": "Cl.Cl.Cl.Cl.N1(CCCC1)[C@@H]1CN(CC1)C1=CC=C(C=C1)[C@@H]1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-((S)-3-(pyrrolidin-1-yl) pyrrolidin-1-yl)phenyl)piperazine (479 mg, 0.957 mmol) in dichloromethane (4 mL) was added 4 N hydrogen chloride in ethyl acetate (4 mL) at room temperature. After stirring for 3 h, the resulting precipitate was collected and dried in vacuo to ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ccccc1.C1CC[NH]C1.C1CC[NH]C1.C1CNCCN1 | HO- | ClCCl.C(C)(=O)OCC | null | 3 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(N3CC[C@H](N4CCCC4)C3)cc2)C1>ClCCl.C(C)(=O)OCC>Cl.Cl.Cl.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-471f5f2b664a47949b2c6a09540a5d53 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1>>Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncc2)cc1=O | Cl.Cl.Cl.Cl.N1(CCCC1)[C@@H]1CN(CC1)C1=CC=C(C=C1)[C@@H]1NCCNC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>N1(CCCC1)C1CN(CC1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:35](=[O:36])[cH:34][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:26]1.[NH:4]1[CH2:5][CH2:6][NH:7][C@@H:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][C@H:16]([N:17]4[CH2:18][CH2:19][CH2:20][CH2:21]4)[CH2:22]3)[cH:23][cH:24]2)[CH2:25]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][NH:7... | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 82.4 | [{"value": 82.0, "product": "N1(CCCC1)C1CN(CC1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.4, "product": "N1(CCCC1)C1CN(CC1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a suspension of (S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl) piperazine tetrahydrochloride (98 mg, 0.22 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.20 mL, 1.40 mmol) and 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (44 mg, 0.20 mmol) at room temperature. After stirring for 24 h, the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCCN1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.C1CC[NH]C1.C1CC[NH]C1.c1ccncc1 | HCl | O1CCCC1 | null | 24 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1>O1CCCC1>Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-550edba2ff7943a2b0d596302e1f3a7e | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1>>Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncn2)cc1=O | Cl.Cl.Cl.Cl.N1(CCCC1)[C@@H]1CN(CC1)C1=CC=C(C=C1)[C@@H]1NCCNC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=NC=NC=C1>>CN1C(=NC(=CC1=O)C1=NC=NC=C1)N1C[C@@H](NCC1)C1=CC=C(C=C1)N1CC(CC1)N1CCCC1 | Cl[c:3]1[n:2]([CH3:1])[c:35](=[O:36])[cH:34][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][n:33]2)[n:26]1.[NH:4]1[CH2:5][CH2:6][NH:7][C@@H:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][C@H:16]([N:17]4[CH2:18][CH2:19][CH2:20][CH2:21]4)[CH2:22]3)[cH:23][cH:24]2)[CH2:25]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][NH:7]... | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1 | Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncn2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncn2)nc(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 66.8 | [{"value": 66.0, "product": "CN1C(=NC(=CC1=O)C1=NC=NC=C1)N1C[C@@H](NCC1)C1=CC=C(C=C1)N1CC(CC1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.8, "product": "CN1C(=NC(=CC1=O)C1=NC=NC=C1)N1C[C@@H](NCC1)C1=CC=C(C=C1)N1CC(CC1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a suspension of (S)-2-(4-((S)-3-(pyrrolidin-1-yl)pyrrolidin-1-yl)phenyl) piperazine tetrahydrochloride (99 mg, 0.22 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.20 mL, 1.40 mmol) and 2-chloro-3-methyl-6-(4-pyrimidinyl)-3H-pyrimidin-4-one (45 mg, 0.20 mmol) at room temperature. After stirring for 24 h, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCCN1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.C1CC[NH]C1.C1CC[NH]C1.c1cncnc1 | HCl | O1CCCC1 | null | 24 | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1cc(N2CC[C@H](N3CCCC3)C2)ccc1[C@H]1CNCCN1>O1CCCC1>Cn1c(N2CCN[C@@H](c3ccc(N4CCC(N5CCCC5)C4)cc3)C2)nc(-c2ccncn2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dddb005d28e743f6bebca0ca50f0b4f6 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC1CCCCC1>>CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1 | BrC1=CC=C(C=C1)[C@@H]1N(CCN(C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.CNC1CCCCC1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C1CCCCC1 | Br[c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][N:9]([C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:17][CH2:18][N:19]2[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][cH:28]1.[CH3:1][NH:2][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][N:9](... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC1CCCCC1 | CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc([C@H]2CNCCN2)ccc1NC1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH;D2;+0:8]-[C;D1;H3:9])-[C:10]>>[C:6]-[C:7](-[N;H0;D3;+0:8](-[C;D1;H3:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:10] | 70.4 | [{"value": 70.4, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl) piperazine (1.21 g, 2.75 mmol), N-methylcyclohexylamine (0.43 mL, 3.30 mmol), palladium acetate (25 mg, 0.11 mmol), 2-(di-t-butylphosphino)biphenyl (66 mg, 0.22 mmol), and sodium t-butoxide (370 mg, 3.85 mmol) in t-butanol (15 mL) was heated at 80° C. for 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O | 80 | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC1CCCCC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O>CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d2e7a374b4a42c0bbc119a338b74a4c | CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1>>CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1 | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C1CCCCC1.Cl>>C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@@H]1NCCNC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][C@H:7]([c:6]2[cH:5][cH:4][c:3]([N:2]([CH3:1])[CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:14][cH:13]2)[N:12](C(=O)OC(C)(C)C)[CH2:11][CH2:10]1>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][NH:9][CH2:10][CH2:11][NH:12]2)[cH:13][cH:14]1)[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][... | CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1 | CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1 | null | null | ClCCl.C(C)(=O)OCC | Reduction | OtherReaction | 5dc6a6e72b840f8254dd5d683a72ad117110578e0dccad8ab46ac333e532cdb4 | 62d6d161f7b7b3cc63e568e66451a46259e0e34072c373a60dd8b9591af3c67b | c1cc([C@H]2CNCCN2)ccc1NC1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4](-C(=O)-O-C(-C)(-C)-C)-[C:5]-[C:6]-1-[c:7]>>[c:7]-[C:6]1-[C:5]-[NH;D2;+0:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 8 | [{"value": 8.0, "product": "C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@@H]1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N-cyclohexyl-N-methylamino)phenyl)piperazine in dichloromethane (4 mL) was added 4 N hydrogen chloride in ethyl acetate (4 mL). After stirring for 40 min, the white precipitate was collected, which included impurities. The mixture was purified by a reverse phase chrom... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ccccc1.C1CNCCN1.C1CCCCC1 | HO- | ClCCl.C(C)(=O)OCC | null | 0.666667 | CN(c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1)C1CCCCC1>ClCCl.C(C)(=O)OCC>CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-191ef9472c454fc186967e24cce1f2d0 | CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>CN(c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1)C1CCCCC1 | C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@@H]1NCCNC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][NH:9][CH2:24][CH2:25][NH:26]2)[cH:27][cH:28]1)[CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1.Cl[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19][c:20](=[O:21])[n:22]1[CH3:23]>>[CH3:1][N:2]([c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][N:9]([c:10]3[... | CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | CN(c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1)C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 12e031c56e3265fed397a3e32360d8e1fccdeedb7d10ff4500339614dfe4903f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@@H](c3ccc(NC4CCCCC4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 88 | [{"value": 88.0, "product": "C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "C1(CCCCC1)N(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | To a solution of (S)-2-(4-(N-cyclohexyl-N-methylamino)phenyl) piperazine (50 mg, 0.183 mmol) and triethylamine (0.077 mL, 0.55 mmol) was added 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (37 mg, 0.17 mmol) at room temperature. After stirring for 4.5 h, the reaction mixture was concentrated in vacuo. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | C1CNCC[NH]1.c1cncnc1 | c1ccccc1.C1CNCC[NH]1.c1cncnc1.c1ccncc1.C1CCCCC1 | HCl | null | null | 4.5 | CN(c1ccc([C@H]2CNCCN2)cc1)C1CCCCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>CN(c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1)C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf440bf12c0741c5950bc22e35b8fa99 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC>>CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1 | BrC1=CC=C(C=C1)[C@@H]1N(CCN(C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.Cl.CNC.