dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9054b5aa3c1b4875811af2b6a2856c29 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.[BH4-].[Na+]>>C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | [CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20]>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20] | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)cc1 | [C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[#16;a:7]:[c:8]>>[C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[#16;a:7]:[c:8] | null | [] | null | null | 15 | MINUTE | To a solution of 3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.084 g, 0.283 mmole) in THF (3 mL), is added to NaBH4 (0.023 g, 0.622 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using saturated... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.25 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>C1CCOC1>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e1267c207b141c1b44d49f744e051d6 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO>>CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO>>C(C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | [CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20] | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccc(-c2cccs2)cc1 | [C:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](-[C;D1;H3:8])=[CH2;D1;+0:9]>>[C:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1-[CH;D3;+0:7](-[C;D1;H3:8])-[CH3;D1;+0:9] | null | [] | null | null | null | null | The solution of [3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-methanol (0.084 g, 0.282 mmole) is stirred under nitrogen gas in presence of 10% palladium on carbon (0.085 g) for 16 hours. The catalyst is removed by filtration, and the filtrate is concentrated to provide the titled compound as white solid, w... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccsc1.c1ccccc1 | null | [Pd] | null | null | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO>[Pd]>CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-617d2c25a5ed444db23b3ce802b6ae6c | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O>>CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)=O | [CH3:1][CH:2]([OH:3])[c:4]1[s:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH3:19]>>[CH3:1][C:2](=[O:3])[c:4]1[s:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH3:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | O=[Mn]=O.O=[Mn]=O | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(-c2cccs2)cc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | null | null | To a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanol (see Preparation 2)(4.40 g, 15.4 mmole), is added MnO2 (7.88 g, 77.0 mmole) in one portion. The mixture is heated under reflux for 16 hours, more MnO2 (7.88 g, 77.0 mmole) is added to the reaction and continued to reflux for 4 hours. The m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccsc1.c1ccccc1 | null | O=[Mn]=O.O=[Mn]=O | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O>O=[Mn]=O.O=[Mn]=O>CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62425f70050d42c1a414238fad5cd29a | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)=O.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[K+]>>COC=C(C)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F | O=[C:4]([CH3:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19][c:20]1[CH3:21].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][O:2][CH3:1])cc1>>[CH3:1][O:2][CH:3]=[C:4]([CH3:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19][c:20]... | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Wittig with Phosphonium | 183135d5dbdf71ecf3df8474088b3eff5f51c5ed39d27c562953dba9cee5701e | bc49b37cfad095ef21edb56cfe703ef15fa2ade769431a305bbc0346ae1ffa96 | c1ccc(-c2cccs2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:7]-[#8:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 30 | MINUTE | To a solution of (methoxymethyl)triphenyl phosphonium chloride (3.96 g, 10.76 mmole) in toluene/THF (2:1, 60 mL), is added potassium t-butoxide (1.21 g, 10.76 mmole) in one portion and stirred for 30 minutes. To the resulting ylide, is injected into a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccsc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | null | 0.5 | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C.C1CCOC1>COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-544a0915018b4af0ad3c53ce5e7a3704 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C=O)C.[BH4-].[Na+]>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(CO)C | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[CH:19]=[O:20]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[CH2:19][OH:20] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)cc1 | [#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-[OH;D1;+0:6] | null | [] | null | null | 15 | MINUTE | To a solution of 2-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-propionaldehyde (1.40 g, 4.69 mmole) in THF (20 mL), is added to NaBH4 (0.266 g, 7.04 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using NH4Cl(a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.25 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O>C1CCOC1>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6f89c9e01fc4555ad8b0887273f9788 | CC(=O)c1cc(-c2ccccc2)sc1C>>Cc1sc(-c2ccccc2)cc1C(C)O | CC=1SC(=CC1C(C)=O)C1=CC=CC=C1.[Li+].[BH4-]>>CC=1SC(=CC1C(C)O)C1=CC=CC=C1 | [CH3:1][c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]1[C:13]([CH3:14])=[O:15]>>[CH3:1][c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]1[CH:13]([CH3:14])[OH:15] | CC(=O)c1cc(-c2ccccc2)sc1C | Cc1sc(-c2ccccc2)cc1C(C)O | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cccs2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[C;D1;H3:9]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[C;D1;H3:9] | null | [] | null | null | 30 | MINUTE | To a solution of 1-(2-Methyl-5-phenyl-thiophen-3-yl)-ethanone (1.08 g, 5.0.0 mmole) in THF (20 mL), is added to LiBH4 (0.327 g, 15.0 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 30 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using NH4Cl(aq) (50 mL) at 0° C. The TH... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.5 | CC(=O)c1cc(-c2ccccc2)sc1C>C1CCOC1>Cc1sc(-c2ccccc2)cc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a0af10095864711a1b8cd8e75ad68c5 | COC(=O)CCc1ccc(O)cc1C.FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1>>COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | ClCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F.COC(CCC1=C(C=C(C=C1)O)C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>COC(CCC1=C(C=C(C=C1)OCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:28][c:29]1[CH3:30].Cl[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[s:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][c:16... | COC(=O)CCc1ccc(O)cc1C.FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1 | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#16;a:4]:[c:5] | null | [] | 50 | CELSIUS | null | null | To a solution of 2-Chloromethyl-5-(4-trifluoromethyl-phenyl)-thiophene (0.210 g, 0.760 mmole) and 3-(4-Hydroxy-2-methyl-phenyl)-propionic acid methyl ester (0.147 g, 0.760 mmole) in acetonitrile (5 mL), is added cesium carbonate (0.248 mL, 0.760 mmole) in one portion. The reaction is heated at 50° C. overnight, then co... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HCl | C(C)#N | 50 | null | COC(=O)CCc1ccc(O)cc1C.FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1>C(C)#N>COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78009c9577e44dcfabb11ce3612f5146 | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C>>Cc1cc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)ccc1CCC(=O)O | COC(CCC1=C(C=C(C=C1)OCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F)C)=O.[OH-].[Na+].C1CCOC1>>CC1=C(C=CC(=C1)OCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F)CCC(=O)O | C[O:29][C:27]([CH2:26][CH2:25][c:24]1[c:2]([CH3:1])[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[s:21]2)[cH:22][cH:23]1)=[O:28]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])... | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | Cc1cc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)ccc1CCC(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | 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 | 3-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester (0.170 g, 0.390 mmole) is treated with a mixture of NaOH(aq) (1 mL)/THF (3 mL)/MeOH (3 mL) at room temperature overnight. The organic solvents are removed on rota-vapor. The residue is diluted with water (10 mL), acidi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | Other | CO | null | null | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C>CO>Cc1cc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)ccc1CCC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3191e85e53f4984b08595ad3d44059a | COC(=O)CCc1ccc(O)cc1C.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1>>COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.FC(C1=CC=C(C=C1)C1=CC=C(S1)CO)(F)F.COC(CCC1=C(C=C(C=C1)O)C)=O.C(CCC)P(CCCC)CCCC>>COC(CCC1=C(C=C(C=C1)OCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:28][c:29]1[CH3:30].O[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[s:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][c:16]... | COC(=O)CCc1ccc(O)cc1C.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | null | null | CCCCCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[#16;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#16;a:4]:[c:5] | null | [] | null | null | 8 | HOUR | To a solution of [5-(4-Trifluoromethyl-phenyl)-thiophen-2-yl]-methanol (0.063 g, 0.232 mmole) and 3-(4-Hydroxy-2-methyl-phenyl)-propionic acid methyl ester (0.045 g, 0.232 mmole) in toluene (2 mL) at room temperature, is added tributylphosphine (0.087 mL, 0.348 mmole) followed by a solution of 1,1′-(azodicarbonyl)-dipi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CCCCCC.C1(=CC=CC=C1)C | null | 8 | COC(=O)CCc1ccc(O)cc1C.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1>CCCCCC.C1(=CC=CC=C1)C>COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abab57cd1c474a29a460a6693f315ad0 | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C>>Cc1cc(OCc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1CCC(=O)O | COC(CCC1=C(C=C(C=C1)OCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F)C)=O.[OH-].[Na+].C1CCOC1>>CC1=C(C=CC(=C1)OCC=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F)CCC(=O)O | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[s:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]3)[cH:20][cH:21]2)[cH:23][cH:24][c:25]1[CH2:26][CH2:27][C:28](=[O:29])[O:30][CH3:22]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[s:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:... | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C | Cc1cc(OCc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1CCC(=O)O | null | null | CO | Miscellaneous | OtherReaction | 6eaa82c9bff7dcd0e914ed4c1704b92012af71ed9c92c02e6e67b81cb6b19c80 | b51da43dbb7140dac708518f8dbf83c5b067214819134afdb3f427285d08d6f8 | c1ccc(OCc2ccc(-c3ccccc3)s2)cc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[CH3;D1;+0:5].[C:6]-[c:7]1:[#16;a:8]:[c:9](-[c:10]):[c:11]:[cH;D2;+0:12]:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:6]-[c:7]1:[#16;a:8]:[c:9](-[c:10]):[c:11]:[c;H0;D3;+0:12]:1-[CH3;D1;+0:5] | null | [] | null | null | null | null | 3-{2-Methyl-4-[5-(4-trifluoromethyl-phenyl)-thiophen-2-ylmethoxy]-phenyl}-propionic acid methyl ester (0.043 g, 0.0959 mmole) is treated with a mixture of NaOH (aq) (1 mL)/THF (3 mL)/MeOH (3 mL) at room temperature overnight. The organic solvents are removed on rota-vapor. The residue is diluted with water (10 mL), aci... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccsc1 | c1ccsc1 | c1ccccc1.c1ccsc1.c1ccccc1 | null | CO | null | null | COC(=O)CCc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)s2)cc1C>CO>Cc1cc(OCc2sc(-c3ccc(C(F)(F)F)cc3)cc2C)ccc1CCC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-618470c700bc4ec5b8d4465d4eb4b009 | CC(O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1I.COC(=O)CCc1ccc(S)cc1C>>COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C | N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.IC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O.COC(CCC1=C(C=C(C=C1)S)C)=O.C(CCC)P(CCCC)CCCC>>COC(CCC1=C(C=C(C=C1)SC(C)C=1SC(=CC1I)C1=CC=C(C=C1)C(F)(F)F)C)=O | O[CH:12]([CH3:13])[c:14]1[s:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[cH:27][c:28]1[I:29].[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([SH:11])[cH:30][c:31]1[CH3:32]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([S:11][CH:12]([CH3:13])[c:1... | CC(O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1I.COC(=O)CCc1ccc(S)cc1C | COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C | null | null | CCCCCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 7cb493581910e8c50a30f8276e25f4f2a94eede984d74451e64f1f8213a0ace9 | 71a01c6a04600b773cc4425dd7382ceba509351bcb3a39361eb82b2bd06d5f60 | c1ccc(SCc2ccc(-c3ccccc3)s2)cc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[SH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:2]-[CH;D3;+0:1](-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 8 | HOUR | To a solution of 1-[3-Iodo-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanol (1.52 g, 3.96 mmole) and 3-(4-Mercapto-2-methyl-phenyl)-propionic acid methyl ester (0.769 g, 3.96 mmole) in toluene (20 mL) at room temperature, is added tributylphosphine (1.98 mL, 7.92 mmole) followed by a solution of 1,1′-(azodicarbonyl)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CCCCCC.C1(=CC=CC=C1)C | null | 8 | CC(O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1I.COC(=O)CCc1ccc(S)cc1C>CCCCCC.C1(=CC=CC=C1)C>COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fe04c369f834c55bf75cf7cae10a5ea | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C>>C=Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)Sc1ccc(CCC(=O)OC)c(C)c1 | COC(CCC1=C(C=C(C=C1)SC(C)C=1SC(=CC1I)C1=CC=C(C=C1)C(F)(F)F)C)=O.C(CCC)[Sn](C=C)(CCCC)CCCC>>COC(CCC1=C(C=C(C=C1)SC(C)C=1SC(=CC1C=C)C1=CC=C(C=C1)C(F)(F)F)C)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].I[c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[s:16][c:17]1[CH:18]([CH3:19])[S:20][c:21]1[cH:22][cH:23][c:24]([CH2:25][CH2:26][C:27](=[O:28])[O:29][CH3:30])[c:31]([CH3:32])[cH:33]1>>[CH2:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C | C=Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)Sc1ccc(CCC(=O)OC)c(C)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_vinyl | 22882a41b1efd9d9d1c0470da8c50df805aff9c8c0e445e747ee85b348dde8dc | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | c1ccc(SCc2ccc(-c3ccccc3)s2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:1]=[C;D1;H2:2].I-[c;H0;D3;+0:3]1:[c:4]:[c:5](-[c:6]):[#16;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#16;a:7]:[c:5](-[c:6]):[c:4]:[c;H0;D3;+0:3]:1-[CH;D2;+0:1]=[C;D1;H2:2] | null | [] | 80 | CELSIUS | null | null | The solution of 3-(4-{1-[3-Iodo-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethylsulfanyl}-2-methyl-phenyl)-propionic acid methyl ester (0.195 g, 0.348 mmole) and tributyl(vinyl)tin (0.331 g, 1.04 mmole) in toluene (3 mL) is bubbled with nitrogen gas for 10 minutes. To it is added tetrakis(triphenylphosphine)palladium(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1.c1ccccc1 | HI.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 80 | null | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.COC(=O)CCc1ccc(SC(C)c2sc(-c3ccc(C(F)(F)F)cc3)cc2I)cc1C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>C=Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)Sc1cc... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58bb9fe142bf4c379013ede835e2d216 | C=O.O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>CN1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCNCC1)(C1=CC=CC=C1)O)F.C=O.C(#N)[BH3-].[Na+]>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C)(C1=CC=CC=C1)O)F | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][CH:5]([O:6][C:7](=[O:8])[C@:9]([OH:10])([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@@H:17]2[CH2:18][CH2:19][C:20]([F:21])([F:22])[CH2:23]2)[CH2:24][CH2:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:6][C:7](=[O:8])[C@:9]([OH:10])([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@@H:17]2[CH2:... | C=O.O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | CN1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | null | [Cl-].[Zn+2].[Cl-] | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | e23db47f33553519e7237e30c3b19a21fcbb90bde44fbb5566021920bc9b7164 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | 30 | MINUTE | To a solution of 17 mg of piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate and 0.03 ml of formaldehyde (35% aqueous solution) in 1 ml of methanol, 0.3 ml of advancedly prepared 0.3 M methanol solution of sodium cyanoborohydride and zinc chloride (1:0.5) was added at room temperature, follo... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | Other | [Cl-].[Zn+2].[Cl-].CO.C(C)(=O)OCC | null | 0.5 | C=O.O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>[Cl-].[Zn+2].[Cl-].CO.C(C)(=O)OCC>CN1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1ff75c1b6ee41e5b300884db48fa03a | CI.CN1CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>C[N+]1(C)CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[I-] | FC1(C[C@@H](CC1)[C@](C(=O)OC1C2CN(CC1CCC2)C)(C2=CC=CC=C2)O)F.CI>>[I-].FC1(C[C@@H](CC1)[C@](C(=O)OC1C2C[N+](CC1CCC2)(C)C)(C2=CC=CC=C2)O)F | [CH3:1][I:30].