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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1574d9bf016a423897aab51d9da5f3e8 | COc1ccccc1[C@H]1O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21>>COc1ccccc1[C@H]1O[C@H](CC(=O)[O-])C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21 | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=C(C=CC=C2)OC)C1.[OH-].[Na+]>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)[O-])C2=C(C=CC=C2)OC)C1.[Na+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@H:9]1[O:10][C@H:11]([CH2:12][C:13](=[O:14])[OH:15])[C:16](=[O:17])[N:18]([CH2:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][c:30]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@H:9]1[O:10][C@H:11]([CH2:12][C:13](=[O:14])[O-:15... | COc1ccccc1[C@H]1O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21 | COc1ccccc1[C@H]1O[C@H](CC(=O)[O-])C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21 | null | null | CO | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | To a suspension of (3R,5S)-7-chloro-5-(2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (12 g) in methanol (200 ml) was added 1N aqueous sodium hydroxide (27.7 ml). After the acid was dissolved completely, the mixture was concentrated in vacuo. To the residue was added ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | CO | null | null | COc1ccccc1[C@H]1O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21>CO>COc1ccccc1[C@H]1O[C@H](CC(=O)[O-])C(=O)N(CC(C)(C)C)c2ccc(Cl)cc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c708472c83f40bf8ae9adf5f16de858 | BrCc1ccccc1.COc1cc(O)ccc1Br>>COc1cc(OCc2ccccc2)ccc1Br | BrC1=C(C=C(C=C1)O)OC.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)Br)OC | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[cH:14][cH:15][c:16]1[Br:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[Br:17] | BrCc1ccccc1.COc1cc(O)ccc1Br | COc1cc(OCc2ccccc2)ccc1Br | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 24 | HOUR | A mixture of 4-bromo-3-methoxyphenol (21 g), benzyl bromide (13.5 ml), potassium carbonate (21.4 g) and acetone (200 ml) was stirred at room temperature for 24 h. The insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CC(=O)C | null | 24 | BrCc1ccccc1.COc1cc(O)ccc1Br>CC(=O)C>COc1cc(OCc2ccccc2)ccc1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a08d4d95931403fb13cf9932fe3b98e | COc1cc(OCc2ccccc2)ccc1C(=O)c1cc(Cl)ccc1N>>COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N | NC1=C(C(=O)C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)C=C(C=C1)Cl.[BH4-].[Na+]>>NC1=C(C(C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)O)C=C(C=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[C:17](=[O:18])[c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[NH2:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[CH:17]([OH:18])[c:19]1[cH:20][c:21... | COc1cc(OCc2ccccc2)ccc1C(=O)c1cc(Cl)ccc1N | COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(COc2ccc(Cc3ccccc3)cc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 94.5 | [{"value": 94.5, "product": "NC1=C(C(C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)O)C=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone (10 g) in methanol (100 ml) was added sodium borohydride (1.4 g). After being stirred for 24 h, the mixture was concentrated in vacuo. The residue was diluted with water (200 ml) and extracted with ethyl acetate (300 ml). The extract was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | CO | null | 24 | COc1cc(OCc2ccccc2)ccc1C(=O)c1cc(Cl)ccc1N>CO>COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b478747f94e9498ba6d526c52d811437 | CC(C)(C)C=O.COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N>>COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1NCC(C)(C)C | C(#N)[BH3-].[Na+].NC1=C(C(C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)O)C=C(C=C1)Cl.C(C(C)(C)C)=O.C(C)(=O)O>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C(C1=C(C=CC(=C1)Cl)NCC(C)(C)C)O)OC | O=[CH:27][C:28]([CH3:29])([CH3:30])[CH3:31].[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][c:16]1[CH:17]([OH:18])[c:19]1[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]1[NH2:26]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:... | CC(C)(C)C=O.COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N | COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1NCC(C)(C)C | null | null | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(COc2ccc(Cc3ccccc3)cc2)cc1 | O=[CH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[CH2;D2;+0:1]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 30 | MINUTE | A mixture of 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g), pivalaldehyde (3.35 ml), acetic acid (1.85 g) and ethanol (200 ml) was stirred for 30 min. To the mixture was added sodium cyanoborohydride (2.33 g) and the mixture was stirred for 24 h. After the mixture was concentrated in vacuo, the... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)O | null | 0.5 | CC(C)(C)C=O.COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N>C(C)O>COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1NCC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0bc1a7edcd584f338aa5705126d111be | CCOC(=O)C=CC(=O)N(CC(C)(C)C)c1ccc(Cl)cc1C(O)c1ccc(OCc2ccccc2)cc1OC>>CCOC(=O)C[C@H]1O[C@H](c2ccc(OCc3ccccc3)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | ClC1=CC(=C(C=C1)N(C(=O)C=CC(=O)OCC)CC(C)(C)C)C(C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)OCC)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][C:39]([N:33]([c:32]1[c:26]([CH:9]([OH:8])[c:10]2[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][c:23]2[O:24][CH3:25])[cH:27][c:28]([Cl:29])[cH:30][cH:31]1)[CH2:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:40]>>[CH3:1][CH2:2][O:3][C:4](=[O... | CCOC(=O)C=CC(=O)N(CC(C)(C)C)c1ccc(Cl)cc1C(O)c1ccc(OCc2ccccc2)cc1OC | CCOC(=O)C[C@H]1O[C@H](c2ccc(OCc3ccccc3)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 99d80846228eaef6ce19530e5c1c07fddd1659a06affdcd620742fe97a34da2c | 46ffa02bcab28066025af1fc8314e1e9a0b26f78b0ff559fab0e87808d67ee23 | O=C1CO[C@H](c2ccc(OCc3ccccc3)cc2)c2ccccc2N1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[C:10])-[c:11]:[c:12](-[CH;D3;+0:13](-[OH;D1;+0:14])-[c:15](:[c:16]):[c:17]):[c:18]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[C@H;D3;+0:6]1-[O;H0;D2;+0:14]-[C@H;D3;+0:13](-[c:15](:[c:16]):[c:17])-[c:12](:[c:18]):[c:11]-[#7:9](... | 81.7 | [{"value": 81.7, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)OCC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a mixture of ethyl 3-[N-[4-chloro-2-(4-benzyloxy-α-hydroxy-2-methoxybenzyl)-phenyl]-N-neopentylcarbamoyl]acrylate (12 g), potassium carbonate (5.9 g) and ethanol (150 ml) was stirred for 24 h. After the mixture was concentrated in vacuo, the residue was diluted with water (200 ml) and extracted with ethyl acetate (2... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester.Ether | null | c1ccc2c(c1)COCC[NH]2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)COCC[NH]2 | null | C(C)O | null | 24 | CCOC(=O)C=CC(=O)N(CC(C)(C)C)c1ccc(Cl)cc1C(O)c1ccc(OCc2ccccc2)cc1OC>C(C)O>CCOC(=O)C[C@H]1O[C@H](c2ccc(OCc3ccccc3)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-077138807f014cf5b7519e136115f695 | CCI.CCOC(=O)C[C@H]1O[C@H](c2ccc(O)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O>>CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)OCC)C2=C(C=C(C=C2)O)OC)C1.C(C)I.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)OCC)C2=C(C=C(C=C2)OCC)OC)C1 | I[CH2:15][CH3:16].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]1[O:8][C@H:9]([c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:17][c:18]2[O:19][CH3:20])[c:21]2[cH:22][c:23]([Cl:24])[cH:25][cH:26][c:27]2[N:28]([CH2:29][C:30]([CH3:31])([CH3:32])[CH3:33])[C:34]1=[O:35]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C@H:7]1[O:8][C@H:9]([... | CCI.CCOC(=O)C[C@H]1O[C@H](c2ccc(O)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 3 | HOUR | A mixture of ethyl trans-7-chloro-5-(4-hydroxy-2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.25 g), ethyl iodide (0.06 ml), potassium carbonate (0.15 g) and N,N-dimethylformamide (200 ml) was stirred for 3 h. The mixture was diluted with water (50 ml) and extracted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | HI | O | null | 3 | CCI.CCOC(=O)C[C@H]1O[C@H](c2ccc(O)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O>O>CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-272d2516523f4474ab76d5851158b256 | CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O>>CCOc1ccc([C@H]2O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c3ccc(Cl)cc32)c(OC)c1 | C(C)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)OCC)OC.C([O-])([O-])=O.[K+].[K+].CO.O1CCCC1>>C(C)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)O)OC | CC[O:14][C:12]([CH2:11][C@H:10]1[O:9][C@H:8]([c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:33][c:30]2[O:31][CH3:32])[c:29]2[c:23]([cH:24][cH:25][c:26]([Cl:27])[cH:28]2)[N:17]([CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:15]1=[O:16])=[O:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C@H:8]2[O:9][C@H:10]([CH2:11][C:... | CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O | CCOc1ccc([C@H]2O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c3ccc(Cl)cc32)c(OC)c1 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CO[C@H](c2ccccc2)c2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A mixture of ethyl trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.18 g), potassium carbonate (0.10 g), methanol (10 ml), tetrahydrofuran (10 ml) and water (5 ml) was refluxed for 1.5 h. The resulting mixture was concentrated in vacuo, acidified with 1N hy... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)COCC[NH]2 | Other | O | null | null | CCOC(=O)C[C@H]1O[C@H](c2ccc(OCC)cc2OC)c2cc(Cl)ccc2N(CC(C)(C)C)C1=O>O>CCOc1ccc([C@H]2O[C@H](CC(=O)O)C(=O)N(CC(C)(C)C)c3ccc(Cl)cc32)c(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-519d1ed0c254438c8f86070fac54bfc1 | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F>>N#Cc1n[nH]c(N)c1SC(F)(F)F | C(#N)C1=NNC(=C1SC(F)(F)F)NC(C(F)(F)F)=O.[OH-].[NH4+].Cl>>C(#N)C1=NNC(=C1SC(F)(F)F)N | O=C(C(F)(F)F)[NH:7][c:6]1[nH:5][n:4][c:3]([C:2]#[N:1])[c:8]1[S:9][C:10]([F:11])([F:12])[F:13]>>[N:1]#[C:2][c:3]1[n:4][nH:5][c:6]([NH2:7])[c:8]1[S:9][C:10]([F:11])([F:12])[F:13] | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F | N#Cc1n[nH]c(N)c1SC(F)(F)F | null | null | CO.C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1cn[nH]c1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1>>[NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5]:[c:6]:1 | 87.6 | [{"value": 87.6, "product": "C(#N)C1=NNC(=C1SC(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | The product of Step E (55 g, 181 mmoles) was dissolved in methanol. 100 ml of ammonium hydroxide were added, the solution was refluxed for 3 hours and then stirred at room temperature for 15 hours. The methanolic solution was brought to pH7 using concentrated aqueous hydrochloric acid and diluted with ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1cn[nH]c1 | Other | CO.C(C)(=O)OCC | null | 15 | N#Cc1n[nH]c(NC(=O)C(F)(F)F)c1SC(F)(F)F>CO.C(C)(=O)OCC>N#Cc1n[nH]c(N)c1SC(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-473dec5ce90f484b83b1114372213153 | CCOC(=S)CC.CCOc1ccc(N)cc1>>CCOc1ccc2c(c1)CC(=O)N2 | C(C)N(CC)CC.C(C)OC1=CC=C(N)C=C1.CCC(=S)OCC.ClCl>>C(C)OC=1C=C2CC(NC2=CC1)=O | CC[O:12][C:11](=S)[CH2:10]C.[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:13])[cH:8][cH:9]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][C:11](=[O:12])[NH:13]2 | CCOC(=S)CC.CCOc1ccc(N)cc1 | CCOc1ccc2c(c1)CC(=O)N2 | null | null | C(Cl)Cl.O | Acylation | OtherReaction | a2a74f97cf7b487de6b223d2dc53dd6aa5e8f47b1840b7ace2677d5fc1e0131e | 7ad4bf7309306986e6cc349c7bc628011e853b7eb203cf188a8de27e64e52865 | O=C1Cc2ccccc2N1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=S)-[CH2;D2;+0:3]-C.[NH2;D1;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:5](:[c:6])-[NH;D2;+0:4]-1 | null | [] | null | null | 5 | MINUTE | 23.6 g of ethyl methylthioacetate in 60 ml of DCM are added to a solution, cooled to about -70° C., of 12.5 g of chlorine in 400 ml of DCM. After stirring for 5 minutes at the same temperature, a solution of 4-ethoxyaniline (48.3 g) in 120 ml of DCM is added. The mixture is stirred for one hour at about -70° C., 39.3 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Thiocarbonyl | Secondary amide | c1ccccc1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | C(Cl)Cl.O | null | 0.083333 | CCOC(=S)CC.CCOc1ccc(N)cc1>C(Cl)Cl.O>CCOc1ccc2c(c1)CC(=O)N2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ae97b39090304851b44154a73304af2d | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1>>O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 | ClC=1C=C2C(C(NC2=CC1)=O)=O.[Cl-].[Al+3].[Cl-].[Cl-].C1=CC=CC=C1>>ClC=1C=C2C(C(NC2=CC1)=O)(C1=CC=CC=C1)C1=CC=CC=C1 | O=[C:11]1[C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]21.[cH:12]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11]1([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1 | O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | dba4da327e7262cdcc29a8207cdf08b13f4d7581c1f62dc179c070e46d100989 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | O=C1Nc2ccccc2C1(c1ccccc1)c1ccccc1 | O=[C;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]:[c:6]-1:[c:7].[c:8]1:[c:9]:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:1>>[O;D1;H0:3]=[C:2]1-[#7:4]-[c:5]:[c:6](:[c:7])-[C;H0;D4;+0:1]-1(-[c:14]1:[cH;D2;+0:13]:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1)-[c;H0;D3;+0:12](:[c:15]:[c:16]):[c:17]:[c:18] | null | [] | null | null | null | null | This compound is prepared by the method described in Helv. Chim. Acta, 1946, 29, 415-431, by the reaction of benzene with 5-chloroisatin in the presence of aluminum chloride. M.p.=281° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound is prepared by the method | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCN2.c1ccccc1.c1ccccc1 | null | null | null | null | O=C1Nc2ccc(Cl)cc2C1=O.c1ccccc1>>O=C1Nc2ccc(Cl)cc2C1(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-82e1641a8537406cb79348a3cda038e6 | CCO.O=C(Cl)c1ccc(F)cc1>>CCOC(=O)c1ccc(F)cc1 | FC1=CC=C(C(=O)Cl)C=C1.C(C)O>>FC1=CC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1 | CCO.O=C(Cl)c1ccc(F)cc1 | CCOC(=O)c1ccc(F)cc1 | null | null | null | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture containing 35 g of 4-fluorobenzoyl chloride in 50 ml of 100% ethanol is refluxed for 15 minutes. 35 g of the ethyl 4-fluorobenzoate obtained are mixed with 22 g of imidazole and 61 g of potassium carbonate in 35 ml of DMSO. The mixture is heated for 18 hours at 120°-130° C. and 500 ml of iced water are then a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | null | null | null | CCO.O=C(Cl)c1ccc(F)cc1>>CCOC(=O)c1ccc(F)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8a2792e0ff14486c99220c32eed53e32 | O=C(O)CCCCC/C=C/CCCCCCCCO>>O=C1CCCCC/C=C\CCCCCCCCO1 | [OH-].[K+].C(CCCCO)CCC/C=C/CCCCCC(=O)O>>C1CCCCOC(=O)CCCCC/C=C\CCC1 | O=[C:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]1 | O=C(O)CCCCC/C=C/CCCCCCCCO | O=C1CCCCC/C=C\CCCCCCCCO1 | null | null | null | Miscellaneous | OtherReaction | d008debc606a42ffabf18996f7a12af8bf05125aaa7394ef1bb59bbb42455bcf | aace2e495d6e25bd670c830d3d27c657c78d937f84a32acc2423ead6678aa7cd | O=C1CCCCC/C=C\CCCCCCCCO1 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4] | null | [] | 180 | CELSIUS | null | null | Alternatively, the ester may be saponified to obtain the ambrettolic acid. The crude ambrettolic acid obtained by saponification was transformed into its glycerine polyester by heating under a slight vacuum at 180° C. for a period of 4 to 5 hours. The resulting polyesters were then depolymerized in the presence of a mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | C1=C\CCCCCCOCCCCCCCC/1 | C1=C\CCCCCCOCCCCCCCC/1 | HO- | null | 180 | null | O=C(O)CCCCC/C=C/CCCCCCCCO>>O=C1CCCCC/C=C\CCCCCCCCO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-99c88818328441daaf858d5d4bfeac19 | Cc1ccc(O)cn1.OO>>O=Cc1ccc(O)cn1 | Cl.OC=1C=CC(=NC1)C.OO.C([O-])([O-])=O.[Na+].[Na+].OO>>C(=O)C1=NC=C(C=C1)O | [CH3:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][n:9]1.O[OH:1]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][n:9]1 | Cc1ccc(O)cn1.OO | O=Cc1ccc(O)cn1 | null | null | C(C)(=O)O.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 7e1870c03b602e61df02a0c51095711e42253be2dbc5d565388a68551b4e83d3 | 9ad8303996fc77b37f471d05459c96affefccf7f394ffdf3b2e3c59a7a7dabb7 | c1ccncc1 | O-[OH;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 32 | [{"value": 32.0, "product": "C(=O)C1=NC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 3 | HOUR | To a stirred solution of 21.8 g of 5-hydroxy-2-picoline (0.2 mol) in 200 mL of glacial acetic acid was added 18 mL of 30% hydrogen peroxide (0.159 mol) in one portion. The mixture was heated in an oil bath at 80°-85° C. with stirring for 3 h. Then another 18 mL of hydrogen peroxide was added and the mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aldehyde | null | null | c1ccncc1 | HO- | C(C)(=O)O.N1=CC=CC=C1 | 120 | 3 | Cc1ccc(O)cn1.OO>C(C)(=O)O.N1=CC=CC=C1>O=Cc1ccc(O)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc420121d02f4dbbbc0f71fe5ec58124 | NNC(=O)Nc1ccccc1.O=Cc1ncccc1O>>O=C(NN=Cc1ncccc1O)Nc1ccccc1 | C1(=CC=CC=C1)NC(NN)=O.OC=1C(=NC=CC1)C=O>>OC=1C(=NC=CC1)C=NNC(=O)NC1=CC=CC=C1 | [O:1]=[C:2]([NH:3][NH2:4])[NH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.O=[CH:5][c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[OH:12]>>[O:1]=[C:2]([NH:3][N:4]=[CH:5][c:6]1[n:7][cH:8][cH:9][cH:10][c:11]1[OH:12])[NH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | NNC(=O)Nc1ccccc1.O=Cc1ncccc1O | O=C(NN=Cc1ncccc1O)Nc1ccccc1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d96921e54ea5a9886efe70451a5b6747abf630b51f5287f460084f46e96e1d54 | 24296832c6ee4d0b5568b975c5df51fd66c85a5bdc41f3275d634cea600f4109 | O=C(NN=Cc1ccccn1)Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[NH2;D1;+0:10]>>[#7:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[N;H0;D2;+0:10]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 99 | [{"value": 99.0, "product": "OC=1C(=NC=CC1)C=NNC(=O)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.2, "product": "OC=1C(=NC=CC1)C=NNC(=O)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 4-Phenyl semicarbazide (4.91 g, 33 mmol) was added to a suspension of 3-hydroxy-2-pyridine carbaldehyde (4.0 g, 33 mmol) in a mixture of ethanol water (30 mL:40 mL). The reaction mixture was stirred at room temperature for 3 h and the yellow product was collected by filtration. The yellow precipitate was washed with Et... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Hydrazone amide | null | null | c1ccncc1.c1ccccc1 | HO- | O.C(C)O | null | 3 | NNC(=O)Nc1ccccc1.O=Cc1ncccc1O>O.C(C)O>O=C(NN=Cc1ncccc1O)Nc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0871baecec9c4c268d5490bd44c95dc8 | CN(C)C(=O)c1cc(O)c(C=NNC(N)=O)[n+](C)c1>>CN(C)C(=O)c1c(O)cc[n+](C)c1C=NNC(N)=O | [Cl-].NC(=O)NN=CC1=[N+](C=C(C=C1O)C(N(C)C)=O)C.C(=O)C1=NC=C(C=C1)O.