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C | Br[c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19][N:20]2[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC | CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)(C)(C)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 705933786518ece8447c3a260ed1708cc50b5b37b829540bc5bba9d6bb1dde91 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc([C@H]2CNCCN2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 53 | [{"value": 53.0, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A suspension of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl) piperazine (1.14 g, 2.59 mmol), N,N-dimethylamine hydrochloride (422 mg, 5.17 mmol), palladium acetate (23 mg, 0.10 mmol), 2-(di-t-butylphosphino)biphenyl(62 mg, 0.21 mmol), and sodium t-butoxide (845 mg, 8.80 mmol) in t-butanol (15 mL) was heated at 90° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O.C(C)(=O)OCC | 90 | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.CNC>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)(C)(C)O.C(C)(=O)OCC>CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46722a4ab12e4015b35c2d141eca1c8d | CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1>>CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cl | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)N(C)C.Cl>>Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@@H]1NCCNC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][C@H:8]([c:7]2[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:15][cH:14]2)[N:13](C(=O)OC(C)(C)C)[CH2:12][CH2:11]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][NH:10][CH2:11][CH2:12][NH:13]2)[cH:14][cH:15]1.[ClH:17].[ClH:18] | CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1 | CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cl | null | null | ClCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 08ac0381a99ce87510db4bc15073b49b2abc743214633aaa7c6faa36177fdebd | 3c4f51b1c1f508215f616109a3309695a74a7c119e69c8c1a7e8536489a089af | c1ccc([C@H]2CNCCN2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4](-C(=O)-O-C(-C)(-C)-C)-[C:5](-[c:6])-[C:7]-1>>[c:6]-[C:5]1-[C:7]-[NH;D2;+0:1]-[C:2]-[C:3]-[NH;D2;+0:4]-1 | 96 | [{"value": 96.0, "product": "Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@@H]1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8.5 | HOUR | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4-(N,N-dimethylamino) phenyl)piperazine (556 mg, 1.37 mmol) in dichloromethane (4 mL) was added 4 N hydrogen chloride in ethyl acetate (4 mL). After stirring for 8.5 h, the white precipitate was collected and dried in vacuo to afford (S)-2-(4-(N,N-dimethylamino) phenyl)p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | HO- | ClCCl.C(C)(=O)OCC | null | 8.5 | CN(C)c1ccc([C@H]2CN(C(=O)OC(C)(C)C)CCN2C(=O)OC(C)(C)C)cc1>ClCCl.C(C)(=O)OCC>CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81d542686bc54120bf1adf8893b40a75 | CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>CN(C)c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1.Cl | Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@@H]1NCCNC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][NH:10][CH2:25][CH2:26][NH:27]2)[cH:28][cH:29]1.[ClH:31].Cl[c:11]1[n:12][c:13](-[c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:20][c:21](=[O:22])[n:23]1[CH3:24]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C@H:8]2[CH2:9][N:10]([c:11]3[n:12][c:13](-[c:14]4[cH... | CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O | CN(C)c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1.Cl | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 12e031c56e3265fed397a3e32360d8e1fccdeedb7d10ff4500339614dfe4903f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@@H](c3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 163.7 | [{"value": 81.0, "product": "Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 163.7, "product": "Cl.Cl.Cl.CN(C)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a suspension of (S)-2-(4-(N,N-dimethylamino)phenyl)piperazine trihydrochloride (115 mg, 0.365 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.28 mL, 2.0 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (74 mg, 0.33 mmol) at room temperature. After stirring for 10 h, the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cncnc1 | C1CNCC[NH]1.c1cncnc1 | c1ccccc1.C1CNCC[NH]1.c1cncnc1.c1ccncc1 | HCl | O1CCCC1 | null | 10 | CN(C)c1ccc([C@H]2CNCCN2)cc1.Cl.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>CN(C)c1ccc([C@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abb46fde9373413eb6000eebdd8e96f9 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.COc1ccc(B(O)O)cc1>>COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)cc1 | BrC1=CC=C(C=C1)[C@@H]1N(CCN(C1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C.COC1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC | Br[c:7]1[cH:8][cH:9][c:10]([C@H:11]2[CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22][N:23]2[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31][cH:32]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:1... | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.COc1ccc(B(O)O)cc1 | COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 75.9 | [{"value": 75.9, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.8, "product": "C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (S)-2-(4-bromophenyl)-1,4-di(t-butoxycarbonyl)piperazine (1.82 g, 4.11 mmol), 4-methoxyphenylboronic acid (937 mg, 6.17 mmol), sodium carbonate (2.18 g, 20.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (238 mg, 0.206 mmol) was dissolved in dimethoxyethane (20 mL) and water (20 mL), and the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC | null | null | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)[C@@H](c2ccc(Br)cc2)C1.COc1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC>COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8ca483842b5438b9455a12d784197ec | COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)cc1>>COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cl | C(C)(C)(C)OC(=O)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C1=CC=C(C=C1)OC.Cl>>Cl.Cl.COC1=CC=C(C2=CC=C(C=C2)[C@@H]2NCCNC2)C=C1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][C@H:11]([c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:20][cH:19]3)[cH:18][cH:17]2)[N:16](C(=O)OC(C)(C)C)[CH2:15][CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C@H:11]3[CH2:12][NH:13][CH2:14][CH2:15][NH:16]3)[cH:17][cH:18]2)[cH:19][cH:20]1.[Cl... | COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)cc1 | COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cl | null | null | ClCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 08ac0381a99ce87510db4bc15073b49b2abc743214633aaa7c6faa36177fdebd | 3c4f51b1c1f508215f616109a3309695a74a7c119e69c8c1a7e8536489a089af | c1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[c:4])-[N;H0;D3;+0:5](-C(=O)-O-C(-C)(-C)-C)-[C:6]-[C:7]-1>>[c:4]-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-[NH;D2;+0:5]-1 | 94 | [{"value": 94.0, "product": "Cl.Cl.COC1=CC=C(C2=CC=C(C=C2)[C@@H]2NCCNC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (S)-1,4-di(t-butoxycarbonyl)-2-(4′-methoxybiphen-4-yl)-piperazine (1.46 g, 3.12 mmol) in dichloromethane (8 mL) was added 4 N hydrogen chloride in ethyl acetate (8 mL) at room temperature. After stirring for 1 h, the precipitate was collected and dried in vacuo to afford (S)-2-(4′-methoxybiphen-4-yl) p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ccccc1.c1ccccc1.C1CNCCN1 | HO- | ClCCl.C(C)(=O)OCC | null | 1 | COc1ccc(-c2ccc([C@H]3CN(C(=O)OC(C)(C)C)CCN3C(=O)OC(C)(C)C)cc2)cc1>ClCCl.C(C)(=O)OCC>COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42c7b84a31604c4091f55d88e4c69265 | COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>COC1([C@@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)C=CC(c2ccccc2)=CC1 | Cl.Cl.COC1=CC=C(C2=CC=C(C=C2)[C@@H]2NCCNC2)C=C1.O1CCCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>COC1(CC=C(C=C1)C1=CC=CC=C1)[C@@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [CH3:1][O:2][c:30]1[cH:29][cH:28][c:27](-[c:26]2[cH:25][cH:24][c:3]([C@H:4]3[CH2:5][NH:6][CH2:21][CH2:22][NH:23]3)[cH:34][cH:33]2)[cH:32][cH:31]1.Cl[c:7]1[n:8][c:9](-[c:10]2[cH:11][cH:12][n:13][cH:14][cH:15]2)[cH:16][c:17](=[O:18])[n:19]1[CH3:20]>>[CH3:1][O:2][C:3]1([C@@H:4]2[CH2:5][N:6]([c:7]3[n:8][c:9](-[c:10]4[cH:11... | COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | COC1([C@@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)C=CC(c2ccccc2)=CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 090c209b89efd2cb8bf43f980bf54f8be24674a82a264d1230342d427215c1d1 | 95e3de0a2bd40f15927b80d8fd8e00d1114047e3c62580ce88b031e60fbcb5f1 | O=c1cc(-c2ccncc2)nc(N2CCN[C@H](C3C=CC(c4ccccc4)=CC3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16](-[C:17]3-[#7:18]-[C:19]-[C:20]-[NH;D2;+0:21]-[C:22]-3):[cH;D2;+0:23]:[cH;D2;+0:24]:2):[c:25]:[c:26]:1>>[C;D1;H3:7]-[O;H0;... | 96 | [{"value": 96.0, "product": "COC1(CC=C(C=C1)C1=CC=CC=C1)[C@@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 28 | HOUR | To a suspension of (S)-2-(4′-methoxybiphen-4-yl)-piperazine dihydrochloride (237 mg, 0.694 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.40 mL, 2.9 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (128 mg, 0.579 mmol) at room temperature. After stirring for 28 h, the resulting mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amine | Ether.Tertiary amine | c1ccccc1.c1ccccc1.C1CNCCN1.c1cncnc1 | C1CNCC[NH]1.c1cncnc1.C1=CCCC=C1.c1ccccc1 | C1CNCC[NH]1.c1cncnc1.c1ccncc1.C1=CCCC=C1.c1ccccc1 | Other | null | null | 28 | COc1ccc(-c2ccc([C@H]3CNCCN3)cc2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>COC1([C@@H]2CN(c3nc(-c4ccncc4)cc(=O)n3C)CCN2)C=CC(c2ccccc2)=CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a40728b054464428beffa3efeff83f72 | CCOC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)OC(C)(C)C>>O=C1CNC(=O)[C@H](Cc2ccccc2)N1 | C(C)OC([C@@H](NC(CNC(=O)OC(C)(C)C)=O)CC1=CC=CC=C1)=O.