[N:2]1([CH3:3])[CH2:4][CH:5]2[CH2:6][CH2:7][CH2:8][CH:9]([CH2:10]1)[CH:11]2[O:12][C:13](=[O:14])[C@:15]([OH:16])([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C@@H:23]1[CH2:24][CH2:25][C:26]([F:27])([F:28])[CH2:29]1>>[CH3:1][N+:2]1([CH3:3])[CH2:4][CH:5]2[CH2:6][CH2:7][CH2:8][CH:9]([CH2:10]1)[CH:11]2[O:12][... | CI.CN1CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | C[N+]1(C)CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 1b2aff627d0c4e49d657f34e1b312c4fe18d1d1e107350bbcb67c0f6519f919a | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | O=C(OC1C2CCCC1C[NH2+]C2)C(c1ccccc1)C1CCCC1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]-[C:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C:7]-[C:8]>>[C:3]-[C:4]-[N+;H0;D4:5](-[C;D1;H3:6])(-[CH3;D1;+0:1])-[C:7]-[C:8].[I-;H0;D0:2] | null | [] | null | null | null | null | Each of the diastereomers of 3-methyl-3-azabicyclo[3.3.1]-non-9-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate was dissolved in 0.5 ml of methyl iodide and heated under reflux for 12 hours. Thereafter the excessive reagent was distilled off under reduced pressure. The residue was purified on a pre... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC2C[NH]CC(C1)C2 | C1CC2C[NH+]CC(C1)C2 | C1CC2C[NH+]CC(C1)C2.c1ccccc1.C1CCCC1 | null | null | null | null | CI.CN1CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>C[N+]1(C)CC2CCCC(C1)C2OC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-73ce964deb3f4062b3be28927b87c3b0 | CC=O.O=C(OC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>>CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCNCC1)(C1=CC=C(C=C1)Cl)O)F.C(C)=O.C(#N)[BH3-].[Na+]>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)CC)(C1=CC=C(C=C1)Cl)O)F | O=[CH:2][CH3:1].[NH:3]1[CH2:4][CH2:5][CH:6]([O:7][C:8](=[O:9])[C@:10]([OH:11])([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[C@@H:19]2[CH2:20][CH2:21][C:22]([F:23])([F:24])[CH2:25]2)[CH2:26][CH2:27]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH:6]([O:7][C:8](=[O:9])[C@:10]([OH:11])([c:12]2[cH:13][cH:14][c:15]([Cl:16])... | CC=O.O=C(OC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1 | null | null | C(Cl)(Cl)Cl.CO | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6]-[C:7] | null | [] | null | null | 2 | HOUR | To a solution of 25 mg of piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-chlorophenyl)ethanoate in 1 ml of methanol, 50 mg of acetaldehyde and 10 mg of sodium cyanoborohydride were added at room temperature, followed by two hours' stirring at the same temperature. The reaction liquid was diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | Other | C(Cl)(Cl)Cl.CO | null | 2 | CC=O.O=C(OC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>C(Cl)(Cl)Cl.CO>CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29997327c820464fae137cc3d6b25a01 | CCI.CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1>>CC[N+]1(CC)CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)CC)(C1=CC=C(C=C1)Cl)O)F.C(C)I>>[I-].FC1(C[C@@H](CC1)[C@](C(=O)OC1CC[N+](CC1)(CC)CC)(C1=CC=C(C=C1)Cl)O)F | [CH3:1][CH2:2][I:30].[N:3]1([CH2:4][CH3:5])[CH2:6][CH2:7][CH:8]([O:9][C:10](=[O:11])[C@:12]([OH:13])([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[C@@H:21]2[CH2:22][CH2:23][C:24]([F:25])([F:26])[CH2:27]2)[CH2:28][CH2:29]1>>[CH3:1][CH2:2][N+:3]1([CH2:4][CH3:5])[CH2:6][CH2:7][CH:8]([O:9][C:10](=[O:11])[C@:12]([OH:... | CCI.CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1 | CC[N+]1(CC)CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 02cf38bf365754a73f6e767e0e41237341aa66c38716b4b65a6c2985c13aa572 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | O=C(OC1CC[NH2+]CC1)C(c1ccccc1)C1CCCC1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[I;H0;D1;+0:3].[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[C;D1;H3:8])-[C:9]-[C:10]>>[C:4]-[C:5]-[N+;H0;D4:6](-[C:7]-[C;D1;H3:8])(-[CH2;D2;+0:2]-[C;D1;H3:1])-[C:9]-[C:10].[I-;H0;D0:3] | null | [] | 70 | CELSIUS | 12 | HOUR | A solution formed by dissolving 1-ethylpiperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-chlorophenyl)-ethanoate in 1 ml of ethyl iodide at room temperature was stirred for 12 hours at 70° C. Excessive reagent was distilled off under reduced pressure, and the residue was purified on preparative thin lay... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CC[NH]CC1 | C1CC[NH+]CC1 | C1CC[NH+]CC1.c1ccccc1.C1CCCC1 | null | null | 70 | 12 | CCI.CCN1CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1>>CC[N+]1(CC)CCC(OC(=O)[C@](O)(c2ccc(Cl)cc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9eddb3ba3f7b4b28b924fddb7597c338 | O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=CC1CCCCCC1>>O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCNCC1)(C1=CC=CC=C1)O)F.C1(CCCCCC1)C=O.C(#N)[BH3-].[Na+]>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)CC1CCCCCC1)(C1=CC=CC=C1)O)F | [O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH2:6][NH:7][CH2:16][CH2:17]1)[C@:18]([OH:19])([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[C@@H:26]1[CH2:27][CH2:28][C:29]([F:30])([F:31])[CH2:32]1.O=[CH:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH:9]2[CH2:10][CH2:11... | O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=CC1CCCCCC1 | O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | [Cl-].[Zn+2].[Cl-] | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(OC1CCN(CC2CCCCCC2)CC1)C(c1ccccc1)C1CCCC1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9])-[C:4] | null | [] | null | null | 30 | MINUTE | To a solution of 9.3 mg of piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 1 ml of methanol, 10 mg of cycloheptanecarbaldehyde and then 0.5 ml of advancedly prepared 0.3 M methanol solution of sodium cyanoborohydride and zinc chloride (1:0.5) were added at room temperature, followed by... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CCCCCC1.c1ccccc1.C1CCCC1 | Other | [Cl-].[Zn+2].[Cl-].CO.C(C)(=O)OCC | null | 0.5 | O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=CC1CCCCCC1>[Cl-].[Zn+2].[Cl-].CO.C(C)(=O)OCC>O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d49d62c3094409599b03a48dfc5e2c3 | CI.O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>C[N+]1(CC2CCCCCC2)CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)CC1CCCCCC1)(C1=CC=CC=C1)O)F.CI>>[I-].C1(CCCCCC1)C[N+]1(CCC(CC1)OC([C@@](C1=CC=CC=C1)(O)[C@H]1CC(CC1)(F)F)=O)C | [CH3:1][I:34].[N:2]1([CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:11][CH2:12][CH:13]([O:14][C:15](=[O:16])[C@:17]([OH:18])([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[C@@H:25]2[CH2:26][CH2:27][C:28]([F:29])([F:30])[CH2:31]2)[CH2:32][CH2:33]1>>[CH3:1][N+:2]1([CH2:3][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8]... | CI.O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | C[N+]1(CC2CCCCCC2)CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] | null | null | null | Functional Group Interconversion | OtherReaction | 09575fe46c8911a98e993e03b5a92296c31ea5be9a52cd39ecdb32e5047f1b98 | 5a8d30abc7481f1c446ec3891ae2e6d38df9cf7a08165b843f1d24fc50c4b9cd | O=C(OC1CC[NH+](CC2CCCCCC2)CC1)C(c1ccccc1)C1CCCC1 | [CH3;D1;+0:1]-[I;H0;D1;+0:2].[C:3]-[C:4]-[N;H0;D3;+0:5](-[C:6]-[C:7])-[C:8]-[C:9]>>[C:3]-[C:4]-[N+;H0;D4:5](-[CH3;D1;+0:1])(-[C:6]-[C:7])-[C:8]-[C:9].[I-;H0;D0:2] | null | [] | null | null | 12 | HOUR | A solution formed by dissolving 1-(cycloheptyl-methyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 0.3 ml of methyl iodide at room temperature was allowed to stand for 12 hours at the same temperature, and excessive reagent was distilled off under reduced pressure. The diastereomers... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | C1CC[NH]CC1 | C1CC[NH+]CC1 | C1CCCCCC1.C1CC[NH+]CC1.c1ccccc1.C1CCCC1 | null | null | null | 12 | CI.O=C(OC1CCN(CC2CCCCCC2)CC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>C[N+]1(CC2CCCCCC2)CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1.[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-018ba7b2b07942aca4d1897b71007bdb | ClCCOCCCl.O=C(O[C@@H]1CCNC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@@H]1CC[N+]2(CCOCC2)C1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[Cl-] | FC1(C[C@@H](CC1)[C@](C(=O)O[C@H]1CNCC1)(C1=CC=CC=C1)O)F.ClCCOCCCl>>[Cl-].FC1(C[C@@H](CC1)[C@](C(=O)O[C@H]1C[N+]2(CC1)CCOCC2)(C2=CC=CC=C2)O)F | Cl[CH2:12][CH2:11][O:10][CH2:9][CH2:8][Cl:29].[O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][CH2:6][NH:7][CH2:13]1)[C@:14]([OH:15])([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C@@H:22]1[CH2:23][CH2:24][C:25]([F:26])([F:27])[CH2:28]1>>[O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][CH2:6][N+:7]2([CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[CH2:13]1)[C... | ClCCOCCCl.O=C(O[C@@H]1CCNC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@@H]1CC[N+]2(CCOCC2)C1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[Cl-] | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 4332b98e22e38a270edcc2417a58bda0463dfb5b7e886ab5e05884c99005faee | 32dad54f9ec634f8b7ad177f2ad334e32120fe3190c0450b793155ec265a25f0 | O=C(O[C@@H]1CC[N+]2(CCOCC2)C1)C(c1ccccc1)C1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-[Cl;H0;D1;+0:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#8:3]1-[C:2]-[CH2;D2;+0:1]-[N+;H0;D4:11]2(-[C:7]-[C:8]-[C:9]-[C:10]-2)-[CH2;D2;+0:5]-[C:4]-1.[Cl-;H0;D0:6] | 19.2 | [{"value": 19.2, "product": "[Cl-].FC1(C[C@@H](CC1)[C@](C(=O)O[C@H]1C[N+]2(CC1)CCOCC2)(C2=CC=CC=C2)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To an acetonitrile solution containing 11 mg of (3R)-pyrrolidin-3-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate, 30 mg of 1-chloro-2-(2-chloroethoxy)ethane was added at room temperature, followed by 12 hours' heating under reflux. Distilling the solvent off under reduced pressure, the residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Secondary amine | null | C1CCNC1 | C1CC[N+]2(C1)CCOCC2 | C1CC[N+]2(C1)CCOCC2.c1ccccc1.C1CCCC1 | HCl | C(C)#N | null | 12 | ClCCOCCCl.O=C(O[C@@H]1CCNC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>C(C)#N>O=C(O[C@@H]1CC[N+]2(CCOCC2)C1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.[Cl-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4318591769994b8d97748cc15b9048f3 | CCOC=N.O=C(OC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>N=CN1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCNCC1)(C1=CC=C(C=C1)Br)O)F.Cl.C(OCC)=N>>Cl.FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C=N)(C1=CC=C(C=C1)Br)O)F | CCO[CH:3]=[NH:2].[NH:4]1[CH2:5][CH2:6][CH:7]([O:8][C:9](=[O:10])[C@:11]([OH:12])([c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]2)[C@@H:20]2[CH2:21][CH2:22][C:23]([F:24])([F:25])[CH2:26]2)[CH2:27][CH2:28]1>>[NH:2]=[CH:3][N:4]1[CH2:5][CH2:6][CH:7]([O:8][C:9](=[O:10])[C@:11]([OH:12])([c:13]2[cH:14][cH:15][c:16]([Br:17... | CCOC=N.O=C(OC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | N=CN1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 186c22f41e8095c322401cf7bd1d3d5e86f00d9c7f683ae4693526b57ca274e2 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C-O-[CH;D2;+0:1]=[N;D1;H1:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH;D2;+0:1]=[N;D1;H1:2])-[C:6]-[C:7] | 60.1 | [{"value": 60.1, "product": "Cl.FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C=N)(C1=CC=C(C=C1)Br)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 13 | HOUR | To a solution of 13 mg of piperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoate in 1 ml of anhydrous ethanol, 4 mg of ethyl formimidate hydrochloride was added, followed by 13 hours' stirring at room temperature. The reaction liquid was condensed to dry solid. Purifying the crude pro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | HO- | C(C)O | null | 13 | CCOC=N.O=C(OC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>C(C)O>N=CN1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8c8b43b0bd547c2a505c1f74f854587 | [Br-]>>Br | Cl.FC1(C[C@@H](CC1)[C@](C(=O)OCCC1CCN(CC1)C=N)(C1=CC=CC=C1)O)F.[Br-].[Na+]>>Br.FC1(C[C@@H](CC1)[C@](C(=O)OCCC1CCN(CC1)C=N)(C1=CC=CC=C1)O)F | [Br-:1]>>[BrH:1] | [Br-] | Br | null | null | O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | null | [Br-;H0;D0:1]>>[BrH;D0;+0:1] | null | [] | null | null | null | null | A solution of 50 mg of 2-(1-(iminomethyl)piperidin-4-yl)ethyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate monohydrochloride in 2 ml of ultrapure water was developed on reversed phase medium pressure liquid chromatography [ODS-AQ 120-S50 (YMC Co.)], and 60 ml of 0.2 M aqueous sodium bromide solutio... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | [Br-]>O>Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46df447b708444abb1cc42d7bd501595 | O=P(O)(O)O>>O=P(O)(O)O | Cl.FC1(C[C@@H](CC1)[C@](C(=O)OCCC1CCN(CC1)C=N)(C1=CC=CC=C1)O)F.[Na].P(O)(O)(O)=O>>P(=O)(O)(O)O.FC1(C[C@@H](CC1)[C@](C(=O)OCCC1CCN(CC1)C=N)(C1=CC=CC=C1)O)F | [O:29]=[P:30]([OH:31])([OH:32])[OH:33]>>[O:29]=[P:30]([OH:31])([OH:32])[OH:33] | O=P(O)(O)O | O=P(O)(O)O | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | A solution of 7.0 g of 2-(1-(iminomethyl)piperidin-4-yl)ethyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate monohydrochloride in 50 ml of ultrapure water was developed on reversed phase medium pressure liquid chromatography [ODS-AQ 120-S50 (YMC Co.)], and 300 ml of 1.0 M aqueous sodium dihydrogeneph... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | O=P(O)(O)O>O>O=P(O)(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56ac07f6175b4f60b76721db3706bd1f | N=C(N)n1cccn1.O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>N=C(N)N1CCC(COC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | FC1(C[C@@H](CC1)[C@](C(=O)OCC1CCNCC1)(C1=CC=CC=C1)O)F.Cl.N1(N=CC=C1)C(=N)N.C(C)(C)N(CC)C(C)C>>Cl.FC1(C[C@@H](CC1)[C@](C(=O)OCC1CCN(CC1)C(N)=N)(C1=CC=CC=C1)O)F | c1cnn([C:3](=[NH:2])[NH2:4])c1.[NH:5]1[CH2:6][CH2:7][CH:8]([CH2:9][O:10][C:11](=[O:12])[C@:13]([OH:14])([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C@@H:21]2[CH2:22][CH2:23][C:24]([F:25])([F:26])[CH2:27]2)[CH2:28][CH2:29]1>>[NH:2]=[C:3]([NH2:4])[N:5]1[CH2:6][CH2:7][CH:8]([CH2:9][O:10][C:11](=[O:12])[C@:13]([OH:14])([c... | N=C(N)n1cccn1.O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | N=C(N)N1CCC(COC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 1d47d8f13664cc303edc1041b5eee58c2592bc1620781673957d71e55ae5fa09 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | O=C(OCC1CCNCC1)C(c1ccccc1)C1CCCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5].[N;D1;H1:6]=[C;H0;D3;+0:7](-[N;D1;H2:8])-n1:c:c:c:n:1>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;H0;D3;+0:7](=[N;D1;H1:6])-[N;D1;H2:8])-[C:4]-[C:5] | 64.3 | [{"value": 64.3, "product": "Cl.FC1(C[C@@H](CC1)[C@](C(=O)OCC1CCN(CC1)C(N)=N)(C1=CC=CC=C1)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 14 mg of piperidin-4-ylmethyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 0.020 ml of anhydrous dimethylformamide, 6.3 mg of 1H-pyrazole-1-carboxamidine hydrochloride and 0.008 ml of diisopropylethylamine were added, followed by stirring at room temperature for 12 hours. The re... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | c1cn[nH]c1.C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | Other | CN(C=O)C | null | 12 | N=C(N)n1cccn1.O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>CN(C=O)C>N=C(N)N1CCC(COC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c589c582224e448c9b111b78989fe13c | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1.CCN(CC(F)(F)F)OS(=O)(=O)O>>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1 | C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)=O.FC(CN(CC)OS(O)(=O)=O)(F)F>>C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)(F)F | O=[C:19]1[CH2:18][CH2:17][C@@H:16]([C@@:9]2([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[C:7](=[O:8])[O:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[O:23]2)[CH2:22]1.CCN(CC(F)([F:20])[F:21])OS(=O)(=O)O>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[O:6][C:7](=[O:8])[C@:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([C@@H:16]2[C... | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1.CCN(CC(F)(F)F)OS(=O)(=O)O | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | d8ce75582cc2085b219bb8e7f0284896b047fb1d56cf73026d9dd21cf5f84c8c | 0f58136e456fc28bfb0d5032c72f56b6abc0d1d18c529a0320bc8a66ee51f94e | O=C1OCO[C@@]1(c1ccccc1)C1CCCC1 | C-C-N(-C-C(-F)(-[F;H0;D1;+0:1])-[F;H0;D1;+0:2])-O-S(-O)(=O)=O.O=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-1>>[F;H0;D1;+0:1]-[C;H0;D4;+0:3]1(-[F;H0;D1;+0:2])-[C:4]-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | 20 | HOUR | To a solution of 2.8 g of (2R, 5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 30 ml of chloroform, 4.89 ml of trifluorodiethylaminosulfuric acid was added under cooling with ice, followed by 20 hours' stirring at room temperature. The reaction liquid was diluted with chloroform, washed success... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ketone.Tertiary amine | Tertiary halide.Tertiary halide | C1CCCC1 | C1CCCC1 | C1COCO1.c1ccccc1.C1CCCC1 | HF | C(Cl)(Cl)Cl | null | 20 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1.CCN(CC(F)(F)F)OS(=O)(=O)O>C(Cl)(Cl)Cl>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29385844d9be4267ac23088a4a6e55f9 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1>>O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)(F)F>>FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=CC=C1)O)F | CC(C)(C)[C@H]1[O:3][C:2](=[O:1])[C@:4]([c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)([C@@H:12]2[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18]2)[O:5]1>>[O:1]=[C:2]([OH:3])[C@:4]([OH:5])([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18]1 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1 | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | null | O.CO.[OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | 5d8aabf78afd0bf8d003243176b5b72a268496612e07f11fa3f64f912faa66f6 | 8e2add5eaa507524491d9d9cabcbcd31fd373281e11b69181789d3583e355db5 | c1ccc(CC2CCCC2)cc1 | C-C(-C)(-C)-[C@@H]1-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5])(-[c:6])-[O;H0;D2;+0:7]-1>>[C:5]-[C:4](-[OH;D1;+0:7])(-[c:6])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 87.6 | [{"value": 87.6, "product": "FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=CC=C1)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2.4 g of (2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 30 ml of methanol, 10 ml of 1N aqueous sodium hydroxide solution was added, followed by 3 hours' stirring at room temperature. Distilling the methanol off under reduced pressure, the reaction liquid was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Tertiary alcohol | C1COCO1 | null | c1ccccc1.C1CCCC1 | Other | O.CO.[OH-].[Na+] | null | 3 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(F)(F)C2)O1>O.CO.[OH-].[Na+]>O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3221c25f13b24b299b9ac30fb17d2e0a | CCCCCC.O=C(O)[C@H](O)c1ccc(Cl)cc1>>CC(C)(C)[C@H]1OC(=O)[C@@H](c2ccc(Cl)cc2)O1 | ClC1=CC=C(C=C1)[C@H](C(=O)O)O.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CCCCCC.C1(=CC=CC=C1)C>>C(C)(C)(C)[C@@H]1O[C@@H](C(O1)=O)C1=CC=C(C=C1)Cl | C([CH2:3][CH2:2][CH3:4])[CH2:5][CH3:1].[OH:6][C:7](=[O:8])[C@@H:9]([c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1)[OH:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[O:6][C:7](=[O:8])[C@@H:9]([c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]2)[O:17]1 | CCCCCC.O=C(O)[C@H](O)c1ccc(Cl)cc1 | CC(C)(C)[C@H]1OC(=O)[C@@H](c2ccc(Cl)cc2)O1 | null | null | C(C)(=O)OCC.C(C(C)(C)C)=O | Heteroatom Alkylation and Arylation | OtherReaction | a3c75a0be150f8d7c9053ca28e350dd64dbc7cebde3ab061901dddbd47e28a78 | 7f05cd01c6e95ada1a19e5e2581aa24ce55853204c19e74f249bfdf96a92ee94 | O=C1OCO[C@@H]1c1ccccc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-C-[CH2;D2;+0:4]-[CH3;D1;+0:5].[O;D1;H0:6]=[C:7](-[OH;D1;+0:8])-[C:9](-[OH;D1;+0:10])-[c:11]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:5])(-[CH3;D1;+0:3])-[C@@H;D3;+0:4]1-[O;H0;D2;+0:10]-[C:9](-[c:11])-[C:7](=[O;D1;H0:6])-[O;H0;D2;+0:8]-1 | null | [] | null | null | 12 | HOUR | To a solution of 16 g of (2R)-2-(4-chlorophenyl)-2-hydroxyacetic acid (cf. JP-Hei 6 (1994)-165695A) in 440 ml of hexane/toluene (10:1), 23 ml of pivalaldehyde and 326 mg of p-toluenesulfonic acid monohydrate were added by the order stated, followed by 12 hours' heating under reflux while removing the generated water wi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester.Ether | null | C1COCO1 | C1COCO1.c1ccccc1 | Other | C(C)(=O)OCC.C(C(C)(C)C)=O | null | 12 | CCCCCC.O=C(O)[C@H](O)c1ccc(Cl)cc1>C(C)(=O)OCC.C(C(C)(C)C)=O>CC(C)(C)[C@H]1OC(=O)[C@@H](c2ccc(Cl)cc2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-debd0f3dfe2643b0a287161a47507876 | COC(=O)[C@H](O)c1ccccc1OC>>COc1ccccc1[C@@H](O)C(=O)O | [OH-].[Na+].COC1=C(C=CC=C1)[C@H](C(=O)OC)O.Cl>>COC1=C(C=CC=C1)[C@H](C(=O)O)O | C[O:13][C:11]([C@@H:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[OH:10])=[O:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@@H:9]([OH:10])[C:11](=[O:12])[OH:13] | COC(=O)[C@H](O)c1ccccc1OC | COc1ccccc1[C@@H](O)C(=O)O | 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] | 62.4 | [{"value": 62.4, "product": "COC1=C(C=CC=C1)[C@H](C(=O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 19 g of methyl (2R)-2-(methoxyphenyl)-2-hydroxyethanoate (cf. Journal of Chemical Society, Parkintrans 1, 2253-2255 (1992)) in 50 ml of methanol, 50 ml of 3N aqueous sodium hydroxide solution was added, followed by 12 hours' stirring at room temperature. Distilling the methanol off under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | 12 | COC(=O)[C@H](O)c1ccccc1OC>CO>COc1ccccc1[C@@H](O)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91385b1b123949878e5a4e4114d92036 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1>>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(O)C2)O1 | C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)=O.[BH4-].[Na+]>>C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)O | [CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[O:6][C:7](=[O:8])[C@:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([C@@H:16]2[CH2:17][CH2:18][C:19](=[O:20])[CH2:21]2)[O:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[O:6][C:7](=[O:8])[C@:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([C@@H:16]2[CH2:17][CH2:18][CH:19]([OH:20])[C... | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(O)C2)O1 | null | null | CO.C(C)OCC | Reduction | Reduction of ketone to secondary alcohol | 87d90128b40d1aec3bafae0cf798ca35261f3c820469cb5c329528b3141a9934 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=C1OCO[C@@]1(c1ccccc1)C1CCCC1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[C:5]-[C:6]-1 | 92.3 | [{"value": 92.3, "product": "C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@H]1CC(CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 169 mg of the (2R,5R)-2-(t-butyl)-5-((1R)-3-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one, as obtained in Step 1 of Referential Example 1, in 2 ml of methanol, 71 mg of sodium borohydride was added under cooling with ice, followed by 30 minutes' stirring at the same temperature. The reaction liquid was d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCC1 | C1CCCC1 | C1COCO1.c1ccccc1.C1CCCC1 | null | CO.C(C)OCC | null | 0.5 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(=O)C2)O1>CO.C(C)OCC>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@@H]2CCC(O)C2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-475821efc53b404d8de49a169e579248 | CC(=O)OC1=CC[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)C1>>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1 | C(C)(=O)OC1=CC[C@H](C1)[C@@]1(O[C@H](OC1=O)C(C)(C)C)C1=CC=CC=C1.C[N+]1(CCOCC1)[O-].S(=O)([O-])[O-].[Na+].[Na+]>>C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@@H]1C[C@H](C(C1)=O)O | CC(=O)[O:21][C:20]1=[CH:18][CH2:17][C@@H:16]([C@@:9]2([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[C:7](=[O:8])[O:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[O:23]2)[CH2:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C@H:5]1[O:6][C:7](=[O:8])[C@:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([C@H:16]2[CH2:17][C:18](=[O:19])[C@H:2... | CC(=O)OC1=CC[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)C1 | CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1 | null | [Os](=O)(=O)(=O)=O | C(C)#N.O.C(C)(=O)OCC | Miscellaneous | OtherReaction | e0e7e70b556eba016d2d7bfc1e6966b877452687ffcffc2d2cef73d195b59662 | 8cb4eb0d760423ba5e32a375db6dd70ea33fa9e372492146081c9fddf2d7b9fc | O=C1CC[C@@H]([C@]2(c3ccccc3)OCOC2=O)C1 | C-C(=O)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C:5]-[C:6]-1>>[O;D1;H0:7]=[C;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C@H;D3;+0:2]-1-[OH;D1;+0:1] | 20.5 | [{"value": 20.5, "product": "C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@@H]1C[C@H](C(C1)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 169 mg of (4R)-4-((2R,4R)-2-(t-butyl)-5-oxo-4-phenyl-1,3-dioxolan-4-yl)-1-cyclopentenyl acetate in 7.5 ml of acetonitrile and water (2:1), 80 mg of N-methyl morpholine-oxide and 0.2 ml of 2% aqueous osmium tetraoxide solution were successively added at 0° C. by the order stated, followed by 3 hours' st... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone.Secondary alcohol | C1=CCCC1 | C1CCCC1 | C1COCO1.c1ccccc1.C1CCCC1 | HO- | [Os](=O)(=O)(=O)=O.C(C)#N.O.C(C)(=O)OCC | null | 3 | CC(=O)OC1=CC[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)C1>[Os](=O)(=O)(=O)=O.C(C)#N.O.C(C)(=O)OCC>CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c59b96b22fe43faa9b95c584f793fef | CC(=O)OC(C)=O.CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1>>CC(=O)O[C@@H]1C[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)CC1=O | C(C)(C)(C)[C@@H]1O[C@@](C(O1)=O)(C1=CC=CC=C1)[C@@H]1C[C@H](C(C1)=O)O.C(C)(=O)OC(C)=O>>C(C)(=O)O[C@H]1C(C[C@@H](C1)[C@@]1(O[C@H](OC1=O)C(C)(C)C)C1=CC=CC=C1)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[CH2:6][C@@H:7]([C@:8]2([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[O:15][C@@H:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[O:21][C:22]2=[O:23])[CH2:24][C:25]1=[O:26]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[CH2:6][C@@H:7]([C@:8]2([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[O:15][C@@H:1... | CC(=O)OC(C)=O.CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1 | CC(=O)O[C@@H]1C[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)CC1=O | null | null | N1=CC=CC=C1.C(C)(=O)OCC | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | O=C1CC[C@@H]([C@]2(c3ccccc3)OCOC2=O)C1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:4]-[C:5](=[O;D1;H0:6])-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:9] | null | [] | null | null | 1 | HOUR | To a solution of 32 mg of (2R,5R)-2-(t-butyl)-5-((1R,3R)-3-hydroxy-4-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 1 ml of pyridine, 0.5 ml of acetic anhydride was added, followed by 1 hour's stirring at room temperature. The reaction liquid was diluted with ethyl acetate, washed successively with water, 1N hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1CCCC1.c1ccccc1.C1COCO1 | HO- | N1=CC=CC=C1.C(C)(=O)OCC | null | 1 | CC(=O)OC(C)=O.CC(C)(C)[C@H]1OC(=O)[C@](c2ccccc2)([C@H]2CC(=O)[C@H](O)C2)O1>N1=CC=CC=C1.C(C)(=O)OCC>CC(=O)O[C@@H]1C[C@@H]([C@]2(c3ccccc3)O[C@@H](C(C)(C)C)OC2=O)CC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-815f58751dcf4a28a4ddffaff22fb0a3 | CC(C)(C)OC(=O)OC(C)(C)C.OC1CCNCC1>>CC(C)(C)OC(=O)N1CCC(O)CC1 | OC1CCNCC1.C(C)(C)(C)OC(OC(C)(C)C)=O>>OC1CCN(CC1)C(=O)OC(C)(C)C | CC(C)(C)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)OC(C)(C)C.OC1CCNCC1 | CC(C)(C)OC(=O)N1CCC(O)CC1 | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC | Protection | Boc amine protection of secondary amine | 916a31927ce671c40c2108c871e1ecded7541035ed125881c0eb3601afbcbaa4 | f0869a0b34976f381b42755ff52efacfde708ff6f8d3c39d434136b4f68fd40e | C1CCNCC1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11]-[C:12] | 90.5 | [{"value": 90.5, "product": "OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 10 g of 4-hydroxypiperidine in 300 ml of chloroform, 20 g of di-t-butylcarbonate was added under cooling with ice, followed by 2 hours' stirring at room temperature. The reaction liquid was diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium s... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HO- | C(Cl)(Cl)Cl.C(C)(=O)OCC | null | 2 | CC(C)(C)OC(=O)OC(C)(C)C.OC1CCNCC1>C(Cl)(Cl)Cl.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d242a990ee9d48b1a9487f812e26cba8 | CC(C)(C)OC(=O)N1CCC(O)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>>CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | OC1CCN(CC1)C(=O)OC(C)(C)C.[H-].[Na+].FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=CC=C1)O)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=CC=C1)O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH2:30][CH2:31]1.O[C:13](=[O:14])[C@:15]([OH:16])([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C@@H:23]1[CH2:24][CH2:25][C:26]([F:27])([F:28])[CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:1... | CC(C)(C)OC(=O)N1CCC(O)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6].[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6])-[C:10] | 55.1 | [{"value": 55.1, "product": "FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=CC=C1)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 128 mg of (2R)-2-((1R)-3,3-difluorocyclo-pentyl)-2-hydroxy-2-phenylacetic acid in 3 ml of dimethylformamide, 81 mg of carbonyldiimidazole was added and stirred for 30 minutes. Then 121 mg of 4-hydroxy-1-t-butoxycarbonylpiperidine and 10 mg of sodium hydride were added successively, followed by another ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 0.5 | CC(C)(C)OC(=O)N1CCC(O)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1>CN(C=O)C.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c15477ac92d84af797455bf7a7578939 | CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1>>O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=CC=C1)O)F>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCNCC1)(C1=CC=CC=C1)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][CH:4]([O:3][C:2](=[O:1])[C@:10]([OH:11])([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@@H:18]2[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]2)[CH2:9][CH2:8]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]1)[C@:10]([OH:11])([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C@@... | CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1 | O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | null | Cl.CO | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | 12 | HOUR | 162 Milligrams of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclo-pentyl)-2-hydroxy-2-phenylethanoyloxy)tetrahydropyridine-1(2H)-carboxylate was dissolved in 5 ml of 10% hydrochloric acid-methanol, stirred for 12 hours, and the solvent was distilled off under reduced pressure. The residue was diluted with water, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.C1CCCC1 | HO- | Cl.CO | null | 12 | CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccccc2)[C@@H]2CCC(F)(F)C2)CC1>Cl.CO>O=C(OC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a324c8fadf9c4d5a9621b3317a7a5cdd | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(CO)CC1 | O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C)(C)(C)OC(=O)N1CCC(C(=O)OCC)CC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C)(C)(C)OC(=O)N1CCC(CC1)CO | CCO[C:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][CH2:15]1 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(CO)CC1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 95.9 | [{"value": 95.9, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 516 mg of ethyl N-t-butoxycarbonyl-isonipecotate in 30 ml of tetrahydrofuran, 200 mg of lithium-aluminum hydride was added under cooling with ice, followed by 20 minutes' stirring at the same temperature. Sodium sulfate decahydrate was added to the reaction liquid, stirred for 30 minutes and filtered w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | HO- | O1CCCC1 | null | 0.333333 | CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a580eccee2b44efb9571d60de05c901 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CCOC(=O)CP(=O)(OCC)OCC>>CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 | [H-].[Na+].C(C)OP(=O)(OCC)CC(=O)OCC.C(C)(C)(C)OC(=O)N1CCC(CC1)=O>>C(C)OC(C=C1CCN(CC1)C(=O)OC(C)(C)C)=O | O=[C:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1.CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CCOC(=O)CP(=O)(OCC)OCC | CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | O1CCCC1.C(C)(=O)OCC | C-C Coupling | Wittig with Phosphonium | f1cc2860cc6808241638b4df406fbf2f5b73713101b0526a537082124324a39f | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | [CH]=C1CCNCC1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1 | null | [] | null | null | 20 | MINUTE | To a solution of 9.1 g of 60% oily sodium hydride in 200 ml of tetrahydrofuran, 38.0 ml of ethyl diethylphosphonoacetate was added dropwise under cooling with ice, stirred for 20 minutes, and thereafter a solution of 31.4 g of 1-t-butoxycarbonyl-4-piperidone in 500 ml of tetrahydrofuran was added dropwise, followed by ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HO- | O1CCCC1.C(C)(=O)OCC | null | 0.333333 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CCOC(=O)CP(=O)(OCC)OCC>O1CCCC1.C(C)(=O)OCC>CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-261116ed74f64cfb8097dccb58c8d003 | CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1>>CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 | C(C)OC(C=C1CCN(CC1)C(=O)OC(C)(C)C)=O.[H][H]>>C(C)OC(CC1CCN(CC1)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18][CH2:19]1 | CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0b630b13701240d196b3b7ae7f8d1027f0f9b3476df9973ccf2f682d0aecd577 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | C1CCNCC1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1 | 93.4 | [{"value": 93.4, "product": "C(C)OC(CC1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 355 mg of t-butyl 4-(2-ethoxy-2-oxoethylidene)tetrahydropyridine-1(2H)-carboxylate in 10 ml of methanol, 50 mg of 10% palladium-on-carbon catalyst was added and stirred for 13 hours in 3 atmospheres' hydrogen pressure. Filtering the catalyst off, the solvent was distilled off under reduced pressure to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | null | [Pd].CO | null | null | CCOC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1>[Pd].CO>CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cc64e404d544f6d9cb4433e828622a6 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(CCO)CC1 | O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+].C(C)OC(CC1CCN(CC1)C(=O)OC(C)(C)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>OCCC1CCN(CC1)C(=O)OC(C)(C)C | CCO[C:13]([CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:16][CH2:15]1)=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][OH:14])[CH2:15][CH2:16]1 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(CCO)CC1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | 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 | 20 | MINUTE | To a solution of 2'mg of t-butyl 4-(2-ethoxy-2-oxoethyl)-tetrahydropyridine-1(2H)-carboxylate in 15 ml of tetrahydrofuran, 100 mg of lithiumaluminum hydride was added under cooling with ice, followed by 20 minutes' stirring at the same temperature. To the reaction liquid sodium sulfate decahydrate was added, stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | HO- | O1CCCC1 | null | 0.333333 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(CCO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a295b1c4a76243d89cb4d499c6467ed8 | CCOC(=O)C=CC1CCN(C(=O)OC(C)(C)C)CC1>>CCOC(=O)CCC1CCN(C(=O)OC(C)(C)C)CC1 | C(C)OC(C=CC1CCN(CC1)C(=O)OC(C)(C)C)=O.