[Cl-].NC(=O)NN=CC1=[N+](C(=CC(=C1C(N(C)C)=O)O)C)C.OC=1C(=NC=CC1)C=O.OC=1C(=NC=CC1)C=O.OC=1C(=NC(=CC1)C)C=O>>[Cl-].NC(=O)NN=CC1=[N+](C=CC(=C1C(N(C)C)=O)O)C | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:9][c:7]([OH:8])[c:13]([CH:14]=[N:15][NH:16][C:17]([NH2:18])=[O:19])[n+:11]([CH3:12])[cH:10]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[c:7]([OH:8])[cH:9][cH:10][n+:11]([CH3:12])[c:13]1[CH:14]=[N:15][NH:16][C:17]([NH2:18])=[O:19] | CN(C)C(=O)c1cc(O)c(C=NNC(N)=O)[n+](C)c1 | CN(C)C(=O)c1c(O)cc[n+](C)c1C=NNC(N)=O | null | null | null | Miscellaneous | OtherReaction | d9b18d697b4d4db9243a5c6f5ddeb225e493174381e1c97208f65b6bb99201d8 | 1208f5f10c31f751480b67448a35dc747ab74c6e532be327ba8985b70d351e81 | c1cc[nH+]cc1 | [C;D1;H3:1]-[#7;a;+:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#7:7](-[C;D1;H3:8])-[C;D1;H3:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11](-[O;D1;H1:12]):[c;H0;D3;+0:13]:1-[C:14]=[#7:15]-[#7:16]-[C:17]=[O;D1;H0:18]>>[C;D1;H3:1]-[#7;a;+:2]1:[cH;D2;+0:3]:[cH;D2;+0:10]:[c;H0;D3;+0:11](-[O;D1;H1:12]):[c;H0;D3;+0:4](-[C:5](=[... | null | [] | null | null | null | null | 2-[[(Aminocarbonyl)hydrazono]methyl]-3-(N,N-dimethylcarbamoyl)hydroxy-1,6-dimethyl pyridinium chloride can be made by the same procedure replacing 3-hydroxy-2-pyridine aldehyde in the above example with 3-hydroxy-6-methyl-2-pyridine aldehyde. 2-[[(Aminocarbonyl)hydrazono] methyl] -5-(N ,N-dimethylcarbamoyl)hydroxy-1-me... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic alcohol | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | null | null | null | CN(C)C(=O)c1cc(O)c(C=NNC(N)=O)[n+](C)c1>>CN(C)C(=O)c1c(O)cc[n+](C)c1C=NNC(N)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0570825de3de42f284cb61b4bb3699df | Cc1ccc(O)c(CO)n1>>Cc1ccc(O)c(C=O)n1 | OC=1C(=NC(=CC1)C)CO.[Se](=O)=O>>OC=1C(=NC(=CC1)C)C=O | [CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([CH2:8][OH:9])[n:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[n:10]1 | Cc1ccc(O)c(CO)n1 | Cc1ccc(O)c(C=O)n1 | null | null | C(C)O.O1CCOCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccncc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 57.3 | [{"value": 56.0, "product": "OC=1C(=NC(=CC1)C)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "OC=1C(=NC(=CC1)C)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Hydroxy-6-methyl-2-pyridine methanol (20.0 g, 0.14 mol) and selenium dioxide(8.0 g, 72 mmol) were dissolved in 140 mL of 1,4-dioxane and 280 mL of absolute ethanol. The resulting mixture was heated at 80°-85° C. for 12 h. The selenium precipitate was removed by filtration and the filtrate was concentrated to dryness ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccncc1 | null | C(C)O.O1CCOCC1 | null | null | Cc1ccc(O)c(CO)n1>C(C)O.O1CCOCC1>Cc1ccc(O)c(C=O)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-45cdb5a182c44dd2b68a1aad0b23d6f4 | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1ccccc1CO2>>CC(O)(C(=O)Nc1cccc2c1C(=O)c1ccccc1CO2)C(F)(F)F | FC(C(C(=O)O)(C)O)(F)F.S(=O)(Cl)Cl.NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3>>FC(C(C(=O)NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3)(C)O)(F)F | O[C:4]([C:2]([CH3:1])([OH:3])[C:23]([F:24])([F:25])[F:26])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[CH2:21][O:22]2>>[CH3:1][C:2]([OH:3])([C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]... | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1ccccc1CO2 | CC(O)(C(=O)Nc1cccc2c1C(=O)c1ccccc1CO2)C(F)(F)F | null | null | CC(=O)N(C)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2COc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[O;D1;H1:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15]>>[C;D1;H3:4]-[C:3](-[O;D1;H1:5])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:... | 30 | [{"value": 30.0, "product": "FC(C(C(=O)NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3)(C)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | In dimethylacetamide (3 ml) was dissolved 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid (0.17 g, 1.1 mmol), and thionyl chloride (80 μl, 1.1 mmol) was added thereto at -15° C., followed by stirring at -15 to -5° C. for one hour. To this reaction mixture was added 1-amino-6,11-dihydrodibenz[b,e]oxepin-11-one obtained... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)COc1ccccc1C2 | HO- | CC(=O)N(C)C.C(C)(=O)OCC | -10 | 1 | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1ccccc1CO2>CC(=O)N(C)C.C(C)(=O)OCC>CC(O)(C(=O)Nc1cccc2c1C(=O)c1ccccc1CO2)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c07975784c3e442c8e7370feccd7700d | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2>>CC(O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F | FC(C(C(=O)O)(C)O)(F)F.S(=O)(Cl)Cl.NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O>>FC(C(C(=O)NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O)(C)O)(F)F | O[C:4]([C:2]([CH3:1])([OH:3])[C:22]([F:23])([F:24])[F:25])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[s:16][cH:17][cH:18][c:19]1[CH2:20][O:21]2>>[CH3:1][C:2]([OH:3])([C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[s:16][cH:17][cH:18][c:19]1[CH2:20][O:21]2... | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2 | CC(O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F | null | null | CC(=O)N(C)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2OCc2ccsc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[O;D1;H1:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15]>>[C;D1;H3:4]-[C:3](-[O;D1;H1:5])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:... | 89 | [{"value": 89.0, "product": "FC(C(C(=O)NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O)(C)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | In dimethylacetamide (3 ml) was dissolved 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid (0.32 g, 2.03 mmol), and thionyl chloride (148 μl, 2.03 mmol) was added thereto at -15° C., followed by stirring at -15° to -5° C. for one hour. To this reaction mixture was added 9-amino-4,10-dihydrothieno[3,2-c][1]benzoxepin-10... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)Cc1sccc1CO2 | HO- | CC(=O)N(C)C.C(C)(=O)OCC | null | 1 | CC(O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2>CC(=O)N(C)C.C(C)(=O)OCC>CC(O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6484a284b0aa46eaae0c0af132625719 | C[C@](O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2>>C[C@](O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F | NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O.FC([C@@](C(=O)O)(C)O)(F)F>>FC([C@@](C(=O)NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O)(C)O)(F)F | O[C:4]([C@:2]([CH3:1])([OH:3])[C:22]([F:23])([F:24])[F:25])=[O:5].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[s:16][cH:17][cH:18][c:19]1[CH2:20][O:21]2>>[CH3:1][C@:2]([OH:3])([C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[C:13](=[O:14])[c:15]1[s:16][cH:17][cH:18][c:19]1[CH2:20][O:21... | C[C@](O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2 | C[C@](O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2OCc2ccsc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[O;D1;H1:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15]>>[C;D1;H3:4]-[C:3](-[O;D1;H1:5])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-[C:14]=[O;D1;H0:15])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:... | 35 | [{"value": 35.0, "product": "FC([C@@](C(=O)NC1=CC=CC2=C1C(C1=C(CO2)C=CS1)=O)(C)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Substantially the same procedure as in Example 1 was repeated using 9-amino-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one obtained in Reference Example 11 (0.840 g, 3.63 mmol) and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid obtained in Reference Example 27 (1.14 g, 7.26 mmol) to give Compound 33 (0.47 g, 35%).... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)Cc1sccc1CO2 | HO- | null | null | null | C[C@](O)(C(=O)O)C(F)(F)F.Nc1cccc2c1C(=O)c1sccc1CO2>>C[C@](O)(C(=O)Nc1cccc2c1C(=O)c1sccc1CO2)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08ed9fc621264a2f9632e16668245bd7 | CC(=O)Nc1cccc(O)c1.COC(=O)c1ccccc1CBr>>COC(=O)c1ccccc1COc1cccc(NC(C)=O)c1 | C([O-])(O)=O.[Na+].BrCC1=C(C(=O)OC)C=CC=C1.C(C)(=O)NC=1C=C(C=CC1)O.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(=O)NC=1C=C(OCC2=C(C(=O)OC)C=CC=C2)C=CC1 | [OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]([NH:18][C:19]([CH3:20])=[O:21])[cH:22]1.Br[CH2:11][c:10]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]([NH:18][C:19]([CH3:20])=[O:21])[cH:22]1 | CC(=O)Nc1cccc(O)c1.COC(=O)c1ccccc1CBr | COC(=O)c1ccccc1COc1cccc(NC(C)=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:3] | 61.2 | [{"value": 61.0, "product": "C(C)(=O)NC=1C=C(OCC2=C(C(=O)OC)C=CC=C2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "C(C)(=O)NC=1C=C(OCC2=C(C(=O)OC)C=CC=C2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-acetamidophenol (1.0 g, 6.6 mmol) in dimethylformamide (10 ml) was added cesium carbonate (1.3 g, 3.9 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 2-bromomethylbenzoate (1.8 g, 7.9 mmol), and the mixture was stirred overnight at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | CC(=O)Nc1cccc(O)c1.COC(=O)c1ccccc1CBr>CN(C=O)C>COC(=O)c1ccccc1COc1cccc(NC(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cca8c52f7ba34625b95aa6d245498aa5 | CC(=O)Nc1cccc2c1C(=O)c1ccccc1CO2>>Nc1cccc2c1C(=O)c1ccccc1CO2 | C(C)(=O)NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3.C([O-])(O)=O.[Na+]>>NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[CH2:16][O:17]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[CH2:16][O:17]2 | CC(=O)Nc1cccc2c1C(=O)c1ccccc1CO2 | Nc1cccc2c1C(=O)c1ccccc1CO2 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C1c2ccccc2COc2ccccc21 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]-[C:5]=[O;D1;H0:6] | 81 | [{"value": 81.0, "product": "NC1=CC=CC=2OCC3=C(C(C21)=O)C=CC=C3", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In concentrated hydrochloric acid (10 ml), 1-acetamido-6,11-dihydrodibenz[b,e]oxepin-11-one obtained in Reference Example 3(0.25 g, 0.94 mmol) was heated under reflux for 2 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate (25 ml). ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)COc1ccccc1C2 | HO- | Cl | null | null | CC(=O)Nc1cccc2c1C(=O)c1ccccc1CO2>Cl>Nc1cccc2c1C(=O)c1ccccc1CO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e2a46196bcf14ceb891b2c6cabfdc4c1 | CC(C)(C)O.O=C(O)c1ccc2c(c1)C(=O)c1ccccc1CO2.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)Nc1ccc2c(c1)C(=O)c1ccccc1CO2 | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C(=O)(O)C1=CC2=C(OCC3=C(C2=O)C=CC=C3)C=C1.C(C)N(CC)CC.C(C)(C)(C)O.C([O-])(O)=O.[Na+]>>C(C)(C)(C)OC(=O)NC1=CC2=C(OCC3=C(C2=O)C=CC=C3)C=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].O[C:6](=[O:7])[c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[CH2:23][O:24]2.[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14]1)[C:15](=[O:16])[... | CC(C)(C)O.O=C(O)c1ccc2c(c1)C(=O)c1ccccc1CO2.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)Nc1ccc2c(c1)C(=O)c1ccccc1CO2 | null | null | null | Protection | OtherReaction | efa4d9f6166f8f9c040ea327d55dafea4e6b153c801300b92bbe2be4bea80c34 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | O=C1c2ccccc2COc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]-[C:8]=[O;D1;H0:9].O=P(-[N;H0;D2;+0:10]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[OH;D1;+0:15]>>[C;D1;H3:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[O;H0;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2... | 41 | [{"value": 41.0, "product": "C(C)(C)(C)OC(=O)NC1=CC2=C(OCC3=C(C2=O)C=CC=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To tert-butanol (8.3 ml) were added diphenylphosphoryl azide (1.1 ml, 5.11 mmol), 2-carboxy-6,11-dihydrodibenz-[b,e]oxepin-11-one (Japanese Published Unexamined Patent Application No. 91040/90) (1.0 g, 3.9 mmol), and triethylamine (0.71 ml, 5.11 mmol) under an atmosphere of argon gas, followed by heating under reflux f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | c1ccc2c(c1)COc1ccccc1C2.c1ccccc1.c1ccccc1 | c1ccc2c(c1)COc1ccccc1C2 | c1ccc2c(c1)COc1ccccc1C2 | HO- | null | null | null | CC(C)(C)O.O=C(O)c1ccc2c(c1)C(=O)c1ccccc1CO2.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)Nc1ccc2c(c1)C(=O)c1ccccc1CO2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29f57c2dee5f49d5a4d2fd451c9a7d4b | CC(=O)Nc1cccc(O)c1.COC(=O)c1sccc1CBr>>COC(=O)c1sccc1COc1cccc(NC(C)=O)c1 | C(C)(=O)NC=1C=C(C=CC1)O.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+].BrCC1=C(SC=C1)C(=O)OC>>C(C)(=O)NC=1C=C(OCC2=C(SC=C2)C(=O)OC)C=CC1 | [OH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[cH:21]1.Br[CH2:10][c:9]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[s:6][cH:7][cH:8]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[cH:21]1 | CC(=O)Nc1cccc(O)c1.COC(=O)c1sccc1CBr | COC(=O)c1sccc1COc1cccc(NC(C)=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccsc2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1-[C:7](-[#8:8])=[O;D1;H0:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#8:8]-[C:7](=[O;D1;H0:9])-[c:6]1:[#16;a:5]:[c:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 75.1 | [{"value": 75.0, "product": "C(C)(=O)NC=1C=C(OCC2=C(SC=C2)C(=O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C(C)(=O)NC=1C=C(OCC2=C(SC=C2)C(=O)OC)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-acetamidophenol (4.79 g, 31.7 mmol) in dimethylformamide (50 ml) was added cesium carbonate (5.67 g, 17.4 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 3-bromomethyl-2-thiophenecarboxylate (8.94 g, 38.0 mmol), and the mixture was stirred ove... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccsc1.c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | CC(=O)Nc1cccc(O)c1.COC(=O)c1sccc1CBr>CN(C=O)C>COC(=O)c1sccc1COc1cccc(NC(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fe0aa9a207b24d63bb0ea46174e05e6e | CC(=O)Nc1ccc2c(c1)OCc1ccsc1C2=O>>Nc1ccc2c(c1)OCc1ccsc1C2=O | C(C)(=O)NC1=CC2=C(C(C3=C(CO2)C=CS3)=O)C=C1.C([O-])(O)=O.[Na+]>>NC1=CC2=C(C(C3=C(CO2)C=CS3)=O)C=C1 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][c:10]1[cH:11][cH:12][s:13][c:14]1[C:15]2=[O:16]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[O:8][CH2:9][c:10]1[cH:11][cH:12][s:13][c:14]1[C:15]2=[O:16] | CC(=O)Nc1ccc2c(c1)OCc1ccsc1C2=O | Nc1ccc2c(c1)OCc1ccsc1C2=O | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C1c2ccccc2OCc2ccsc21 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 78 | [{"value": 78.0, "product": "NC1=CC2=C(C(C3=C(CO2)C=CS3)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In concentrated hydrochloric acid (15 ml), 7-acetamido-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one obtained in Reference Example 9(0.41 g, 1.51 mmol) was heated under reflux for 2 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)Cc1sccc1CO2 | HO- | Cl | null | null | CC(=O)Nc1ccc2c(c1)OCc1ccsc1C2=O>Cl>Nc1ccc2c(c1)OCc1ccsc1C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f5ea82e1d125454e8bce94b7fc33917f | COC(=O)c1sccc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COC(=O)c1sccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | BrCC1=C(SC=C1)C(=O)OC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].COC(=O)C=1SC=CC1C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[CH2:10][Br:30].[P:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[CH2:10][P+:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:... | COC(=O)c1sccc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COC(=O)c1sccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc([P+](Cc2ccsc2)(c2ccccc2)c2ccccc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[c:8]:1-[CH2;D2;+0:9]-[Br;H0;D1;+0:10].[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[c:8]:1-[CH2;D2;+0:9]-[P+;H0;D4:13](-[c:12](:[c:11]):[c:20])(-[c:14](:[c:15]):[c:... | 70.4 | [{"value": 70.4, "product": "[Br-].COC(=O)C=1SC=CC1C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.4, "product": "[Br-].COC(=O)C=1SC=CC1C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of methyl 3-bromomethyl-2-thiophenecarboxylate (7.31 g, 31.1 mmol) in toluene (90 ml) was added triphenylphosphine (7.92 g, 30.2 mmol) under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 2 days. The precipitated crystals were collected by filtration a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccsc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | 48 | COC(=O)c1sccc1CBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>COC(=O)c1sccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-26cdb6c868e440d6955dd972d622308f | CC(C)(C)C(=O)Nc1ccc2c(c1)CCc1ccsc1C2=O>>Nc1ccc2c(c1)CCc1ccsc1C2=O | CC(C(=O)NC=1C=CC2=C(CCC3=C(SC=C3)C2=O)C1)(C)C.Cl>>NC=1C=CC2=C(CCC3=C(SC=C3)C2=O)C1 | CC(C)(C)C(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][c:10]1[cH:11][cH:12][s:13][c:14]1[C:15]2=[O:16]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[CH2:8][CH2:9][c:10]1[cH:11][cH:12][s:13][c:14]1[C:15]2=[O:16] | CC(C)(C)C(=O)Nc1ccc2c(c1)CCc1ccsc1C2=O | Nc1ccc2c(c1)CCc1ccsc1C2=O | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=C1c2ccccc2CCc2ccsc21 | C-C(-C)(-C)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98.8 | [{"value": 98.8, "product": "NC=1C=CC2=C(CCC3=C(SC=C3)C2=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In ethanol (10 ml) was suspended 7-trimethylacetamido-4,5-dihydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophen-10-one obtained in Reference Example 17 (0.40 g, 1.28 mmol), and 6N hydrochloric acid (5 ml) was added thereto, followed by heating under reflux for 6 hours. After the reaction was completed, ethanol was distilled ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2c(c1)CCc1ccsc1C2 | HO- | C(C)O | null | null | CC(C)(C)C(=O)Nc1ccc2c(c1)CCc1ccsc1C2=O>C(C)O>Nc1ccc2c(c1)CCc1ccsc1C2=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61670ca8f3ee46f6b6f8d3342a1692cf | CC(=O)OC(C)=O.COC(=O)c1sccc1/C=C\c1cccc([N+](=O)[O-])c1>>COC(=O)c1sccc1/C=C\c1cccc(NC(C)=O)c1 | [N+](=O)([O-])C=1C=C(\C=C/C2=C(SC=C2)C(=O)OC)C=CC1.C(C)(=O)OC(C)=O>>C(C)(=O)NC=1C=C(\C=C/C2=C(SC=C2)C(=O)OC)C=CC1 | CC(=O)O[C:18]([CH3:19])=[O:20].O=[N+:17]([O-])[c:16]1[cH:15][cH:14][cH:13][c:12](/[CH:11]=[CH:10]\[c:9]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[s:6][cH:7][cH:8]2)[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1/[CH:10]=[CH:11]\[c:12]1[cH:13][cH:14][cH:15][c:16]([NH:17][C:18]([CH3:19])=[O:20])[cH:21]1 | CC(=O)OC(C)=O.COC(=O)c1sccc1/C=C\c1cccc([N+](=O)[O-])c1 | COC(=O)c1sccc1/C=C\c1cccc(NC(C)=O)c1 | null | null | null | Acylation | OtherReaction | e42a085282c3a07a051d4fb8d2fca17494e60eb1125ef7dc723a241b4f07d443 | f3ba867686f6df7397dc4715602a55649ceb24345966ae3ca69ac9bcc38b3956 | C(=C\c1ccsc1)\c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O=[N+;H0;D3:4](-[O-])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 91.3 | [{"value": 91.3, "product": "C(C)(=O)NC=1C=C(\\C=C/C2=C(SC=C2)C(=O)OC)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Substantially the same procedure as in Reference Example 14 was repeated using methyl (Z)-3-(3-nitrostyryl)-2-thiophenecarboxylate obtained in Reference Example 13 (3.51 g, 12.1 mmol), and also using acetic anhydride (3.43 ml, 36.3 mmol) instead of trimethylacetyl chloride, to give methyl (Z)-3-(3-acetamidostyryl)-2-th... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Nitro group | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HO- | null | null | null | CC(=O)OC(C)=O.COC(=O)c1sccc1/C=C\c1cccc([N+](=O)[O-])c1>>COC(=O)c1sccc1/C=C\c1cccc(NC(C)=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-614e99a357bf4013896cb29a932850fc | C=C[Si](Cl)(Cl)Cl.CCCCc1ccccc1>>CCCCc1c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c1CC[Si](Cl)(Cl)Cl | CCCCC=1C=CC=CC1.C(=C)[Si](Cl)(Cl)Cl>>Cl[Si](Cl)(Cl)CCC1=C(C(=C(C(=C1CCCC)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl | [CH2:7]=[CH:8][Si:9]([Cl:10])([Cl:31])[Cl:40].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:14][cH:13][cH:29][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[c:6]([CH2:7][CH2:8][Si:9]([Cl:10])([Cl:11])[Cl:12])[c:13]([CH2:14][CH2:15][Si:16]([Cl:17])([Cl:18])[Cl:19])[c:20]([CH2:21][CH2:22][Si:23]([Cl:24])([Cl:25])[Cl:26])[c:27... | C=C[Si](Cl)(Cl)Cl.CCCCc1ccccc1 | CCCCc1c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c1CC[Si](Cl)(Cl)Cl | null | [Cl-].[Al+3].[Cl-].[Cl-] | null | Functional Group Addition | OtherReaction | 84472cee9e18c6d957af5cab860570501d7c23416d2cb3f223907c01d09026ed | f39406e104622d7b50ce34fddb8ff597d6739d136261cbef91e2d935503b02ea | c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[Si;H0;D4;+0:3](-[Cl;D1;H0:4])(-[Cl;H0;D1;+0:5])-[Cl;H0;D1;+0:6].[C:7]-[C:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:1>>[#14:15]-[C:16]-[CH2;D2;+0:13]-[c;H0;D3;+0:12]1:[c:17](-[C:18]):[c:19](-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[#14:20](-[Cl;D1;H0:21])(... | 102.2 | [{"value": 2.68, "product": "Cl[Si](Cl)(Cl)CCC1=C(C(=C(C(=C1CCCC)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 102.2, "product": "Cl[Si](Cl)(Cl)CCC1=C(C(=C(C(=C1CCCC)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl", "... | null | null | null | null | In the same apparatus and by the same procedure described in EXAMPLE 1, n-butylbenzene 0.86 g (6.40 mmol), vinyltrichlorosilane 5.17 g (32.00 mmol) and aluminum chloride 0.047 g (0.35 mmol) were reacted at 80° C. for 6 hours under a dry nitrogen atmosphere. Recrystallization of solid product from THF gave 6.16 g (yield... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl.Silyl protective group | Silyl protective group.Silyl protective group.Silyl protective group.Silyl protective group.Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cl-].[Al+3].[Cl-].[Cl-] | null | null | C=C[Si](Cl)(Cl)Cl.CCCCc1ccccc1>[Cl-].[Al+3].[Cl-].[Cl-]>CCCCc1c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c(CC[Si](Cl)(Cl)Cl)c1CC[Si](Cl)(Cl)Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2bfdd368208a447a97e7268f9780631d | N#CCO.O=C(O)CNCCO>>N#CCN(CCO)CC(=O)O | C(=O)(O)CNCCO.C(CO)#N>>C(=O)(O)CN(CC#N)CCO | O[CH2:3][C:2]#[N:1].[NH:4]([CH2:5][CH2:6][OH:7])[CH2:8][C:9](=[O:10])[OH:11]>>[N:1]#[C:2][CH2:3][N:4]([CH2:5][CH2:6][OH:7])[CH2:8][C:9](=[O:10])[OH:11] | N#CCO.O=C(O)CNCCO | N#CCN(CCO)CC(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f33a8d71b7dbaa463dcb87d1e5073e084c21a5fbc935ce82a22b6d65293f45d1 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | null | O-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10])-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3] | null | [] | null | null | null | null | The hydrolysis of (I) with base gives N-carboxymethylamino-2-ethanol (II). Compound (II) is then reacted with additional glycolonitrile to form N-carboxymethyl-N-cyanomethylamino-2-ethanol (III). The molar ratio of (II) to glycolonitrile is generally about 1:1. In the above reactions, hydrogen cyanide and formaldehyde ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | null | null | HO- | null | null | null | N#CCO.O=C(O)CNCCO>>N#CCN(CCO)CC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1fb9d43185c941be8156961fc5f37329 | CC(=O)[O-].O=C1NC(=O)C(=Nc2c(O)[nH]c(=O)[nH]c2=O)C(=O)N1>>O=C(O)CN(CCO)CC(=O)O | O.C1(=C(NC(=O)NC1=O)[O-])N=C2C(=O)NC(=O)NC2=O.[NH4+].C1(=C(NC(=O)NC1=O)O)N=C2C(=O)NC(=O)NC2=O.N.C(C)(=O)[O-].[Na+]>>C(CO)N(CC(=O)O)CC(=O)O | [O-:3][C:7]([CH3:6])=[O:8].O=C1NC(=[O:12])N[C:10](=[O:11])[C:9]1=[N:5][c:4]1c(=O)[nH]c(=O)[nH][c:2]1[OH:1]>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]([CH2:6][CH2:7][OH:8])[CH2:9][C:10](=[O:11])[OH:12] | CC(=O)[O-].O=C1NC(=O)C(=Nc2c(O)[nH]c(=O)[nH]c2=O)C(=O)N1 | O=C(O)CN(CCO)CC(=O)O | null | [Cu](Cl)Cl.[Cu] | null | Acylation | OtherReaction | 9872d15baae7386e238a714f7ab5cbb218e52e231f5916ade8e1ce865d9d8097 | b67b6a3dad4b38052a431f993a20517f031191df13ef18b037a0b3d7fb52a40d | null | O=C1-N-C(=[O;H0;D1;+0:1])-N-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C;H0;D3;+0:4]-1=[N;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[c;H0;D3;+0:7](-[OH;D1;+0:8]):[nH]:c(=O):[nH]:c:1=O.[CH3;D1;+0:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;H0;D1;+0:12]>>[O;D1;H0:3]=[C;H0;D3;+0:2](-[OH;D1;+0:1])-[CH2;D2;+0:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:6]-[C;H0;D3;+0:7]... | null | [] | null | null | null | null | Copper titration value is used to measure the extent of biodegradation of the chelating agents during the procedure. Titration is performed using ammonium purpurate (indicator for complexometric titration, commercially available from Aldrich Chemical Co., Inc. under the trade designation Murexide) as the indicator at a... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Substituted imine.Unsubstituted dicarboximide.Unsubstituted dicarboximide.Aromatic alcohol | Carboxylic acid.Carboxylic acid.Primary alcohol.Tertiary amine | C1CNCNC1.c1cncnc1 | null | null | Other | [Cu](Cl)Cl.[Cu] | null | null | CC(=O)[O-].O=C1NC(=O)C(=Nc2c(O)[nH]c(=O)[nH]c2=O)C(=O)N1>[Cu](Cl)Cl.[Cu]>O=C(O)CN(CCO)CC(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2ed9fcf75bbf4af59779e91e6297c949 | O=Cc1ccc(Cl)c(Cl)c1.[C-]#N>>N#CC(O)c1ccc(Cl)c(Cl)c1 | [C-]#N.[K+].ClC=1C=C(C=O)C=CC1Cl>>ClC=1C=C(C=CC1Cl)C(C#N)O | [CH:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH:3]([OH:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[c:10]([Cl:11])[cH:12]1 | O=Cc1ccc(Cl)c(Cl)c1.[C-]#N | N#CC(O)c1ccc(Cl)c(Cl)c1 | null | null | O | C-C Coupling | OtherReaction | 236cd56a92cf15f00d53dce2793575c5ed7c3ec173ebae4a1233543c0db3ac9d | 68cad6670aea61b0290696d3ddb6b46e4783b1c98982f76fc6b06e18aa6719c1 | c1ccccc1 | [C-;H0;D1:1]#[N;D1;H0:2].[O;H0;D1;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[CH;D3;+0:4](-[OH;D1;+0:3])-[c:5](:[c:6]):[c:7] | 100.5 | [{"value": 100.5, "product": "ClC=1C=C(C=CC1Cl)C(C#N)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 25 g of 3,4-dichlorobenzaldehyde are added to a solution of 32.5 g of Na2S2O5 in 100 ml of water and the mixture is heated at 40°-45° C. for 1 hour. After one night at room temperature, the reaction mixture is cooled and a solution of 19.5 g of KCN in 40 ml of water is added slowly. After stirring for 30 minutes at RT,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Nitrile.Secondary alcohol | null | null | c1ccccc1 | null | O | null | 0.5 | O=Cc1ccc(Cl)c(Cl)c1.[C-]#N>O>N#CC(O)c1ccc(Cl)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f2cd038ec84e4a03a81609c6e7029c63 | CNCCO.O=Cc1ccc(Cl)c(Cl)c1>>CN(CCO)C(C#N)c1ccc(Cl)c(Cl)c1 | ClC=1C=C(C=O)C=CC1Cl.C(#N)[Si](C)(C)C.CNCCO>>ClC=1C=C(C=CC1Cl)C(C#N)N(C)CCO | [CH3:1][NH:2][CH2:3][CH2:4][OH:5].O=[CH:6][c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1>>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[CH:6]([C:7]#[N:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1 | CNCCO.O=Cc1ccc(Cl)c(Cl)c1 | CN(CCO)C(C#N)c1ccc(Cl)c(Cl)c1 | null | [I-].[Zn+2].[I-] | CO | Heteroatom Alkylation and Arylation | OtherReaction | 65895308b5f67b585ddaa37f306e495e36985cf3c70224ad6c8aa7852833472c | 860dd54cb9329ea0e96b0cf04a71152378c5b5aab7f54c5a6ec1d7b1b585ad63 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[CH;D3;+0:1](-[C:9]#[N;D1;H0:10])-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | MINUTE | A mixture of 10 g of 3,4-dichlorobenzaldehyde and 9.5 ml of cyanotrimethylsilane is cooled in an ice bath, 0.01 g of zinc iodide is added and the mixture is stirred for 15 minutes at RT. A solution of 4.5 g of 2-(methylamino)ethanol in 50 ml of MeOH is then added and the reaction mixture is heated at 60° C. for 2 hours... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Nitrile.Tertiary amine | null | null | c1ccccc1 | HO- | [I-].[Zn+2].[I-].CO | null | 0.25 | CNCCO.O=Cc1ccc(Cl)c(Cl)c1>[I-].[Zn+2].[I-].CO>CN(CCO)C(C#N)c1ccc(Cl)c(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2ea15a5f5b1a44b1851d5776c77eecc6 | BrCc1ccccc1.C1CCOC1.CCOCC.N#CC1CCNCC1>>N#CC1(Cc2ccccc2)CCN(Cc2ccccc2)CC1 | C(C1=CC=CC=C1)Br.C(C)(C)[N-]C(C)C.[Li+].CCOCC.C(#N)C1CCNCC1.C1CCOC1>>C(C1=CC=CC=C1)N1CCC(CC1)(C#N)CC1=CC=CC=C1 | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.O1[CH2:7][CH2:6][CH2:5][CH2:10]1.C[CH2:4]O[CH2:8][CH3:9].[N:1]#[C:2][CH:3]1[CH2:11][CH2:12][NH:13][CH2:21][CH2:22]1>>[N:1]#[C:2][C:3]1([CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][C... | BrCc1ccccc1.C1CCOC1.CCOCC.N#CC1CCNCC1 | N#CC1(Cc2ccccc2)CCN(Cc2ccccc2)CC1 | null | null | C1CCCCC1 | Aromatic Heterocycle Formation | OtherReaction | d921e7522bf8776c1b967ac12f340ec2076285c08bd5b01e4d9da413aba257b9 | 6af2cbbe2292f8983804f000c10af2ef039866a3ad561dd0c7834578d992cd0f | c1ccc(CC2CCN(Cc3ccccc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[CH2;D2;+0:5]-O-[CH2;D2;+0:6]-[CH3;D1;+0:7].O1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1.[N;D1;H0:12]#[C:13]-[CH;D3;+0:14]1-[C:15]-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[N;D1;H0:12]#[C:13]-[C;H0;D4;+0:14]1(-[CH2;D2;+0:5]-[c;H0;D3;+0:9]2:[cH;D2;+0:8]:[cH;D2;+0:7]:... | null | [] | -50 | CELSIUS | 30 | MINUTE | A solution of 15 g of 4-cyanopiperidine in 250 ml of THF is cooled to -50° C., 190 ml of a 1.5M solution of lithium diisopropylamide in cyclohexane are added dropwise and the mixture is stirred for 30 minutes at -50° C. 34 ml of benzyl bromide are then added and the mixture is stirred for 3 hours after the temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Secondary amine | Tertiary amine | C1CCOC1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | C1CCCCC1 | -50 | 0.5 | BrCc1ccccc1.C1CCOC1.CCOCC.N#CC1CCNCC1>C1CCCCC1>N#CC1(Cc2ccccc2)CCN(Cc2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c7a3ca41e01d4efebb1bd0e9b36a8939 | CN(CC(OCCOC1CCCCO1)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C>>CN(CC(OCCO)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C | C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.CN(CC(OCCOC1OCCCC1)C1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C>>CN(CC(OCCO)C1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C | C1CCC([O:8][CH2:7][CH2:6][O:5][CH:4]([CH2:3][N:2]([CH3:1])[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:9]2[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]2)OC1>>[CH3:1][N:2]([CH2:3][CH:4]([O:5][CH2:6][CH2:7][OH:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1)[C:17](=[O:18])[O:19][C:20]([C... | CN(CC(OCCOC1CCCCO1)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C | CN(CC(OCCO)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C | null | null | CO | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccccc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3] | 100.9 | [{"value": 100.9, "product": "CN(CC(OCCO)C1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.56 g of pyridinium paratoluenesulfonate is added to a solution of 10 g of the compound obtained in EXAMPLE 8, step C), in 100 ml of MeOH and the reaction mixture is refluxed for 1 hour 15 minutes. It is concentrated under vacuum and the residue is taken up with ether, washed with water and with a buffer solution of p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1ccccc1 | HO- | CO | null | null | CN(CC(OCCOC1CCCCO1)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C>CO>CN(CC(OCCO)c1ccc(Cl)c(Cl)c1)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ef8b43a3b744c0190064171c4bf7822 | CCC(=O)Cl.CCCl.CCN(CC)CC.CN(CC(OCCN1CCC(O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1)C(=O)OCc1ccccc1.Cl>>CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.Cl.O | CCCl.C(C)N(CC)CC.C(CC)(=O)Cl.Cl.OC1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1>>O.Cl.C1(=CC=CC=C1)C1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)OC(CC)=O.C1(=CC=CC=C1)C1(CCN(CC1)CCOC(CN(C)C(=O)OCC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)OC(CC)=O.Cl | [CH3:43][CH2:44][C:45](=[O:46])[Cl:85].[CH3:1][CH2:2][Cl:81].[CH2:3]([N:21]([CH2:62][CH3:61])[CH2:68][CH3:69])[CH3:77].[O:4]=[C:65]([O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[N:63]([CH2:20][CH:19]([O:18][CH2:17][CH2:16][N:15]1[CH2:14][CH2:13][C:6]([OH:5])([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:42... | CCC(=O)Cl.CCCl.CCN(CC)CC.CN(CC(OCCN1CCC(O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1)C(=O)OCc1ccccc1.Cl | CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.Cl.O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 57073be6faedcc2d5bb06d1e6b9e9ffa3359ccf5259f4ee5b3dbebbb1e979158 | 9c547aac983238d738640532f12fa6284b51a1c211c6d3e928557125ecee582a | O=C(NCC(OCCN1CCC(c2ccccc2)CC1)c1ccccc1)OCc1ccccc1.O=C(NCC(OCCN1CCC(c2ccccc2)CC1)c1ccccc1)OCc1ccccc1 | [#8:1]-[C:2](-[c:3])-[CH2;D2;+0:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[O;H0;D2;+0:9]-[C:10]-[c:11].[C:12]-[C:13](-[OH;D1;+0:14])(-[c:15])-[C:16].[C;D1;H3:17]-[CH2;D2;+0:18]-[Cl;H0;D1;+0:19].[C;D1;H3:20]-[C:21]-[C;H0;D3;+0:22](-[Cl;H0;D1;+0:23])=[O;D1;H0:24].[CH3;D1;+0:25]-[CH2;D2;+0:26]-[N;H0;... | null | [] | null | null | 15 | MINUTE | 670 mg of the compound obtained in EXAMPLE 9 are dissolved in 10 ml of methylene chloride, and 0.2 ml of triethylamine and 0.2 ml of propionyl chloride are then added, with stirring. After 15 minutes, the reaction mixture is washed with water and then with 10% Na2CO3 solution and the organic phase is dried over MgSO4 a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide.Carbamic ester.Ether.Tertiary alcohol.Tertiary amine | Aromatic halide.Aromatic halide.Carbamic ester.Carbamic ester.Ester.Ester.Ether.Ether.Ether.Tertiary amine | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 0.25 | CCC(=O)Cl.CCCl.CCN(CC)CC.CN(CC(OCCN1CCC(O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1)C(=O)OCc1ccccc1.Cl>C(Cl)Cl>CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CCC(=O)OC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.Cl.O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d504e6d31bb4728a49a96e042f2ee0f | CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.O=C(Cl)OCc1ccccc1>>CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 | CCCl.C(C)N(CC)CC.Cl.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CNC)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.ClC(=O)OCC1=CC=CC=C1>>Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][O:17][CH:18]([CH2:19][NH:20][CH3:21])[c:32]2[cH:33][cH:34][c:35]([Cl:36])[c:37]([Cl:38])[cH:39]2)[CH2:40][CH2:41]1.Cl[C:22](=[O:23])[O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][C:2](=[O... | CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.O=C(Cl)OCc1ccccc1 | CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 | null | null | C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(NCC(OCCN1CCC(c2ccccc2)CC1)c1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | 0 | CELSIUS | null | null | 0.41 ml of triethylamine is added to a solution of 0.5 g of the compound obtained in EXAMPLE 11, step B), in 10 ml of DCM, the mixture is then cooled to 0° C. and 0.14 ml of benzyl chloroformate is added dropwise. The reaction mixture is washed twice with water, dried over MgSO4 and concentrated under vacuum. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | null | CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.O=C(Cl)OCc1ccccc1>C(Cl)Cl>CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)OCc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b505007df247456aa881670aca334437 | CCCl.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.Cl.O=C(O)Cc1ccccc1>>CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.O | CCCl.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.Cl.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CNC)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.C1(=CC=CC=C1)CC(=O)O>>O.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C(=O)CC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C)C(=O)CC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C... | [CH2:24]([CH3:25])[Cl:37].n1[n:44][c:45]2[cH:38][cH:36][cH:34][cH:51][c:46]2[n:54]1[O:43][P+](N([CH3:18])[CH3:31])(N([CH3:19])[CH3:41])[N:20]([CH3:21])[CH3:22].[CH3:1][C:2](=[O:3])[NH:4][C:5]1([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]([CH2:15][CH2:16][O:17][CH:58]([CH2:59][NH:60][CH3:61])[c:71]2[cH... | CCCl.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.Cl.O=C(O)Cc1ccccc1 | CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.O | null | null | C(Cl)Cl.C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | fbc1bf9e9850da35158abf121e62080f85848c864fb1d301d05d27533a5f2ea4 | 6f50c022d88226844c1ec51d75aba7a23d86bfccd362a324d39ca7a98259aa0c | O=C(Cc1ccccc1)NCC(OCCN1CCC(c2ccccc2)CC1)c1ccccc1.O=C(Cc1ccccc1)NCC(OCCN1CCC(c2ccccc2)CC1)c1ccccc1 | [C;D1;H3:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:3])-[P+](-[O;H0;D2;+0:4]-[n;H0;D3;+0:5]1:n:[n;H0;D2;+0:6]:[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12]:2:1)(-N(-[CH3;D1;+0:13])-[CH3;D1;+0:14])-N(-[CH3;D1;+0:15])-[CH3;D1;+0:16].[CH3;D1;+0:17]-[CH2;D2;+0:18]-[Cl;H0;D1;+0:19].[C:20]-[C:21]-[... | null | [] | null | null | null | null | 0.46 ml of triethylamine and then 0.5 g of BOP are added to a mixture of 0.5 g of the compound obtained in EXAMPLE 11, step B), 0.127 g of phenylacetic acid and 10 ml of DCM. The resulting mixture is concentrated under vacuum and the residue is taken up with AcOEt, washed with water, with 1N NaOH solution and with satu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Ether.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | Aromatic halide.Aromatic halide.Ether.Ether.Secondary amide.Tertiary amide.Tertiary amide.Tertiary amine | c1ccc2[nH]nnc2c1 | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl.C(C)N(CC)CC | null | null | CCCl.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.CNCC(OCCN1CCC(NC(C)=O)(c2ccccc2)CC1)c1ccc(Cl)c(Cl)c1.Cl.O=C(O)Cc1ccccc1>C(Cl)Cl.C(C)N(CC)CC>CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.CC(=O)NC1(c2ccccc2)CCN(CCOC(CN(C)C(=O)Cc2ccccc2)c2ccc(Cl)c(Cl)c2)CC1.Cl.O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f25fd50f39249598d47f6ff669d7346 | O=P(Cl)(Cl)Cl.Oc1nc(Cc2ccc(F)cc2)ncc1F>>Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1 | FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)O.