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)[C@H]1C(NCC(N1)=O)=O | CCO[C:5](=[O:6])[C@H:7]([CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[NH:15][C:2](=[O:1])[CH2:3][NH:4]C(=O)OC(C)(C)C>>[O:1]=[C:2]1[CH2:3][NH:4][C:5](=[O:6])[C@H:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15]1 | CCOC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)OC(C)(C)C | O=C1CNC(=O)[C@H](Cc2ccccc2)N1 | null | null | ClCCl | Miscellaneous | OtherReaction | 65fa34161ca2d5064a14663b709a4d219252d9fbe2cc1fea3c317c98b8af4179 | b0e3e4341a5ddf0d97948d9b8973adb58a5f8a4ab6888767daa512773c94bb45 | O=C1CNC(=O)[C@H](Cc2ccccc2)N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-C(=O)-O-C(-C)(-C)-C>>[C:4]-[C:3]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)[C@H]1C(NCC(N1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "C(C1=CC=CC=C1)[C@H]1C(NCC(N1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of Boc-glycylphenylalanine ethyl ester (5.96 g) in dichloromethane (20 ml) was added trifluoroacetic acid (20 mL) at room temperature. After stirring 1.5 h, the resulting solution was concentrated in vacuo. The residue was dissolved in water, into which sodium bicarbonate was added until the pH was 9. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Secondary amide | null | C1CNCCN1 | C1CNCCN1.c1ccccc1 | HO- | ClCCl | null | 1.5 | CCOC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)OC(C)(C)C>ClCCl>O=C1CNC(=O)[C@H](Cc2ccccc2)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1d429434cc449ce9006358226a97478 | O=C1CNC(=O)[C@H](Cc2ccccc2)N1>>c1ccc(C[C@H]2CNCCN2)cc1 | C(C1=CC=CC=C1)[C@H]1C(NCC(N1)=O)=O.B.O1CCCC1>>C(C1=CC=CC=C1)[C@@H]1NCCNC1 | O=[C:7]1[C@H:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:13][cH:12]2)[NH:11][C:10](=O)[CH2:9][NH:8]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][C@H:6]2[CH2:7][NH:8][CH2:9][CH2:10][NH:11]2)[cH:12][cH:13]1 | O=C1CNC(=O)[C@H](Cc2ccccc2)N1 | c1ccc(C[C@H]2CNCCN2)cc1 | null | null | O1CCCC1 | Reduction | OtherReaction | 590622dd9a2e8c2d281165576d60ec19eab5d22e33abf2760741e66901de6344 | 8cc0e36b0114c9604f5816aff3deb5718780146046d1c51c89e29421ba87e915 | c1ccc(C[C@H]2CNCCN2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3](-[C:4])-[C;H0;D3;+0:5](=O)-[#7:6]-[C:7]-1>>[C:4]-[C:3]1-[#7:2]-[CH2;D2;+0:1]-[C:7]-[#7:6]-[CH2;D2;+0:5]-1 | 40.3 | [{"value": 40.3, "product": "C(C1=CC=CC=C1)[C@@H]1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.3, "product": "C(C1=CC=CC=C1)[C@@H]1NCCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of (S)-3-benzyl-2,5-dioxopiperazine (2.284 g, 11.18 mmol) in tetrahydrofuran (20 mL) was added borane-tetrahydrofuran complex (49 mL, 1.0 M solution in THF, 49 mmol) at room temperature. The resulting mixture was refluxed for several hours before it was quenched with methanol at 0° C. After concentratio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amide | null | C1CNCCN1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | Other | O1CCCC1 | null | null | O=C1CNC(=O)[C@H](Cc2ccccc2)N1>O1CCCC1>c1ccc(C[C@H]2CNCCN2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6979c03fb01b40ae888e2ba66d8f690a | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1ccc(C[C@H]2CNCCN2)cc1>>Cn1c(N2CCN[C@@H](Cc3ccccc3)C2)nc(-c2ccncc2)cc1=O | ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1.C(C1=CC=CC=C1)[C@@H]1NCCNC1.C(C)N(CC)CC>>C(C1=CC=CC=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:26](=[O:27])[cH:25][c:18](-[c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[n:17]1.[NH:4]1[CH2:5][CH2:6][NH:7][C@@H:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][NH:7][C@@H:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:16]2)[n:1... | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1ccc(C[C@H]2CNCCN2)cc1 | Cn1c(N2CCN[C@@H](Cc3ccccc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@@H](Cc3ccccc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 81.4 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C(C1=CC=CC=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (S)-2-benzylpiperazine (48 mg, 0.27 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.10 mL, 0.74 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (55 mg, 0.248 mmol) at room temperature. After refluxing for 24 h, the resulting mixture was concentrated in vacuo. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCCN1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1 | null | null | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1ccc(C[C@H]2CNCCN2)cc1>O1CCCC1>Cn1c(N2CCN[C@@H](Cc3ccccc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03eb49fdf0444d6d8aa0fdb011cd32d7 | BrBr.CC(=O)c1ccc(C#N)cc1>>N#Cc1ccc(C(=O)CBr)cc1 | CC(=O)C1=CC=C(C=C1)C#N.BrBr>>C(#N)C1=CC=C(C(CBr)=O)C=C1 | Br[Br:10].[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH3:9])[cH:11][cH:12]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][Br:10])[cH:11][cH:12]1 | BrBr.CC(=O)c1ccc(C#N)cc1 | N#Cc1ccc(C(=O)CBr)cc1 | null | null | ClCCl | 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] | 101.5 | [{"value": 101.5, "product": "C(#N)C1=CC=C(C(CBr)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-cyanoacetophenone (11.32 g, 77.98 mmol) in dichloromethane (200 mL) was added bromine (4.00 mL, 78.0 mmol) dropwise at room temperature. After stirring several minutes, the reaction mixture was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 4-cyanophenacyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | ClCCl | null | null | BrBr.CC(=O)c1ccc(C#N)cc1>ClCCl>N#Cc1ccc(C(=O)CBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf025574da9c425ca0c750432e9a196e | N#Cc1ccc(C(=O)CBr)cc1.O>>N#Cc1ccc(C(=O)C=O)cc1 | C(#N)C1=CC=C(C(CBr)=O)C=C1.O>>C(#N)C1=CC=C(C=C1)C(=O)C=O | Br[CH2:9][C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:12][cH:11]1)=[O:8].[OH2:10]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH:9]=[O:10])[cH:11][cH:12]1 | N#Cc1ccc(C(=O)CBr)cc1.O | N#Cc1ccc(C(=O)C=O)cc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | e6f195d0eaa3dbf60a64865dd520e91a9420a32204416749e54032cc8ab6f41e | 0dd4cbb38ec6423de2cbac32f3512efe0313fd055cf8857f20d4712b6549de8d | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[OH2;D0;+0:5]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D2;+0:1]=[O;H0;D1;+0:5] | 64.1 | [{"value": 64.1, "product": "C(#N)C1=CC=C(C=C1)C(=O)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.1, "product": "C(#N)C1=CC=C(C=C1)C(=O)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 4-cyanophenacyl bromide (11.20 g, 49.99 mmol) in dimethylsulfoxide (83 mL) was treated with water (0.90 mL, 49.99 mmol). After stirring for 24 h at room temperature, it was poured into ice-water, and extracted with ether. The organic layer was washed with water and then brine, dried over anhydrous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Aldehyde | null | null | c1ccccc1 | HBr | CS(=O)C | null | 24 | N#Cc1ccc(C(=O)CBr)cc1.O>CS(=O)C>N#Cc1ccc(C(=O)C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57958516d5ce48d287e37d493ccef38f | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(c2ccc(-c3ncon3)cc2)C1>>Cl.c1nc(-c2ccc(C3CNCCN3)cc2)no1 | C(C)(C)(C)OC(=O)N1C(CN(CC1)C(=O)OC(C)(C)C)C1=CC=C(C=C1)C1=NOC=N1.Cl>>Cl.Cl.O1N=C(N=C1)C1=CC=C(C=C1)C1NCCNC1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH:10]([c:9]2[cH:8][cH:7][c:6](-[c:5]3[n:4][cH:3][o:19][n:18]3)[cH:17][cH:16]2)[N:15](C(=O)OC(C)(C)C)[CH2:14][CH2:13]1>>[ClH:2].[cH:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][NH:12][CH2:13][CH2:14][NH:15]3)[cH:16][cH:17]2)[n:18][o:19]1 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(c2ccc(-c3ncon3)cc2)C1 | Cl.c1nc(-c2ccc(C3CNCCN3)cc2)no1 | null | null | ClCCl.C(C)(=O)OCC | Miscellaneous | OtherReaction | 08ac0381a99ce87510db4bc15073b49b2abc743214633aaa7c6faa36177fdebd | 3c4f51b1c1f508215f616109a3309695a74a7c119e69c8c1a7e8536489a089af | c1nc(-c2ccc(C3CNCCN3)cc2)no1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](-[c:4])-[N;H0;D3;+0:5](-C(=O)-O-C(-C)(-C)-C)-[C:6]-[C:7]-1>>[c:4]-[C:3]1-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-[NH;D2;+0:5]-1 | 98 | [{"value": 98.0, "product": "Cl.Cl.O1N=C(N=C1)C1=CC=C(C=C1)C1NCCNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 1,4-di(t-butoxycarbonyl)-2-(4-(1,2,4-oxadiazol-3-yl) phenyl)piperazine (464 mg, 1.08 mmol) in dichloromethane (2 mL) was added 4 N hydrogen chloride in ethyl acetate (3 mL) at room temperature. After stirring for 1.5 h, the precipitate was collected and dried in vacuo to afford 2-(4-(1,2,4-oxadiazol-3-... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine.Secondary amine | C1C[NH]CC[NH]1 | C1CNCCN1 | c1ncon1.c1ccccc1.C1CNCCN1 | HO- | ClCCl.C(C)(=O)OCC | null | 1.5 | CC(C)(C)OC(=O)N1CCN(C(=O)OC(C)(C)C)C(c2ccc(-c3ncon3)cc2)C1>ClCCl.C(C)(=O)OCC>Cl.c1nc(-c2ccc(C3CNCCN3)cc2)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02640808f39546fa99ccda8cbe00e9f0 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1nc(-c2ccc(C3CNCCN3)cc2)no1>>Cn1c(N2CCN[C@@H](c3ccc(-c4ncon4)cc3)C2)nc(-c2ccncc2)cc1=O | Cl.Cl.O1N=C(N=C1)C1=CC=C(C=C1)C1NCCNC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>O1N=C(N=C1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:30](=[O:31])[cH:29][c:22](-[c:23]2[cH:24][cH:25][n:26][cH:27][cH:28]2)[n:21]1.