[H][H]>>C(C)OC(CCC1CCN(CC1)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1 | CCOC(=O)C=CC1CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)CCC1CCN(C(=O)OC(C)(C)C)CC1 | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | C1CCNCC1 | [C:1]-[C:2](-[CH;D2;+0:3]=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[C:9]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[C:9] | 69.5 | [{"value": 69.5, "product": "C(C)OC(CCC1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1.0 g of t-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-tetrahydropyridine-1(2H)-carboxylate (cf. WO9501336) in 20 ml of ethanol, 300 mg of 10% palladium-on-carbon catalyst, and stirred for 3 hours in a hydrogen atmosphere, at ambient temperature and pressure. After filtering the catalyst off, the solvent was d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | C1CC[NH]CC1 | null | [Pd].C(C)O | null | null | CCOC(=O)C=CC1CCN(C(=O)OC(C)(C)C)CC1>[Pd].C(C)O>CCOC(=O)CCC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2402196d174e41a0a2ae765d4df993a4 | CC(=O)OCC[C@@H]1CCN(C(=O)OC(C)(C)C)C1>>CC(C)(C)OC(=O)N1CC[C@@H](CCO)C1 | C(C)(=O)OCC[C@H]1CN(CC1)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+]>>OCC[C@H]1CN(CC1)C(=O)OC(C)(C)C | CC(=O)[O:14][CH2:13][CH2:12][C@@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([CH2:12][CH2:13][OH:14])[CH2:15]1 | CC(=O)OCC[C@@H]1CCN(C(=O)OC(C)(C)C)C1 | CC(C)(C)OC(=O)N1CC[C@@H](CCO)C1 | null | null | C(Cl)(Cl)Cl.CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 101.9 | [{"value": 101.9, "product": "OCC[C@H]1CN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 34 mg of t-butyl (3S)-3-(2-acetyloxyethyl)-pyrrolidine-1-carboxylate in 1 ml of methanol, 54 mg of potassium carbonate was added, and stirred for 2.5 hours at room temperature. The reaction liquid was diluted with chloroform, washed successively with water and saturated brine and dried over anhydrous s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1 | HO- | C(Cl)(Cl)Cl.CO | null | 2.5 | CC(=O)OCC[C@@H]1CCN(C(=O)OC(C)(C)C)C1>C(Cl)(Cl)Cl.CO>CC(C)(C)OC(=O)N1CC[C@@H](CCO)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27b625f7f1d74977bde5b563f9b0aa0a | CC(C)(C)OC(=O)N1CCC(=O)CC1>>C=C1CCN(C(=O)OC(C)(C)C)CC1 | O=C1CCN(CC1)C(=O)OC(C)(C)C.O1CCCC1.O1CCCC1>>C=C1CCN(CC1)C(=O)OC(C)(C)C | O=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14]1>>[CH2:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1 | C=C1CCN(C(=O)OC(C)(C)C)CC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C(CCC)[Li].CCCCCC.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 84f2bc928f1ef1235d526c5737341c242f9e69bd5bf9fcfa4d907666d076cc2e | f395a9efbb80a99833acb686d4944d4880257993d074f4e04e21822999af09fe | C=C1CCNCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[C;D1;H2:7]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | 50 | MINUTE | To a solution of 986 mg of methyltriphenylphosphonium bromide in 20 ml of tetrahydrofuran, 1.87 ml of 1.63 M n-butyl lithium/hexane solution was added dropwise at 0° C., under cooling with ice. The temperature then was immediately raised to room temperature, and the system was stirred for 50 minutes. The reaction liqui... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Vinyl | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | null | [Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li].CCCCCC.C(C)(=O)OCC | null | 0.833333 | CC(C)(C)OC(=O)N1CCC(=O)CC1>[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li].CCCCCC.C(C)(=O)OCC>C=C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfed5481dc9c401e99dea675414aa0e6 | C=C1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(O)(CO)CC1 | C=C1CCN(CC1)C(=O)OC(C)(C)C.C[N+]1(CCOCC1)[O-].O1CCCC1.O.S(=O)([O-])[O-].[Na+].[Na+]>>OC1(CCN(CC1)C(=O)OC(C)(C)C)CO | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[CH2:13])[CH2:15][CH2:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([OH:12])([CH2:13][OH:14])[CH2:15][CH2:16]1 | C=C1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(O)(CO)CC1 | null | [Os](=O)(=O)(=O)=O | C(C)(=O)OCC | Oxidation | Alkene to diol | a9601858eec5f8f28bd409fc6d595e766f2d642498d7b396df275335e387de82 | 86d8a5113266bb51fa4a374fff1e7c7e54f992c26d50d72a0dd8479b9175ed13 | C1CCNCC1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1>>[O;D1;H1:8]-[C;H0;D4;+0:2]1(-[CH2;D2;+0:1]-[O;D1;H1:9])-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1 | null | [] | null | null | 2 | HOUR | To a solution of 98 mg of t-butyl 4-methylenetetrahydro-pyridine-1(2H)-carboxylate in 2 ml of tetrahydrofuran-water (1:1), 88 mg of N-methyl morpholine-oxide and 0.1 ml of 2% osmium tetraoxide were added at 0° C., followed by 2 hours' stirring at the same temperature. Adding sodium sulfite to the reaction liquid, the r... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Primary alcohol.Tertiary alcohol | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | [Os](=O)(=O)(=O)=O.C(C)(=O)OCC | null | 2 | C=C1CCN(C(=O)OC(C)(C)C)CC1>[Os](=O)(=O)(=O)=O.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(O)(CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bddf77c75f9a41f1bfd40bd9b6a5a45c | NCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=Cc1ccccc1>>O=C(OCCCNCc1ccccc1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | [BH4-].[Na+].CO.FC1(C[C@@H](CC1)[C@](C(=O)OCCCN)(C1=CC=CC=C1)O)F.C(C1=CC=CC=C1)=O>>FC1(C[C@@H](CC1)[C@](C(=O)OCCCNCC1=CC=CC=C1)(C1=CC=CC=C1)O)F | [O:1]=[C:2]([O:3][CH2:4][CH2:5][CH2:6][NH2:7])[C@:15]([OH:16])([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C@@H:23]1[CH2:24][CH2:25][C:26]([F:27])([F:28])[CH2:29]1.O=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][CH2:6][NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C@:15]([... | NCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=Cc1ccccc1 | O=C(OCCCNCc1ccccc1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(OCCCNCc1ccccc1)C(c1ccccc1)C1CCCC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a methanol solution of 87 mg of 3-aminopropyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate, 35 mg of benzaldehyde was added at room temperature, stirred for 30 minutes at the same temperature, sodium borohydride was added, and further stirred for 30 minutes. The reaction liquid was diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCC1 | Other | C(C)(=O)OCC | null | 0.5 | NCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.O=Cc1ccccc1>C(C)(=O)OCC>O=C(OCCCNCc1ccccc1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8218e48e8a834f22a8b9a07fa9eada15 | CN(CCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1)Cc1ccccc1>>CNCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)OCCCN(C)CC1=CC=CC=C1)(C1=CC=CC=C1)O)F>>FC1(C[C@@H](CC1)[C@](C(=O)OCCCNC)(C1=CC=CC=C1)O)F | c1ccc(C[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7](=[O:8])[C@:9]([OH:10])([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[C@@H:17]2[CH2:18][CH2:19][C:20]([F:21])([F:22])[CH2:23]2)cc1>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7](=[O:8])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C@@H:17]1[CH2:18][CH2:19... | CN(CCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1)Cc1ccccc1 | CNCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | [OH-].[Pd+2].[OH-].[C] | [H][H].CO | Deprotection | Hydrogenolysis of tertiary amines | c7b12980b0925f19f153d220e0d23df430cf55f157d3497ce9d59af5c5715792 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(CC2CCCC2)cc1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4] | 99.5 | [{"value": 99.5, "product": "FC1(C[C@@H](CC1)[C@](C(=O)OCCCNC)(C1=CC=CC=C1)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 41 mg of 3-(benzyl(methyl)amino)propyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 2 ml of methanol, 10 mg of palladium hydroxide-carbon catalyst was added, followed by 2 hours' stirring at ambient temperature and pressure in hydrogen atmosphere. The reaction liquid was filtere... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccccc1.C1CCCC1 | Other | [OH-].[Pd+2].[OH-].[C].[H][H].CO | null | 2 | CN(CCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1)Cc1ccccc1>[OH-].[Pd+2].[OH-].[C].[H][H].CO>CNCCCOC(=O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a92957934934b2aabfa270d7030fb61 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1>>C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)Br)O)F.C(=C)[Sn](CCCC)(CCCC)CCCC>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)C=C)O)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]([C@@:7]([OH:8])([C:9](=[O:10])[O:11][CH:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]2)[C@@H:25]2[CH2:26][CH2:27][C:28]([F:29])([F:30])[CH2:31]2)[cH:32][cH:33]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5... | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1 | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | null | null | O1CCOCC1 | C-C Coupling | Stille reaction_vinyl | 70c70ea31829ab76af60acb09a55c00bc191f62cf69589ba5bf99dde81769bb5 | ec03c739f58696d2a3659a73884744e1a490a20a587da6f115be382b663cf23d | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[CH;D2;+0:6]=[C;D1;H2:7]>>[C;D1;H2:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 110 | CELSIUS | 24 | HOUR | To a solution of 125 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 52 in 4 ml of dioxane, 0.10 ml of vinyl tri-n-butyltin and 20 mg of tetrakistriphenylpalladium were added at room temperature, f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl.Tin | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.C1CCCC1 | HBr.Sn | O1CCOCC1 | 110 | 24 | C=[CH][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(Br)cc2)[C@@H]2CCC(F)(F)C2)CC1>O1CCOCC1>C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77988b43a5fe474bafcefd9ab43ee5ca | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>>CCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)C=C)O)F>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)CC)O)F | [CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([C@@:7]([OH:8])([C:9](=[O:10])[O:11][CH:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]2)[C@@H:25]2[CH2:26][CH2:27][C:28]([F:29])([F:30])[CH2:31]2)[cH:32][cH:33]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C@@:7]([OH:8])([C:9](=[O:10... | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | CCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | null | [Pd] | [H][H].CO | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 6 | HOUR | To a solution of 50 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-vinylphenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 56 in 3 ml of methanol, 10 mg of palladium-on-carbon catalyst was added, followed by 6 hours' stirring at ambient temperature and... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCC1 | null | [Pd].[H][H].CO | null | 6 | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>[Pd].[H][H].CO>CCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44ea4f623b554ee5b9186fbc14c5ea0e | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>>CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)C=C)O)F.S(=O)([O-])[O-].[Na+].[Na+]>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)CO)O)F | C=[CH:21][c:20]1[cH:19][cH:18][c:17]([C@:15]([C:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)=[O:14])([OH:16])[C@@H:25]2[CH2:26][CH2:27][C:28]([F:29])([F:30])[CH2:31]2)[cH:24][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:1... | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1 | null | [Os](=O)(=O)(=O)=O | O1CCCC1.O.C(C)(=O)OCC | Oxidation | OtherReaction | 47da4cae537af04b95e2008a4a76932a9bd3ee8dabc4da584512d2d2f7c10bdd | 393450bfe890fed79a323246fd64e6714faf5fe6acf694c6a491bf9280244151 | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | C=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[O;D1;H1:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a solution of 69 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-vinylphenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 56 in 2 ml of tetrahydrofuran-water (1:1), 85 mg of sodium periodide and 0.1 ml of 2% osmium tetraoxide were added at 0° C., foll... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | Primary alcohol | null | null | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | null | [Os](=O)(=O)(=O)=O.O1CCCC1.O.C(C)(=O)OCC | null | 0.5 | C=Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>[Os](=O)(=O)(=O)=O.O1CCCC1.O.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de7e1269efe741ef877a9100d62df71e | CC(=O)OC(C)=O.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1>>CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)CO)O)F.CN(C)C1=NC=CC=C1.C(C)(=O)OC(C)=O>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)COC(C)=O)O)F | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([C@@:10]([OH:11])([C:12](=[O:13])[O:14][CH:15]2[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[C@@H:28]2[CH2:29][CH2:30][C:31]([F:32])([F:33])[CH2:34]2)[cH:35][cH:36]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6... | CC(=O)OC(C)=O.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1 | CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | null | null | C(C)N(CC)CC.C(Cl)(Cl)Cl.C(C)(=O)OCC | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C:5]-[c:6] | null | [] | null | null | null | null | To a solution of 42 mg of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-(hydroxymethyl)phenyl)-ethanoyloxy)tetrahydropyridine-1(2H)-carboxylate in 2 ml of chloroform, 0.015 ml of triethylamine, 0.01 ml of acetic anhydride and 2 mg of dimethylaminopyridine were added successively, followed by an hour's... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCC1 | HO- | C(C)N(CC)CC.C(Cl)(Cl)Cl.C(C)(=O)OCC | null | null | CC(=O)OC(C)=O.CC(C)(C)OC(=O)N1CCC(OC(=O)[C@](O)(c2ccc(CO)cc2)[C@@H]2CCC(F)(F)C2)CC1>C(C)N(CC)CC.C(Cl)(Cl)Cl.C(C)(=O)OCC>CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2637beb2e7147119ea334fb03e2a2bd | CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>>Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)COC(C)=O)O)F>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)C)O)F | CC(=O)O[CH2:1][c:2]1[cH:3][cH:4][c:5]([C@@:6]([OH:7])([C:8](=[O:9])[O:10][CH:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]2)[C@@H:24]2[CH2:25][CH2:26][C:27]([F:28])([F:29])[CH2:30]2)[cH:31][cH:32]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C@@:6]([OH:7])([C:8](=[O:9])[O:10][... | CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 | null | [OH-].[Pd+2].[OH-].[C] | [H][H].CO | Reduction | OtherReaction | bbe4aa74424ca2aa68ccc284976164429303e3793b330c9b63e6e77a951d8d58 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=C(OC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.4 | [{"value": 99.4, "product": "FC1(C[C@@H](CC1)[C@](C(=O)OC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=C(C=C1)C)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 42 mg of t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-((acetyloxy)methyl)phenyl)-ethanoyloxy)tetrahydropyridine-1(2H)-carboxylate in 1 ml of methanol, 20 mg of palladium hydroxide-carbon catalyst was added, followed by 16 hours' stirring at ambient temperature and pressure in hydroge... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | null | null | c1ccccc1.C1CC[NH]CC1.C1CCCC1 | HO- | [OH-].[Pd+2].[OH-].[C].[H][H].CO | null | 16 | CC(=O)OCc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1>[OH-].[Pd+2].[OH-].[C].[H][H].CO>Cc1ccc([C@@](O)(C(=O)OC2CCN(C(=O)OC(C)(C)C)CC2)[C@@H]2CCC(F)(F)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1573abc0add4415a85f489b522faf3da | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)Cl)O)F.C(C)(C)(C)OC(=O)N1CCC(CC1)CO>>FC1(C[C@@H](CC1)[C@](C(=O)OCC1CCNCC1)(C1=CC=C(C=C1)Cl)O)F | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][OH:3])[CH2:10][CH2:9]1.O[C:2](=[O:1])[C@:11]([OH:12])([c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1)[C@@H:20]1[CH2:21][CH2:22][C:23]([F:24])([F:25])[CH2:26]1>>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[C@:11]([OH:12])([c:13]1[cH:14][cH:15]... | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | O=C(OCC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 9c9e293d6958deeabb63603a3df6dc3546c1fc2c695cac6c006a11693e87990f | 069bc07be5850cdc179014895714841ff72d0727af3e4d028febfe6f3b2878c2 | O=C(OCC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:7]-[C:8]-1.