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC=C1F)CC1=CC=C(C=C1)F | O=P(Cl)(Cl)[Cl:13].O[c:12]1[c:10]([F:11])[cH:9][n:8][c:7]([CH2:6][c:5]2[cH:4][cH:3][c:2]([F:1])[cH:16][cH:15]2)[n:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][c:7]2[n:8][cH:9][c:10]([F:11])[c:12]([Cl:13])[n:14]2)[cH:15][cH:16]1 | O=P(Cl)(Cl)Cl.Oc1nc(Cc2ccc(F)cc2)ncc1F | Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(Cc2ncccn2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[C:5]):[#7;a:6]:[c:7]:[c:8]:1-[F;D1;H0:9]>>[C:5]-[c:4]1:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:8](-[F;D1;H0:9]):[c:7]:[#7;a:6]:1 | 90 | [{"value": 90.0, "product": "ClC1=NC(=NC=C1F)CC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.93 g (8.7 mmol) of 5-fluoro-2-(4-fluorobenzyl)-4-hydroxypyrimidine, from Step 1, and 15 mL of phosphorus oxychloride was heated in an oil bath at 90° C. for 1.5 hours and then concentrated in vacuo. The residue was triturated with 75 mL of ice water and the aqueous mixture was adjusted to pH 8-9 by the a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.Oc1nc(Cc2ccc(F)cc2)ncc1F>>Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f9fb1d3a7e54201b973e3a877894221 | CN1CCNCC1.Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1>>CN1CCN(c2nc(Cc3ccc(F)cc3)ncc2F)CC1 | ClC1=NC(=NC=C1F)CC1=CC=C(C=C1)F.CN1CCNCC1>>FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:21][CH2:22]1.Cl[c:6]1[n:7][c:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[F:20]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([CH2:9][c:10]3[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]3)[n:17][cH:18][c:19]2[F:20])[CH2:21][CH2:22]1 | CN1CCNCC1.Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1 | CN1CCN(c2nc(Cc3ccc(F)cc3)ncc2F)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a9178a48f510c186744480d82f1e9a1a3beb7a148197ba9ff5ade9c935d3afea | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Cc2nccc(N3CCNCC3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 96.9 | [{"value": 95.0, "product": "FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of 0.48 g (2 mmol) of 4-chloro-5-fluoro-2-(4-fluorobenzyl)-pyrimidine from Step 2 and 1.53 mL (14 mmol) of 4-methylpiperazine in 10 mL of methylene chloride was stirred at ambient temperature for 1.5 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in methylene chloride. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cncnc1 | C1C[NH]CC[NH]1.c1cncnc1 | C1C[NH]CC[NH]1.c1cncnc1.c1ccccc1 | HCl | C(Cl)Cl | null | 1.5 | CN1CCNCC1.Fc1ccc(Cc2ncc(F)c(Cl)n2)cc1>C(Cl)Cl>CN1CCN(c2nc(Cc3ccc(F)cc3)ncc2F)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c692bc85106744069adc7052796b1100 | CCC[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.CCOC(=O)c1ccc2cc(Cl)ccn2c1=O>>CCC[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 | ClC=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O.NC1CN(CC1)CC1=CC=CC=C1.C(C)(C)(C)OC(=O)N[C@@H](CCC)C(=O)O.C(=O)(OC(C)(C)C)N[C@@H](CCC)C(=O)NC1CNCC1.ON1C(CCC1=O)=O>>N[C@@H](CCC)C(=O)NC1CN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)O)=O | CC(C)(C)OC(=O)[NH:5][C@@H:4]([CH2:3][CH2:2][CH3:1])[C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:27]1.CC[O:22][C:20]([c:19]1[c:17](=[O:18])[n:16]2[cH:15][cH:14][c:13](Cl)[cH:26][c:25]2[cH:24][cH:23]1)=[O:21]>>[CH3:1][CH2:2][CH2:3][C@H:4]([NH2:5])[C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH... | CCC[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.CCOC(=O)c1ccc2cc(Cl)ccn2c1=O | CCC[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3372844e8874019375346d6c944b99477e0efc73838c38032f67789541cb28f9 | 5c530bc185fdf54956090e5ff31b4625247366cd666dcae789cfd53ed04cb8aa | O=c1cccc2cc(N3CCCC3)ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-1.C-C-[O;H0;D2;+0:12]-[C:13](=[O;D1;H0:14])-[c:15]:[c:16]:[#7;a:17]1:[c:18]:[c:19]:[c;H0;D3;+0:20](-Cl):[c:21]:[c:22]:1:[c:23]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]1-[C:8]-[C:9]-[N;H... | null | [] | null | null | null | null | 3-Amino-1-benzylpyrrolidine (I. Sumio and T. Matsuo, Japanese Kokai JP 5328161, published Mar. 16, 1978) is coupled to N-t-butoxycarbonyl norvaline (Boc-nVal) using conventional N-hydroxysuccinimide coupling procedures. The 1-benzyl group is removed by hydrogenolysis in methanol using palladium on carbon catalyst. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Carboxylic acid.Primary amine.Tertiary amine | C1CCNC1.c1cn2ccccc2cc1 | C1CC[NH]C1.c1cn2ccccc2cc1 | C1CC[NH]C1.c1cn2ccccc2cc1 | HCl | null | null | null | CCC[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.CCOC(=O)c1ccc2cc(Cl)ccn2c1=O>>CCC[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1417262cbeb4dcfb27be135b8b405b2 | CCOC(=O)c1ccc2cc(Cl)ccn2c1=O.CN1CCNCC1>>CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O | ClC=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O.ClC=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O.CN1CCNCC1>>CN1CCN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O | Cl[c:11]1[cH:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:22](=[O:23])[n:21]2[cH:20][cH:19]1.[NH:12]1[CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[cH:10][c:11]([N:12]3[CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18]3)[cH:19][cH:20][n:21]2[c... | CCOC(=O)c1ccc2cc(Cl)ccn2c1=O.CN1CCNCC1 | CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d1eef4f8c0aa68dde2b04e6a19bf2997a325e5677cab2bf9db6ffa7b61f605c2 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cccc2cc(N3CCNCC3)ccn12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]):[#7;a:5](:[c:6]):[c:7]:[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[#7;a:5]1:[c:7]:[c:8]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1:[c:4] | 106.8 | [{"value": 106.8, "product": "CN1CCN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate (755 mg, 3.0 mmol), the product of Step 3 of Example 58, was suspended in 12 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 6.0 mL (6.0 mmol) of N-methylpiperazine and the reaction mixture was heated at 70° C. for 8 hours. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cn2ccccc2cc1.C1CNCC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | HCl | N1=CC=CC=C1 | 70 | null | CCOC(=O)c1ccc2cc(Cl)ccn2c1=O.CN1CCNCC1>N1=CC=CC=C1>CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9f579710cd264918b47252784f610bcf | CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O>>CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 | Cl.[OH-].[Na+].CN1CCN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O>>Cl.CN1CCN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)O)=O | CC[O:15][C:13]([c:12]1[c:10](=[O:11])[n:9]2[cH:8][cH:7][c:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:21][CH2:20]3)[cH:19][c:18]2[cH:17][cH:16]1)=[O:14]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9]3[c:10](=[O:11])[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]3[cH:19]2)[CH2:20][CH2:21]1 | CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O | CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cccc2cc(N3CCNCC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 75 | CELSIUS | 8 | HOUR | A mixture of 0.865 g (2.75 mmol) of ethyl 8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 12 mL of THF and 16.5 mL of a 0.5N aqueous solution of sodium hydroxide was heated, with stirring, at 75° C. for 8 hours. The THF was removed from the reaction mixture by distillation during the react... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1C[NH]CC[NH]1.c1cn2ccccc2cc1 | Other | C1CCOC1 | 75 | 8 | CCOC(=O)c1ccc2cc(N3CCN(C)CC3)ccn2c1=O>C1CCOC1>CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-05fc3ca2347f436aa6a5c4b9b479ce81 | CCI.Cc1cc(Cl)ccn1>>CCCc1cc(Cl)ccn1 | [Li+].CC(C)[N-]C(C)C.[Li+].CC(C)[N-]C(C)C.CCCCCC.[N+](=O)(O)[O-].C(C)I.ClC1=CC(=NC=C1)C>>ClC1=CC(=NC=C1)CCC | I[CH2:2][CH3:1].[CH3:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][n:10]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([Cl:7])[cH:8][cH:9][n:10]1 | CCI.Cc1cc(Cl)ccn1 | CCCc1cc(Cl)ccn1 | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccncc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[CH3;D1;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7] | 60 | [{"value": 60.0, "product": "ClC1=CC(=NC=C1)CCC", "details": "PERCENTYIELD", "is_desired": false}] | -60 | CELSIUS | 0.5 | HOUR | A 1.5M solution of LDA in hexane (100 mL, 150 mmol) was cooled to -60° C. in an isopropyl alcohol/dry ice bath. To the stirred LDA solution, under nitrogen, was added, dropwise over a 0.5 hours period, a solution of 17.466 g (137 mmol) of 4-chloro-2-picoline (the product of Step 1 of Example 58) in 80 mL of dry THF. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccncc1 | HI | C1CCOC1 | -60 | 0.5 | CCI.Cc1cc(Cl)ccn1>C1CCOC1>CCCc1cc(Cl)ccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-919d466c679b402eab41fc7f145b2864 | C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NC1CCN(Cc2ccccc2)C1.O=C1CCC(=O)N1O>>C[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 | ON1C(CCC1=O)=O.C(=O)(OC(C)(C)C)N[C@@H](C)C(=O)NC1CNCC1.NC1CN(CC1)CC1=CC=CC=C1.C(C)(C)(C)OC(=O)N[C@@H](C)C(=O)O>>N[C@@H](C)C(=O)NC1CN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)O)=O | CC(C)(C)OC(=O)[NH:3][C@@H:2]([CH3:1])[C:4](=[O:5])[NH:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:25]1.C[C@H](NC(=O)OC(C)(C)C)[C:18](=[O:19])[OH:20].N[CH:11]1[CH2:12][CH2:13]N(C[c:23]2ccccc2)[CH2:24]1.O=[C:22]1[N:14](O)[C:15](=[O:16])[CH2:17][CH2:21]1>>[CH3:1][C@H:2]([NH2:3])[C:4](=[O:5])[NH:6][CH:7]1[CH2:8][CH2:9][N:10]([c:11]... | C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NC1CCN(Cc2ccccc2)C1.O=C1CCC(=O)N1O | C[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 | null | null | null | C-C Coupling | OtherReaction | 36b19e8a44a944846ed8e7bd03188901c7f52265adcb2d98574ac4841adb71f8 | bb3d9244575be890562eeba770fd313c4a09fcf6f990dcd0e29c445795cfa2b1 | O=c1cccc2cc(N3CCCC3)ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1.C-[C@H](-N-C(=O)-O-C(-C)(-C)-C)-[C;H0;D3;+0:12](=[O;D1;H0:13])-[O;D1;H1:14].N-[CH;D3;+0:15]1-[CH2;D2;+0:16]-[CH2;D2;+0:17]-N(-C-[c;H0;D3;+0:18]2:c:c:c:c:c:2)-[CH2;D2;+0:19]-1.O-[N;H0;D3;+0:20]1-[C;H... | null | [] | null | null | null | null | 3-Amino-1-benzylpyrrolidine (I. Sumio and T. Matsuo, Japanese Kokai JP 5328161, published Mar. 16, 1978) is coupled to N-t-butoxycarbonyl alanine (Boc-Ala) using conventional N-hydroxysuccinimide coupling procedures. The 1-benzyl group is removed by hydrogenolysis in methanol using palladium on carbon catalyst. The 3-(... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Carboxylic acid.Ether.Ether.Tertiary amide.Tertiary amide.Primary amine.Secondary amine.Tertiary amine.Boc.Boc | Carboxylic acid.Primary amine.Tertiary amine | C1CCNC1.C1CCNC1.c1ccccc1.C1CC[NH]C1 | C1CC[NH]C1.c1cn2ccccc2cc1 | C1CC[NH]C1.c1cn2ccccc2cc1 | HO- | null | null | null | C[C@H](NC(=O)OC(C)(C)C)C(=O)NC1CCNC1.C[C@H](NC(=O)OC(C)(C)C)C(=O)O.NC1CCN(Cc2ccccc2)C1.O=C1CCC(=O)N1O>>C[C@H](N)C(=O)NC1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dbb3e314646f42c4828e49ee8c678c63 | CC1CNCCN1.CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O>>CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O | ClC=1C=CN2C(C(=CC(=C2C1)CC)C(=O)OCC)=O.CC1NCCNC1>>C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)OCC | [NH:14]1[CH2:15][CH2:16][NH:17][CH:18]([CH3:19])[CH2:20]1.Cl[c:13]1[cH:12][c:11]2[c:8]([CH2:9][CH3:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:24](=[O:25])[n:23]2[cH:22][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][CH3:10])[c:11]2[cH:12][c:13]([N:14]3[CH2:15][CH2:16][NH:17][CH:18]([CH3:19]... | CC1CNCCN1.CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O | CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 666b4849793ff533c8edd054666569c3e8ecb55f1bf04ec78a4aed522f7676e2 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cccc2cc(N3CCNCC3)ccn12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]):[#7;a:5](:[c:6]):[c:7]:[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[#7;a:5]1:[c:7]:[c:8]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1:[c:4] | 100.5 | [{"value": 100.5, "product": "C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (558 mg, 2.0 mmol), the product of Step 3 of Example 62, was dissolved in 10 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 600 mg (6.0 mmol) of 2-methylpiperazine and the stirred reaction mixture was heated at 65° C. for 3 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cn2ccccc2cc1 | c1cn2ccccc2cc1.C1C[NH]CCN1 | c1cn2ccccc2cc1.C1C[NH]CCN1 | HCl | N1=CC=CC=C1 | 65 | null | CC1CNCCN1.CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O>N1=CC=CC=C1>CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9473a5b4f44b4bc8b8cc65bad100e385 | CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O>>CCc1cc(C(=O)O)c(=O)n2ccc(N3CCNC(C)C3)cc12 | [OH-].[Na+].C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)OCC.Cl>>Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)O | CC[O:8][C:6]([c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:23]2[n:11]([c:9]1=[O:10])[cH:12][cH:13][c:14]([N:15]1[CH2:16][CH2:17][NH:18][CH:19]([CH3:20])[CH2:21]1)[cH:22]2)=[O:7]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[n:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][NH:18][CH:19]([CH3:20])[CH2:21]3)... | CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O | CCc1cc(C(=O)O)c(=O)n2ccc(N3CCNC(C)C3)cc12 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cccc2cc(N3CCNCC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 55 | [{"value": 55.0, "product": "Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 3 | HOUR | To a suspension of 0.686 g (2 mmol) of ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 8 mL of THF was added 8.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture was heated, with stirring, at 65° C. for 3 hours. The THF was removed from the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cn2ccccc2cc1.C1C[NH]CCN1 | Other | C1CCOC1 | 65 | 3 | CCOC(=O)c1cc(CC)c2cc(N3CCNC(C)C3)ccn2c1=O>C1CCOC1>CCc1cc(C(=O)O)c(=O)n2ccc(N3CCNC(C)C3)cc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ba268a942a684f5bae96f7015e014325 | CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O.CN1CCNCC1>>CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O | ClC=1C=CN2C(C(=CC(=C2C1)CC)C(=O)OCC)=O.CN1CCNCC1>>C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)OCC | Cl[c:13]1[cH:12][c:11]2[c:8]([CH2:9][CH3:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:24](=[O:25])[n:23]2[cH:22][cH:21]1.[NH:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][CH3:10])[c:11]2[cH:12][c:13]([N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19... | CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O.CN1CCNCC1 | CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d1eef4f8c0aa68dde2b04e6a19bf2997a325e5677cab2bf9db6ffa7b61f605c2 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cccc2cc(N3CCNCC3)ccn12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]):[#7;a:5](:[c:6]):[c:7]:[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[c:6]:[#7;a:5]1:[c:7]:[c:8]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[c:2]:[c:3]:1:[c:4] | 99.9 | [{"value": 99.9, "product": "C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Ethyl 8-chloro-1-ethyl-4H-quinolizin-4-one-3-carboxylate (279 mg, 1.0 mmol), the product of Step 3 of Example 62, was dissolved in 5 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution was added 2 mL (2.0 mmol) of N-methylpiperazine and the stirred reaction mixture was heated at 85° C. for 2.5 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cn2ccccc2cc1.C1CNCC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | HCl | N1=CC=CC=C1 | 85 | null | CCOC(=O)c1cc(CC)c2cc(Cl)ccn2c1=O.CN1CCNCC1>N1=CC=CC=C1>CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f8eca8686f04fab850d92ff0dd05c7a | CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O>>CCc1cc(C(=O)O)c(=O)n2ccc(N3CCN(C)CC3)cc12 | Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)OCC.[OH-].[Na+]>>Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)O | CC[O:8][C:6]([c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:23]2[n:11]([c:9]1=[O:10])[cH:12][cH:13][c:14]([N:15]1[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]1)[cH:22]2)=[O:7]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[n:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]3)... | CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O | CCc1cc(C(=O)O)c(=O)n2ccc(N3CCN(C)CC3)cc12 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cccc2cc(N3CCNCC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 68 | [{"value": 68.0, "product": "Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 4.5 | HOUR | To a solution of 171 mg (0.5 mmol) of ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 4 mL of THF was added 4.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture was heated, with stirring, at 75° C. for 4.5 hours. The reaction mixture was cooled to ambie... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | Other | C1CCOC1 | 75 | 4.5 | CCOC(=O)c1cc(CC)c2cc(N3CCN(C)CC3)ccn2c1=O>C1CCOC1>CCc1cc(C(=O)O)c(=O)n2ccc(N3CCN(C)CC3)cc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-784765bd050b4df79dbabcefd7283ef9 | O=C([O-])CC(CC(=O)[O-])c1ccc([N+](=O)[O-])cn1>>Cc1ccc([N+](=O)[O-])cn1 | [OH-].[Na+].[N+](=O)([O-])C=1C=CC(=NC1)C(CC(=O)[O-])CC(=O)[O-]>>[N+](=O)([O-])C=1C=CC(=NC1)C | O=C([O-])C[CH:1](CC(=O)[O-])[c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][n:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][n:10]1 | O=C([O-])CC(CC(=O)[O-])c1ccc([N+](=O)[O-])cn1 | Cc1ccc([N+](=O)[O-])cn1 | null | null | S(O)(O)(=O)=O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccncc1 | O=C(-[O-])-C-[CH;D3;+0:1](-C-C(=O)-[O-])-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 92 | [{"value": 92.0, "product": "[N+](=O)([O-])C=1C=CC(=NC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "[N+](=O)([O-])C=1C=CC(=NC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 102.0 g (0.361 mol) of 2-(5-nitro-2-pyridyl)-1,3-propanedicarboxylate, from Step 1, in 600 mL of 20% aqueous sulfuric acid solution was heated at 95° C. for 24 hours. The resultant solution was poured onto 1 kg of ice and the aqueous mixture was adjusted to a pH within the range pH 10-12 with 50% aqueou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccncc1 | HO- | S(O)(O)(=O)=O | null | null | O=C([O-])CC(CC(=O)[O-])c1ccc([N+](=O)[O-])cn1>S(O)(O)(=O)=O>Cc1ccc([N+](=O)[O-])cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5f292609ba64fafa75e76f067d6b75e | Cc1ccc(F)cn1.OO>>Cc1ccc(F)c[n+]1[O-] | FC=1C=CC(=NC1)C.C(C)(=O)OO.OO.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C([N+](=C1)[O-])C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][n:8]1.O[OH:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][n+:8]1[O-:9] | Cc1ccc(F)cn1.OO | Cc1ccc(F)c[n+]1[O-] | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | d7f3c84fb751fef5567bc0e84a2e7c0afb271257e8dfb17aa871e038ff1a84c7 | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1cc[nH+]cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | 22 | [{"value": 22.0, "product": "FC1=CC=C([N+](=C1)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 4 | HOUR | To the solution of 5-fluoro-2-picoline obtained in Step 4, at 0° C., was added, with vigorous stirring, a cold solution of 40% peracetic acid (prepared by carefully adding 50 mL of 30% hydrogen peroxide solution to 150 mL of glacial acetic acid). The reaction mixture was heated at reflux temperature (50° C.) for 4 days... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | C(C)(=O)O | 50 | 4 | Cc1ccc(F)cn1.OO>C(C)(=O)O>Cc1ccc(F)c[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2f9949b0e5874a0b8b55bdaaeb8c3283 | Cc1ccc(F)c[n+]1[O-]>>Cc1cc([N+](=O)[O-])c(F)c[n+]1[O-] | S(O)(O)(=O)=O.[N+](=O)([O-])[O-].[K+].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].FC1=CC=C([N+](=C1)[O-])C.FC1=CC=C([N+](=C1)[O-])C.[N+](=O)([O-])[O-].[K+]>>FC1=C(C=C([N+](=C1)[O-])C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:8]([F:9])[cH:10][n+:11]1[O-:12]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[c:8]([F:9])[cH:10][n+:11]1[O-:12] | Cc1ccc(F)c[n+]1[O-] | Cc1cc([N+](=O)[O-])c(F)c[n+]1[O-] | null | null | null | Functional Group Addition | OtherReaction | d1758a3dd09d130b0b6f98cf4f20aa520271dd0a99b430b7cead3eb29332a65b | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1cc[nH+]cc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[c:5](-[F;D1;H0:6]):[c:7]:[#7;a;+:8]:1-[O;-;D1;H0:9]>>[C;D1;H3:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-[#7;+:10](-[O;-;D1;H0:11])=[O;D1;H0:12]):[c:5](-[F;D1;H0:6]):[c:7]:[#7;a;+:8]:1-[O;-;D1;H0:9] | 80 | [{"value": 80.0, "product": "FC1=C(C=C([N+](=C1)[O-])C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 18 | HOUR | The reaction was carried out in a flask vented to a gas scrubber containing aqueous sodium hydroxide solution. The product of Step 5, 5-fluoro-2-picoline-N-oxide (1.0 g, 7.86 mmol) was cooled to 0° C. and concentrated sulfuric acid (4.2 mL) was slowly added, with stirring. Solid potassium nitrate (1.27 g, 12.5 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | Other | null | 50 | 18 | Cc1ccc(F)c[n+]1[O-]>>Cc1cc([N+](=O)[O-])c(F)c[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c15659462ee47fb96bbf189ac58fe27 | Cc1cc(Cl)c(F)c[n+]1[O-]>>Cc1cc(Cl)c(F)cn1 | ClC=1C=C([N+](=CC1F)[O-])C.C([O-])([O-])=O.[K+].[K+]>>ClC1=CC(=NC=C1F)C | [O-][n+:9]1[c:2]([CH3:1])[cH:3][c:4]([Cl:5])[c:6]([F:7])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([F:7])[cH:8][n:9]1 | Cc1cc(Cl)c(F)c[n+]1[O-] | Cc1cc(Cl)c(F)cn1 | null | [Fe] | C(C)(=O)O | Functional Group Interconversion | OtherReaction | 8660dc08f9c4d3b8c6814ee1b12714454b2bd6ddbe4d55cbaaeb274a83637cea | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccncc1 | [C;D1;H3:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-]):[c:5]:[c:6]>>[C;D1;H3:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6] | 142.1 | [{"value": 71.0, "product": "ClC1=CC(=NC=C1F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 142.1, "product": "ClC1=CC(=NC=C1F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 4-Chloro-5-fluoro-2-picoline-N-oxide (12.43 g, 76.93 mmol), from Step 7, was dissolved in 52 mL of glacial acetic acid in a 3-necked flask equiped with a mechanical stirrer, a condenser and a thermometer. Iron powder (6.45 g, 115.5 mmol) was added to the solution at ambient temperature and the reaction mixture was care... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | Other | [Fe].C(C)(=O)O | null | 0.166667 | Cc1cc(Cl)c(F)c[n+]1[O-]>[Fe].C(C)(=O)O>Cc1cc(Cl)c(F)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1ecb12c0a720485081b2a903dedaad68 | CC(C)(C)OCl.Cc1cc(Cl)c(F)cn1>>Cc1ncc(F)c(Cl)c1Cl | O.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)C.C(C)(C)(C)OCl>>ClC=1C(=NC=C(C1Cl)F)C | CC(C)(C)O[Cl:10].[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[cH:9]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[c:9]1[Cl:10] | CC(C)(C)OCl.Cc1cc(Cl)c(F)cn1 | Cc1ncc(F)c(Cl)c1Cl | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | C-C(-C)(-C)-O-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9]:1-[Cl;H0;D1;+0:1] | null | [] | 0 | CELSIUS | 2 | HOUR | To 0.87 g (6 mmol) of 4-chloro-5-fluoro-2-picoline, the product of Example 66, in 20 mL of chloroform cooled to -45° C., is added 0.75 mL of t-butylhypochlorite. The reaction mixture is stirred at -45° C. for 2 hours and at 0° C. for 2 hours. The reaction mixture is then poured into water and the resultant aqueous mixt... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | C(Cl)(Cl)Cl | 0 | 2 | CC(C)(C)OCl.Cc1cc(Cl)c(F)cn1>C(Cl)(Cl)Cl>Cc1ncc(F)c(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a549bdf2b11747b18714efb6d4d43a8c | BrBr.Cc1cc(Cl)c(F)cn1>>Cc1ncc(F)c(Cl)c1Br | S(O)(O)(=O)=O.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)C.BrBr>>BrC=1C(=NC=C(C1Cl)F)C | Br[Br:10].[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[cH:9]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[c:9]1[Br:10] | BrBr.Cc1cc(Cl)c(F)cn1 | Cc1ncc(F)c(Cl)c1Br | null | null | null | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:3](-[C;D1;H3:2]):[#7;a:4]:[c:5]:[c:6]:[c:7]:1-[Cl;D1;H0:8] | null | [] | null | null | null | null | 4-Chloro-5-fluoro-2-picoline, the product of Example 66, is treated with bromine in fuming sulfuric acid containing 65% sulfur trioxide for 7 hours at 80° C. as described by L. van der Does and H. J. Hertog in Rec Trav Chim 81: 864 (1965) to afford the title compound.
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | null | BrBr.Cc1cc(Cl)c(F)cn1>>Cc1ncc(F)c(Cl)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6be519bfa24b404b82af4b0e9d174bb5 | CC(=O)OF.Cc1cc(Cl)c(F)cn1>>Cc1ncc(F)c(Cl)c1F | ClC1=CC(=NC=C1F)C.FOC(C)=O>>ClC1=C(C(=NC=C1F)C)F | CC(=O)O[F:10].[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[cH:9]1>>[CH3:1][c:2]1[n:3][cH:4][c:5]([F:6])[c:7]([Cl:8])[c:9]1[F:10] | CC(=O)OF.Cc1cc(Cl)c(F)cn1 | Cc1ncc(F)c(Cl)c1F | null | null | null | Functional Group Interconversion | OtherReaction | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | C-C(=O)-O-[F;H0;D1;+0:1].[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[cH;D2;+0:9]:1>>[C;D1;H3:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](-[Cl;D1;H0:8]):[c;H0;D3;+0:9]:1-[F;H0;D1;+0:1] | null | [] | null | null | null | null | 4-Chloro-5-fluoro-2-picoline is treated with 1.1 equivalents of acetyl hypofluorite as described by O. Lerman, et al. J Org Chem, 49: 806-813 (1984) to afford the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | null | null | null | CC(=O)OF.Cc1cc(Cl)c(F)cn1>>Cc1ncc(F)c(Cl)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40d48fdd456840b9bb764160e1bbdceb | CCI.Cc1cc(Cl)c(F)cn1>>CCCc1cc(Cl)c(F)cn1 | C(C)I.C(CCC)[Li].ClC1=CC(=NC=C1F)C.C(C)(C)NC(C)C.C(C)(C)[N-]C(C)C.[Li+].C(C)(C)[N-]C(C)C.[Li+]>>ClC1=CC(=NC=C1F)CCC | I[CH2:2][CH3:1].[CH3:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][n:11]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][n:11]1 | CCI.Cc1cc(Cl)c(F)cn1 | CCCc1cc(Cl)c(F)cn1 | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccncc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[CH3;D1;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | -78 | CELSIUS | 5 | HOUR | Diisopropylamine (924 μL, 6.59 mmol) was dissolved in 9 mL of dry THF and the resultant solution was cooled to 0° C. in an ice bath. n-Butyllithium (3.07 mL of a 2.05M solution in THF, 6.29 mmol) was added via syringe to the amine solution and the resultant solution was stirred for 30 minutes at 0° C. The lithium diiso... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccncc1 | HI | C1CCOC1 | -78 | 5 | CCI.Cc1cc(Cl)c(F)cn1>C1CCOC1>CCCc1cc(Cl)c(F)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35690c6e645f4d1f972faf4b4a3c07c5 | CCCc1cc(Cl)c(F)cn1>>CCCc1ncc(F)c(Cl)c1Cl | ClC1=CC(=NC=C1F)CCC.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)CCC>>ClC=1C(=NC=C(C1Cl)F)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[c:11]1[Cl:12] | CCCc1cc(Cl)c(F)cn1 | CCCc1ncc(F)c(Cl)c1Cl | null | null | null | Functional Group Addition | Aromatic chlorination | 7c108e53aa6849672ac0ea1998cfd24df7835b0d1bc5738d16f4d561a472c88e | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccncc1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[cH;D2;+0:8]:1>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[c;H0;D3;+0:8]:1-[Cl;D1;H0:9] | null | [] | null | null | null | null | By following the procedures described in Example 67 and replacing 4-chloro-5-fluoro-2-picoline (the product of Example 66) with 4-chloro-5-fluoro-2-propyl-pyridine (the product of Example 70), the title compound can be prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | CCCc1cc(Cl)c(F)cn1>>CCCc1ncc(F)c(Cl)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf330283adb847978dd3b58700a37b8c | CCCc1cc(Cl)c(F)cn1>>CCCc1ncc(F)c(Cl)c1F | ClC1=CC(=NC=C1F)CCC.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)CCC>>ClC1=C(C(=NC=C1F)CCC)F | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[cH:11]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][cH:6][c:7]([F:8])[c:9]([Cl:10])[c:11]1[F:12] | CCCc1cc(Cl)c(F)cn1 | CCCc1ncc(F)c(Cl)c1F | null | null | null | Functional Group Addition | Aromatic fluorination | 7c108e53aa6849672ac0ea1998cfd24df7835b0d1bc5738d16f4d561a472c88e | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccncc1 | [C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[cH;D2;+0:8]:1>>[C:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[Cl;D1;H0:7]):[c;H0;D3;+0:8]:1-[F;D1;H0:9] | null | [] | null | null | null | null | By following the procedures described in Example 69 and replacing 4-chloro-5-fluoro-2-picoline (the product of Example 66) with 4-chloro-5-fluoro-2-propyl-pyridine (the product of Example 70), the title compound can be prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | null | null | null | CCCc1cc(Cl)c(F)cn1>>CCCc1ncc(F)c(Cl)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9b54b14eaa34567839b3bc713494b14 | Cc1cc(Cl)c(F)cn1.O=C1CCC(=O)N1Br>>CC1(Br)C=C(Cl)C(F)=CN1 | CC(C)(C#N)N=NC(C)(C)C#N.ClC1=CC(=NC=C1F)C.ClC1=CC(=NC=C1F)C.BrN1C(CCC1=O)=O>>ClC1=CC(NC=C1F)(C)Br | [CH3:1][c:2]1[cH:4][c:5]([Cl:6])[c:7]([F:8])[cH:9][n:10]1.O=C1CCC(=O)N1[Br:3]>>[CH3:1][C:2]1([Br:3])[CH:4]=[C:5]([Cl:6])[C:7]([F:8])=[CH:9][NH:10]1 | Cc1cc(Cl)c(F)cn1.O=C1CCC(=O)N1Br | CC1(Br)C=C(Cl)C(F)=CN1 | null | null | C(Cl)Cl.ClCCCl | Functional Group Interconversion | OtherReaction | a5011706c3b542cad82b76bbbf2532a9330903bdef3a651fec89f9efae3345a4 | d68a01110e168c02e5a14d46a91c97d2353cca8f6d85d864624a3298918472b0 | C1=CCNC=C1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C;D1;H3:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[Cl;D1;H0:6]):[c;H0;D3;+0:7](-[F;D1;H0:8]):[cH;D2;+0:9]:[n;H0;D2;+0:10]:1>>[Br;H0;D1;+0:1]-[C;H0;D4;+0:3]1(-[C;D1;H3:2])-[CH;D2;+0:4]=[C;H0;D3;+0:5](-[Cl;D1;H0:6])-[C;H0;D3;+0:7](-[F;D1;H0:8])=[CH;D2;+0:9]-[NH;D2;+0:10]-1 | 69 | [{"value": 69.0, "product": "ClC1=CC(NC=C1F)(C)Br", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | null | null | 4-Chloro-5-fluoro-2-picoline (2.9 g, 20 mmol), the product of Example 66, was dissolved in 50 mL of 1,2-dichloroethane in a dry flask. The resultant solution was heated, with stirring, to 75° C. and 4.09 (23 mmol) of N-bromosuccinimide was added, followed by 100 mG (0.7 mmol) of 2,2-azobisisobutyronirile (AIBN), a free... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide.Tertiary amide | Enamine.Tertiary halide.Alkenyl halide.Alkenyl halide | c1ccncc1.C1CCNC1 | C1=CCNC=C1 | C1=CCNC=C1 | HO- | C(Cl)Cl.ClCCCl | 75 | null | Cc1cc(Cl)c(F)cn1.O=C1CCC(=O)N1Br>C(Cl)Cl.ClCCCl>CC1(Br)C=C(Cl)C(F)=CN1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a310f335f3e844efadd43206c4a310e4 | CC1(Br)C=C(Cl)C(F)=CN1.CN>>CNCc1cc(Cl)c(F)cn1 | ClC1=CC(NC=C1F)(C)Br.CN>>ClC1=CC(=NC=C1F)CNC | Br[C:4]1([CH3:3])[CH:5]=[C:6]([Cl:7])[C:8]([F:9])=[CH:10][NH:11]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]([Cl:7])[c:8]([F:9])[cH:10][n:11]1 | CC1(Br)C=C(Cl)C(F)=CN1.CN | CNCc1cc(Cl)c(F)cn1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 89c5e51da84b17b94a10ac0183ba706b07e9fdcd804405a5bd1f7d8228653361 | b2680e4f3eb35cf11f81268e8fcd711678a40fd9bd43a0fd5cc2b47a013eabce | c1ccncc1 | Br-[C;H0;D4;+0:1]1(-[CH3;D1;+0:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[Cl;D1;H0:5])-[C;H0;D3;+0:6](-[F;D1;H0:7])=[CH;D2;+0:8]-[NH;D2;+0:9]-1.[C;D1;H3:10]-[NH2;D1;+0:11]>>[C;D1;H3:10]-[NH;D2;+0:11]-[CH2;D2;+0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[Cl;D1;H0:5]):[c;H0;D3;+0:6](-[F;D1;H0:7]):[cH;D2;+0:8]:[n;H0;D2;+0:9]... | 70 | [{"value": 70.0, "product": "ClC1=CC(=NC=C1F)CNC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | 4-Chloro-5-fluoro-alpha-bromo-2-picoline (1.37 g, 6.1 mmol), from Step 1 was dissolved in 15 mL of methanol in a pressure tube. Methylamine (3 mL of 40% aqueous solution) was added to the tube and the tube was sealed. The reaction mixture was stirred at ambient temperature for 26 hours and then the solvent was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Tertiary halide.Alkenyl halide.Alkenyl halide.Primary amine | Aromatic halide.Aromatic halide.Secondary amine | C1=CCNC=C1 | c1ccncc1 | c1ccncc1 | HBr | CO | null | 26 | CC1(Br)C=C(Cl)C(F)=CN1.CN>CO>CNCc1cc(Cl)c(F)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7367f512f50b4d5a8670fe6f388da171 | CCOC(=O)c1cc(NC)c2cc(Cl)c(F)cn2c1=O.CN1CCNCC1>>CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O | ClC=1C(=CN2C(C(=CC(=C2C1)NC)C(=O)OCC)=O)F.ClC=1C(=CN2C(C(=CC(=C2C1)NC)C(=O)OCC)=O)F.CN1CCNCC1>>FC1=CN2C(C(=CC(=C2C=C1N1CCN(CC1)C)NC)C(=O)OCC)=O | Cl[c:13]1[cH:12][c:11]2[c:8]([NH:9][CH3:10])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:25](=[O:26])[n:24]2[cH:23][c:21]1[F:22].[NH:14]1[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH:9][CH3:10])[c:11]2[cH:12][c:13]([N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2... | CCOC(=O)c1cc(NC)c2cc(Cl)c(F)cn2c1=O.CN1CCNCC1 | CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d1eef4f8c0aa68dde2b04e6a19bf2997a325e5677cab2bf9db6ffa7b61f605c2 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cccc2cc(N3CCNCC3)ccn12 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]):[#7;a:5](:[c:6]):[c:7]:[c:8]:1-[F;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[F;D1;H0:9]-[c:8]1:[c:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1 | null | [] | 70 | CELSIUS | null | null | Ethyl 8-chloro-7-fluoro-1-methylamino-4H-quinolizin-4-one-3-carboxylate (899 mg, 3.0 mmol), the product of Step 6, is suspended in 12 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution is added 6.0 mL (6.0 mmol) of N-methylpiperazine and the reaction mixture is heated at 70° C. for 8 hours. The r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cn2ccccc2cc1.C1CNCC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | c1cn2ccccc2cc1.C1C[NH]CC[NH]1 | HCl | N1=CC=CC=C1 | 70 | null | CCOC(=O)c1cc(NC)c2cc(Cl)c(F)cn2c1=O.CN1CCNCC1>N1=CC=CC=C1>CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abe903ec14e54584b4ff8c0f401a1f41 | CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O>>CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 | Cl.[OH-].[Na+].FC1=CN2C(C(=CC(=C2C=C1N1CCN(CC1)C)NC)C(=O)OCC)=O>>Cl.CN1CCN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)O)=O | CC[O:15][C:13]([c:12]1[c:10](=[O:11])[n:9]2[cH:8][c:7](F)[c:6]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:21][CH2:20]3)[cH:19][c:18]2[c:17](NC)[cH:16]1)=[O:14]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][n:9]3[c:10](=[O:11])[c:12]([C:13](=[O:14])[OH:15])[cH:16][cH:17][c:18]3[cH:19]2)[CH2:20][CH2:21]1 | CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O | CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 | null | null | C1CCOC1 | Deprotection | OtherReaction | d767766159eca04a31c6462e9304a3b76a67df1aacf006354a10347433d804b2 | 6108969b3e8e27263fe6331bef502f27a92cbd29e30aa832f75c68e6238d47c8 | O=c1cccc2cc(N3CCNCC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]2:[c:7]:[c;H0;D3;+0:8](-F):[c:9](-[#7:10]):[c:11]:[c:12]:2:[c;H0;D3;+0:13](-N-C):[c:14]:1>>[#7:10]-[c:9]1:[c:11]:[c:12]2:[cH;D2;+0:13]:[c:14]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:5]:[#7;a:6]:2:[c:7]:[cH;D2;+0:8]:1 | null | [] | 75 | CELSIUS | 8 | HOUR | A mixture of 1 g (2.75 mmol) of ethyl 7-fluoro-1-methylamino-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate, from Step 7, in 12 mL of THF and 16.5 mL of a 0.5N aqueous solution of sodium hydroxide is heated, with stirring, at 75° C. for 8 hours. The THF is removed from the reaction mixture by distillation... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Carboxylic acid | c1cn2ccccc2cc1 | c1cn2ccccc2cc1 | C1C[NH]CC[NH]1.c1cn2ccccc2cc1 | HF | C1CCOC1 | 75 | 8 | CCOC(=O)c1cc(NC)c2cc(N3CCN(C)CC3)c(F)cn2c1=O>C1CCOC1>CN1CCN(c2ccn3c(=O)c(C(=O)O)ccc3c2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1624c7c809f4abaa8b97cad497ea554 | [O-][n+]1c(F)c(F)c(F)c(F)c1F>>Cc1c(F)c(F)c(F)c(F)[n+]1[O-] | FC1=[N+](C(=C(C(=C1F)F)F)F)[O-].C[Mg]I.[Cl-].[NH4+].FC1=NC(=C(C(=C1F)F)F)F>>CC1=[N+](C(=C(C(=C1F)F)F)F)[O-] | F[c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[n+:11]1[O-:12]>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([F:8])[c:9]([F:10])[n+:11]1[O-:12] | [O-][n+]1c(F)c(F)c(F)c(F)c1F | Cc1c(F)c(F)c(F)c(F)[n+]1[O-] | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | cc6f4b6d0d543ddd6c55aed1efc961c75ac719a3837cf61a932da33e493678b7 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cc[nH+]cc1 | F-[c;H0;D3;+0:1](:[#7;a;+:2](-[O;-;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7]>>[C;D1;H3:8]-[c;H0;D3;+0:1](:[#7;a;+:2](-[O;-;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7] | null | [] | null | null | null | null | 2,3,4,5,6-Pentafluoropyridine (commercially available from Aldich Chemical Co.) is oxidized to the corresponding N-oxide following the procedures described in Step 6 of Example 66. The 2,3,4,5,6-pentafluoropyridine N-oxide is treated at ambient temperature with one equivalent of methylmagnesium iodide in diethyl ether ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(C)OCC | null | null | [O-][n+]1c(F)c(F)c(F)c(F)c1F>C(C)OCC>Cc1c(F)c(F)c(F)c(F)[n+]1[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-487343b7458b49df9d5c356386d96e9c | CCI.Cc1nc(F)c(F)c(F)c1F>>CCCc1nc(F)c(F)c(F)c1F | FC=1C(=NC(=C(C1F)F)F)C.[Li+].CC(C)[N-]C(C)C.[Li+].CC(C)[N-]C(C)C.CCCCCC.C(C)I>>C(CC)C1=NC(=C(C(=C1F)F)F)F | I[CH2:2][CH3:1].[CH3:3][c:4]1[n:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]([F:7])[c:8]([F:9])[c:10]([F:11])[c:12]1[F:13] | CCI.Cc1nc(F)c(F)c(F)c1F | CCCc1nc(F)c(F)c(F)c1F | null | null | [Cl-].[Na+].O.C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 15973705e8ad8fc52aace4e951dc2397c95f8af8fb2361e425388262f1895099 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccncc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[CH3;D1;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | -60 | CELSIUS | 0.5 | HOUR | A 1.5M solution of LDA in hexane (100 mL, 150 mmol) is cooled to -60° C. in an isopropyl alcohol/dry ice bath. To the stirred LDA solution, under nitrogen, is added, dropwise over a 0.5 hours period, a solution of 22.617 g (137 mmol) of 3,4,5,6-tetrafluoro-2-picoline, the product of Step 1, in 80 mL of dry THF. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccncc1 | HI | [Cl-].[Na+].O.C1CCOC1 | -60 | 0.5 | CCI.Cc1nc(F)c(F)c(F)c1F>[Cl-].[Na+].O.C1CCOC1>CCCc1nc(F)c(F)c(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ab0b347450d44f97b1ec59d5fd17f704 | CCOC(=O)C1C=C(CC)C2=C(F)C(F)(Cl)C(F)=C(F)N2C1=O.CN1CCNCC1>>CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O | ClC1(C(=C(N2C(C(C=C(C2=C1F)CC)C(=O)OCC)=O)F)F)F.CN1CCNCC1>>C(C)C=1C=C(C(N2C(=C(C(=C(C12)F)N1CCN(CC1)C)F)F)=O)C(=O)OCC | F[C:14]1(Cl)[C:12]([F:13])=[C:11]2[C:8]([CH2:9][CH3:10])=[CH:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:27](=[O:28])[N:26]2[C:24]([F:25])=[C:22]1[F:23].