[NH:4]1[CH2:5][CH2:6][NH:7][CH:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[n:14][cH:15][o:16][n:17]3)[cH:18][cH:19]2)[CH2:20]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][NH:7][C@@H:8]([c:9]3[cH:10][cH:11][c:12](-[c:13]4[n:14... | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1nc(-c2ccc(C3CNCCN3)cc2)no1 | Cn1c(N2CCN[C@@H](c3ccc(-c4ncon4)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 20777ae9d5a363a48071462fee2ac360794a4b33f519e76040bff714d38f1488 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCN[C@@H](c3ccc(-c4ncon4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 74.4 | [{"value": 74.0, "product": "O1N=C(N=C1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "O1N=C(N=C1)C1=CC=C(C=C1)[C@H]1CN(CCN1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a suspension of 2-(4-(1,2,4-oxadiazol-3-yl)phenyl)piperazine dihydrochloride (102 mg, 0.34 mmol) in tetrahydrofuran (6 mL) was added triethylamine (0.23 mL, 1.65 mmol) and then 2-chloro-3-methyl-6-(4-pyridyl)-3H-pyrimidin-4-one (73 mg, 0.33 mmol) at room temperature. After stirring for 24 h, the resulting mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCCN1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1.c1ccccc1.c1ncon1.c1ccncc1 | HCl | O1CCCC1 | null | 24 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1nc(-c2ccc(C3CNCCN3)cc2)no1>O1CCCC1>Cn1c(N2CCN[C@@H](c3ccc(-c4ncon4)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cbdbb9184be4011b7fdd5dca6457d7a | CC(C)(C)OC(=O)N1CCC(=O)CC1.COc1ccc(N)cc1>>COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1 | COC1=CC=C(C=C1)N.C(C)(C)(C)OC(=O)N1CCC(CC1)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].CO>>C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=C(C=CC=C1)OC | O=[C:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:8]([NH2:9])[cH:7][cH:6]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:2... | CC(C)(C)OC(=O)N1CCC(=O)CC1.COc1ccc(N)cc1 | COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5b886caafb447af2c42b25994145ceba06be89ff436920103b9b647b7e02dc3e | 7162e3d0527cbbe0cdc8721f12ca2525ced194aa00f43bb910be06dbeae3b0ad | c1ccc(NC2CCNCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[C;D1;H3:7]-[#8:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[NH2;D1;+0:13]):[c:14]:[cH;D2;+0:15]:1>>[C;D1;H3:7]-[#8:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:15]:[c:14]:[c;H0;D3;+0:12]:1-[NH;D2;+0:13]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 35 | [{"value": 35.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of anisidine (3.1 g, 25.2 mmol) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 25.1 mmol) in methanol (100 mL) was added sodium triacetoxyborohydride (13.4 g, 63.2 mmol) at room temperature. After stirring for 6 h, the resulting suspension was partitioned between ethyl acetate and 1N sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Primary amine | Ether.Secondary amine | C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | null | null | 6 | CC(C)(C)OC(=O)N1CCC(=O)CC1.COc1ccc(N)cc1>>COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ecb189bad7f45de80b6db393d2d5e90 | COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1>>COc1ccccc1NC1CCNCC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)NC1=C(C=CC=C1)OC.Cl>>COC1=C(C=CC=C1)NC1CCNCC1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][CH:10]([NH:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:15][CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1 | COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1 | COc1ccccc1NC1CCNCC1 | null | null | CO.C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(NC2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 99 | [{"value": 99.0, "product": "COC1=C(C=CC=C1)NC1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "COC1=C(C=CC=C1)NC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-(2-methoxyphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.7 g, 8.8 mmol) in methanol (30 mL) was added 4N hydrochloric acid in ethyl acetate (20 mL) at room temperature. After stirring for 1 h, the resulting suspension was concentrated in vacuo. The residue was partitioned between chlor... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | CO.C(C)(=O)OCC | null | 1 | COc1ccccc1NC1CCN(C(=O)OC(C)(C)C)CC1>CO.C(C)(=O)OCC>COc1ccccc1NC1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e37bd646fe8849b39e69b4fe53b217cd | COc1ccccc1NC1CCNCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>COc1ccccc1NC1CCN(c2nc(-c3ccncc3)cc(=O)n2C)CC1 | COC1=C(C=CC=C1)NC1CCNCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>COC1=C(C=CC=C1)NC1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH:10]1[CH2:11][CH2:12][NH:13][CH2:28][CH2:29]1.Cl[c:14]1[n:15][c:16](-[c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[cH:23][c:24](=[O:25])[n:26]1[CH3:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][CH:10]1[CH2:11][CH2:12][N:13]([c:14]2[n:15][c:16](-[c:17]... | COc1ccccc1NC1CCNCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | COc1ccccc1NC1CCN(c2nc(-c3ccncc3)cc(=O)n2C)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCC(Nc3ccccc3)CC2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 85 | [{"value": 85.0, "product": "COC1=C(C=CC=C1)NC1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.0, "product": "COC1=C(C=CC=C1)NC1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 4-(2-methoxyphenylamino)-piperidine (0.8 g, 3.87 mmol) and triethylamine (1.3 g, 12.8 mmol) in tetrahydrofuran (20 mL) was added 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.8 g, 3.61 mmol) portionwise. After stirring for 12 h, the resulting suspension was partitioned between chloroform and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1cncnc1 | C1CC[NH]CC1.c1cncnc1 | c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccncc1 | HCl | O1CCCC1 | null | 12 | COc1ccccc1NC1CCNCC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>COc1ccccc1NC1CCN(c2nc(-c3ccncc3)cc(=O)n2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cb2562ed8414c3ebd14754b80b80c00 | CC(C)(C)OC(=O)NCCCBr.CCOC(=O)Cc1ccc(Br)cc1>>CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1 | C(C)(C)(C)OC(NCCCBr)=O.C(C)OC(CC1=CC=C(C=C1)Br)=O.[H-].[Na+]>>C(C)OC(CC(CCCNC(=O)OC(C)(C)C)C1=CC=C(C=C1)Br)=O | Br[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:19].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:19]1[cH:... | CC(C)(C)OC(=O)NCCCBr.CCOC(=O)Cc1ccc(Br)cc1 | CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | c22d47ded1042e398953cfffd3fa039330d7e66db03ea63bcedf5b9b13400342 | f22c98686e1db86af9a686c666f03659457e1eabd3a4d1243f8afc820848db7b | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[CH3;D1;+0:11].[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[C:16]-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[c:19]:[c:20]:[c:21]:[cH;D2;+0:22]:1>>[C:12]-[#8:13]-[C:14](=[O;D1;H0:15])-[C:16]-[CH;D3;+0:17](-[CH2;D2;+0:1]-[C:2]-[C:3]-... | 137.7 | [{"value": 74.0, "product": "C(C)OC(CC(CCCNC(=O)OC(C)(C)C)C1=CC=C(C=C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 137.7, "product": "C(C)OC(CC(CCCNC(=O)OC(C)(C)C)C1=CC=C(C=C1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | MINUTE | A solution of (4-bromo-phenyl)-acetic acid ethyl ester (2.31 g, 9.50 mmol) in dimethylsulfoxide (6 mL) was added to the suspension of sodium hydride (407 mg, 60% in oil, 10.17 mmol) and stirred 3 min. A solution of (3-bromo-propyl)-carbamic acid tert-butyl ester (2.03 g, 8.52 mmol) in dimethylsulfoxide (6 mL) was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Boc | Ether.Boc | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CS(=O)C | null | 0.05 | CC(C)(C)OC(=O)NCCCBr.CCOC(=O)Cc1ccc(Br)cc1>CS(=O)C>CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b08306b43794c0caae6c50d5fc43b55 | CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1>>CCOC(=O)CC(CCCN)c1ccc(Br)cc1 | C(C)OC(CC(CCCNC(=O)OC(C)(C)C)C1=CC=C(C=C1)Br)=O.Cl>>Cl.C(C)OC(CC(CCCN)C1=CC=C(C=C1)Br)=O | CC(C)(C)OC(=O)[NH:11][CH2:10][CH2:9][CH2:8][CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH2:8][CH2:9][CH2:10][NH2:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1 | CCOC(=O)CC(CCCN)c1ccc(Br)cc1 | null | null | C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | 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 | 30 | MINUTE | To a solution of 3-(4-Bromo-phenyl)-6-tert-butoxycarbonylamino-hexanoic acid ethyl ester (2.43 g, 6.32 mmol) in ethyl acetate (3 mL) was added 4 N hydrogen chloride in ethyl acetate (6 mL) at room temperature. Removal of the solvent in vacuo after stirring for 30 min afforded 6-Amino-3-(4-bromo-phenyl)-hexanoic acid et... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(C)(=O)OCC | null | 0.5 | CCOC(=O)CC(CCCNC(=O)OC(C)(C)C)c1ccc(Br)cc1>C(C)(=O)OCC>CCOC(=O)CC(CCCN)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1fbf437c99243d6ad6d224e40c0c375 | CCOC(=O)CC(CCCN)c1ccc(Br)cc1>>O=C1NCCCC1c1ccc(Br)cc1 | Cl.C(C)OC(CC(CCCN)C1=CC=C(C=C1)Br)=O.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=C(C=C1)C1C(NCCC1)=O | CCOC(=[O:1])[CH2:2][CH:7]([CH2:6][CH2:5][CH2:4][NH2:3])[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][CH2:6][CH:7]1[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CCOC(=O)CC(CCCN)c1ccc(Br)cc1 | O=C1NCCCC1c1ccc(Br)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 65d5f5abf1905df28bc78504907575768cc1961fce3cba5ae648e8698d72a683 | 92bd4402d90a419a2f8338f9414db9222f74d64e606e4b1a47fea24edc8b3ea6 | O=C1NCCCC1c1ccccc1 | C-C-O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[C:3](-[c:4])-[C:5]-[C:6]-[C:7]-[NH2;D1;+0:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[NH;D2;+0:8]-[C:7]-[C:6]-[C:5]-[C:3]-1-[c:4] | 86 | [{"value": 86.0, "product": "BrC1=CC=C(C=C1)C1C(NCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-amino-3-(4-bromo-phenyl)-hexanoic acid ethyl ester hydrochloride, potassium carbonate (1039 mg, 7.52 mmol) in ethanol (50 ml) was refluxed for 20 hr. Solvent was removed in vacuo after addition of dilute hydrochloric acid and water was added to the residue. Filtration, wash with water and dryness afford... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | C1CCNCC1 | C1CCNCC1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)CC(CCCN)c1ccc(Br)cc1>C(C)O>O=C1NCCCC1c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d4e95c7133d42b48eeb2ffe5e987cab | O=C1NCCCC1c1ccc(Br)cc1>>Brc1ccc(C2CCCNC2)cc1 | Cl.BrC1=CC=C(C=C1)C1C(NCCC1)=O.B.O1CCCC1>>BrC1=CC=C(C=C1)C1CNCCC1 | O=[C:11]1[CH:6]([c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:13][cH:12]2)[CH2:7][CH2:8][CH2:9][NH:10]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][NH:10][CH2:11]2)[cH:12][cH:13]1 | O=C1NCCCC1c1ccc(Br)cc1 | Brc1ccc(C2CCCNC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | edc142430f5f6289e7d9f9629acd70dfaf6c042d8ee247558b104f4a86ec0340 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(C2CCCNC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[c:5])-[C:6]>>[C:6]-[C:4](-[c:5])-[CH2;D2;+0:1]-[#7:2]-[C:3] | 90 | [{"value": 90.0, "product": "BrC1=CC=C(C=C1)C1CNCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "BrC1=CC=C(C=C1)C1CNCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To an ice-cooled solution of 3-(4-bromo-phenyl)-piperidin-2-one (37.97 g, 149 mmol) in tetrahydrofuran (250 ml) was added borane-tetrahydrofuran complex (335 ml, 1.0 M solution in THF, 335 mmol). The solution was stirred overnight at room temperature, and then refluxed 1.5 hr after addition of 10% aqueous hydrochloric ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CCNCC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | Other | O1CCCC1 | null | 8 | O=C1NCCCC1c1ccc(Br)cc1>O1CCCC1>Brc1ccc(C2CCCNC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63f98dd0911049c8ac37e68b334e3a3e | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.CN1CCNCC1>>CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1 | C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)Br.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+].CN1CCNCC1>>C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C | Br[c:6]1[cH:7][cH:8][c:9]([CH:10]2[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22]2)[cH:23][cH:24]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:1... | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.CN1CCNCC1 | CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)ccc1C1CCCNC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 63.2 | [{"value": 63.0, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.2, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a suspension of 3-(4-bromophenyl)-piperidine-1-carboxylic acid tert-butyl ester (3.0 g, 8.8 mmol), palladium acetate (80 mg, 0.36 mmol), 2-(di-t-butyl phosphino)biphenyl (210 mg, 0.70 mmol), and sodium t-butoxide (1.2 g, 125 mmol) in toluene (30 mL) was added N-methylpiperazine (1.3 g, 13.0 mmol) at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.C1CC[NH]CC1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | 90 | null | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.CN1CCNCC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d8506b1c879405883e373c628aeb02c | CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1>>CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cl.Cl | C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C.Cl>>Cl.Cl.Cl.CN1CCN(CC1)C1=CC=C(C=C1)C1CNCCC1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][CH2:11][CH:10]([c:9]2[cH:8][cH:7][c:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:19][CH2:18]3)[cH:17][cH:16]2)[CH2:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:14][CH2:15]3)[cH:16][cH:17]2)[CH2:18][CH2:19]1.[ClH:21].[ClH:22] | CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1 | CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cl.Cl | null | null | CO.C(C)(=O)OCC | Miscellaneous | Boc amine deprotection | 0d17b1cd8faa9642170a265595f8fea596067098aa2d20db6ef6a923fda4571d | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | c1cc(N2CCNCC2)ccc1C1CCCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 90 | [{"value": 90.0, "product": "Cl.Cl.Cl.CN1CCN(CC1)C1=CC=C(C=C1)C1CNCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-(4-(4-methylpiperazin-1-yl)-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (2.0 g, 5.56 mmol) in methanol (20 mL) was added 4N hydrochloric acid in ethyl acetate (20 mL) at room temperature. After stirring for 1 h, the resulting suspension was concentrated in vacuo. The residue was washed with... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1C[NH]CC[NH]1.c1ccccc1.C1CCNCC1 | HO- | CO.C(C)(=O)OCC | null | 1 | CN1CCN(c2ccc(C3CCCN(C(=O)OC(C)(C)C)C3)cc2)CC1>CO.C(C)(=O)OCC>CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5756c3fc9e6b4483bf935bfc4dd79987 | CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>CN1CCN(c2ccc(C3CCCN(c4nc(-c5ccncc5)cc(=O)n4C)C3)cc2)CC1 | Cl.Cl.Cl.CN1CCN(CC1)C1=CC=C(C=C1)C1CNCCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:14][CH2:29]3)[cH:30][cH:31]2)[CH2:32][CH2:33]1.Cl[c:15]1[n:16][c:17](-[c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[cH:24][c:25](=[O:26])[n:27]1[CH3:28]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([CH:10]3[CH2:11][C... | CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | CN1CCN(c2ccc(C3CCCN(c4nc(-c5ccncc5)cc(=O)n4C)C3)cc2)CC1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCCC(c3ccc(N4CCNCC4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 71 | [{"value": 71.0, "product": "CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CC(CCC1)C1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 3-(4-(4-methylpiperazin-1-yl)-phenyl)-piperidine trihydrochloride salt (0.4 g, 1.08 mmol) and triethylamine (0.6 g, 5.93 mmol) in tetrahydrofuran (10 mL) was added 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.22 g, 0.99 mmol) portionwise. After stirring for 12 h, the resulting suspension wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1cncnc1 | C1CC[NH]CC1.c1cncnc1 | C1C[NH]CC[NH]1.c1ccccc1.C1CC[NH]CC1.c1cncnc1.c1ccncc1 | HCl | O1CCCC1 | null | 12 | CN1CCN(c2ccc(C3CCCNC3)cc2)CC1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>CN1CCN(c2ccc(C3CCCN(c4nc(-c5ccncc5)cc(=O)n4C)C3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3969d37275cb4f06a9a9b44160e37bd3 | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.NC1CCCCC1>>CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1 | C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)Br.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+].C1(CCCCC1)N>>C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)NC1CCCCC1 | Br[c:16]1[cH:15][cH:14][c:13]([CH:12]2[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26]2)[cH:25][cH:24]1.[NH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([NH:17... | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.NC1CCCCC1 | CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(C2CCCNC2)ccc1NC1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9] | 80 | [{"value": 80.0, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)NC1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)NC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a suspension of 3-(4-bromophenyl)-piperidine-1-carboxylic acid tert-butyl ester (8.0 g, 23.5 mmol), palladium acetate (210 mg, 0.94 mmol), 2-(di-t-butyl phosphino)biphenyl (560 mg, 1.88 mmol), and sodium t-butoxide (3.2 g, 33.3 mmol) in toluene (80 mL) was added cyclohexylamine (2.8 g, 28.2 mmol) at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | C1CC[NH]CC1.c1ccccc1.C1CCCCC1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | 90 | null | CC(C)(C)OC(=O)N1CCCC(c2ccc(Br)cc2)C1.NC1CCCCC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ba6a1f9797a494c9bc614151c07d222 | CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1>>Cl.c1cc(C2CCCNC2)ccc1NC1CCCCC1 | C(C)(C)(C)OC(=O)N1CC(CCC1)C1=CC=C(C=C1)NC1CCCCC1.Cl>>Cl.Cl.C1(CCCCC1)NC1=CC=C(C=C1)C1CNCCC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][CH2:7][CH:6]([c:5]2[cH:4][cH:3][c:14]([NH:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[cH:13][cH:12]2)[CH2:11]1>>[ClH:2].[cH:3]1[cH:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][NH:10][CH2:11]2)[cH:12][cH:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1 | CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1 | Cl.c1cc(C2CCCNC2)ccc1NC1CCCCC1 | null | null | CO.C(C)(=O)OCC | Miscellaneous | Boc amine deprotection | 0d17b1cd8faa9642170a265595f8fea596067098aa2d20db6ef6a923fda4571d | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | c1cc(C2CCCNC2)ccc1NC1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 94 | [{"value": 94.0, "product": "Cl.Cl.C1(CCCCC1)NC1=CC=C(C=C1)C1CNCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-(4-cyclohexylaminophenyl)-piperidine-1-carboxylic acid tert-butyl ester (6.74 g, 18.8 mmol) in methanol (50 mL) was added 4N hydrochloric acid in ethyl acetate (40 mL) at room temperature. After stirring for 1 h, the resulting suspension was concentrated in vacuo. The residue was washed with ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1.C1CCCCC1 | HO- | CO.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N1CCCC(c2ccc(NC3CCCCC3)cc2)C1>CO.C(C)(=O)OCC>Cl.c1cc(C2CCCNC2)ccc1NC1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-688e675da1f149ee9f2c802eb3e0d146 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(C2CCCNC2)ccc1NC1CCCCC1>>Cn1c(N2CCCC(c3ccc(NC4CCCCC4)cc3)C2)nc(-c2ccncc2)cc1=O | Cl.Cl.C1(CCCCC1)NC1=CC=C(C=C1)C1CNCCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>C1(CCCCC1)NC1=CC=C(C=C1)C1CN(CCC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:32](=[O:33])[cH:31][c:24](-[c:25]2[cH:26][cH:27][n:28][cH:29][cH:30]2)[n:23]1.