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[C:12])(-[O;D1;H1:13])-[c:14]>>[C:12]-[C:11](-[O;D1;H1:13])(-[c:14])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:6]-[C:5]-[C:4]1-[C:7]-[C:8]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-chlorophenyl)acetic acid and N-t-butoxycarbonyl-4-piperidine-methanol, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary alcohol.Boc | Ester.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-353e21b8fa334511aba7ecd4e0898589 | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)Br)O)F.C(C)(C)(C)OC(=O)N1CCC(CC1)CO>>FC1(C[C@@H](CC1)[C@](C(=O)OCC1CCNCC1)(C1=CC=C(C=C1)Br)O)F | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][OH:3])[CH2:10][CH2:9]1.O[C:2](=[O:1])[C@:11]([OH:12])([c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1)[C@@H:20]1[CH2:21][CH2:22][C:23]([F:24])([F:25])[CH2:26]1>>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[C@:11]([OH:12])([c:13]1[cH:14][cH:15]... | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | O=C(OCC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 9c9e293d6958deeabb63603a3df6dc3546c1fc2c695cac6c006a11693e87990f | 069bc07be5850cdc179014895714841ff72d0727af3e4d028febfe6f3b2878c2 | O=C(OCC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:7]-[C:8]-1.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[C:12])(-[O;D1;H1:13])-[c:14]>>[C:12]-[C:11](-[O;D1;H1:13])(-[c:14])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:6]-[C:5]-[C:4]1-[C:7]-[C:8]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)acetic acid and N-t-butoxycarbonyl-4-piperidine-methanol, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary alcohol.Boc | Ester.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c687c5dab8f84dc3aaa0009d8fe80a86 | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1 | FC1(C[C@@H](C[C@H]1O)[C@](C(=O)O)(C1=CC=CC=C1)O)F.C(C)(C)(C)OC(=O)N1CCC(CC1)CO>>FC1(C[C@@H](C[C@H]1O)[C@](C(=O)OCC1CCNCC1)(C1=CC=CC=C1)O)F | CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][OH:3])[CH2:10][CH2:9]1.O[C:2](=[O:1])[C@:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2:20][C@@H:21]([OH:22])[C:23]([F:24])([F:25])[CH2:26]1>>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[C@:11]([OH:12])([c:13]1[cH:14][cH:1... | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1 | O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1 | null | null | null | Acylation | OtherReaction | 9c9e293d6958deeabb63603a3df6dc3546c1fc2c695cac6c006a11693e87990f | 069bc07be5850cdc179014895714841ff72d0727af3e4d028febfe6f3b2878c2 | O=C(OCC1CCNCC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[OH;D1;+0:6])-[C:7]-[C:8]-1.O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11](-[C:12])(-[O;D1;H1:13])-[c:14]>>[C:12]-[C:11](-[O;D1;H1:13])(-[c:14])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:6]-[C:5]-[C:4]1-[C:7]-[C:8]-[NH;D2;+0:1]-[C:2]-[C:3]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R,4R)-3,3-difluoro-4-hydroxycyclopentyl)-2-hydroxy-2-phenylacetic acid and N-t-butoxycarbonyl-4-piperidine-methanol, the title compound was prepared by a method similar to steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary alcohol.Boc | Ester.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CO)CC1.O=C(O)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1>>O=C(OCC1CCNCC1)[C@](O)(c1ccccc1)[C@@H]1C[C@@H](O)C(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cbb865464f746e1989dfb24ba43b7f9 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)F)O)F.O[C@H]1CN(CC1)C(=O)OC(C)(C)C>>FC1(C[C@@H](CC1)[C@](C(=O)O[C@H]1CNCC1)(C1=CC=C(C=C1)F)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@@H:4]([OH:3])[CH2:8]1.O[C:2](=[O:1])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1)[C@@H:18]1[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]1>>[O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][CH2:6][NH:7][CH2:8]1)[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1... | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 0f32895f86307496d881270b5893142b7e6f0bfad36a2f8bb676e27359041532 | 9370f47be85b7f762f9dfe0f3c726311efbbb1800d75f07f1880fc727c84fc15 | O=C(O[C@@H]1CCNC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-1.O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])(-[O;D1;H1:11])-[c:12]>>[C:10]-[C:9](-[O;D1;H1:11])(-[c:12])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-fluorophenyl)acetic acid and t-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol.Boc | Ester.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d264fb6259cd4ae3ab134495266d8294 | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)Br)O)F.O[C@H]1CN(CC1)C(=O)OC(C)(C)C>>FC1(C[C@@H](CC1)[C@](C(=O)O[C@H]1CNCC1)(C1=CC=C(C=C1)Br)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@@H:4]([OH:3])[CH2:8]1.O[C:2](=[O:1])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1)[C@@H:18]1[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]1>>[O:1]=[C:2]([O:3][C@@H:4]1[CH2:5][CH2:6][NH:7][CH2:8]1)[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17... | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 0f32895f86307496d881270b5893142b7e6f0bfad36a2f8bb676e27359041532 | 9370f47be85b7f762f9dfe0f3c726311efbbb1800d75f07f1880fc727c84fc15 | O=C(O[C@@H]1CCNC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-1.O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])(-[O;D1;H1:11])-[c:12]>>[C:10]-[C:9](-[O;D1;H1:11])(-[c:12])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)acetic acid and t-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol.Boc | Ester.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09ea3120aac043509456e0fed5ca0a23 | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)F)O)F.O[C@@H]1CN(CC1)C(=O)OC(C)(C)C>>FC1(C[C@@H](CC1)[C@](C(=O)O[C@@H]1CNCC1)(C1=CC=C(C=C1)F)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@H:4]([OH:3])[CH2:8]1.O[C:2](=[O:1])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1)[C@@H:18]1[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]1>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][CH2:6][NH:7][CH2:8]1)[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1)[... | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 0f32895f86307496d881270b5893142b7e6f0bfad36a2f8bb676e27359041532 | 9370f47be85b7f762f9dfe0f3c726311efbbb1800d75f07f1880fc727c84fc15 | O=C(O[C@H]1CCNC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-1.O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])(-[O;D1;H1:11])-[c:12]>>[C:10]-[C:9](-[O;D1;H1:11])(-[c:12])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-fluorophenyl)acetic acid and t-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol.Boc | Ester.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(F)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-91bc23d348744d3785b40c93d9614944 | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)Cl)O)F.O[C@@H]1CN(CC1)C(=O)OC(C)(C)C>>FC1(C[C@@H](CC1)[C@](C(=O)O[C@@H]1CNCC1)(C1=CC=C(C=C1)Cl)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@H:4]([OH:3])[CH2:8]1.O[C:2](=[O:1])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[C@@H:18]1[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]1>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][CH2:6][NH:7][CH2:8]1)[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1... | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 0f32895f86307496d881270b5893142b7e6f0bfad36a2f8bb676e27359041532 | 9370f47be85b7f762f9dfe0f3c726311efbbb1800d75f07f1880fc727c84fc15 | O=C(O[C@H]1CCNC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-1.O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])(-[O;D1;H1:11])-[c:12]>>[C:10]-[C:9](-[O;D1;H1:11])(-[c:12])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-chlorophenyl)acetic acid and t-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol.Boc | Ester.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Cl)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca24b7697ed54f53aea5fc4b195e0479 | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=C(C=C1)Br)O)F.O[C@@H]1CN(CC1)C(=O)OC(C)(C)C>>FC1(C[C@@H](CC1)[C@](C(=O)O[C@@H]1CNCC1)(C1=CC=C(C=C1)Br)O)F | CC(C)(C)OC(=O)[N:7]1[CH2:6][CH2:5][C@H:4]([OH:3])[CH2:8]1.O[C:2](=[O:1])[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1)[C@@H:18]1[CH2:19][CH2:20][C:21]([F:22])([F:23])[CH2:24]1>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][CH2:6][NH:7][CH2:8]1)[C@:9]([OH:10])([c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1... | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Acylation | OtherReaction | 0f32895f86307496d881270b5893142b7e6f0bfad36a2f8bb676e27359041532 | 9370f47be85b7f762f9dfe0f3c726311efbbb1800d75f07f1880fc727c84fc15 | O=C(O[C@H]1CCNC1)C(c1ccccc1)C1CCCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-1.O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[C:9](-[C:10])(-[O;D1;H1:11])-[c:12]>>[C:10]-[C:9](-[O;D1;H1:11])(-[c:12])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-1 | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)acetic acid and t-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate, the title compound was prepared by a method similar to Steps 2 and 3 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary alcohol.Boc | Ester.Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CC[C@H](O)C1.O=C(O)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1>>O=C(O[C@H]1CCNC1)[C@](O)(c1ccc(Br)cc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37614793e01048b6aa3def03b23c9708 | COC(=O)C[C@@H]1COC(C)(C)O1>>CC1(C)OC[C@@H](CCO)O1 | O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+].CC1(OC[C@H](O1)CC(=O)OC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC1(OC[C@H](O1)CCO)C | CO[C:8]([CH2:7][C@@H:6]1[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:10]1)=[O:9]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([CH2:7][CH2:8][OH:9])[O:10]1 | COC(=O)C[C@@H]1COC(C)(C)O1 | CC1(C)OC[C@@H](CCO)O1 | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COCO1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]-[#8:5]>>[#8:5]-[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 93.2 | [{"value": 93.2, "product": "CC1(OC[C@H](O1)CCO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | To a solution of 1.0 g of methyl 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)acetate in 29 ml of diethyl ether, 110 mg of lithium aluminum hydride was added under cooling with ice, followed by 12 hours' stirring at the same temperature. Sodium sulfate decahydrate was added to the reaction liquid which was then stirred for 3... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COCO1 | Other | C(C)OCC | null | 12 | COC(=O)C[C@@H]1COC(C)(C)O1>C(C)OCC>CC1(C)OC[C@@H](CCO)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5888c27d571a46b3b6c9f69781d6646f | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC[C@@H]1CCNC(=S)N1>>O=C(OC[C@@H]1CCNC(=S)N1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=CC=C1)O)F.OC[C@H]1NC(NCC1)=S>>FC1(C[C@@H](CC1)[C@](C(=O)OC[C@H]1NC(NCC1)=S)(C1=CC=CC=C1)O)F | O[C:2](=[O:1])[C@:12]([OH:13])([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C@@H:20]1[CH2:21][CH2:22][C:23]([F:24])([F:25])[CH2:26]1.[OH:3][CH2:4][C@@H:5]1[CH2:6][CH2:7][NH:8][C:9](=[S:10])[NH:11]1>>[O:1]=[C:2]([O:3][CH2:4][C@@H:5]1[CH2:6][CH2:7][NH:8][C:9](=[S:10])[NH:11]1)[C@:12]([OH:13])([c:14]1[cH:15][cH:16][cH:17]... | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC[C@@H]1CCNC(=S)N1 | O=C(OC[C@@H]1CCNC(=S)N1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OC[C@@H]1CCNC(=S)N1)C(c1ccccc1)C1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6].[#7:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#7:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6] | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and (4S)-4-(hydroxymethyl)tetrahydropyrimidine-2(1H)-thione, the title compound was prepared by a method similar to Step 2 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CNCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC[C@@H]1CCNC(=S)N1>>O=C(OC[C@@H]1CCNC(=S)N1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c99d31c5adb24599b80a14ac0842751a | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC1CNC(=S)NC1>>O=C(OC1CNC(=S)NC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | FC1(C[C@@H](CC1)[C@](C(=O)O)(C1=CC=CC=C1)O)F.OC1CNC(NC1)=S>>FC1(C[C@@H](CC1)[C@](C(=O)OC1CNC(NC1)=S)(C1=CC=CC=C1)O)F | O[C:2](=[O:1])[C@:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@H:19]1[CH2:20][CH2:21][C:22]([F:23])([F:24])[CH2:25]1.[OH:3][CH:4]1[CH2:5][NH:6][C:7](=[S:8])[NH:9][CH2:10]1>>[O:1]=[C:2]([O:3][CH:4]1[CH2:5][NH:6][C:7](=[S:8])[NH:9][CH2:10]1)[C@:11]([OH:12])([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[C@@... | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC1CNC(=S)NC1 | O=C(OC1CNC(=S)NC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 | null | null | null | Protection | Esterification of Carboxylic Acids | 624bf219458ba212c982344d7c3d6088244bf818423b8912fbf03efe5373c5bf | 547c73c17c71bc10d21cd3cdbafe9d7a279f866fe729eea28fdc1be18f1a2791 | O=C(OC1CNC(=S)NC1)C(c1ccccc1)C1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6].[#7:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]-[#7:12]>>[#7:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[O;D1;H1:5])-[c:6])-[C:11]-[#7:12] | null | [] | null | null | null | null | Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | C1CNCNC1.c1ccccc1.C1CCCC1 | HO- | null | null | null | O=C(O)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1.OC1CNC(=S)NC1>>O=C(OC1CNC(=S)NC1)[C@](O)(c1ccccc1)[C@@H]1CCC(F)(F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3995c5ded094789b555339d723dd692 | O=[N+]([O-])c1ccc(CN2CCCC2)cc1>>Nc1ccc(CN2CCCC2)cc1 | [N+](=O)([O-])C1=CC=C(CN2CCCC2)C=C1.ClCCl.CO>>N1(CCCC1)CC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][cH:13]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[cH:12][cH:13]1 | O=[N+]([O-])c1ccc(CN2CCCC2)cc1 | Nc1ccc(CN2CCCC2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CN2CCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 36.9 | [{"value": 36.9, "product": "N1(CCCC1)CC1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-(4-nitro-benzyl)-pyrrolidine (1.37 g) in ethanol (66 mL) tin(II)-chloride dihydrate (9.0 g) was added portionwise and the resulting mixture refluxed for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the aqueous phase extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]C1 | Other | C(C)O | null | null | O=[N+]([O-])c1ccc(CN2CCCC2)cc1>C(C)O>Nc1ccc(CN2CCCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bcf2537d748471a9ecfb404bfad1fc6 | Clc1ncc(Br)c(NCCc2c[nH]cn2)n1.Nc1ccc(CN2CCCC2)cc1>>Brc1cnc(Nc2ccc(CN3CCCC3)cc2)nc1NCCc1c[nH]cn1 | ClCCl.CO.BrC=1C(=NC(=NC1)Cl)NCCC=1N=CNC1.N1(CCCC1)CC1=CC=C(C=C1)N.Cl>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)CN1CCCC1)NCCC=1N=CNC1 | Cl[c:5]1[n:4][cH:3][c:2]([Br:1])[c:20]([NH:21][CH2:22][CH2:23][c:24]2[cH:25][nH:26][cH:27][n:28]2)[n:19]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17][cH:18]1>>[Br:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][N:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[cH:17]... | Clc1ncc(Br)c(NCCc2c[nH]cn2)n1.Nc1ccc(CN2CCCC2)cc1 | Brc1cnc(Nc2ccc(CN3CCCC3)cc2)nc1NCCc1c[nH]cn1 | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NCCc2c[nH]cn2)nc(Nc2ccc(CN3CCCC3)cc2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 4.6 | [{"value": 4.6, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)CN1CCCC1)NCCC=1N=CNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-bromo-4-(2-(1H-imidazol-4-yl)-ethylamino)-2-chloro-pyrimidine (60 mg), 4-pyrrolidin-1-ylmethyl-phenylamine (35 mg) and hydrochloric acid (37% in water, 40 μL) in methanol (2 mL) was refluxed overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate sol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.C1CC[NH]C1.c1c[nH]cn1 | HCl | CO | null | null | Clc1ncc(Br)c(NCCc2c[nH]cn2)n1.Nc1ccc(CN2CCCC2)cc1>CO>Brc1cnc(Nc2ccc(CN3CCCC3)cc2)nc1NCCc1c[nH]cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27783949e23b42948a00d34f6d795f4c | C#CCN.FC(F)(F)c1cnc(Cl)nc1Cl>>C#CCNc1nc(Cl)ncc1C(F)(F)F | ClC1=NC=C(C(=N1)Cl)C(F)(F)F.C(C#C)N>>ClC1=NC=C(C(=N1)NCC#C)C(F)(F)F | [CH:1]#[C:2][CH2:3][NH2:4].Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15]>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | C#CCN.FC(F)(F)c1cnc(Cl)nc1Cl | C#CCNc1nc(Cl)ncc1C(F)(F)F | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10].[C;D1;H1:11]#[C:12]-[C:13]-[NH2;D1;+0:14]>>[C;D1;H1:11]#[C:12]-[C:13]-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10] | null | [] | null | null | 48 | HOUR | To a solution of 2,4-dichloro-5-trifluoromethyl-pyrimidine (3-47 g) in acetonitrile (16 mL) a solution of propargylamine (1.76 g) in acetonitrile (16 mL) was added dropwise at 0° C., the mixture warmed to r.t. and stirred at r.t. for 48 h. The suspension was diluted with ethyl acetate, washed with brine, dried (Na2SO4)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | C(C)#N.C(C)(=O)OCC | null | 48 | C#CCN.FC(F)(F)c1cnc(Cl)nc1Cl>C(C)#N.C(C)(=O)OCC>C#CCNc1nc(Cl)ncc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f6531e17c464e9e8521ddfd18dbd2c7 | C#CCNc1nc(Cl)ncc1C(F)(F)F.Nc1ccc(CNC(=O)C(F)(F)F)cc1>>C#CCNc1nc(Nc2ccc(CN)cc2)ncc1C(F)(F)F | ClCCl.CO.ClC1=NC=C(C(=N1)NCC#C)C(F)(F)F.NC1=CC=C(CNC(C(F)(F)F)=O)C=C1.Cl>>NCC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)C(F)(F)F | Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][C:2]#[CH:1])[c:19]([C:20]([F:21])([F:22])[F:23])[cH:18][n:17]1.O=C(C(F)(F)F)[NH:14][CH2:13][c:12]1[cH:11][cH:10][c:9]([NH2:8])[cH:16][cH:15]1>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][NH2:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]([F:21])([... | C#CCNc1nc(Cl)ncc1C(F)(F)F.Nc1ccc(CNC(=O)C(F)(F)F)cc1 | C#CCNc1nc(Nc2ccc(CN)cc2)ncc1C(F)(F)F | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 63b053341316c499262ea0ca714177f06ddc9253641938fa2055841d36a30307 | 8b6ae2d35861183c434122f7abcf95b5448537ccbb9959a2e0360f24d60e99dc | c1ccc(Nc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].F-C(-F)(-F)-C(=O)-[NH;D2;+0:6]-[C:7]-[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[NH2;D1;+0:6]-[C:7]-[c:8].