[NH:15]1[CH2:16][CH2:17][N:18]([CH3:19])[CH2:20][CH2:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH2:9][CH3:10])[c:11]2[c:12]([F:13])[c:14]([N:15]3[CH2:1... | CCOC(=O)C1C=C(CC)C2=C(F)C(F)(Cl)C(F)=C(F)N2C1=O.CN1CCNCC1 | CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 61141502804def142624ebf6de9457c7ce12c3d0914157ecbf5cc024f28f95db | 46bebd2a54663dfaa5a326dc4633e4fab960d5e57724fa2874aa798ef8a6827f | O=c1cccc2cc(N3CCNCC3)ccn12 | Cl-[C;H0;D4;+0:1]1(-F)-[C;H0;D3;+0:2](-[F;D1;H0:3])=[C;H0;D3;+0:4]2-[C;H0;D3;+0:5](-[C:6]-[C;D1;H3:7])=[CH;D2;+0:8]-[CH;D3;+0:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C;H0;D3;+0:14](=[O;D1;H0:15])-[N;H0;D3;+0:16]-2-[C;H0;D3;+0:17](-[F;D1;H0:18])=[C;H0;D3;+0:19]-1-[F;D1;H0:20].[#7:21]1-[C:22]-[C:23]-[NH;D2;+0:24]-[C:2... | null | [] | 85 | CELSIUS | null | null | Ethyl 8-chloro-1-ethyl-6,7,8,9-tetrafluoro-4H-quinolizin-4-one-3-carboxylate (317 mg, 1.0 mmol), from Step 4, is dissolved in 5 mL of dry pyridine under a nitrogen atmosphere. To the resultant solution is added 2 mL (2.0 mmol) of N-methylpiperazine and the stirred reaction mixture is heated at 85° C. for 2.5 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Enamine.Tertiary halide.Tertiary halide.Alkenyl halide.Alkenyl halide.Alkenyl halide.Ester.Tertiary amide.Secondary amine | Aromatic halide.Aromatic halide.Aromatic halide.Ester.Tertiary amine | C1=CN2CCC=CC2=CC1.C1CNCC[NH]1 | c1ccn2ccccc2c1.C1C[NH]CC[NH]1 | c1ccn2ccccc2c1.C1C[NH]CC[NH]1 | HF | N1=CC=CC=C1 | 85 | null | CCOC(=O)C1C=C(CC)C2=C(F)C(F)(Cl)C(F)=C(F)N2C1=O.CN1CCNCC1>N1=CC=CC=C1>CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc06e3b96a4d464db4a5d7e744be556b | CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O>>CCc1cc(C(=O)O)c(=O)n2c(F)c(F)c(N3CCN(C)CC3)c(F)c12 | Cl.C(C)C=1C=C(C(N2C(=C(C(=C(C12)F)N1CCN(CC1)C)F)F)=O)C(=O)OCC.[OH-].[Na+]>>Cl.C(C)C=1C=C(C(N2C(=C(C(=C(C12)F)N1CCN(CC1)C)F)F)=O)C(=O)O | CC[O:8][C:6]([c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:26]2[n:11]([c:9]1=[O:10])[c:12]([F:13])[c:14]([F:15])[c:16]([N:17]1[CH2:18][CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]1)[c:24]2[F:25])=[O:7]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9](=[O:10])[n:11]2[c:12]([F:13])[c:14]([F:15])[c:16]([N:17]3[CH2:18][CH2:19][... | CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O | CCc1cc(C(=O)O)c(=O)n2c(F)c(F)c(N3CCN(C)CC3)c(F)c12 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cccc2cc(N3CCNCC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 75 | CELSIUS | 4.5 | HOUR | To a solution of 199 mg (0.5 mmol) of ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-6,7,9-trifluoro-4H-quinolizin-4-one-3-carboxylate, from Step 5, in 4 mL of THF is added 4.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture is heated, with stirring, at 75° C. for 4.5 hours. The reaction mixture is co... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccn2ccccc2c1.C1C[NH]CC[NH]1 | Other | C1CCOC1 | 75 | 4.5 | CCOC(=O)c1cc(CC)c2c(F)c(N3CCN(C)CC3)c(F)c(F)n2c1=O>C1CCOC1>CCc1cc(C(=O)O)c(=O)n2c(F)c(F)c(N3CCN(C)CC3)c(F)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4f295b3d715849a297bcad06075e2348 | CC(COC1CCCCO1)c1ncc(F)c(Cl)c1F>>CC(CO)c1ncc(F)c(Cl)c1F | ClC1=C(C(=NC=C1F)C(COC1OCCCC1)C)F.O.C(C)(=O)O>>ClC1=C(C(=NC=C1F)C(CO)C)F | C1CCC([O:4][CH2:3][CH:2]([CH3:1])[c:5]2[n:6][cH:7][c:8]([F:9])[c:10]([Cl:11])[c:12]2[F:13])OC1>>[CH3:1][CH:2]([CH2:3][OH:4])[c:5]1[n:6][cH:7][c:8]([F:9])[c:10]([Cl:11])[c:12]1[F:13] | CC(COC1CCCCO1)c1ncc(F)c(Cl)c1F | CC(CO)c1ncc(F)c(Cl)c1F | null | null | C1CCOC1 | Reduction | Ether cleavage to primary alcohol | 69ac283008defddd09d640f7879e86f66dd29371b5c835a2facf24163ef14e9f | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccncc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1>>[C:1]-[C:2]-[OH;D1;+0:3] | null | [] | 45 | CELSIUS | null | null | The product of Step 1 is dissolved in 200 mL of 2:1 THF:water and to this solution is added 6 mL of acetic acid. The reaction mixture is heated at 45° C. for approximately 5 hours. The THF is removed under reduced pressure and the aqueous reaction mixture is adjusted to a pH in the range of 8 to 9 with 10% sodium carbo... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | C1CCOCC1 | null | c1ccncc1 | HO- | C1CCOC1 | 45 | null | CC(COC1CCCCO1)c1ncc(F)c(Cl)c1F>C1CCOC1>CC(CO)c1ncc(F)c(Cl)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c191750ca7b54fdb8dafaf0853defb9d | CC(C)(C)Oc1cc(F)nc(F)c1F.OO>>CC(C)(C)Oc1c(O)c(F)nc(F)c1F | C(C)(C)(C)OC1=C(C(=NC(=C1)F)F)F.[Li+].CC(C)[N-]C(C)C.OO.[OH-].[Na+].COB(OC)OC>>C(C)(C)(C)OC1=C(C(=NC(=C1O)F)F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][c:6]1[cH:7][c:9]([F:10])[n:11][c:12]([F:13])[c:14]1[F:15].O[OH:8]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][c:6]1[c:7]([OH:8])[c:9]([F:10])[n:11][c:12]([F:13])[c:14]1[F:15] | CC(C)(C)Oc1cc(F)nc(F)c1F.OO | CC(C)(C)Oc1c(O)c(F)nc(F)c1F | null | null | C(C)(=O)O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1d486e404d15e1f03f247400e5680334f540a293783abe66ffa8f2f1b3c56e68 | a2fdf414569b219d462bc05c91ebf31e5426b96645f5c78cb091f50cc92fc345 | c1ccncc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11](-[F;D1;H0:12]):[cH;D2;+0:13]:1>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:13]:1-[OH;D1;+0:1] | null | [] | -78 | CELSIUS | 30 | MINUTE | A 11.16 g (54.39 mmol) sample of 4-t-butoxy-2,3,6-trifluoropyridine, from Example 253 step b above, was dissolved in 50 mL of THF, and the solution was cooled to -78° C. To this solution was added LDA (65.6 mmol) with stirring for 30 min, during which a solid preciptated. To this mixture was added 7.5 mL of trimethoxyb... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aromatic alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1 | HO- | C(C)(=O)O.C1CCOC1 | -78 | 0.5 | CC(C)(C)Oc1cc(F)nc(F)c1F.OO>C(C)(=O)O.C1CCOC1>CC(C)(C)Oc1c(O)c(F)nc(F)c1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-60ba32da8a3a420db576adcfd7bcef8c | CC(C)(C)Oc1c(O)c(F)nc(F)c1F.CO>>COc1c(F)nc(F)c(F)c1OC(C)(C)C | CCOC(=O)/N=N/C(=O)OCC.C(C)(C)(C)OC1=C(C(=NC(=C1O)F)F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CO>>C(C)(C)(C)OC1=C(C(=NC(=C1OC)F)F)F | [OH:2][c:3]1[c:4]([F:5])[n:6][c:7]([F:8])[c:9]([F:10])[c:11]1[O:12][C:13]([CH3:14])([CH3:15])[CH3:16].O[CH3:1]>>[CH3:1][O:2][c:3]1[c:4]([F:5])[n:6][c:7]([F:8])[c:9]([F:10])[c:11]1[O:12][C:13]([CH3:14])([CH3:15])[CH3:16] | CC(C)(C)Oc1c(O)c(F)nc(F)c1F.CO | COc1c(F)nc(F)c(F)c1OC(C)(C)C | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 4622e7934dd5328af1014056d8882932e5f303d08f873e671539ebf0ad57f848 | 51e77d0fe280879eec2f84298441067b61501ac5af19ab94008f56517f7456b2 | c1ccncc1 | O-[CH3;D1;+0:1].[F;D1;H0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[CH3;D1;+0:1]-[O;H0;D2;+0:7]-[c:6](:[c:8]):[c:3](-[F;D1;H0:2]):[#7;a:4]:[c:5] | 85.7 | [{"value": 85.7, "product": "C(C)(C)(C)OC1=C(C(=NC(=C1OC)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Methanol | Ether | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.166667 | CC(C)(C)Oc1c(O)c(F)nc(F)c1F.CO>C1CCOC1>COc1c(F)nc(F)c(F)c1OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-42ec8884ab714360a71d7169f934632f | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>>Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.C(C)(C)(C)OC(=O)N[C@@H](C)[C@H]1CNCC1>>Cl.N[C@@H](C)[C@H]1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | CC[O:21][C:19]([c:18]1[c:16](=[O:17])[n:15]2[cH:14][c:12]([F:13])[c:3]([Cl:28])[c:2]([CH3:1])[c:27]2[c:23]([CH:24]2[CH2:25][CH2:26]2)[cH:22]1)=[O:20].CC(C)(C)OC(=O)[NH:10][C@H:8]([C@@H:7]1[CH2:6][CH2:5][NH:4][CH2:11]1)[CH3:9]>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@@H:7]([C@H:8]([CH3:9])[NH2:10])[CH2:11]2)[c:12]([F:... | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1 | Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b96865a2ff8714677ca5bb9121091de64fb42c9ead83b6dbe92c6b4491a8f051 | 5c530bc185fdf54956090e5ff31b4625247366cd666dcae789cfd53ed04cb8aa | O=c1ccc(C2CC2)c2cc(N3CCCC3)ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.C-C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]:[#7;a:14]1:[c:15]:[c:16](-[F;D1;H0:17]):[c;H0;D3;+0:18](-[Cl;H0;D1;+0:19]):[c:20](-[C;D1;H3:21]):[c:22]:1:[c:23]>>[C;D1;H3:21]-[c:20]1:[c:22](:[c:23]):[#7;a:14](:[c:15]:[c:... | null | [] | null | null | null | null | A sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in anhydrous acetonitrile, reacted with (3R,1S)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Carboxylic acid.Primary amine.Tertiary amine | c1ccn2ccccc2c1.C1CCNC1 | C1CC[NH]C1.c1ccn2ccccc2c1 | C1CC[NH]C1.c1ccn2ccccc2c1.C1CC1 | HO- | C(C)#N | null | null | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>C(C)#N>Cc1c(N2CC[C@@H]([C@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-55cfd45f05674e829002cb383c59d3b6 | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1>>Cc1c(N2CC[C@H]([C@@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.C(=O)(O)[O-].[Na+].C(C)(C)(C)OC(=O)N[C@H](C)[C@@H]1CNCC1>>Cl.N[C@H](C)[C@@H]1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | CC[O:21][C:19]([c:18]1[c:16](=[O:17])[n:15]2[cH:14][c:12]([F:13])[c:3]([Cl:28])[c:2]([CH3:1])[c:27]2[c:23]([CH:24]2[CH2:25][CH2:26]2)[cH:22]1)=[O:20].CC(C)(C)OC(=O)[NH:10][C@@H:8]([C@H:7]1[CH2:6][CH2:5][NH:4][CH2:11]1)[CH3:9]>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@H:7]([C@@H:8]([CH3:9])[NH2:10])[CH2:11]2)[c:12]([F:... | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1 | Cc1c(N2CC[C@H]([C@@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b96865a2ff8714677ca5bb9121091de64fb42c9ead83b6dbe92c6b4491a8f051 | 5c530bc185fdf54956090e5ff31b4625247366cd666dcae789cfd53ed04cb8aa | O=c1ccc(C2CC2)c2cc(N3CCCC3)ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.C-C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]:[#7;a:14]1:[c:15]:[c:16](-[F;D1;H0:17]):[c;H0;D3;+0:18](-[Cl;H0;D1;+0:19]):[c:20](-[C;D1;H3:21]):[c:22]:1:[c:23]>>[C;D1;H3:21]-[c:20]1:[c:22](:[c:23]):[#7;a:14](:[c:15]:[c:... | null | [] | null | null | null | null | A 0.44 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 1.51 g of NaHCO3 were dissolved in 40 mL of anhydrous acetonitrile, reacted with (3S,1R)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (1.06 g, prepared as described by Schroeder ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Carboxylic acid.Primary amine.Tertiary amine | c1ccn2ccccc2c1.C1CCNC1 | C1CC[NH]C1.c1ccn2ccccc2c1 | C1CC[NH]C1.c1ccn2ccccc2c1.C1CC1 | HO- | C(C)#N | null | null | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1>C(C)#N>Cc1c(N2CC[C@H]([C@@H](C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f80d09c9ce4641f588bcb7b3d9cdf66d | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>>Cc1cc(F)cn2c(=O)c(C(=O)O)c(N3CCC(C(C)N)C3)c(C3CC3)c12.Cl | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.C([O-])(O)=O.[Na+].C(C)(C)(C)OC(=O)N[C@H](C)[C@H]1CNCC1>>Cl.NC(C)C1CN(CC1)C=1C(=C2C(=CC(=CN2C(C1C(=O)O)=O)F)C)C1CC1 | CC[O:13][C:11]([c:10]1[c:8](=[O:9])[n:7]2[cH:6][c:4]([F:5])[c:3]([Cl:28])[c:2]([CH3:1])[c:27]2[c:23]([CH:24]2[CH2:25][CH2:26]2)[cH:14]1)=[O:12].CC(C)(C)OC(=O)[NH:21][C@@H:19]([C@@H:18]1[CH2:17][CH2:16][NH:15][CH2:22]1)[CH3:20]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][n:7]2[c:8](=[O:9])[c:10]([C:11](=[O:12])[OH:13])[c:14]... | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1 | Cc1cc(F)cn2c(=O)c(C(=O)O)c(N3CCC(C(C)N)C3)c(C3CC3)c12.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b96865a2ff8714677ca5bb9121091de64fb42c9ead83b6dbe92c6b4491a8f051 | 5c530bc185fdf54956090e5ff31b4625247366cd666dcae789cfd53ed04cb8aa | O=c1cc(N2CCCC2)c(C2CC2)c2ccccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C@H;D3;+0:2](-[C;D1;H3:3])-[C@@H;D3;+0:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-1.C-C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[cH;D2;+0:13]:[c:14](-[C:15]):[c:16]2:[#7;a:17](:[c:18]:[c:19](-[F;D1;H0:20]):[c;H0;D3;+0:21](-[Cl;H0;D1;+0:22]):[c:23]:2-[C;D1;H3:24]):[c:25]:1=[O;D1;H0:26]>>[C... | null | [] | null | null | null | null | A 0.35 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 0.73 g of sodium bicarbonate were dissolved in 24 mL of anhydrous acetonitrile, reacted with (3R,1R)-3-(1-(t-butoxycarbonylamino)ethyl)-pyrrolidine (0.51 g, prepared as described ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Carboxylic acid.Primary amine.Tertiary amine | c1ccn2ccccc2c1.C1CCNC1 | c1ccn2ccccc2c1.C1CC[NH]C1 | c1ccn2ccccc2c1.C1CC[NH]C1.C1CC1 | HO- | C(C)#N | null | null | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.C[C@@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>C(C)#N>Cc1cc(F)cn2c(=O)c(C(=O)O)c(N3CCC(C(C)N)C3)c(C3CC3)c12.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-021e1069b0ae4865bfe08ff43a38ea27 | C1CCN(C2CCNCC2)CC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>>Cc1c(N2CCC(N3CCCCC3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.N1(CCCCC1)C1CCNCC1>>N1(CCCCC1)C1CCN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | [NH:4]1[CH2:5][CH2:6][CH:7]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:14][CH2:15]1.CC[O:25][C:23]([c:22]1[c:20](=[O:21])[n:19]2[cH:18][c:16]([F:17])[c:3](Cl)[c:2]([CH3:1])[c:31]2[c:27]([CH:28]2[CH2:29][CH2:30]2)[cH:26]1)=[O:24]>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH:7]([N:8]3[CH2:9][CH2:10][CH2:11][CH2:1... | C1CCN(C2CCNCC2)CC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O | Cc1c(N2CCC(N3CCCCC3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 75e3478f1935539f46d5bed9d67d6223d61ee486643b0274563c38d0f0705c86 | 154ad2504fb7aaca0f52c4b8eebdfca329f4106b95adc3c71ff059886f074b58 | O=c1ccc(C2CC2)c2cc(N3CCC(N4CCCCC4)CC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]1:[c:7]:[c:8](-[F;D1;H0:9]):[c;H0;D3;+0:10](-Cl):[c:11](-[C;D1;H3:12]):[c:13]:1:[c:14].[C:15]-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]>>[C:15]-[C:16]-[N;H0;D3;+0:17](-[c;H0;D3;+0:10]1:[c:8](-[F;D1;H0:9]):[c:7]:[#7;a:6](:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[... | null | [] | null | null | null | null | A 70 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 4-(1-piperidyl)piperidine (70 mg, 0.4 mmol, Aldrich Chem. Co.), and carried forward as described in Example 253j-k to give... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | C1CCNCC1.c1ccn2ccccc2c1 | C1CC[NH]CC1.c1ccn2ccccc2c1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccn2ccccc2c1.C1CC1 | HCl | C(C)#N | null | null | C1CCN(C2CCNCC2)CC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>C(C)#N>Cc1c(N2CCC(N3CCCCC3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-972b3424b54942c0a0dc54962740941f | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.c1ccc(N2CCNCC2)nc1>>Cc1c(N2CCN(c3ccccn3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.N1=C(C=CC=C1)N1CCNCC1>>N1=C(C=CC=C1)N1CCN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | CC[O:25][C:23]([c:22]1[c:20](=[O:21])[n:19]2[cH:18][c:16]([F:17])[c:3](Cl)[c:2]([CH3:1])[c:31]2[c:27]([CH:28]2[CH2:29][CH2:30]2)[cH:26]1)=[O:24].[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[CH2:14][CH2:15]1>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][N:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[C... | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.c1ccc(N2CCNCC2)nc1 | Cc1c(N2CCN(c3ccccn3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 3d13f06a25d11dec98bfced8d30fa8db832cfa5df664b10802b8dba845979727 | 154ad2504fb7aaca0f52c4b8eebdfca329f4106b95adc3c71ff059886f074b58 | O=c1ccc(C2CC2)c2cc(N3CCN(c4ccccn4)CC3)ccn12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]1:[c:7]:[c:8](-[F;D1;H0:9]):[c;H0;D3;+0:10](-Cl):[c:11](-[C;D1;H3:12]):[c:13]:1:[c:14].[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[C;D1;H3:12]-[c:11]1:[c:13](:[c:14]):[#7;a:6](:[c:7]:[c:8](-[F;D1;H0:9]):[c;H0;D3;+0:10]:1-[N;H0;D3;+0:18]1-[C:17]-[C:16... | null | [] | null | null | null | null | A 60 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 4-(2-pyridyl)piperazine (63.5 mg, 0.39 mmol, Aldrich Chem. Co.), and carried forward as described in Example 253j-k to giv... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | c1ccn2ccccc2c1.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ccn2ccccc2c1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccn2ccccc2c1.C1CC1 | HCl | C(C)#N | null | null | CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O.c1ccc(N2CCNCC2)nc1>C(C)#N>Cc1c(N2CCN(c3ccccn3)CC2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92c1e74f55654031bf26bcc5f6384595 | C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>>Cc1c(N2CCC(C(C)(C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.N1CCCC1>>Cl.NC(C)(C)C1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | [NH:4]1[CH2:5][CH2:6][CH2:7][CH2:12]1.[CH3:1][c:2]1[c:3]([Cl:29])[c:13]([F:14])[cH:15][n:16]2[c:17](=[O:18])[c:19]([C:20](=[O:21])[O:22][CH2:8][CH3:9])[cH:23][c:24]([CH:25]3[CH2:10][CH2:26]3)[c:28]12>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][CH:7]([C:8]([CH3:9])([CH3:10])[NH2:11])[CH2:12]2)[c:13]([F:14])[cH:15][n:16]2[c... | C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O | Cc1c(N2CCC(C(C)(C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl | null | null | C(C)#N | Functional Group Addition | OtherReaction | 2a14acf5dad08302fea9e0bd4232a3eaeb821e0070a4f67f5349da5b06b8412a | 9483057e46e532308f07004ea2e319dd166b11d42f3c6073c033a07678c4faf6 | O=c1ccc(C2CC2)c2cc(N3CCCC3)ccn12 | [C;D1;H3:1]-[c:2]1:[c:3]2:[#7;a:4](:[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8]:1-[Cl;H0;D1;+0:9]):[c:10]:[c:11](-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[CH2;D2;+0:15]-[C;D1;H3:16]):[c:17]:[c:18]:2-[CH;D3;+0:19]1-[CH2;D2;+0:20]-[CH2;D2;+0:21]-1.[C:22]1-[CH2;D2;+0:23]-[C:24]-[C:25]-[NH;D2;+0:26]-1>>[C;D1;H3:1]-[c:2]1:[c:3]2... | null | [] | null | null | null | null | A 150 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 1-amino-1-methylethyl)pyrrolidine (155 mg, 0.77 mmol, prepared by standard method from the free base described by Hayakaw... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine | Carboxylic acid.Primary amine.Tertiary amine | C1CCNC1.c1ccn2ccccc2c1.C1CC1 | C1CC[NH]C1.c1ccn2ccccc2c1.C1CC1 | C1CC[NH]C1.c1ccn2ccccc2c1.C1CC1 | Other | C(C)#N | null | null | C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>C(C)#N>Cc1c(N2CCC(C(C)(C)N)C2)c(F)cn2c(=O)c(C(=O)O)cc(C3CC3)c12.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1497b876ea1b4e33b1825cfea95b6d86 | CCCC(NC(=O)OC(C)(C)C)C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>>CCCC(N)C1CCN(c2c(F)cn3c(=O)c(C(=O)O)cc(C4CC4)c3c2C)C1.Cl | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1.C(=O)(OC(C)(C)C)NC(CCC)C1CNCC1>>Cl.NC(CCC)C1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F | CC(C)(C)OC(=O)[NH:5][CH:4]([CH2:3][CH2:2][CH3:1])[CH:6]1[CH2:7][CH2:8][NH:9][CH2:29]1.CC[O:20][C:18]([c:17]1[c:15](=[O:16])[n:14]2[cH:13][c:11]([F:12])[c:10]([Cl:30])[c:27]([CH3:28])[c:26]2[c:22]([CH:23]2[CH2:24][CH2:25]2)[cH:21]1)=[O:19]>>[CH3:1][CH2:2][CH2:3][CH:4]([NH2:5])[CH:6]1[CH2:7][CH2:8][N:9]([c:10]2[c:11]([F:... | CCCC(NC(=O)OC(C)(C)C)C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O | CCCC(N)C1CCN(c2c(F)cn3c(=O)c(C(=O)O)cc(C4CC4)c3c2C)C1.Cl | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b96865a2ff8714677ca5bb9121091de64fb42c9ead83b6dbe92c6b4491a8f051 | 5c530bc185fdf54956090e5ff31b4625247366cd666dcae789cfd53ed04cb8aa | O=c1ccc(C2CC2)c2cc(N3CCCC3)ccn12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]1-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.C-C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]:[#7;a:14]1:[c:15]:[c:16](-[F;D1;H0:17]):[c;H0;D3;+0:18](-[Cl;H0;D1;+0:19]):[c:20](-[C;D1;H3:21]):[c:22]:1:[c:23]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4]1-[C:5]-[N;H0;D3;+0:6](-[c;H0;D... | null | [] | null | null | null | null | A 238 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 5 mL of anhydrous acetonitrile, reacted with 3-(1-(N-BOC-amino)butyl)pyrrolidine (620 mg, 1.83 mmol, prepared in step 314d above), and carried forward as described in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Secondary amine.Boc | Carboxylic acid.Primary amine.Tertiary amine | C1CCNC1.c1ccn2ccccc2c1 | C1CC[NH]C1.c1ccn2ccccc2c1 | C1CC[NH]C1.c1ccn2ccccc2c1.C1CC1 | HO- | C(C)#N | null | null | CCCC(NC(=O)OC(C)(C)C)C1CCNC1.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>C(C)#N>CCCC(N)C1CCN(c2c(F)cn3c(=O)c(C(=O)O)cc(C4CC4)c3c2C)C1.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93761b963a124e92971caa48a87616c1 | Nc1ccc2[nH]ccc2c1>>NC1CCC2NCCC2C1 | NC=1C=C2C=CNC2=CC1>>NC1CC2CCNC2CC1 | [NH2:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[cH:10]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][CH:5]2[NH:6][CH2:7][CH2:8][CH:9]2[CH2:10]1 | Nc1ccc2[nH]ccc2c1 | NC1CCC2NCCC2C1 | null | null | C(C)(=O)O | Reduction | OtherReaction | 1a8bda49366775c1ecaa868ff827f72b98c3b352605f1d6dd7d013f9a334a693 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCC2NCCC2C1 | [N;D1;H2:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[nH;D2;+0:7]:[c;H0;D3;+0:8]:2:[cH;D2;+0:9]:[cH;D2;+0:10]:1>>[N;D1;H2:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[CH;D3;+0:4]2-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[NH;D2;+0:7]-[CH;D3;+0:8]-2-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1 | null | [] | null | null | null | null | A 1.0 g sample of 5-aminoindole was hydrogenated at 4 atm H2 in 50 mL of acetic acid over 2 g of Pt2O at room temperature for 90 hours. The solution was filtered, and the solvent was removed