[NH:4]1[CH2:5][CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([NH:13][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][cH:21]2)[CH2:22]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH2:7][CH:8]([c:9]3[cH:10][cH:1... | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(C2CCCNC2)ccc1NC1CCCCC1 | Cn1c(N2CCCC(c3ccc(NC4CCCCC4)cc3)C2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCCC(c3ccc(NC4CCCCC4)cc3)C2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 96 | [{"value": 96.0, "product": "C1(CCCCC1)NC1=CC=C(C=C1)C1CN(CCC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.8, "product": "C1(CCCCC1)NC1=CC=C(C=C1)C1CN(CCC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 3-(4-cyclohexylaminophenyl)-piperidine dihydrochloride salt (1.0 g, 3.02 mmol) and triethylamine (1.5 g, 14.8 mmol) in tetrahydrofuran (20 mL) was added 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.64 g, 2.89 mmol) portionwise. After stirring for 12 h, the resulting suspension was partition... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CCNCC1 | c1cncnc1.C1CC[NH]CC1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.C1CCCCC1.c1ccncc1 | HCl | O1CCCC1 | null | 12 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(C2CCCNC2)ccc1NC1CCCCC1>O1CCCC1>Cn1c(N2CCCC(c3ccc(NC4CCCCC4)cc3)C2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f849f56ce6d459792352a6feaaeea00 | CCOC(=O)C(C(=O)OCC)C(c1ccc(Br)cc1)C(C(=O)OCC)C(=O)OCC>>O=C(O)CC(CC(=O)O)c1ccc(Br)cc1 | C(C)OC(C(C(C(C(=O)OCC)C(=O)OCC)C1=CC=C(C=C1)Br)C(=O)OCC)=O>>BrC1=CC=C(C=C1)C(CC(=O)O)CC(=O)O | CCOC(=O)[CH:4]([C:2](=[O:1])[O:3]CC)[CH:5]([CH:6](C(=O)OCC)[C:7](=[O:8])[O:9]CC)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([CH2:6][C:7](=[O:8])[OH:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1 | CCOC(=O)C(C(=O)OCC)C(c1ccc(Br)cc1)C(C(=O)OCC)C(=O)OCC | O=C(O)CC(CC(=O)O)c1ccc(Br)cc1 | null | null | Cl.C(C)(=O)O | Reduction | OtherReaction | c66b299b40f3bbe41ba1575d603bfa618c1cfd61a8332cce6a45cf083197b05c | 710ca63f65f20afd2d083b70f6465deae8116e1dce84a7e30ca74e667dfb146a | c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C)-[C:5](-[c:6])-[CH;D3;+0:7](-C(=O)-O-C-C)-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:4])-[CH2;D2;+0:1]-[C:5](-[c:6])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10] | null | [] | null | null | null | null | A solution of 3-(4-bromo-phenyl)-2,4-bis-ethoxycarbonyl-pentanedioic acid diethyl ester in concentrated hydrochloric acid (100 ml) and acetic acid (100 ml) was refluxed for 8 h. Removal of the solvent in vacuo and recrystallization of the residue from acetonitrile yielded 3-(4-bromo-phenyl)-pentanedioic acid (22.84 g i... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | HO- | Cl.C(C)(=O)O | null | null | CCOC(=O)C(C(=O)OCC)C(c1ccc(Br)cc1)C(C(=O)OCC)C(=O)OCC>Cl.C(C)(=O)O>O=C(O)CC(CC(=O)O)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-085f94f171c14756b7758395c55c699e | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1>>Brc1ccc(C2CCNCC2)cc1 | C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)Br.Cl>>Cl.BrC1=CC=C(C=C1)C1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][CH:6]([c:5]2[cH:4][cH:3][c:2]([Br:1])[cH:13][cH:12]2)[CH2:11][CH2:10]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[cH:12][cH:13]1 | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1 | Brc1ccc(C2CCNCC2)cc1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(C2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 98 | [{"value": 98.0, "product": "Cl.BrC1=CC=C(C=C1)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of furnished 4-(4-bromophenyl)-piperidine-1-carboxylic acid tert-butyl ester (1114 mg, 3.27 mmol) in ethyl acetate (1 mL) was added 4 N hydrogen chloride in ethyl acetate (2 mL) at room temperature. After stirring for 5 h, solvent was removed in vacuo, and the resulting solid was washed with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CCNCC1 | HO- | C(C)(=O)OCC | null | 5 | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1>C(C)(=O)OCC>Brc1ccc(C2CCNCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2cc3198a190426a81ba2c14e9af8b9a | Brc1ccc(C2CCNCC2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>>Cn1c(N2CCC(c3ccc(Br)cc3)CC2)nc(-c2ccncc2)cc1=O | Cl.BrC1=CC=C(C=C1)C1CCNCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>BrC1=CC=C(C=C1)C1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1 | [NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1.Cl[c:3]1[n:2]([CH3:1])[c:26](=[O:27])[cH:25][c:18](-[c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[n:17]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH:7]([c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[CH2:15][CH2:16]2)[n:17]... | Brc1ccc(C2CCNCC2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O | Cn1c(N2CCC(c3ccc(Br)cc3)CC2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCC(c3ccccc3)CC2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 93.1 | [{"value": 93.0, "product": "BrC1=CC=C(C=C1)C1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "BrC1=CC=C(C=C1)C1CCN(CC1)C1=NC(=CC(N1C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (4-(4-bromophenyl)-piperidine hydrochloride (279 mg, 1.01 mmol) and triethylamine (554 mg, 5.47 mmol), 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (206 mg, 0.929 mmol) in tetrahydrofuran (20 mL) was stirred for 3 hr. The resulting solution was diluted with tetrahydrofuran and filtrated. After re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1cncnc1 | c1cncnc1.C1CC[NH]CC1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1 | null | null | Brc1ccc(C2CCNCC2)cc1.Cn1c(Cl)nc(-c2ccncc2)cc1=O>O1CCCC1>Cn1c(N2CCC(c3ccc(Br)cc3)CC2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcbbc628771c47e0b6e6fc681d9349d2 | C1CCNC1.CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1>>CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)Br.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+].N1CCCC1>>C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)N1CCCC1 | [NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.Br[c:15]1[cH:14][cH:13][c:12]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:24][CH2:23]2)[cH:22][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH2:18][CH2:19... | C1CCNC1.CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1 | CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCCC2)ccc1C1CCNCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:4]:[c:5] | null | [] | 90 | CELSIUS | null | null | A suspension of 4-(4-Bromophenyl)-piperidine-1-carboxylic acid tert-butyl ester (1.97 g, 5.79 mmol), palladium acetate (54 mg, 0.24 mmol), 2-(di-t-butylphosphino)biphenyl (154 mg, 0.52 mmol), and sodium t-butoxide (846 mg, 8.80 mmol), pyrrolidine (587 mg, 8.25 mmol) in toluene (80 mL) was heated at 90° C. for 3 h under... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | 90 | null | C1CCNC1.CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)CC1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3042e115b414872ac51f3148119a39d | CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1>>c1cc(N2CCCC2)ccc1C1CCNCC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC=C(C=C1)N1CCCC1.Cl>>N1(CCCC1)C1=CC=C(C=C1)C1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][CH:12]([c:11]2[cH:1][cH:2][c:3]([N:4]3[CH2:5][CH2:6][CH2:7][CH2:8]3)[cH:9][cH:10]2)[CH2:17][CH2:16]1>>[cH:1]1[cH:2][c:3]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8]2)[cH:9][cH:10][c:11]1[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1 | c1cc(N2CCCC2)ccc1C1CCNCC1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(N2CCCC2)ccc1C1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 76 | [{"value": 76.0, "product": "N1(CCCC1)C1=CC=C(C=C1)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of furnished 4-(4-Pyrrolidin-1-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester in ethyl acetate (5 mL) was added 4 N hydrogen chloride in ethyl acetate (10 mL) at room temperature. After stirring for 3 h, solvent was removed in vacuo, and the resulting solid was purified by HPLC. Sodium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.C1CC[NH]C1.C1CCNCC1 | HO- | C(C)(=O)OCC | null | 3 | CC(C)(C)OC(=O)N1CCC(c2ccc(N3CCCC3)cc2)CC1>C(C)(=O)OCC>c1cc(N2CCCC2)ccc1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12034e504d8748dcb585172770766ce8 | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CCCC2)ccc1C1CCNCC1>>Cn1c(N2CCC(c3ccc(N4CCCC4)cc3)CC2)nc(-c2ccncc2)cc1=O | N1(CCCC1)C1=CC=C(C=C1)C1CCNCC1.C(C)N(CC)CC.ClC1=NC(=CC(N1C)=O)C1=CC=NC=C1>>CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CCC(CC1)C1=CC=C(C=C1)N1CCCC1 | Cl[c:3]1[n:2]([CH3:1])[c:30](=[O:31])[cH:29][c:22](-[c:23]2[cH:24][cH:25][n:26][cH:27][cH:28]2)[n:21]1.