[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:12] | 37.4 | [{"value": 37.4, "product": "NCC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-chloro-4-(prop-2-ynylamino)-5-trifluoromethyl-pyrimidine (235 mg), N-(4-aminobenzyl)-2,2,2-trifluoro-acetamide (410 mg) and hydrochloric acid (37% in water, 0.2 mL) in methanol (5 mL) was refluxed for 1 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Secondary amide.Primary amine | Primary amine.Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | Other | CO | null | null | C#CCNc1nc(Cl)ncc1C(F)(F)F.Nc1ccc(CNC(=O)C(F)(F)F)cc1>CO>C#CCNc1nc(Nc2ccc(CN)cc2)ncc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ce7055e0983477da284dafc7868d5ab | CC(C)(C)OC(=O)NCCCN.Clc1ncc(Br)c(Cl)n1>>CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br | BrC=1C(=NC(=NC1)Cl)Cl.C(C)N(CC)CC.CC(C)(C)OC(NCCCN)=O>>C(C)(C)(C)OC(NCCCNC1=NC(=NC=C1Br)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH2:12].Cl[c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Br:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[Br:20] | CC(C)(C)OC(=O)NCCCN.Clc1ncc(Br)c(Cl)n1 | CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[Br;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[Br;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:10]-[C:9]-[C:8] | 85.8 | [{"value": 85.8, "product": "C(C)(C)(C)OC(NCCCNC1=NC(=NC=C1Br)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-bromo-2,4-dichloro-pyrimidine (1.4 g) in acetonitrile (10 mL) at 0° C. was added triethylamine (0.94 mL) and 3-aminopropylcarbamic acid-1,1-dimethylethyl ester (1.0 g). After removing the cooling bath the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | C(C)#N | null | 8 | CC(C)(C)OC(=O)NCCCN.Clc1ncc(Br)c(Cl)n1>C(C)#N>CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cd4beb4e75a4046901fce5d34fec6e7 | CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br.Nc1ccc(S(N)(=O)=O)cc1>>Cl.NCCCNc1nc(Nc2ccc(S(N)(=O)=O)cc2)ncc1Br | NC1=CC=C(C=C1)S(=O)(=O)N.CC(C)(C)OC(NCCCNC1=NC(=NC=C1Br)Cl)=O>>Cl.NCCCNC1=NC(=NC=C1Br)NC1=CC=C(C=C1)S(=O)(=O)N | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]([Cl:1])[n:21][cH:22][c:23]1[Br:24].[NH2:10][c:11]1[cH:12][cH:13][c:14]([S:15]([NH2:16])(=[O:17])=[O:18])[cH:19][cH:20]1>>[ClH:1].[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]([S:15]([NH2:16])(=[O:17])=[O:18])[cH:19][... | CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br.Nc1ccc(S(N)(=O)=O)cc1 | Cl.NCCCNc1nc(Nc2ccc(S(N)(=O)=O)cc2)ncc1Br | null | null | Cl.C(C)#N.O | Heteroatom Alkylation and Arylation | OtherReaction | 0740faf4895077f4f6df85298369c1e2a11932716b6f9f960df9d4c4a9f64cab | b189e21881719932ff7e93d2cee73d5d9b679e27f974877dd5fa270130c3c7ff | c1ccc(Nc2ncccn2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:3]-[C:2]-[NH2;D1;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9]):[c:13].[ClH;D0;+0:4] | 74.3 | [{"value": 74.3, "product": "Cl.NCCCNC1=NC(=NC=C1Br)NC1=CC=C(C=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-aminobenzenesulfonamide (190 mg) in acetonitrile (20 mL), hydrochloric acid solution (4M in dioxane, 0.3 mL) and water (0.3 mL) was added (3-((5-bromo-2-chloro-4-pyrimidinyl)amino)propyl)-carbamic acid-1,1-dimethylethyl ester (360 mg). The resulting mixture was refluxed overnight. The precipitate was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary amine.Boc | Primary amine.Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | Cl.C(C)#N.O | null | null | CC(C)(C)OC(=O)NCCCNc1nc(Cl)ncc1Br.Nc1ccc(S(N)(=O)=O)cc1>Cl.C(C)#N.O>Cl.NCCCNc1nc(Nc2ccc(S(N)(=O)=O)cc2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bd4d18dca2e4c3794abb96b4dfe9ef5 | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1>>C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br | BrC=1C(=NC(=NC1)Cl)OCC#C.NC=1C=C(C(=O)OC)C=C(C1)N.Cl>>COC(C1=CC(=CC(=C1)NC1=NC=C(C(=N1)OCC#C)Br)N)=O | Cl[c:7]1[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:22]([Br:23])[cH:21][n:20]1.[NH2:8][c:9]1[cH:10][c:11]([NH2:12])[cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19]1>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19]2)[n:20][cH:21][c:22]1[Br:23] | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1 | C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 60.4 | [{"value": 60.4, "product": "COC(C1=CC(=CC(=C1)NC1=NC=C(C(=N1)OCC#C)Br)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | A mixture of 5-bromo-2-chloro-4-(prop-2-ynyloxy)pyrimidine (15 g), methyl 3,5-diaminobenzoate (45 g) and concentrated hydrochloric acid (15 ml) in methanol (600 ml) was stirred at 65° C. for 8 h. After concentration to half the volume water was added and the precipitate collected by filtration. The precipitate then was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CO | 65 | 8 | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1>CO>C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04aa12cb8d11464998828cf5c8985bfd | C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])cc(NC(=O)N3CCCC3)c2)ncc1Br>>C#CCOc1nc(Nc2cc(NC(=O)[C@H](N)Cc3ccccc3)cc(NC(=O)N3CCCC3)c2)ncc1Br | CC(C)(ON(C([O-])=O)[C@@H](C(=O)NC1=CC(=CC(=C1)NC(=O)N1CCCC1)NC1=NC=C(C(=N1)OCC#C)Br)CC1=CC=CC=C1)C.S(O)(O)(=O)=O.O>>N[C@@H](C(=O)NC=1C=C(C=C(C1)NC1=NC=C(C(=N1)OCC#C)Br)NC(=O)N1CCCC1)CC1=CC=CC=C1 | CC(C)(C)O[N:16](C(=O)[O-])[C@@H:15]([C:13]([NH:12][c:11]1[cH:10][c:9]([NH:8][c:7]2[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:37]([Br:38])[cH:36][n:35]2)[cH:34][c:25]([NH:26][C:27](=[O:28])[N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:24]1)=[O:14])[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH:1]#[C:2][CH2:3][O:4][... | C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])cc(NC(=O)N3CCCC3)c2)ncc1Br | C#CCOc1nc(Nc2cc(NC(=O)[C@H](N)Cc3ccccc3)cc(NC(=O)N3CCCC3)c2)ncc1Br | null | null | O1CCOCC1 | Reduction | OtherReaction | 017509a577522918fcd61b79a78a9b03bf1c8337f1c76e29f10765017faab5c3 | ac6f378f3e5e6c9b4b710d4e542f71f04a708f2a748ed8cf03d2a10006d6bc94 | O=C(CCc1ccccc1)Nc1cc(NC(=O)N2CCCC2)cc(Nc2ncccn2)c1 | C-C(-C)(-C)-O-[N;H0;D3;+0:1](-C(=O)-[O-])-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7] | 86.8 | [{"value": 86.8, "product": "N[C@@H](C(=O)NC=1C=C(C=C(C1)NC1=NC=C(C(=N1)OCC#C)Br)NC(=O)N1CCCC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,1-Dimethylethoxy[(1R)-2-[[3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-[[(pyrrolidin-1-yl)carbonyl]amino]phenyl]amino]-2-oxo-1(phenylmethyl)ethyl]carbamate (105 mg) and sulfuric acid (0.5 ml; 2 n) were stirred in dioxane (5 ml) at 85° C. for 3.5 h. After cooling and dilution with water saturated NaHCO3-solut... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | HO- | O1CCOCC1 | null | null | C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])cc(NC(=O)N3CCCC3)c2)ncc1Br>O1CCOCC1>C#CCOc1nc(Nc2cc(NC(=O)[C@H](N)Cc3ccccc3)cc(NC(=O)N3CCCC3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b16ead9bbb0d438d90be65935a9f0c13 | CCOC(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>>CCOC(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.ClC(=O)OCC>>C(C)OC(NCCCNC1=NC(=NC=C1Br)NC1=CC(=CC=C1)NC(=O)N1CCCC1)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28]2)[n:29][cH:30][c:31]1[Br:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][c:13]([... | CCOC(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | CCOC(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1cccc(Nc2ncccn2)c1)N1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 6.6 | [{"value": 6.6, "product": "C(C)OC(NCCCNC1=NC(=NC=C1Br)NC1=CC(=CC=C1)NC(=O)N1CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (150 mg, 0.30 mmol) in pyridine (5 mL) was added ethyl chloroformate (38.5 mg, 0.35 mmol) at 0° C. under N2. The resulting reaction mixture was stirred at 0° C. for 1 h and then was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1cncnc1.c1ccccc1.C1CC[NH]C1 | HCl | N1=CC=CC=C1 | 0 | 1 | CCOC(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>N1=CC=CC=C1>CCOC(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c9f1cd31f1645a28bbbe1d7ff675661 | CCCS(=O)(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>>CCCS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.CCN(C(C)C)C(C)C.C(CC)S(=O)(=O)Cl>>BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNS(=O)(=O)CCC | Cl[S:4]([CH2:3][CH2:2][CH3:1])(=[O:5])=[O:6].[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][c:12]1[n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[cH:29]2)[n:30][cH:31][c:32]1[Br:33]>>[CH3:1][CH2:2][CH2:3][S:4](=[O:5])(=[O:6])[NH:7][CH2:8][CH2:9][CH2:10][NH:11... | CCCS(=O)(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | CCCS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | null | CN(C)C=1C=CN=CC1 | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(Nc1cccc(Nc2ncccn2)c1)N1CCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:5]-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:8]-[C:7]-[C:6] | 41.3 | [{"value": 41.3, "product": "BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNS(=O)(=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | To a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (150 mg, 0.30 mmol) in dichloromethane (4 mL) was added DIEA (0.16 mL, 0.92 mmol) and DMAP (1.4 mg, 0.011 mmol) at 0° C., then a solution of 1-propanesulfonyl chloride (51 mg, 0.36 mmol) in dichloromethane (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1cncnc1.c1ccccc1.C1CC[NH]C1 | HCl | CN(C)C=1C=CN=CC1.ClCCl | 0 | 8 | CCCS(=O)(=O)Cl.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>CN(C)C=1C=CN=CC1.ClCCl>CCCS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9afebf5c36f34a3ca3961af93d651cd2 | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=Nc1ccccc1>>O=C(NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br)Nc1ccccc1 | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.CCN(C(C)C)C(C)C.C1(=CC=CC=C1)N=C=O>>BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNC(=O)NC1=CC=CC=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[cH:25]2)[n:26][cH:27][c:28]1[Br:29].[O:1]=[C:2]=[N:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[n:9][c:10](... | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=Nc1ccccc1 | O=C(NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br)Nc1ccccc1 | null | null | O1CCOCC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCCNc1ccnc(Nc2cccc(NC(=O)N3CCCC3)c2)n1)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 61.4 | [{"value": 61.4, "product": "BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNC(=O)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (100 mg, 0.2 mmol) and DIEA (0.14 mL, 0.8 mmol) in 1,4-dioxane (5 mL) was added phenyl isocyanate (35 mg, 0.3 mmol). The resulting solution was stirred overnight and concentrated. The crude residue was direct... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cncnc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | null | O1CCOCC1 | null | 8 | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=Nc1ccccc1>O1CCOCC1>O=C(NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br)Nc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d94129faff384dacbbcf2e6310915cfd | CCSN=C=O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>>CCNC(=S)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.CCN(C(C)C)C(C)C.C(C)SN=C=O>>BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNC(=S)NCC | O=[C:4]=[N:3][S:5][CH2:2][CH3:1].[NH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:28]2)[n:29][cH:30][c:31]1[Br:32]>>[CH3:1][CH2:2][NH:3][C:4](=[S:5])[NH:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[n:12][c:13]([N... | CCSN=C=O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | CCNC(=S)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 28d8b5f204086df6b757dfa4474e7c65e6f4ceb8253365e9687ab34e3d541aef | 0e293b57a79fbb4b3e56abffbe4729147ea3208588cc79d4fe92f2040d00840d | O=C(Nc1cccc(Nc2ncccn2)c1)N1CCCC1 | O=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[S;H0;D2;+0:3]-[CH2;D2;+0:4]-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[S;H0;D1;+0:3])-[NH;D2;+0:2]-[CH2;D2;+0:4]-[C;D1;H3:5] | 92.5 | [{"value": 92.5, "product": "BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNC(=S)NCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (100 mg, 0.20 mmol) and DMF (5 mL) was treated with DIEA (0.1 mL, 0.6 mmol, 3eq) and ethylthioisocyanate (15 mg, 0.17 mmol, 0.9 eq). The resulting mixture was stirred at RT for 2 hr. Then the crude mixture was pur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Thiourea | null | null | c1cncnc1.c1ccccc1.C1CC[NH]C1 | Other | CN(C)C=O | null | 2 | CCSN=C=O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br>CN(C)C=O>CCNC(=S)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cc5d5ff710a4e5c8fc9fd4d32199cdd | CC(C)(C)O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=NS(=O)(=O)Cl>>CC(C)(C)OC(=O)NS(=O)(=O)Cl.NS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.CCN(C(C)C)C(C)C.ClS(=O)(=O)N=C=O.C(C)(C)(C)O>>ClS(NC(=O)OC(C)(C)C)(=O)=O.NS(=O)(=O)NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1 | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][c:22]1[n:23][c:24]([NH:25][c:26]2[cH:27][cH:28][cH:29][c:30]([NH:31][C:32](=[O:33])[N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[cH:39]2)[n:40][cH:41][c:42]1[Br:43].[C:6](=[O:7])=[N:8][S:9](=[O:10])(=[O:11])[Cl:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[... | CC(C)(C)O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=NS(=O)(=O)Cl | CC(C)(C)OC(=O)NS(=O)(=O)Cl.NS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br | null | CN(C)C=1C=CN=CC1 | ClCCl | Oxidation | OtherReaction | c7681a9bc491ddfb97b6a1fa5fb53fbc6428630512a123a3b8f2094c948cae2a | c1ef13bfaa9ceebe37ba6c4b18490eba4fe43735e855933840eac0c739522c30 | O=C(Nc1cccc(Nc2ncccn2)c1)N1CCCC1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[OH;D1;+0:5].[C:6]-[C:7]-[NH2;D1;+0:8].[Cl;D1;H0:9]-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[N;H0;D2;+0:13]=[C;H0;D2;+0:14]=[O;D1;H0:15]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:5]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[NH;D2;+0:13]-[#16:10](-[Cl;D1;H0:9])(=[O;D1;... | 50.8 | [{"value": 50.8, "product": "NS(=O)(=O)NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 2.5 | HOUR | Chloro[[(1,1-dimethylethoxy)carbonyl]amino]-sulfane dioxide was prepared by adding chlorosulfonyl isocyanate (32 mg, 0.23 mmol, 1.0 eq.) to a cooled solution of tert-butyl alcohol (17 mg, 0.23 mmol, 1.0eq.) and dichloromethane (2 mL) in an ice-water bath. The resulting mixture was stirred at 0-5° C. for 2-3 hr. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Primary amine | Sulfonamide.Sulfonamide.Sulfonamide.Carbamic ester | null | null | c1cncnc1.c1ccccc1.C1CC[NH]C1 | Other | CN(C)C=1C=CN=CC1.ClCCl | 2.5 | 2.5 | CC(C)(C)O.NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=C=NS(=O)(=O)Cl>CN(C)C=1C=CN=CC1.ClCCl>CC(C)(C)OC(=O)NS(=O)(=O)Cl.NS(=O)(=O)NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72664d7b391f4e4499752a268ef7893b | N.O=C=Nc1cccc([N+](=O)[O-])c1>>NC(=O)Nc1cccc([N+](=O)[O-])c1 | N.[N+](=O)([O-])C=1C=C(C=CC1)N=C=O>>[N+](=O)([O-])C=1C=C(C=CC1)NC(=O)N | [NH3:1].[C:2](=[O:3])=[N:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | N.O=C=Nc1cccc([N+](=O)[O-])c1 | NC(=O)Nc1cccc([N+](=O)[O-])c1 | null | null | null | Acylation | OtherReaction | 82d635e934cbc8e99aff24e37cc3fdf86fb44efb1229c53f437de32ca182fae3 | f3bad38766fe150121cf3a3df1206de539fb081636141fb4c19828594d9c6230 | c1ccccc1 | [NH3;D0;+0:1].[O;D1;H0:2]=[C;H0;D2;+0:3]=[N;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:3](=[O;D1;H0:2])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Ammonia was bubbled into a solution of 3-nitrophenylisocyanate (1.5 g, 9.1 mmol) for ten minutes. The reaction mixture was then concentrated and the resulting yellow solid was washed with ether (200 mL) to afford N-(3-nitrophenyl)-urea (1.35 g, 7.5 mmol).
Conditions: See reaction.notes.procedure_details.
Workup: The re... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate | Urea | null | null | c1ccccc1 | null | null | null | null | N.O=C=Nc1cccc([N+](=O)[O-])c1>>NC(=O)Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27525ecb4b4a4ca99e802618e7fc8b19 | NC(=O)Nc1cccc([N+](=O)[O-])c1>>NC(=O)Nc1cccc(N)c1 | [N+](=O)([O-])C=1C=C(C=CC1)NC(=O)N>>NC=1C=C(C=CC1)NC(=O)N | O=[N+:10]([O-])[c:9]1[cH:8][cH:7][cH:6][c:5]([NH:4][C:2]([NH2:1])=[O:3])[cH:11]1>>[NH2:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([NH2:10])[cH:11]1 | NC(=O)Nc1cccc([N+](=O)[O-])c1 | NC(=O)Nc1cccc(N)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A solution of N-(3-nitrophenyl)-urea (1.0 g, 5-5 mmol) and methanol (40 mL) was treated with 10% Pd/C (250 mg) and placed under H2 (45 psi) for 2 h. The mixture was then filtered through celite and concentrated to afford N-(3-aminophenyl)-urea (828 mg, 5.5 mmol).