Conditions: See reaction.notes.procedure_details.
Workup: The solution was filtered; the solvent was removed | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2[nH]ccc2c1 | C1CCC2NCCC2C1 | C1CCC2NCCC2C1 | null | C(C)(=O)O | null | null | Nc1ccc2[nH]ccc2c1>C(C)(=O)O>NC1CCC2NCCC2C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c6f52c74e1f4a55a7103d040ea32d13 | O=C(NC1CCN(Cc2ccccc2)C1)C(F)(F)F>>FC(F)(F)CNC1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)NC(C(F)(F)F)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)N1CC(CC1)NCC(F)(F)F | O=[C:5]([C:2]([F:1])([F:3])[F:4])[NH:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1>>[F:1][C:2]([F:3])([F:4])[CH2:5][NH:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1 | O=C(NC1CCN(Cc2ccccc2)C1)C(F)(F)F | FC(F)(F)CNC1CCN(Cc2ccccc2)C1 | null | null | CCOCC | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CN2CCCC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]>>[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7] | null | [] | 0 | CELSIUS | 1 | HOUR | A 2.64 g sample of the compound from step 447a was added dropwise to a suspension of 1.11 g of LAH in ether stirred under N2 at 0° C. After one hour, the reaction was stirred at room temperature for 6 hours. The reaction was quenched by sequential addition of 1.2 mL of water, 1.2 mL of 15% NaOH and 2.4 mL of water. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | C1CC[NH]C1.c1ccccc1 | Other | CCOCC | 0 | 1 | O=C(NC1CCN(Cc2ccccc2)C1)C(F)(F)F>CCOCC>FC(F)(F)CNC1CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e4fd5c455c0c484e90968bd95fad35ab | CC(C)(C)OC(=O)N(CCF)C1CCN(Cc2ccccc2)C1>>CC(C)(C)OC(=O)N(CCF)C1CCNC1 | C(C1=CC=CC=C1)N1CC(CC1)N(CCF)C(=O)OC(C)(C)C.C(=O)[O-].[NH4+]>>C(=O)(OC(C)(C)C)N(CCF)C1CNCC1 | c1ccc(C[N:15]2[CH2:14][CH2:13][CH:12]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][F:11])[CH2:16]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][F:11])[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16]1 | CC(C)(C)OC(=O)N(CCF)C1CCN(Cc2ccccc2)C1 | CC(C)(C)OC(=O)N(CCF)C1CCNC1 | null | [Pd] | null | Deprotection | Hydrogenolysis of tertiary amines | 846a35f8c83fa58d2c714915319a8bc96745602a4dd9ac20dbad14bc1e16a470 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CCNC1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | null | [] | null | null | null | null | A 225 mg sample of the compound from step 448a was treated with ammonium formate and 10% Pd/C according to the procedure of step 445b for 1 hour, and the title compound was isolated (190 mg).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | Other | [Pd] | null | null | CC(C)(C)OC(=O)N(CCF)C1CCN(Cc2ccccc2)C1>[Pd]>CC(C)(C)OC(=O)N(CCF)C1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7b48bd4f78a1409eb2c2a20f041bf0c4 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C>>O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 | FC(C(C(=O)O)=C)(F)F.C(C1=CC=CC=C1)N(COC)C[Si](C)(C)C.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F | [O:1]=[C:2]([OH:3])[C:4]([C:5]([F:6])([F:7])[F:8])=[CH2:9].CO[CH2:10][N:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][Si](C)(C)C>>[O:1]=[C:2]([OH:3])[C:4]1([C:5]([F:6])([F:7])[F:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C | O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 236b0889f225c4fc56be294ba6ec85e0ad852c9bba072b2a4bee1d1f43481d20 | 9d56b9958d991884e2b22d7e7d6939373591b095fa4dc9cd59ac7938f5dd12b3 | c1ccc(CN2CCCC2)cc1 | C-O-[CH2;D2;+0:1]-[#7:2](-[C:3])-[CH2;D2;+0:4]-[Si](-C)(-C)-C.[CH2;D1;+0:5]=[C;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[C:3]-[#7:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[C;H0;D4;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])(-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13])-[... | null | [] | null | null | 2 | HOUR | A 2.48 g sample of 2-(trifluoromethyl)acrylic acid was dissolved in 40 mL of dry methylene chloride, and a solution of 4.75 g of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this mixture was added 2 mL of trifluoroacetic acid, and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl.Silyl protective group | null | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C>C(Cl)Cl>O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c14aa7c3cf94af8afc09046f03b475b | CC(C)(C)O.O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)NC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].CN(C)C.C(C)(C)(C)O>>C(C1=CC=CC=C1)N1CC(CC1)(C(F)(F)F)NC(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].O[C:6](=[O:7])[C:9]1([C:10]([F:11])([F:12])[F:13])[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1.[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([C:10]([F:11])([F:12])[F:13])[CH2:14][CH2:15][N... | CC(C)(C)O.O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)NC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | null | null | null | Protection | OtherReaction | 1baf304561413bd40a0af5d9e8984f017d308e72c1984fccd5cfccfb8e775719 | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | c1ccc(CN2CCCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])-[C:8]-[C:9]-[#7:10](-[C:11])-[C:12]-1.O=P(-[N;H0;D2;+0:13]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[OH;D1;+0:18]>>[C:11]-[#7:10]1-[C:9]-[C:8]-[C;H0;D4;+0:3](-[NH;D2;+0:13]-... | 96.7 | [{"value": 96.7, "product": "C(C1=CC=CC=C1)N1CC(CC1)(C(F)(F)F)NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | C1CC[NH]C1.c1ccccc1.c1ccccc1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | null | null | null | CC(C)(C)O.O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)NC1(C(F)(F)F)CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-593685df77934601a60a768a24ebbaa0 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C>>O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 | FC(C(C(=O)O)=C)(F)F.C(C1=CC=CC=C1)N(COC)C[Si](C)(C)C.C(=O)(C(F)(F)F)O>>C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F | [O:1]=[C:2]([OH:3])[C:4]([C:5]([F:6])([F:7])[F:8])=[CH2:9].CO[CH2:10][N:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][Si](C)(C)C>>[O:1]=[C:2]([OH:3])[C:4]1([C:5]([F:6])([F:7])[F:8])[CH2:9][CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C | O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 236b0889f225c4fc56be294ba6ec85e0ad852c9bba072b2a4bee1d1f43481d20 | 9d56b9958d991884e2b22d7e7d6939373591b095fa4dc9cd59ac7938f5dd12b3 | c1ccc(CN2CCCC2)cc1 | C-O-[CH2;D2;+0:1]-[#7:2](-[C:3])-[CH2;D2;+0:4]-[Si](-C)(-C)-C.[CH2;D1;+0:5]=[C;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]>>[C:3]-[#7:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[C;H0;D4;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9])(-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13])-[... | 58.9 | [{"value": 58.9, "product": "C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-(Trifluoromethyl)acrylic acid (2.48 g, 20 mmol) was dissolved in 30 mL of dry methylene chloride, a solution of 4.75 g (20 mmol) of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this solution was added 2 mL of TFA, and the solution was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Vinyl.Silyl protective group | null | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | C=C(C(=O)O)C(F)(F)F.COCN(Cc1ccccc1)C[Si](C)(C)C>C(Cl)Cl>O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2fa90453573642919084e8719e36a12a | O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1>>OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C1=CC=CC=C1)N1CC(CC1)(CO)C(F)(F)F | O=[C:2]([OH:1])[C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1>>[OH:1][CH2:2][C:3]1([C:4]([F:5])([F:6])[F:7])[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18]1 | O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1 | OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | null | null | C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(CN2CCCC2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])(-[C:8])-[C:9]-[#7:10]>>[#7:10]-[C:9]-[C:3](-[CH2;D2;+0:1]-[O;D1;H1:2])(-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])-[C:8] | 99.9 | [{"value": 99.9, "product": "C(C1=CC=CC=C1)N1CC(CC1)(CO)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | The compound from step 456a (2.32 g) was dissolved in 60 mL of dry THF, 1.12 eq of LAH (1N in dry THF) was added, and the reaction was stirred under N2 for 3 hours. The reaction was quenched by the sequential dropwise addition of 0.35 mL water, 0.35 mL of 15% NaOH and 1.3 mL of water, then the mixture was stirred for 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC[NH]C1.c1ccccc1 | Other | C1CCOC1 | null | 3 | O=C(O)C1(C(F)(F)F)CCN(Cc2ccccc2)C1>C1CCOC1>OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e94dfad47a4a48328c7cf02bef7e5975 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1>>Cc1ccccc1S(=O)(=O)OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)(CO)C(F)(F)F.N1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.N1=CC=CC=C1>>C(C1=CC=CC=C1)N1CC(CC1)(COS(=O)(=O)C=1C(=CC=CC1)C)C(F)(F)F | Cl[S:8]([c:7]1[cH:4][cH:3][c:2]([CH3:1])[cH:5][cH:6]1)(=[O:9])=[O:10].[OH:11][CH2:12][C:13]1([C:14]([F:15])([F:16])[F:17])[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[O:11][CH2:12][C:13]1([C:14]([F:15])([F:16])[F:... | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | Cc1ccccc1S(=O)(=O)OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 05fa5c39bec607db4d2ecbdc0d03c290b9a310bbf0fb1c4f6cab56ff403f2979 | cac1a51abad701d3f26583520679a70ff72a7c9f3ad49ba72aafddf242cb8589 | O=S(=O)(OCC1CCN(Cc2ccccc2)C1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[c:9]:[cH;D2;+0:10]:1.[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:10]:[c:9]:[c;H0;D3;+0:7]:1-[C;D1;H3:8] | null | [] | 0 | CELSIUS | null | null | The compound from step 456b (1.61 g) was dissolved in dry pyridine, and the solution was cooled to 0° C. To this was added 1.458 g of p-toluenesulfonyl chloride in 4 mL of dry pyridine, and the reaction was stirred at 0.C for 4 days. The mixture was diluted with 300 mL of methylene chloride, then washed with water and ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Sulfonate | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HCl | C(Cl)Cl | 0 | null | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1>C(Cl)Cl>Cc1ccccc1S(=O)(=O)OCC1(C(F)(F)F)CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a4ea40c7f75d4214b8389b24edce6e3b | CCOC(=O)C1CN(Cc2ccccc2)CC1C(=O)OCC.N>>O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1 | [Cl-].[NH4+].C(C)OC(=O)C1CN(CC1C(=O)OCC)CC1=CC=CC=C1.C1CCOC1.N>>C(C1=CC=CC=C1)N1CC2C(NC(CC2C1)=O)=O | CCO[C:3](=[O:1])[CH:4]1[CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH:15]1[C:16](OCC)=[O:17].[NH3:18]>>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][N:6]([CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[CH2:14][CH:15]2[C:16](=[O:17])[NH:18]1 | CCOC(=O)C1CN(Cc2ccccc2)CC1C(=O)OCC.N | O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1 | null | null | null | Acylation | OtherReaction | 040b55450bf31cac5dd8c67e6fe10643f123c9e4d81d04727113c7719ce7596b | ddd529cd6613435ea56b03afd8160ee4423a1103a480d9c38d135c487ceb3c06 | O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[#7:5]-[C:6]-[C:7]-1-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-O-C-C.[NH3;D0;+0:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:10]-[C:11](=[O;H0;D1;+0:9])-[CH2;D2;+0:8]-[C:7]2-[C:6]-[#7:5]-[C:4]-[C:3]-2-1 | null | [] | -40 | CELSIUS | null | null | A solution of 9.00 mmol of Na in liquid NH3 was prepared at -78° C. To this was added 15 mg of FeCl3, and the reaction mixture was warmed to -40° C. To this solution, stirred under N2, a cooled (-40° C.) solution of the compound (957 mg) from step 457a in THF was added over a 10 minute period, and the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Unsubstituted dicarboximide | null | C1CC2C[NH]CC2CN1 | C1CC2C[NH]CC2CN1.c1ccccc1 | HO- | null | -40 | null | CCOC(=O)C1CN(Cc2ccccc2)CC1C(=O)OCC.N>>O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb07eb00507a464db46f471df4d8364d | BrCc1ccccc1.O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1>>O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1Cc1ccccc1 | C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)N1CC2C(NC(CC2C1)=O)=O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1CC2C(N(C(CC2C1)=O)CC1=CC=CC=C1)=O | Br[CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][N:6]([CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[CH2:14][CH:15]2[C:16](=[O:17])[NH:18]1>>[O:1]=[C:2]1[CH2:3][CH:4]2[CH2:5][N:6]([CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[CH2:14][CH:15]2[C:16](=[O:17])[N:18]1[CH2:19][c:... | BrCc1ccccc1.O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1 | O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1Cc1ccccc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0594d38779d714bd65d325cc095c7894514d8dcb6fbbf3a456b8ee9ec8e0de46 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[C:11]>>[C:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[C:11] | 111.4 | [{"value": 111.4, "product": "C(C1=CC=CC=C1)N1CC2C(N(C(CC2C1)=O)CC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6.5 | HOUR | To a mixture of 905 mg of K2CO3 and 400 mg of the compound from step 457b in 5 mL of DMF was added 308 mg of benzyl bromide, and the reaction mixture was stirred at room temperature under N2 for 6.5 hours. The mixture was diluted with ethyl acetate, which was washed with water and brine, dried and concentrated to give ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | C1CC2C[NH]CC2CN1 | C1CC2C[NH]CC2C[NH]1 | C1CC2C[NH]CC2C[NH]1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O.C(C)(=O)OCC | null | 6.5 | BrCc1ccccc1.O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1>CN(C)C=O.C(C)(=O)OCC>O=C1CC2CN(Cc3ccccc3)CC2C(=O)N1Cc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-88b5cc36e3014d199d30d93dc27d1375 | O=C1CC2CNCC2C(=O)N1Cc1ccccc1>>c1ccc(CN2CCC3CNCC3C2)cc1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C1=CC=CC=C1)N1C(C2C(CC1=O)CNC2)=O>>C(C1=CC=CC=C1)N1CC2C(CC1)CNC2 | O=[C:7]1[N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:16][cH:15]2)[C:14](=O)[CH:13]2[CH:9]([CH2:8]1)[CH2:10][NH:11][CH2:12]2>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH:9]3[CH2:10][NH:11][CH2:12][CH:13]3[CH2:14]2)[cH:15][cH:16]1 | O=C1CC2CNCC2C(=O)N1Cc1ccccc1 | c1ccc(CN2CCC3CNCC3C2)cc1 | null | null | CCOCC.C(Cl)Cl | Reduction | OtherReaction | 51bf16baee6b2913e4f7b53e52cb314a9dfb39221c7bf5f3f490de44e84bc2de | 5c48d2345eb2fa995a1eb3dce1782e140f14b5faddfaad3c600fc635c2b998a2 | c1ccc(CN2CCC3CNCC3C2)cc1 | O=[C;H0;D3;+0:1]1-[#7:2](-[C:3])-[C;H0;D3;+0:4](=O)-[C:5]-[C:6]-[C:7]-1-[C:8]-[#7:9]>>[#7:9]-[C:8]-[C:7]1-[C:6]-[C:5]-[CH2;D2;+0:4]-[#7:2](-[C:3])-[CH2;D2;+0:1]-1 | 81.4 | [{"value": 81.4, "product": "C(C1=CC=CC=C1)N1CC2C(CC1)CNC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | A suspension of 266 mg of LAH in 10 mL of ether was stirred at 10° C. under N2. To this suspension was added 540 mg of the compound from step 457d dissolved in 10 mL of methylene chloride. The mixture was stirred under N2 for 1.5 hours. The reaction was quenched by the sequential dropwise addition of 0.3 mL water, 0.3 ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | null | C1CC2CNCC2C[NH]1 | C1CC2CNCC2C[NH]1 | c1ccccc1.C1CC2CNCC2C[NH]1 | Other | CCOCC.C(Cl)Cl | 10 | null | O=C1CC2CNCC2C(=O)N1Cc1ccccc1>CCOCC.C(Cl)Cl>c1ccc(CN2CCC3CNCC3C2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fab91be0255847869bf52f34533aab78 | O=C(C1CC1)C1CCN(Cc2ccccc2)C1.[NH4+]>>NC(C1CC1)C1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1CC(CC1)C(=O)C1CC1.C(C)(=O)[O-].[NH4+].[BH3-]C#N.[Na+]>>C(C1=CC=CC=C1)N1CC(CC1)C(C1CC1)N | O=[C:2]([CH:3]1[CH2:4][CH2:5]1)[CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1.[NH4+:1]>>[NH2:1][CH:2]([CH:3]1[CH2:4][CH2:5]1)[CH:6]1[CH2:7][CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1 | O=C(C1CC1)C1CCN(Cc2ccccc2)C1.[NH4+] | NC(C1CC1)C1CCN(Cc2ccccc2)C1 | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccc(CN2CCC(CC3CC3)C2)cc1 | O=[C;H0;D3;+0:1](-[C:2]1-[C:3]-[C:4]-1)-[C:5](-[C:6])-[C:7]-[#7:8].[NH4+;D0:9]>>[#7:8]-[C:7]-[C:5](-[CH;D3;+0:1](-[NH2;D1;+0:9])-[C:2]1-[C:3]-[C:4]-1)-[C:6] | null | [] | null | null | 16 | HOUR | A 1 g sample of the compound from step 470b, 3.37 g of ammonium acetate and 274 mg of NaBH3CN were dissolved in 15 mL of methanol, 1.2 g of 4 Å molecular sieves were added, and the mixture was stirred at room temperature under N2 for 16 hours. The mixture was filtered, the sieves washed with methanol, the wash and filt... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | C1CC1.C1CC[NH]C1.c1ccccc1 | HO- | CO | null | 16 | O=C(C1CC1)C1CCN(Cc2ccccc2)C1.