[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17][cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH:7]([c:8]3[cH:9][cH:10][c:11]([N:12]4[CH2:13]... | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CCCC2)ccc1C1CCNCC1 | Cn1c(N2CCC(c3ccc(N4CCCC4)cc3)CC2)nc(-c2ccncc2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncc2)nc(N2CCC(c3ccc(N4CCCC4)cc3)CC2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 81 | [{"value": 81.0, "product": "CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CCC(CC1)C1=CC=C(C=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "CN1C(=NC(=CC1=O)C1=CC=NC=C1)N1CCC(CC1)C1=CC=C(C=C1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(4-pyrrolidin-1-yl-phenyl)-piperidine (215 mg, 0.933 mmol) and triethylamine (391 mg, 3.86 mmol), 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (187 mg, 0.844 mmol) in tetrahydrofuran (10 mL) was refluxed for 5 hr. The resulting solution was diluted with tetrahydrofuran and filtrated. After remo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CCNCC1 | c1cncnc1.C1CC[NH]CC1 | c1cncnc1.C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccncc1 | HCl | O1CCCC1 | null | null | Cn1c(Cl)nc(-c2ccncc2)cc1=O.c1cc(N2CCCC2)ccc1C1CCNCC1>O1CCCC1>Cn1c(N2CCC(c3ccc(N4CCCC4)cc3)CC2)nc(-c2ccncc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e86ce32564d64cb9b307b22e1e227e9e | Fc1cccc(F)c1.O=C(O)C1CCN(C(=O)c2ccccc2)CC1>>O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1 | C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(=O)O.S(=O)(Cl)Cl.FC1=CC=CC(=C1)F.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(C1=C(C=C(C=C1)F)F)=O | [cH:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10].O[C:2](=[O:1])[CH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[F:10])[CH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:2... | Fc1cccc(F)c1.O=C(O)C1CCN(C(=O)c2ccccc2)CC1 | O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | c192095061656f3fd26b35f75625f8f38ff1c48733635e4bb5643912a6b658c7 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)C1CCN(C(=O)c2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[F;D1;H0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[F;D1;H0:6]):[c:8])-[C:5] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(C1=C(C=C(C=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(C1=C(C=C(C=C1)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 1-benzoylpiperidine-4-carboxylic acid (66 g, 285 mmol) in dichloromethane (160 mL) was added thionyl chloride (26 mL, 388 mmol). After stirring at 60° C. for 1 h, the mixture was added portionwise to a stirred suspension of 2,4-difluorobenzene (45 g, 397 mmol) and anhydrous aluminum chloride (88 g, 666... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | ClCCl | 60 | 1 | Fc1cccc(F)c1.O=C(O)C1CCN(C(=O)c2ccccc2)CC1>ClCCl>O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b25fa8f7b0bf4611ae0ad75b5ca0c225 | COC(=O)CS.O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1>>O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1 | C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(C1=C(C=C(C=C1)F)F)=O.C(CS)(=O)OC>>C(C1=CC=CC=C1)(=O)N1CCC(CC1)C=1C2=C(SC1C(=O)O)C=C(C=C2)F | C[O:3][C:2](=[O:1])[CH2:4][SH:5].O=[C:13]([c:12]1[c:6](F)[cH:7][c:8]([F:9])[cH:10][cH:11]1)[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[s:5][c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]2[c:13]1[CH:14]1[CH2:15][CH2:16][N:17]([C:18](... | COC(=O)CS.O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1 | O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 10b65f0bde8c4376e88f9f47bea0fa6b2c5917e28382d62dfc4040fc35d45b8a | 951eb9f72bc66879928a7a36fe41efe1ec642d4ea021c6c4817587d69da3f78c | O=C(c1ccccc1)N1CCC(c2csc3ccccc23)CC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[SH;D1;+0:5].F-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C;H0;D3;+0:10](=O)-[C:11](-[C:12])-[C:13]):[c:14]>>[C:12]-[C:11](-[c;H0;D3;+0:10]1:[c:9](:[c:14]):[c;H0;D3;+0:6](:[c:7]:[c:8]):[s;H0;D2;+0:5]:[c;H0;D3;+0:4]:1-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:13] | 26 | [{"value": 26.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)C=1C2=C(SC1C(=O)O)C=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.6, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)C=1C2=C(SC1C(=O)O)C=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-benzoyl-4-(2,4-difluorobenzoyl)piperidine (40 g, 120 mmol), methyl thioglycolate (12 mL, 130 mmol) in dimethylformamide (500 mL) was stirred at room temperatute for 12 h. The solvent was evaporated off in vacuo and the residue treated with water and ethyl acetate. The organic layer was dried over sodium... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester.Aliphatic thiol | Carboxylic acid | c1ccccc1 | c1ccc2sccc2c1 | c1ccc2sccc2c1.C1CC[NH]CC1.c1ccccc1 | HF | CN(C=O)C | null | null | COC(=O)CS.O=C(c1ccc(F)cc1F)C1CCN(C(=O)c2ccccc2)CC1>CN(C=O)C>O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81940f2bc5ad4c58a4fb7712597babf4 | O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1>>O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1 | C(C1=CC=CC=C1)(=O)N1CCC(CC1)C=1C2=C(SC1C(=O)O)C=C(C=C2)F>>FC=1C=CC2=C(SC=C2C2CCN(CC2)C(=O)C2=CC=CC=C2)C1 | O=C(O)[c:14]1[c:13]([CH:12]2[CH2:11][CH2:10][N:9]([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][cH:8]3)[CH2:24][CH2:23]2)[c:22]2[c:16]([s:15]1)[cH:17][c:18]([F:19])[cH:20][cH:21]2>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][CH:12]([c:13]2[cH:14][s:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21... | O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1 | O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1 | null | null | N1=CC=CC2=CC=CC=C12 | Reduction | Decarboxylation | e7181c38396648ce3877e00f49e821995a538b0b9fe74fd60bef7293cca4fe64 | 292164ffdf89eeb341ee9424f24084b252a703a26bb77721b558b0f8a8528c45 | O=C(c1ccccc1)N1CCC(c2csc3ccccc23)CC1 | O-C(=O)-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1-[C:6]>>[C:6]-[c:5]1:[c:4]:[c:3]:[#16;a:2]:[cH;D2;+0:1]:1 | 56.7 | [{"value": 48.0, "product": "FC=1C=CC2=C(SC=C2C2CCN(CC2)C(=O)C2=CC=CC=C2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "FC=1C=CC2=C(SC=C2C2CCN(CC2)C(=O)C2=CC=CC=C2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 1 | HOUR | 3-(1-Benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acid (10 g, 26 mmol) was suspended in quinoline (100 mL) and cupper powder (0.5 g) was added. After stirring at 200° C. for 1 h, the mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2sccc2c1 | Other | N1=CC=CC2=CC=CC=C12 | 200 | 1 | O=C(O)c1sc2cc(F)ccc2c1C1CCN(C(=O)c2ccccc2)CC1>N1=CC=CC2=CC=CC=C12>O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a29d55a57be492b83495bffda71cec5 | O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1>>Fc1ccc2c(C3CCNCC3)csc2c1 | FC=1C=CC2=C(SC=C2C2CCN(CC2)C(=O)C2=CC=CC=C2)C1.Cl.C(C)(=O)OCC>>Cl.FC=1C=CC2=C(SC=C2C2CCNCC2)C1 | O=C(c1ccccc1)[N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[c:6]3[cH:5][cH:4][c:3]([F:2])[cH:17][c:16]3[s:15][cH:14]2)[CH2:13][CH2:12]1>>[F:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH:8]3[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]3)[cH:14][s:15][c:16]2[cH:17]1 | O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1 | Fc1ccc2c(C3CCNCC3)csc2c1 | null | null | C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | 202dfbde63054fe0c1be1860e0a18d51d73a6e2bf4eb055d21534a1f1bf746b3 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(C3CCNCC3)csc2c1 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 89 | [{"value": 89.0, "product": "Cl.FC=1C=CC2=C(SC=C2C2CCNCC2)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (4-(6-fluorobenzo[b]thiophen-3-yl)piperidin-1-yl) phenylmethanone (6.5 g, 19 mmol) in acetic acid (100 mL) and concentrated hydrochloric acid (100 mL) was stirred at 90° C. for 10 h. To a solution of reaction mixture was added ethyl acetate. The precipitated crystals were collected by filtration and washe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2sccc2c1 | HO- | C(C)(=O)O | null | null | O=C(c1ccccc1)N1CCC(c2csc3cc(F)ccc23)CC1>C(C)(=O)O>Fc1ccc2c(C3CCNCC3)csc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eca6b135471b4a8f969414b2b1546cd5 | Cn1c(Cl)nc(-c2ccncn2)cc1=O.Fc1ccc2c(C3CCNCC3)csc2c1>>Cn1c(N2CCC(c3csc4cc(F)ccc34)CC2)nc(-c2ccncn2)cc1=O | Cl.FC=1C=CC2=C(SC=C2C2CCNCC2)C1.ClC=1N(C(C=C(N1)C1=NC=NC=C1)=O)C.C(C)N(CC)CC>>FC=1C=CC2=C(SC=C2C2CCN(CC2)C=2N(C(C=C(N2)C2=NC=NC=C2)=O)C)C1 | Cl[c:3]1[n:2]([CH3:1])[c:29](=[O:30])[cH:28][c:21](-[c:22]2[cH:23][cH:24][n:25][cH:26][n:27]2)[n:20]1.[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][s:10][c:11]3[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH:7]([c:8]3[cH:9][s:10][c:11]4[cH:12][c:13]([F:14])[cH:15][cH... | Cn1c(Cl)nc(-c2ccncn2)cc1=O.Fc1ccc2c(C3CCNCC3)csc2c1 | Cn1c(N2CCC(c3csc4cc(F)ccc34)CC2)nc(-c2ccncn2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | eef6e7871bcca39724d18f42f2d65d53e5e87d35a7d42bc7183442776a681ce5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncn2)nc(N2CCC(c3csc4ccccc34)CC2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6])-[C:10]-[C:11] | 96 | [{"value": 96.0, "product": "FC=1C=CC2=C(SC=C2C2CCN(CC2)C=2N(C(C=C(N2)C2=NC=NC=C2)=O)C)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "FC=1C=CC2=C(SC=C2C2CCN(CC2)C=2N(C(C=C(N2)C2=NC=NC=C2)=O)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 6 | HOUR | To a solution of 4-(6-fluorobenzo[b]thiophen-3-yl)piperidine hydrochloride (200 mg, 0.74 mmol) and 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (160 mg, 0.70 mmol) in tetrahydrofuran (10 mL) was added triethylamine (212 mg, 2.1 mmol). The mixture was stirred at 90° C. for 6 h. The solvent was evaporated off in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CCNCC1 | c1cncnc1.C1CC[NH]CC1 | c1cncnc1.C1CC[NH]CC1.c1ccc2sccc2c1.c1cncnc1 | HCl | O1CCCC1 | 90 | 6 | Cn1c(Cl)nc(-c2ccncn2)cc1=O.Fc1ccc2c(C3CCNCC3)csc2c1>O1CCCC1>Cn1c(N2CCC(c3csc4cc(F)ccc34)CC2)nc(-c2ccncn2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7af9c45bb3404c878b7fcaa3923c6f9c | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1ccc(-c2ccccc2N2CCNCC2)cc1>>Cn1c(N2CCN(c3ccccc3-c3ccccc3)CC2)nc(-c2ccncn2)cc1=O | Cl.Cl.C1(=C(C=CC=C1)N1CCNCC1)C1=CC=CC=C1.ClC=1N(C(C=C(N1)C1=NC=NC=C1)=O)C.C(C)N(CC)CC>>C1(=C(C=CC=C1)N1CCN(CC1)C=1N(C(C=C(N1)C1=NC=NC=C1)=O)C)C1=CC=CC=C1 | Cl[c:3]1[n:2]([CH3:1])[c:31](=[O:32])[cH:30][c:23](-[c:24]2[cH:25][cH:26][n:27][cH:28][n:29]2)[n:22]1.