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 2 | NC(=O)Nc1cccc([N+](=O)[O-])c1>[Pd].CO>NC(=O)Nc1cccc(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cbb34cd19a849b0a82cafe0f9ba6d7b | COC(=O)CN.O=C=Nc1cccc([N+](=O)[O-])c1>>COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC1)N=C=O.Cl.COC(CN)=O.C(C)N(CC)CC>>COC(CNC(=O)NC1=CC(=CC=C1)[N+](=O)[O-])=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][NH2:6].[C:7](=[O:8])=[N:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][C:7](=[O:8])[NH:9][c:10]1[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | COC(=O)CN.O=C=Nc1cccc([N+](=O)[O-])c1 | COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | 97.1 | [{"value": 97.1, "product": "COC(CNC(=O)NC1=CC(=CC=C1)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 3-nitrophenyl isocyanate (10 g, 61 mmol) and glycine methyl ester hydrochloride (8.4 g, 67 mmol, 1.1 equiv.) in dichloromethane (250 mL) was added triethylamine (10 mL, 72 mmol, 1.2 equiv.) at 0° C. The resulting solution was stirred at room temperature overnight. The resulting dark brown solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1 | null | ClCCl | null | 8 | COC(=O)CN.O=C=Nc1cccc([N+](=O)[O-])c1>ClCCl>COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79780408d8904b6aa7c78e70c80f72ef | COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1>>Nc1cccc(N2C(=O)CNC2=O)c1 | COC(CNC(=O)NC1=CC(=CC=C1)[N+](=O)[O-])=O>>NC=1C=C(C=CC1)N1C(NCC1=O)=O | CO[C:8](=[O:9])[CH2:10][NH:11][C:12]([NH:7][c:6]1[cH:5][cH:4][cH:3][c:2]([N+:1](=O)[O-])[cH:14]1)=[O:13]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[C:8](=[O:9])[CH2:10][NH:11][C:12]2=[O:13])[cH:14]1 | COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1 | Nc1cccc(N2C(=O)CNC2=O)c1 | null | null | Cl.CC(=O)C | Functional Group Interconversion | OtherReaction | e7083db3778a14a4c7c9357783c1aaa3d31f302b0e948a636b8b263ef060dacc | 7b6fbc0f2504d3806fceb2cc29925b7f1251f68de5e6d478678b4df3ed8148ad | O=C1CNC(=O)N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]:[c:11](-[N+;H0;D3:12](=O)-[O-]):[c:13]>>[NH2;D1;+0:12]-[c:11](:[c:13]):[c:10]:[c:8](-[N;H0;D3;+0:7]1-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1]-1=[O;D1;H0:2]):[c:9] | 85.2 | [{"value": 85.2, "product": "NC=1C=C(C=CC1)N1C(NCC1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of [[[(3-nitrophenyl)amino]carbonyl]aminoacetic acid methyl ester (6.9 g, 27 mmol) in 6N aqueous hydrochloride solution (40 mL) and acetone (20 mL) was stirred at reflux overnight. The resulting solution was cooled and concentrated. The resulting yellowish suspension was filtered and the filter cake was wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Urea.Nitro group | Urea.Substituted dicarboximide.Primary amine | null | C1CNC[NH]1 | c1ccccc1.C1CNC[NH]1 | HO- | Cl.CC(=O)C | null | null | COC(=O)CNC(=O)Nc1cccc([N+](=O)[O-])c1>Cl.CC(=O)C>Nc1cccc(N2C(=O)CNC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a14981d6c4d40c19cd39b640375616d | O=C1CNC(=O)N1c1cccc([N+](=O)[O-])c1>>Nc1cccc(N2C(=O)CNC2=O)c1 | [N+](=O)([O-])C=1C=C(C=CC1)N1C(NCC1=O)=O>>NC=1C=C(C=CC1)N1C(NCC1=O)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[C:8](=[O:9])[CH2:10][NH:11][C:12]2=[O:13])[cH:14]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[C:8](=[O:9])[CH2:10][NH:11][C:12]2=[O:13])[cH:14]1 | O=C1CNC(=O)N1c1cccc([N+](=O)[O-])c1 | Nc1cccc(N2C(=O)CNC2=O)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CNC(=O)N1c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.4 | [{"value": 99.4, "product": "NC=1C=C(C=CC1)N1C(NCC1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 3-(3-nitrophenyl)-2,4-imidazolidinedione (4.4 g, 20 mmol) and methanol (100 mL) was treated with 10% Pd/C (1.0 g) and placed under H2 (40 psi) for 2 h. The mixture was then filtered through celite and concentrated to afford the title compound (3.8 g).
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CNC[NH]1 | Other | [Pd].CO | null | 2 | O=C1CNC(=O)N1c1cccc([N+](=O)[O-])c1>[Pd].CO>Nc1cccc(N2C(=O)CNC2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8116cce19894db296c8126ece6ea845 | CC(C)(C)OC(=O)NCCCBr.Nc1nccs1>>CC(C)(C)OC(=O)NCCCNc1nccs1 | CC(C)(C)OC(NCCCBr)=O.NC=1SC=CN1.C(=O)([O-])[O-].[Cs+].[Cs+]>>CC(C)(C)OC(NCCCNC=1SC=CN1)=O | Br[CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:12][c:13]1[n:14][cH:15][cH:16][s:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][c:13]1[n:14][cH:15][cH:16][s:17]1 | CC(C)(C)OC(=O)NCCCBr.Nc1nccs1 | CC(C)(C)OC(=O)NCCCNc1nccs1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cscn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[#7;a:9]:1 | 23.3 | [{"value": 23.3, "product": "CC(C)(C)OC(NCCCNC=1SC=CN1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of (3-bromopropyl)-carbamic acid 1,1-dimethylethyl ester (1.2 g, 5.0 mmol) and 2-aminothiazole (1.0 g, 10 mmol, 2 equiv.) in DMF 20 (mL) was added Cs2CO3 (2.5 g, 7.7 mmol, 1.5 equiv.). The resulting mixture was heated at 85° C. under N2 overnight. The reaction mixture was diluted with ethyl acetate (200 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1cscn1 | HBr | CN(C)C=O.C(C)(=O)OCC | 85 | null | CC(C)(C)OC(=O)NCCCBr.Nc1nccs1>CN(C)C=O.C(C)(=O)OCC>CC(C)(C)OC(=O)NCCCNc1nccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c62d6942a1764086a9a3583d853317c0 | CC(C)(C)OC(=O)CCN.Clc1ncc(Br)c(Cl)n1>>CC(C)(C)OC(=O)CCNc1nc(Cl)ncc1Br | BrC=1C(=NC(=NC1)Cl)Cl.C(C)N(CC)CC.NCCC(=O)OC(C)(C)C.Cl>>CC(C)(C)OC(CCNC1=NC(=NC=C1Br)Cl)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][NH2:10].Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Br:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][NH:10][c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[Br:18] | CC(C)(C)OC(=O)CCN.Clc1ncc(Br)c(Cl)n1 | CC(C)(C)OC(=O)CCNc1nc(Cl)ncc1Br | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[Br;D1;H0:7].[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12]-[NH2;D1;+0:13]>>[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[Br;D1;H0:7] | 35.1 | [{"value": 35.1, "product": "CC(C)(C)OC(CCNC1=NC(=NC=C1Br)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 5-bromo-2,4-dichloropyrimidine (1.0 g, 4.4 mmol, 1 equiv.) in acetonitrile (10 mL) at 0° C. was added triethylamine (0.672 mL, 4.8 mmol, 1.1 equiv.) and H-beta-Ala-OtBu HCl (0.8 g, 4.4 mmol, 1 equiv.). After removing the cooling bath the reaction mixture was stirred at room temperature overnight. The r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | C(C)#N | null | 8 | CC(C)(C)OC(=O)CCN.Clc1ncc(Br)c(Cl)n1>C(C)#N>CC(C)(C)OC(=O)CCNc1nc(Cl)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58bee59f13cb4b3ea42a1a24ff3ce534 | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=Cc1cccs1>>O=C(Nc1cccc(Nc2ncc(Br)c(NCCCNCc3ccsc3)n2)c1)N1CCCC1 | NCCCNC1=NC(=NC=C1Br)NC=1C=C(C=CC1)NC(=O)N1CCCC1.S1C(=CC=C1)C=O.C(C)N(CC)CC.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>BrC=1C(=NC(=NC1)NC=1C=C(C=CC1)NC(=O)N1CCCC1)NCCCNCC1=CSC=C1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([Br:14])[c:15]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])[n:27]2)[cH:28]1)[N:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.O=[CH:21][c:22]1[cH:23][cH:24][cH:26][s:25]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]... | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=Cc1cccs1 | O=C(Nc1cccc(Nc2ncc(Br)c(NCCCNCc3ccsc3)n2)c1)N1CCCC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | f7cd85fecff841c6a583c5a6b4960012627577d9ab64c9a8f8a1f57e17525696 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(Nc1cccc(Nc2nccc(NCCCNCc3ccsc3)n2)c1)N1CCCC1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[s;H0;D2;+0:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[cH;D2;+0:4]:[s;H0;D2;+0:6]:[cH;D2;+0:5]:1 | null | [] | null | null | 8 | HOUR | To a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (1.0 g, 1.97 mmol) in THF (30 mL) was added 2-thiophenecarboxaldehyde (184 mg, 1.64 mmol, 0.8 equiv.), triethylamine (362 mg, 3-6 mmol, 1.8 equiv.) and sodium triacetoxyborohydride (688 mg, 3.25 mmol, 1.6 equiv... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | c1ccsc1 | c1ccsc1 | c1ccccc1.c1cncnc1.c1ccsc1.C1CC[NH]C1 | Other | C1CCOC1 | null | 8 | NCCCNc1nc(Nc2cccc(NC(=O)N3CCCC3)c2)ncc1Br.O=Cc1cccs1>C1CCOC1>O=C(Nc1cccc(Nc2ncc(Br)c(NCCCNCc3ccsc3)n2)c1)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01a4b9c186eb4e21abd5dce0df225a6e | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1>>C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br | BrC=1C(=NC(=NC1)Cl)OCC#C.NC=1C=C(C(=O)OC)C=C(C1)N.Cl>>NC=1C=C(C(=O)OC)C=C(C1)NC1=NC=C(C(=N1)OCC#C)Br | Cl[c:7]1[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:22]([Br:23])[cH:21][n:20]1.[NH2:8][c:9]1[cH:10][c:11]([NH2:12])[cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19]1>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19]2)[n:20][cH:21][c:22]1[Br:23] | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1 | C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br | null | null | CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | 60.4 | [{"value": 60.4, "product": "NC=1C=C(C(=O)OC)C=C(C1)NC1=NC=C(C(=N1)OCC#C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | A mixture of 5-bromo-2-chloro-4-(prop-2-ynyloxy)pyrimidine (15 g), methyl 3,5-diaminobenzoate (45 g) and concentrated hydrochloric acid (15 ml) in methanol (600 ml) was stirred at 65° C. for 8 h. After concentration to half the volume water was added and the precipitate collected by filtration. The precipitate then was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CO | 65 | 8 | C#CCOc1nc(Cl)ncc1Br.COC(=O)c1cc(N)cc(N)c1>CO>C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-445f6cf854b840fb9be84fa43e1027e6 | C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O>>C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)NC(=O)OC(C)(C)C)cc(C(=O)OC)c2)ncc1Br | NC=1C=C(C(=O)OC)C=C(C1)NC1=NC=C(C(=N1)OCC#C)Br.C(=O)(OC(C)(C)C)N[C@H](CC1=CC=CC=C1)C(=O)O.O.ON1N=NC2=C1C=CC=C2.Cl.CN(CCCN=C=NCC)C>>BrC=1C(=NC(=NC1)NC=1C=C(C=C(C(=O)OC)C1)NC([C@@H](CC1=CC=CC=C1)NC(=O)OC(C)(C)C)=O)OCC#C | [CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:31][c:32]([C:33](=[O:34])[O:35][CH3:36])[cH:37]2)[n:38][cH:39][c:40]1[Br:41].O[C:13](=[O:14])[C@@H:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30]>>[CH:1]#[C:2][CH2:3][O... | C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O | C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)NC(=O)OC(C)(C)C)cc(C(=O)OC)c2)ncc1Br | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccccc1)Nc1cccc(Nc2ncccn2)c1 | 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].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[c:14](:[c:15... | 83.4 | [{"value": 83.4, "product": "BrC=1C(=NC(=NC1)NC=1C=C(C=C(C(=O)OC)C1)NC([C@@H](CC1=CC=CC=C1)NC(=O)OC(C)(C)C)=O)OCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-BOC-D-phenylalanine (3.3 g), 1-hydroxy-1H-benzotriazole hydrate(1.9 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimid hydrochloride (2.37 g) were stirred in DMF (30 ml) for 30 minutes Then methyl 3-amino-5-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]benzoate (3.88 g) were added and the mixture stirred over ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | null | null | C#CCOc1nc(Nc2cc(N)cc(C(=O)OC)c2)ncc1Br.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O>CN(C)C=O.C(C)(=O)OCC>C#CCOc1nc(Nc2cc(NC(=O)[C@@H](Cc3ccccc3)NC(=O)OC(C)(C)C)cc(C(=O)OC)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4bdb9387c724a968584a1275d955be4 | C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])c2)ncc1Br>>C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@H](N)Cc3ccccc3)c2)ncc1Br | CC(C)(ON(C([O-])=O)[C@@H](C(=O)NC1=CC(=CC(=C1)CO)NC1=NC=C(C(=N1)OCC#C)Br)CC1=CC=CC=C1)C.S(O)(O)(=O)=O.O>>N[C@@H](C(=O)NC1=CC(=CC(=C1)CO)NC1=NC=C(C(=N1)OCC#C)Br)CC1=CC=CC=C1 | CC(C)(C)O[N:20](C(=O)[O-])[C@@H:19]([C:17]([NH:16][c:15]1[cH:14][c:11]([CH2:12][OH:13])[cH:10][c:9]([NH:8][c:7]2[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:31]([Br:32])[cH:30][n:29]2)[cH:28]1)=[O:18])[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([CH2:... | C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])c2)ncc1Br | C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@H](N)Cc3ccccc3)c2)ncc1Br | null | null | O1CCOCC1 | Reduction | OtherReaction | 017509a577522918fcd61b79a78a9b03bf1c8337f1c76e29f10765017faab5c3 | ac6f378f3e5e6c9b4b710d4e542f71f04a708f2a748ed8cf03d2a10006d6bc94 | O=C(CCc1ccccc1)Nc1cccc(Nc2ncccn2)c1 | C-C(-C)(-C)-O-[N;H0;D3;+0:1](-C(=O)-[O-])-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7] | 56 | [{"value": 56.0, "product": "N[C@@H](C(=O)NC1=CC(=CC(=C1)CO)NC1=NC=C(C(=N1)OCC#C)Br)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,1-Dimethylethoxy[(1R)-2-[[3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-(hydroxymethyl)phenyl]amino]-2-oxo-1-(phenylmethyl)ethyl]carbamate (22 mg) and sulfuric acid (0.3 ml; 2 n) were stirred in dioxane (3 ml) at 100° C. for 2.5 h. After cooling and dilution with water saturated NaHCO3-solution was added and ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic acid | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1 | null | null | C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@@H](Cc3ccccc3)N(OC(C)(C)C)C(=O)[O-])c2)ncc1Br>O1CCOCC1>C#CCOc1nc(Nc2cc(CO)cc(NC(=O)[C@H](N)Cc3ccccc3)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99d9a06d5e2b4a3b974b6a414fedab08 | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)OC)c2)ncc1Br>>C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br | COC(C1=CC(=CC(=C1)NCCO)NC1=NC=C(C(=N1)OCC#C)Br)=O>>BrC=1C(=NC(=NC1)NC=1C=C(C(=O)O)C=C(C1)NCCO)OCC#C | C[O:20][C:18]([c:17]1[cH:16][c:11]([NH:12][CH2:13][CH2:14][OH:15])[cH:10][c:9]([NH:8][c:7]2[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:24]([Br:25])[cH:23][n:22]2)[cH:21]1)=[O:19]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([NH:12][CH2:13][CH2:14][OH:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21]2)[... | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)OC)c2)ncc1Br | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br | null | null | O1CCCC1.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ncccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 100.5 | [{"value": 100.5, "product": "BrC=1C(=NC(=NC1)NC=1C=C(C(=O)O)C=C(C1)NCCO)OCC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Methyl3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-[(2-hydroxyethyl)amino]benzoate (350 mg) in a mixture of tetrahydrofuran (6 ml) and sodium hydroxide solution (2 n; 6 ml) was stirred for 48 h at room temperature. After evaporation the residue was diluted with water and acidified until the product precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1 | Other | O1CCCC1.[OH-].[Na+] | null | 48 | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)OC)c2)ncc1Br>O1CCCC1.[OH-].[Na+]>C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f49c32b0920a4499b5b919e358e164f0 | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br>>C#CCOc1nc(Nc2cc(CO)cc(NCCO)c2)ncc1Br | BrC=1C(=NC(=NC1)NC=1C=C(C(=O)O)C=C(C1)NCCO)OCC#C.C(C)N(CC)CC.[BH4-].[Na+].CO>>BrC=1C(=NC(=NC1)NC=1C=C(C=C(C1)CO)NCCO)OCC#C | O=[C:12]([c:11]1[cH:10][c:9]([NH:8][c:7]2[n:6][c:5]([O:4][CH2:3][C:2]#[CH:1])[c:23]([Br:24])[cH:22][n:21]2)[cH:20][c:15]([NH:16][CH2:17][CH2:18][OH:19])[cH:14]1)[OH:13]>>[CH:1]#[C:2][CH2:3][O:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]([NH:16][CH2:17][CH2:18][OH:19])[cH:20]2)[n:21][cH:22]... | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br | C#CCOc1nc(Nc2cc(CO)cc(NCCO)c2)ncc1Br | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(Nc2ncccn2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | To a mixture of 3-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-5-[(2-hydroxyethyl)amino]benzoic acid and triethylamine (57 μl) in tetrahydrofuran (4 ml) was added ethyl chloroformiate (37 μl) at −10° C. After stirring for 15 minutes at 0° C. sodium borohydride (44 mg) and methanol (3.6 ml) were added and stirring ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1cncnc1.c1ccccc1 | Other | O1CCCC1 | null | null | C#CCOc1nc(Nc2cc(NCCO)cc(C(=O)O)c2)ncc1Br>O1CCCC1>C#CCOc1nc(Nc2cc(CO)cc(NCCO)c2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb73efa892f046989ff7f735192fbd01 | CC(C)OC(=O)c1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1>>CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | [N+](=O)([O-])C=1C=C(C=CC1)NC1=NC=C(C(=N1)NCCCNC(=O)OCC1=CC=CC=C1)C(=O)OC(C)C>>C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO)NC1=CC(=CC=C1)NC(=O)NCC)=O | [O-][N+:3](=[O:5])[c:7]1[cH:8][cH:9][cH:10][c:11]([NH:12][c:13]2[n:14][cH:15][c:16]([C:17](O[CH:2]([CH3:1])[CH3:4])=[O:18])[c:19]([NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[n:35]2)[cH:36]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:... | CC(C)OC(=O)c1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1 | CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | cc7d62ef756462c45a0c5e2c1d8b668a6c4aaed2a6e42070d24a1d2787108d67 | 124b7dee9aef043ef39c8bceaa9cef27a3b4c841ab5b7c20205299cdb3a68a5d | O=C(NCCCNc1ccnc(Nc2ccccc2)n1)OCc1ccccc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-O-[CH;D3;+0:10](-[C;D1;H3:11])-[CH3;D1;+0:12].[O-]-[N+;H0;D3:13](=[O;H0;D1;+0:14])-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[OH;D1;+0:9].[C;D1;H3:11]-[CH2;D2;+0:10]... | 78.8 | [{"value": 78.8, "product": "C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO)NC1=CC(=CC=C1)NC(=O)NCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-Methylethyl 2-[(3-nitrophenyl)amino]-4-[[3-[[(phenylmethoxy)carbonyl]amino]propyl]amino]pyrimidine-5-carboxylate (1.7 g) in tetrahydrofuran (100 ml) LiAlH4 (410 mg) was added in portions at 0° C. After 6 h at 0° C. the reaction was quenched by addition of saturated ammonium chloride solution. Ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Urea.