[NH4+]>CO>NC(C1CC1)C1CCN(Cc2ccccc2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-599ef965de604788a8f4493886ac4c46 | CC(C)(C)OC(=O)NC(C1CC1)C1CCN(Cc2ccccc2)C1>>CC(C)(C)OC(=O)NC(C1CC1)C1CCNC1 | C(=O)(OC(C)(C)C)NC(C1CC1)C1CN(CC1)CC1=CC=CC=C1>>C(=O)(OC(C)(C)C)NC(C1CC1)C1CNCC1 | c1ccc(C[N:16]2[CH2:15][CH2:14][CH:13]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:10]3[CH2:11][CH2:12]3)[CH2:17]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]([CH:10]1[CH2:11][CH2:12]1)[CH:13]1[CH2:14][CH2:15][NH:16][CH2:17]1 | CC(C)(C)OC(=O)NC(C1CC1)C1CCN(Cc2ccccc2)C1 | CC(C)(C)OC(=O)NC(C1CC1)C1CCNC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 846a35f8c83fa58d2c714915319a8bc96745602a4dd9ac20dbad14bc1e16a470 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CC(CC2CC2)CN1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | 35.1 | [{"value": 35.1, "product": "C(=O)(OC(C)(C)C)NC(C1CC1)C1CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 42 | HOUR | A sample (548 mg) of the compound from step 470d was dissolved in methanol, 140 mg of 10% Pd/C was added, and the mixture was hydrogenated at 4 atm H2 for 42 hours at room temperature. The solution was filtered, and the solvent was removed to give 140 mg of the title compound.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | C1CC1.C1CCNC1 | Other | [Pd].CO | null | 42 | CC(C)(C)OC(=O)NC(C1CC1)C1CCN(Cc2ccccc2)C1>[Pd].CO>CC(C)(C)OC(=O)NC(C1CC1)C1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd232c0b8b38439bb9e8a89504c75742 | CCOC(=O)C[C@H](C[N+](=O)[O-])[C@@H]1CCCN1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-] | C(=O)(OC(C)(C)C)N1[C@@H](CCC1)[C@H](CC(=O)OCC)C[N+](=O)[O-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(=O)(OC(C)(C)C)N1[C@@H](CCC1)[C@H](CCO)C[N+](=O)[O-] | CCO[C:15]([CH2:14][C@@H:13]([C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1)[CH2:17][N+:18](=[O:19])[O-:20])=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[C@H:13]([CH2:14][CH2:15][OH:16])[CH2:17][N+:18](=[O:19])[O-:20] | CCOC(=O)C[C@H](C[N+](=O)[O-])[C@@H]1CCCN1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-] | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | A 7.5 g sample of ethyl 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanoate (prepared according to the procedure of Hayakawa et al., U.S. Pat. No. 5,098,912, issued Mar. 24, 1992) was dissolved in 35 mL of ether and treated with 0.76 g of LAH. After careful quenching of the excess reagents, the title compound was extract... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1 | HO- | CCOCC | null | null | CCOC(=O)C[C@H](C[N+](=O)[O-])[C@@H]1CCCN1C(=O)OC(C)(C)C>CCOCC>CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d35336a8d63f46faa12cbe3c8194e4f3 | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-].CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCOS(C)(=O)=O)C[N+](=O)[O-] | C(=O)(OC(C)(C)C)N1[C@@H](CCC1)[C@H](CCO)C[N+](=O)[O-].CS(=O)(=O)Cl>>CS(=O)(=O)OCC[C@H](C[N+](=O)[O-])[C@H]1N(CCC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[C@H:13]([CH2:14][CH2:15][OH:16])[CH2:21][N+:22](=[O:23])[O-:24].Cl[S:17]([CH3:18])(=[O:19])=[O:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[C@H:13]([CH2:14][CH2:15][O:16][S:17]([CH3:18])... | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-].CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCOS(C)(=O)=O)C[N+](=O)[O-] | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CCNC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | A 3.5 g sample of the alcohol from step 471a above was dissolved in 25 mL of methylene chloride and treated with methanesulfonyl chloride an TEA at 0° C. for 2 hours. The reaction mixture was washed with NaHCO3 solution and water, and the solvent was removed. The residue was chromatographed on silica gel to give 3 g of... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]C1 | HCl | C(Cl)Cl | null | null | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-].CS(=O)(=O)Cl>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCOS(C)(=O)=O)C[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-722fc1c8e1ff43a08b3a226da745e8d4 | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]>>CC(C)(C)OC(=O)N1CCC[C@H]1[C@@H]1CCNC1 | C(=O)(OC(C)(C)C)N1[C@@H](CCC1)[C@H](CCO)C[N+](=O)[O-]>>C(=O)(OC(C)(C)C)N1[C@@H](CCC1)[C@H]1CNCC1 | O=[N+:16]([O-])[CH2:17][C@H:13]([C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1)[CH2:14][CH2:15]O>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[C@@H:13]1[CH2:14][CH2:15][NH:16][CH2:17]1 | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-] | CC(C)(C)OC(=O)N1CCC[C@H]1[C@@H]1CCNC1 | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | 48828c3c93909116a9ae11bcb1915303abfc7a49ed11087299d13a2c0f45df78 | 764b36840e9259f724a61c40582ce8fb4279526cbcc6fde89825049b30b4f9a4 | C1CN[C@H]([C@@H]2CCNC2)C1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[N+;H0;D3:5](=O)-[O-]>>[C:3]1-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C:4]-1 | null | [] | null | null | null | null | The ether compound from step 471a was treated by hydrogenation at 4 atm H2 over Pd/C in methanol to give the tile compound.
Conditions: See reaction.notes.procedure_details.
Workup: to give the tile compound | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Secondary amine | null | C1CCNC1 | C1CC[NH]C1.C1CCNC1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CCC[C@H]1[C@H](CCO)C[N+](=O)[O-]>[Pd].CO>CC(C)(C)OC(=O)N1CCC[C@H]1[C@@H]1CCNC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bb91f751bb204267a4e371b6462d78b9 | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>>CCOC(=O)c1cc(C2CC2)c2c(C)c(CC(=O)OC(c3ccccc3)c3ccccc3)c(F)cn2c1=O | O.C(CC(=O)OC(C)(C)C)(=O)OC(C)(C)C.[H-].[Na+].C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1>>C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)CC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C)C1CC1 | O=[C:24](O[C:26]([CH3:21])([CH3:22])[CH3:25])[CH2:16][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:27])[CH3:31].Cl[c:15]1[c:13]([CH3:14])[c:12]2[c:8]([CH:9]3[CH2:10][CH2:11]3)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:37](=[O:38])[n:36]2[cH:35][c:33]1[F:34]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH:9]2[C... | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O | CCOC(=O)c1cc(C2CC2)c2c(C)c(CC(=O)OC(c3ccccc3)c3ccccc3)c(F)cn2c1=O | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 2f864c10139aa052df1f1d82796d030c15fc9d3baed31fefa0f2c376331a7931 | 308879df3a0fd871e75ae976291abb2a3f6f52c3704a24fb5ddea62844558dfc | O=C(Cc1ccn2c(=O)ccc(C3CC3)c2c1)OC(c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4](:[c:5]):[#7;a:6](:[c:7]):[c:8]:[c:9]:1-[F;D1;H0:10].O=[C;H0;D3;+0:11](-O-[C;H0;D4;+0:12](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[CH3;D1;+0:15])-[CH2;D2;+0:16]-[C:17](=[O;D1;H0:18])-[#8:19]-[C;H0;D4;+0:20](-[CH3;D1;+0:21])(-[CH3;D1;+0:22])-[CH3;D1;+0:23]>>[C;D1;H3:3]-[c:2]1:[c:4](... | null | [] | null | null | null | null | To a suspension of NaH in DMF with ice bath cooling is added di-t-butyl malonate. After the addition, 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester from Example 253i above is added. The reaction is then heated to 50° to 60° C., and the mixture is poured into water and acidi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Boc.Boc | Ester | c1ccn2ccccc2c1 | c1ccn2ccccc2c1.c1ccccc1.c1ccccc1 | C1CC1.c1ccn2ccccc2c1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | null | CC(C)(C)OC(=O)CC(=O)OC(C)(C)C.CCOC(=O)c1cc(C2CC2)c2c(C)c(Cl)c(F)cn2c1=O>CN(C)C=O>CCOC(=O)c1cc(C2CC2)c2c(C)c(CC(=O)OC(c3ccccc3)c3ccccc3)c(F)cn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9a35b5778f84e018ef46a7daf51dbfd | CC(C)(C)O.CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(NC(=O)OC(C)(C)C)CC3)c(F)cn2c1=O | C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)C1(CC1)C(=O)O)C)C1CC1.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C(C)(C)(C)O.C(C)N(CC)CC>>C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)C1(CC1)NC(=O)OC(C)(C)C)C)C1CC1 | [OH:20][C:21]([CH3:22])([CH3:23])[CH3:24].O[C:18]([C:16]1([c:15]2[c:13]([CH3:14])[c:12]3[c:8]([CH:9]4[CH2:10][CH2:11]4)[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:31](=[O:32])[n:30]3[cH:29][c:27]2[F:28])[CH2:25][CH2:26]1)=[O:19].[N-]=[N+]=[N:17]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c... | CC(C)(C)O.CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(NC(=O)OC(C)(C)C)CC3)c(F)cn2c1=O | null | null | O1CCOCC1 | Protection | OtherReaction | 14cfb34213c56f76d6c0b0fbad6fbcbdb23f6c7be623f3f9740afd7d91c67e5f | b944663b5278c281edc6c72611c69e4309c3f5728dcd63d51413085e18c1d2e7 | O=c1ccc(C2CC2)c2cc(C3CC3)ccn12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[c:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2)-[C:10]-[C:11]-1.O=P(-[N;H0;D2;+0:12]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[OH;D1;+0:17]>>[C;D1;H3:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[O;H0;D2;+0:17]-[C;H0;D3;+0:1](=[O... | null | [] | null | null | null | null | A sample of the product from Step 477d is heated with diphenylphosphoryl azide, t-butanol, triethylamine and dioxane. The solvents is removed under vacuum. The residue is dissolved in methylene chloride, washed with water and dried over MgSO4 and concentrated under vacuum. The title compound is purified by chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol | Carbamic ester.Ether.Boc | C1CC1.c1ccccc1.c1ccccc1 | C1CC1 | C1CC1.c1ccn2ccccc2c1.C1CC1 | HO- | O1CCOCC1 | null | null | CC(C)(C)O.CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O1CCOCC1>CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(NC(=O)OC(C)(C)C)CC3)c(F)cn2c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-683f6b06ba0444c18452d135760784ee | N#Cc1ccccc1.[N-]=[N+]=[N-]>>c1ccc(-c2nnn[nH]2)cc1 | Cl.CN(C=O)C.C(C1=CC=CC=C1)#N.[N-]=[N+]=[N-].[Na+]>>C1(=CC=CC=C1)C1=NN=NN1 | [cH:1]1[cH:2][cH:3][c:4]([C:5]#[N:6])[cH:10][cH:11]1.[N+:7](=[N-:8])=[N-:9]>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7][n:8][nH:9]2)[cH:10][cH:11]1 | N#Cc1ccccc1.[N-]=[N+]=[N-] | c1ccc(-c2nnn[nH]2)cc1 | null | [Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-] | O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nnn[nH]2)cc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:[nH;D2;+0:3]:1):[c:9]:[c:10] | 90.1 | [{"value": 90.0, "product": "C1(=CC=CC=C1)C1=NN=NN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "C1(=CC=CC=C1)C1=NN=NN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Zinc chloride (3.3 g, 24.3 mmol, 0.5 eq) was added to 15 mL of N,N-dimethylformamide in small portions while maintaining the temperature below 60° C. The suspension of zinc chloride was cooled to room temperature and treated with 5.0 g of benzonitrile (48.5 mmol, 1.0 eq) followed by 3.2 g of sodium azide (48.5 mmol, 1.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | null | [Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-].O | null | null | N#Cc1ccccc1.[N-]=[N+]=[N-]>[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].[Cl-].O>c1ccc(-c2nnn[nH]2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6cdb42c88e1c4050ae28ae6ce211a291 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(-c2nnn[nH]2)cc1>>c1ccc(-c2nnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | O.C(C)N(CC)CC.C1(=CC=CC=C1)C1=NN=NN1.C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl>>C1(=CC=CC=C1)C=1N=NN(N1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7][n:8][nH:28]2)[cH:29][cH:30]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7][n:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)([c:16]3... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(-c2nnn[nH]2)cc1 | c1ccc(-c2nnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | null | null | O1CCCC1.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c814b61f4411b43802c99c033287485a681b4494d43aabc070529707b2f4fba2 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | c1ccc(-c2nnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[c:11]-[c:12]1:[#7;a:13]:[#7;a:14]:[n;H0;D2;+0:15]:[nH;D2;+0:16]:1>>[c:3]:[c:2](-[C;H0;D4;+0:1](-[c:5](:[c:6]):[c:7])(-[c:8](:[c:9]):[c:10])-[n;H0;D3;+0:15]1:[#7;a:14]:[#7;a:13]:[c:12](-[c:11]):[n;H0;D2;+0:16]:1):[c:4] | 100 | [{"value": 100.0, "product": "C1(=CC=CC=C1)C=1N=NN(N1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "C1(=CC=CC=C1)C=1N=NN(N1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of 5.0 g (34.2 mmol) of 5-phenyltetrazole in 55 mL of acetone was added 5.0 mL of triethylamine (3.6 g, 35.6 mmol, 1.04 eq). After 15 minutes, a solution of 10.0 g of triphenylmethyl chloride (35.9 mmol, 1.05 eq) in 20 mL of tetrahydrofuran was added and the mixture stirred at room temperature for one h... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1nnn[nH]1 | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | O1CCCC1.CC(=O)C | null | 0.25 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(-c2nnn[nH]2)cc1>O1CCCC1.CC(=O)C>c1ccc(-c2nnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b176a6bf0704d8d9641aa04cf712b48 | COC(=O)CC(C)(C)C(=O)O.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>COC(=O)CC(C)(C)NC(=O)OCc1ccccc1 | C(C1=CC=CC=C1)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].COC(CC(C(=O)O)(C)C)=O.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(=O)NC(CC(=O)OC)(C)C | O[C:10]([C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])([CH3:7])[CH3:8])=[O:11].[OH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[N-]=[N+]=[N:9]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]([CH3:7])([CH3:8])[NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | COC(=O)CC(C)(C)C(=O)O.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | COC(=O)CC(C)(C)NC(=O)OCc1ccccc1 | null | null | C1=CC=CC=C1 | Protection | OtherReaction | 1e58f6d4d49ad6167ca3c26ac5f42436cf03d7623c1813226bf87246cca930d2 | aa6034c174fc48fa7e86a3e3e456bc7f49699778f1361299699fbbc966318b2e | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10].O=P(-[N;H0;D2;+0:11]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[OH;D1;+0:12]-[C:13]-[c:14]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C:6]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH;D2;+0:11]-[C;H... | 75.1 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC(=O)OC)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC(=O)OC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To 14.7 g (91.8 mmol) of 2,2-dimethylbutanedioic acid-4-methyl ester in 150 mL of benzene was added 13 mL of triethylamine (9.4 g, 93 mmol) followed by 21.8 mL of diphenylphosphoryl azide (27.8 g, 101 mmol). The mixture was heated under nitrogen at reflux for 45 minutes then 19 mL (19.9 g, 184 mmol) of benzyl alcohol w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Primary alcohol | Carbamic ester.Ether | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C1=CC=CC=C1 | null | 16 | COC(=O)CC(C)(C)C(=O)O.OCc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1=CC=CC=C1>COC(=O)CC(C)(C)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-17ae2f40160841b6afa956e1bf8b3a72 | COC(=O)CC(C)(C)NC(=O)OCc1ccccc1>>CC(C)(CC(=O)O)NC(=O)OCc1ccccc1 | COC(CC(C)(C)NC(=O)OCC1=CC=CC=C1)=O.[OH-].[Na+]>>C(C1=CC=CC=C1)OC(=O)NC(CC(=O)O)(C)C | C[O:7][C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:6]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[OH:7])[NH:8][C:9](=[O:10])[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COC(=O)CC(C)(C)NC(=O)OCc1ccccc1 | CC(C)(CC(=O)O)NC(=O)OCc1ccccc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 99.7 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C(C1=CC=CC=C1)OC(=O)NC(CC(=O)O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 18.27 g (68.9 mmol) of 3-benzyloxycarbonylamino-3-methylbutanoic acid methyl ester in 20 mL of methanol at room temperature was treated dropwise with 51 mL of 2N NaOH (102 mmol). The mixture was stirred at room temperature for 16 hours then transferred to a separatory funnel and washed with hexane (3×). T... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 16 | COC(=O)CC(C)(C)NC(=O)OCc1ccccc1>CO>CC(C)(CC(=O)O)NC(=O)OCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a78a3036fc884a618177322321075319 | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CC[C@@H](N)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1>>CC[C@@H](NC(=O)CC(C)(C)NC(=O)OC(C)(C)C)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1 | Cl.N[C@@H](C(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)C1=CC=CC=C1)CC.C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C>>C(C)(C)(C)OC(=O)NC(CC(=O)N[C@@H](C(=O)N(CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)C1=CC=CC=C1)CC)(C)C | O[C:5](=[O:6])[CH2:7][C:8]([CH3:9])([CH3:10])[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][C@@H:3]([NH2:4])[C:19](=[O:20])[N:21]([CH2:22][c:23]1[cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2-[c:33]2[n:34][n:35][n:36][nH:37]2)[cH:38][cH:39]1)[c:40]1[cH:41][cH:42][cH:43][... | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CC[C@@H](N)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1 | CC[C@@H](NC(=O)CC(C)(C)NC(=O)OC(C)(C)C)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(NCc2ccc(-c3ccccc3-c3nnn[nH]3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[#7:6](-[c:7])-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[NH2;D1;+0:12]>>[C:5]-[#7:6](-[c:7])-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | Prepared as in Example 1, Step N from (R)-2-amino-N-phenyl-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]butanamide, hydrochloride and 3-t-butoxycarbonylamino-3-methylbutanoic acid, N-hydroxysuccinimide ester.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1 | HO- | null | null | null | CC(C)(CC(=O)O)NC(=O)OC(C)(C)C.CC[C@@H](N)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1>>CC[C@@H](NC(=O)CC(C)(C)NC(=O)OC(C)(C)C)C(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d15441bff9244cf8bac899003f74801 | CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.OCc1ccccc1>>CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | O.C(C)(C)(C)OC(=O)N[C@H](CC1=CNC2=CC=CC=C12)C(=O)O.C(C1=CC=CC=C1)O.Cl.CN(CCCN=C=NCC)C>>C(C1=CC=CC=C1)OC([C@H](NC(=O)OC(C)(C)C)CC1=CNC2=CC=CC=C12)=O | O[C:20]([C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][nH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12)=[O:21].[OH:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][c:11]1[cH:12][nH:13][c:14]2[cH:15][cH... | CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.OCc1ccccc1 | CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(CCc1c[nH]c2ccccc12)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[OH;D1;+0:13]-[C:14]-[c:15]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:13]-[C:14]-[c:15] | null | [] | null | null | null | null | Finely divided t-butoxycarbonyl-D-tryptophan (3 g, 10 mmol) was suspended in methylene chloride and benzyl alcohol (1.08 mL, 10 mmol) and 4-dimethylaminopyridine (0.12 g, 1 mmol) were added and stirred at room temperature. Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10 mmol) was then adde... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | null | CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O.OCc1ccccc1>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)(C)OC(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1 |
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