[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[CH3:1][n:2]1[c:3]([N:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3-[... | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1ccc(-c2ccccc2N2CCNCC2)cc1 | Cn1c(N2CCN(c3ccccc3-c3ccccc3)CC2)nc(-c2ccncn2)cc1=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89a9e7e1366d55004dcd9e6694ddaa661145a78e26c30f61d46c470b984e6100 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccncn2)nc(N2CCN(c3ccccc3-c3ccccc3)CC2)[nH]1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4](-[C;D1;H3:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[C;D1;H3:5]-[#7;a:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[#7;a:2]:[c:3] | 65 | [{"value": 65.0, "product": "C1(=C(C=CC=C1)N1CCN(CC1)C=1N(C(C=C(N1)C1=NC=NC=C1)=O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "C1(=C(C=CC=C1)N1CCN(CC1)C=1N(C(C=C(N1)C1=NC=NC=C1)=O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 4 | HOUR | To a solution of 1-biphenyl-2-yl-piperazine dihydrochloride (311 mg, 1.0 mmol) and 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (202 mg, 0.91 mmol) in tetrahydrofuran (20 mL) was added triethylamine (404 mg, 4.0 mmol). The mixture was stirred at 90° C. for 4 h. The solvent was evaporated off in vacuo and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.c1cncnc1 | HCl | O1CCCC1 | 90 | 4 | Cn1c(Cl)nc(-c2ccncn2)cc1=O.c1ccc(-c2ccccc2N2CCNCC2)cc1>O1CCCC1>Cn1c(N2CCN(c3ccccc3-c3ccccc3)CC2)nc(-c2ccncn2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07aff546efab4ea98c8878d08510434b | CC(C)(C)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1>>CC(C)(C)c1cn2cc([N+](=O)[O-])ccc2n1 | BrCC(C(C)(C)C)=O.NC1=NC=C(C=C1)[N+](=O)[O-]>>C(C)(C)(C)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1 | O=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6]Br.[n:7]1[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]1[NH2:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7]2[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][cH:14][c:15]2[n:16]1 | CC(C)(C)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1 | CC(C)(C)c1cn2cc([N+](=O)[O-])ccc2n1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccn2ccnc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:10](:[c:11]:[c:12]):[c:8](:[c:9]):[n;H0;D2;+0:7]:1 | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using 1-bromopinacolone and 2-amino-5-nitropyridine. The solid whereupon obtained was suspended in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate solution to provide the title compound as yellow solid.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)(=O)OCC | null | null | CC(C)(C)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>CC(C)(C)c1cn2cc([N+](=O)[O-])ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08e9c128559343a49cfbb57ed99de03f | CC(Br)C=O.Nc1ccc([N+](=O)[O-])cn1>>Cc1cnc2ccc([N+](=O)[O-])cn12 | BrC(C=O)C.NC1=NC=C(C=C1)[N+](=O)[O-]>>CC1=CN=C2N1C=C(C=C2)[N+](=O)[O-] | O=[CH:3][CH:2](Br)[CH3:1].[NH2:4][c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13]12 | CC(Br)C=O.Nc1ccc([N+](=O)[O-])cn1 | Cc1cnc2ccc([N+](=O)[O-])cn12 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=O.[NH2;D1;+0:4]-[c:5](:[c:6]):[n;H0;D2;+0:7]:[c:8]:[c:9]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c:5](:[c:6]):[n;H0;D3;+0:7]:1:[c:8]:[c:9] | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using 2-bromopropionaldehyde and 2-amino-5-nitropyridine. The solid whereupon obtained was suspended in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate solution to provide the title compound as yellow solid.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)(=O)OCC | null | null | CC(Br)C=O.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>Cc1cnc2ccc([N+](=O)[O-])cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddf90a8fa25e4e26a87c88dcaf38753b | CC(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1>>Cc1nc2ccc([N+](=O)[O-])cn2c1C | BrC(C(C)=O)C.NC1=NC=C(C=C1)[N+](=O)[O-]>>CC=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C | O=[C:13]([CH:2](Br)[CH3:1])[CH3:14].[NH2:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12]2[c:13]1[CH3:14] | CC(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1 | Cc1nc2ccc([N+](=O)[O-])cn2c1C | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 68f76555483972bc3db5d3d4b5e479a66c1f89ab1b71b2a0fb941126aa9c191a | 235fd48cd394ba1137abde2ba7484c051be6ffcae187060d6065fe5adf0e90a3 | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=O)-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using 3-bromo-2-butanone and 2-amino-5-nitropyridine. The solid whereupon obtained was suspended in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate. After concentration under reduced pressure, the residue was recrystallized from eth... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)(=O)OCC | null | null | CC(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>Cc1nc2ccc([N+](=O)[O-])cn2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32ddb5a084364fa9ab87a80524035d5d | CCC(=O)C1CC1.Nc1ccc([N+](=O)[O-])cn1>>Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12 | C1(CC1)C(CC)=O.NC1=NC=C(C=C1)[N+](=O)[O-]>>C1(CC1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C1C | O=[C:3]([CH2:2][CH3:1])[CH:4]1[CH2:5][CH2:6]1.[NH2:7][c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][n:16]1>>[CH3:1][c:2]1[c:3]([CH:4]2[CH2:5][CH2:6]2)[n:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][n:16]12 | CCC(=O)C1CC1.Nc1ccc([N+](=O)[O-])cn1 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | cbc7e6c5e0a09d2e514fd60fb099adf259bb478395dbd8e339a49821fedd9120 | 8182c33d66a1c51620dac2e3d5b839c3fec60d5b5668262efc6be8b10c115a58 | c1ccn2cc(C3CC3)nc2c1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;D1;H3:3])-[C:4]1-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C;D1;H3:3]-[c;H0;D3;+0:2]1:[c;H0;D3;+0:1](-[C:4]2-[C:5]-[C:6]-2):[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | null | [] | null | null | null | null | Operations similar to Production Example 1-(1) were conducted using 1-cyclopropyl-1-propanone, and successively those of Production 1-(2) were conducted using 2-amino-5-nitropyridine. The solid whereupon obtained was suspended in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and purifie... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | C1CC1.c1ccn2ccnc2c1 | HO- | C(C)(=O)OCC | null | null | CCC(=O)C1CC1.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7accd1d7f1664bb3b1f3bc86e215ca2e | CCOC(=O)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1>>CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1 | BrCC(C(=O)OCC)=O.NC1=NC=C(C=C1)[N+](=O)[O-]>>[N+](=O)([O-])C=1C=CC=2N(C1)C=C(N2)C(=O)OCC | O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7]Br.[n:8]1[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]1[NH2:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]2[n:17]1 | CCOC(=O)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1 | CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1 | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | d3be5f205f769cfbcd36c6b3c07b14ecde02aad10f74db526231235b2a6ee955 | 9db5e3e6f9ecdf6e7efe58729c5de8c8b341b06179a94217349f28a43071e423 | c1ccn2ccnc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:10](:[c:11]:[c:12]):[c:8](:[c:9]):[n;H0;D2;+0:7]:1 | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using ethyl bromopyruvate and 2-amino-5-nitropyridine. The solid whereupon obtained was suspended in ethyl acetate, and washed with saturated aqueous sodium hydrogencarbonate to provide the title compound as brown solid.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Primary amine | Ester | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)(=O)OCC | null | null | CCOC(=O)C(=O)CBr.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>CCOC(=O)c1cn2cc([N+](=O)[O-])ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46262c6d7e1642fcbad221c17aa8a3f8 | COC(=O)C(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1>>COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C | BrC(C(C(=O)OC)=O)C.NC1=NC=C(C=C1)[N+](=O)[O-]>>CC1=C(N=C2N1C=C(C=C2)[N+](=O)[O-])C(=O)OC | O=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:16](Br)[CH3:17].[NH2:6][c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15]2[c:16]1[CH3:17] | COC(=O)C(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1 | COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 65d99abd6169d4159eeb9f7445bf1dc8119822b7e7ac05f0cb17c1cfb89ebf03 | 31aa25659cf5accd41f8ff85a49e4d2b829110bf1926ff7161f2261cc71e0db2 | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=O)-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]):[n;H0;D2;+0:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1:[c:12]:[c:13] | null | [] | null | null | null | null | Operations similar to Production Example 1-(2) were conducted using methyl 3-bromo-2-oxobutanoate and 2-amino-5-nitropyridine. The resulting solid was suspended in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and purified by silica gel column chromatography (hexane/ethyl acetate=2/1) t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Primary amine | Ester | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | C(C)(=O)OCC | null | null | COC(=O)C(=O)C(C)Br.Nc1ccc([N+](=O)[O-])cn1>C(C)(=O)OCC>COC(=O)c1nc2ccc([N+](=O)[O-])cn2c1C |
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