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)OC(=O)c1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1>O1CCCC1>CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3967056d9c0a4471a1236afc9b9afaef | CC(C)(C)[Si](C)(C)Cl.O=C(NCCCNc1nc(Nc2cccc([N+](=O)[O-])c2)ncc1CO)OCc1ccccc1>>CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1 | OCC=1C(=NC(=NC1)NC1=CC(=CC=C1)[N+](=O)[O-])NCCCNC(OCC1=CC=CC=C1)=O.Cl[Si](C)(C)C(C)(C)C.N1C=NC=C1>>C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)[N+](=O)[O-])=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][c:10]1[cH:11][n:12][c:13]([NH:14][c:15]2[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23]2)[n:24][c:25]1[NH:26][CH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:32])[O:33][CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[CH3:1][C:2]([CH3:3])([... | CC(C)(C)[Si](C)(C)Cl.O=C(NCCCNc1nc(Nc2cccc([N+](=O)[O-])c2)ncc1CO)OCc1ccccc1 | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | O=C(NCCCNc1ccnc(Nc2ccccc2)n1)OCc1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[#7;a:8]:[c:9]:[c:10](-[C:11]-[OH;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:8]:[c:9]:[c:10](-[C:11]-[O;H0;D2;+0:12]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]):[c:13]:[#7;a:14] | 95.8 | [{"value": 95.8, "product": "C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A DMF solution (5 ml) of phenylmethyl [3-[[5-(hydroxymethyl)-2-[(3-nitrophenyl)amino]pyrimidin-4-yl]amino]propyl]carbamate (250 mg), chloro(1,1-dimethylethyl)dimethylsilane (190 mg) and 1H-imidazole (170 mg) was stirred at room temperature (48 h). After addition of ice water the mixture was extracted with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | null | CC(C)(C)[Si](C)(C)Cl.O=C(NCCCNc1nc(Nc2cccc([N+](=O)[O-])c2)ncc1CO)OCc1ccccc1>CN(C)C=O>CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09cb6bfd4238434398cf6768dc9852a4 | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1>>CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1 | C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)[N+](=O)[O-])=O.N.O>>C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)N)=O | O=[N+:20]([O-])[c:19]1[cH:18][cH:17][cH:16][c:15]([NH:14][c:13]2[n:12][cH:11][c:10]([CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[c:23]([NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][CH2:32][c:33]3[cH:34][cH:35][cH:36][cH:37][cH:38]3)[n:22]2)[cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si... | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1 | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(NCCCNc1ccnc(Nc2ccccc2)n1)OCc1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.5 | [{"value": 99.5, "product": "C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Phenylmethyl[3-[[5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-[(3-nitrophenyl)amino]pyrimidin-4-yl]amino]propyl]carbamate (244 mg), dissolved in ethanol (30 ml), was slowly added to a mixture of FeSO4 heptahydrate (1.25 g), concentrated ammonia solution (25%; 1.25 ml) and water (5 ml). After refluxing for 3 h th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1.c1ccccc1.c1ccccc1 | Other | C(C)O | null | null | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc([N+](=O)[O-])c2)nc1NCCCNC(=O)OCc1ccccc1>C(C)O>CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7173e206bdff49b69b309cc8ba97cc57 | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1>>CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NCCCNC(OCC1=CC=CC=C1)=O)CO[Si](C)(C)C(C)(C)C>>CC(C)(C)[Si](OCC=1C(=NC(=NC1)NC1=CC(=CC=C1)NC(=O)NCC)NCCCNC(OCC1=CC=CC=C1)=O)(C)C | [CH3:1][C:22]([Si:19]([CH3:2])([CH3:4])[O:18][CH2:17][c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]([NH2:3])[cH:43]2)[n:42][c:26]1[NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:5][CH2:35][c:36]1[cH:37][cH:38][cH:39][cH:40][cH:41]1)=[O:33])([CH3:23])[CH3:25]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c... | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1 | CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | null | N | C(C)#N | Functional Group Addition | OtherReaction | bb87f41c2905c78fce5d2cb55018460275b4e0d1c509c8abfb13e13cc2bdae48 | fdb2ef2902d6d2bf915f5849663b91110db2c85adfc51d2b8c1e9136f1486fe0 | O=C(NCCCNc1ccnc(Nc2ccccc2)n1)OCc1ccccc1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9].[C:10]-[#8:11]-[Si;H0;D4;+0:12](-[CH3;D1;+0:13])(-[CH3;D1;+0:14])-[C;H0;D4;+0:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[CH3;D1;+0:18].[NH2;D1;+0:19]-[c;H0;D3;+0:20](:[c:21]:[c:22]):[c:23]:[c:24]>>[CH3;D1;+0:18]-[CH2;D2;+0:13]-[NH;D2;+0:... | null | [] | null | null | 18 | HOUR | To a solution of phenylmethyl [3-[[2-[(3-aminophenyl)amino]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]pyrimidin-4-yl]amino]propyl]carbamate (225 mg) in acetonitrile (5 ml) ethyl isocyanate (33 μl) was added and the mixture stirred for 18 h at room temperature. Then 5 drops of ammonia solution (25%) were added an... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine.TMS ether protective group | Carbamic ester.Ether.Urea.TMS ether protective group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | Other | N.C(C)#N | null | 18 | CC(C)(C)[Si](C)(C)OCc1cnc(Nc2cccc(N)c2)nc1NCCCNC(=O)OCc1ccccc1>N.C(C)#N>CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f346902533df4fd98198e0b4e178b846 | CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1>>CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | C1(=CC=CC=C1)COC(NCCCNC1=NC(=NC=C1CO[Si](C)(C)C(C)(C)C)NC1=CC(=CC=C1)NC(=O)NCC)=O.C(=O)(O)[O-].[Na+].C(C)(=O)OCC>>C(C)NC(=O)NC=1C=C(C=CC1)NC1=NC=C(C(=N1)NCCCNC(OCC1=CC=CC=C1)=O)CO | CC(C)(C)[Si](C)(C)[O:18][CH2:17][c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[cH:36]2)[n:35][c:19]1[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][CH2:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH... | CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 | null | null | Cl.C(C)O | Deprotection | Alcohol deprotection from silyl ethers | 6ff8c9c41093ab5237b871dd4689ba6431022d615e227d3774901a983c846e4b | 84d9f5b4e7757c58e584c26c7d52c9a3f594fbcb0c0d22f34765a93a932fcd5b | O=C(NCCCNc1ccnc(Nc2ccccc2)n1)OCc1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[c:3](:[c:4]:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4]:[c:3](-[C:2]-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | null | null | null | null | Phenylmethyl[3-[[5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-[[3[[(ethylamino)carbonyl]amino]phenyl]amino]pyrimidin-4-yl]amino]propyl]carbamate (145 mg) were stirred in a mixture of ethanol (10 ml) and hydrochloric acid (4 n; 1 ml) for 3 h at room temperature. Then halfconcentrated NaHCO3-solution and ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | Cl.C(C)O | null | null | CCNC(=O)Nc1cccc(Nc2ncc(CO[Si](C)(C)C(C)(C)C)c(NCCCNC(=O)OCc3ccccc3)n2)c1>Cl.C(C)O>CCNC(=O)Nc1cccc(Nc2ncc(CO)c(NCCCNC(=O)OCc3ccccc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-377186965de8430eb780d36727c57999 | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F>>Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(C(F)(F)F)=O)NCCC=1NC=NC1.CO.O.[Li+].[OH-]>>NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br | O=C(C(F)(F)F)[NH:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([Br:11])[c:12]([NH:13][CH2:14][CH2:15][c:16]3[cH:17][n:18][cH:19][nH:20]3)[n:21]2)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([Br:11])[c:12]([NH:13][CH2:14][CH2:15][c:16]3[cH:17][n:18][cH:19][nH:20]3)[n:21]2)[cH:2... | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F | Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | null | null | C1CCOC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49.2 | [{"value": 49.2, "product": "NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | N-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl)-trifluoro acetamide (1 g, 1.9 mmole) was dissolved in THF (10 ml), MeOH (10 ml) and water (5 ml) and LiOH (455 mg) was added in one portion at room temperature. The reaction mixture was stirred at room temperature for two days, the solvent r... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccccc1.c1cncnc1.c1c[nH]cn1 | Other | C1CCOC1 | null | 48 | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F>C1CCOC1>Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1564ff70795a482fa888e2302884bf02 | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1>>S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | CN(C)C=O.C(=S)(C=1NC=CN1)C=1NC=CN1.C1(CC1)N.NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(=S)NC1CC1)NCCC=1NC=NC1 | [NH2:26][CH:27]1[CH2:28][CH2:29]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[c:14]([NH:15][CH2:16][CH2:17][c:18]3[cH:19][n:20][cH:21][nH:22]3)[n:23]2)[cH:24][cH:25]1.c1c[nH]c([C:2](c2ncc[nH]2)=[S:1])n1>>[S:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[c:14]... | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1 | S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6b1e4ecc617dc935afacd8266ef8ca1fdaa3b65e35e36b03deeb6f97e81ff17a | f385afadc4d64db6d7d6253d013b21a1921f2b7e30e4a57e45fce8954d8e6e1a | S=C(Nc1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | [NH2;D1;+0:1]-[C:2]1-[C:3]-[C:4]-1.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[S;D1;H0:9]=[C;H0;D3;+0:10](-c1:[nH]:c:c:n:1)-c1:[nH]:c:c:n:1>>[S;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 10.2 | [{"value": 10.2, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(=S)NC1CC1)NCCC=1NC=NC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Cyclopropyl amine (0.275 mmole) was dissolved in THF (2 ml) and thiocarbonyl diimidazole (0.28 mmole) was added. The reaction was stirred at room temperature overnight and N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (0.26 mmole) was added as a solution in THF (3 ml) and DMF (1 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Thiocarbonyl | Thiourea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1cncnc1.c1c[nH]cn1.C1CC1 | Other | C1CCOC1 | null | 8 | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1>C1CCOC1>S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24ba1b0af016409f808c2396f3f5079a | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F>>Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(C(F)(F)F)=O)NCCC=1NC=NC1.CO.O.[Li+].[OH-]>>NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br | O=C(C(F)(F)F)[NH:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([Br:11])[c:12]([NH:13][CH2:14][CH2:15][c:16]3[cH:17][n:18][cH:19][nH:20]3)[n:21]2)[cH:22][cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]([Br:11])[c:12]([NH:13][CH2:14][CH2:15][c:16]3[cH:17][n:18][cH:19][nH:20]3)[n:21]2)[cH:2... | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F | Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | null | null | C1CCOC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | c1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 49.2 | [{"value": 49.2, "product": "NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | N-(4-{5-Bromo-4-[2-(3H-imidazol-4-yl)-ethylamino]-pyrimidin-2-ylamino}-phenyl)-trifluoro acetamide (1 g, 1.9 mmole) was dissolved in THF (10 ml), MeOH (10 ml) and water (5 ml) and LiOH (455 mg) was added in one portion at room temperature. The reaction mixture was stirred at room temperature for two days, the solvent r... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | c1ccccc1.c1cncnc1.c1c[nH]cn1 | Other | C1CCOC1 | null | 48 | O=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)C(F)(F)F>C1CCOC1>Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81227650337c4c01a0bd12b44a807581 | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1>>S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | CN(C)C=O.C(=S)(C=1NC=CN1)C=1NC=CN1.C1(CC1)N.NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(=S)NC1CC1)NCCC=1NC=NC1 | [NH2:26][CH:27]1[CH2:28][CH2:29]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[c:14]([NH:15][CH2:16][CH2:17][c:18]3[cH:19][n:20][cH:21][nH:22]3)[n:23]2)[cH:24][cH:25]1.c1c[nH]c([C:2](c2ncc[nH]2)=[S:1])n1>>[S:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[c:14]... | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1 | S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6b1e4ecc617dc935afacd8266ef8ca1fdaa3b65e35e36b03deeb6f97e81ff17a | f385afadc4d64db6d7d6253d013b21a1921f2b7e30e4a57e45fce8954d8e6e1a | S=C(Nc1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1)NC1CC1 | [NH2;D1;+0:1]-[C:2]1-[C:3]-[C:4]-1.[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[S;D1;H0:9]=[C;H0;D3;+0:10](-c1:[nH]:c:c:n:1)-c1:[nH]:c:c:n:1>>[S;D1;H0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 10.2 | [{"value": 10.2, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(=S)NC1CC1)NCCC=1NC=NC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Cyclopropyl amine (0.275 mmole) was dissolved in THF (2 ml) and thiocarbonyl diimidazole (0.28 mmole) was added. The reaction was stirred at room temperature overnight and N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (0.26 mmole) was added as a solution in THF (3 ml) and DMF (1 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Thiocarbonyl | Thiourea | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1cncnc1.c1c[nH]cn1.C1CC1 | Other | C1CCOC1 | null | 8 | NC1CC1.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1.S=C(c1ncc[nH]1)c1ncc[nH]1>C1CCOC1>S=C(Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1)NC1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42efd63911934d84afb4ce4a8c2b54cc | CCCC=O.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1>>CCCCNc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br.C(CCC)=O.C(#N)[BH3-].[Na+]>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NCCCC)NCCC=1NC=NC1 | O=[CH:4][CH2:3][CH2:2][CH3:1].[NH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Br:15])[c:16]([NH:17][CH2:18][CH2:19][c:20]3[cH:21][n:22][cH:23][nH:24]3)[n:25]2)[cH:26][cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13][c:14]([Br:15])[c:16]([NH:17][CH2:18][CH2... | CCCC=O.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | CCCCNc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 11.6 | [{"value": 11.6, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NCCCC)NCCC=1NC=NC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (1 g, 2.6 mmole, prepared according to procedure 21) was dissolved in MeOH (10 ml), butanal (2.6 ml, 2.9 mmole) was added at room temperature and the reaction mixture was stirred at room temperature for 20 minutes. Sodium cyanoborohydrid... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1cncnc1.c1c[nH]cn1 | Other | CO | null | 0.333333 | CCCC=O.Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1>CO>CCCCNc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78753cfe6dbd453bb7a910a347da8ed0 | CSc1ccc(C(=O)O)cc1[N+](=O)[O-]>>CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-] | CSC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].CO.OOS(=O)[O-].[K+]>>CS(=O)(=O)C1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-] | [CH3:1][S:2][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16] | CSc1ccc(C(=O)O)cc1[N+](=O)[O-] | CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-] | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccccc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | 89 | [{"value": 89.0, "product": "CS(=O)(=O)C1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 8 | HOUR | 4-Methylsulfanyl-3-nitro-benzoic acid (1 g, 4.69 mmole) was dissolved in methanol (25 ml) and cooled to 5° C. A solution of Oxone® (5.8 g) in water (20 ml) was added portionwise at the same temperature. The reaction mixture was allowed to stir overnight at ambient temperature, methanol was removed under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1 | null | O | 5 | 8 | CSc1ccc(C(=O)O)cc1[N+](=O)[O-]>O>CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7374dfe2c0c34fff95de0663074bc577 | CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-].Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1>>CS(=O)(=O)c1ccc(C(=O)Nc2ccc(Nc3ncc(Br)c(NCCc4cnc[nH]4)n3)cc2)cc1[N+](=O)[O-] | CS(=O)(=O)C1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].S(=O)(Cl)Cl.NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCCC=1NC=NC1)Br>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(C1=CC(=C(C=C1)S(=O)(=O)C)[N+](=O)[O-])=O)NCCC=1NC=NC1 | O[C:9]([c:8]1[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:35]([N+:36](=[O:37])[O-:38])[cH:34]1)=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([NH:16][c:17]2[n:18][cH:19][c:20]([Br:21])[c:22]([NH:23][CH2:24][CH2:25][c:26]3[cH:27][n:28][cH:29][nH:30]3)[n:31]2)[cH:32][cH:33]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH... | CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-].Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1 | CS(=O)(=O)c1ccc(C(=O)Nc2ccc(Nc3ncc(Br)c(NCCc4cnc[nH]4)n3)cc2)cc1[N+](=O)[O-] | null | null | CC(=O)N(C)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccc(Nc2nccc(NCCc3cnc[nH]3)n2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | 23.7 | [{"value": 23.0, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(C1=CC(=C(C=C1)S(=O)(=O)C)[N+](=O)[O-])=O)NCCC=1NC=NC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(C1=CC(=C(C=C1)S(=O)(=O)C)[N+](=O)[O-])=O)NCCC=1NC=NC1", "details": "CALCULATEDPERCENTYIELD",... | null | null | 8 | HOUR | 4-Methanesulfonyl-3-nitro-benzoic acid (72 mg, 0.29 mmole) was dissolved in DMA (3 ml) and thionyl chloride (0.29 mmole) was added at ambient temperature. After the mixture was stirred for 5 minutes N2-(4-Amino-phenyl)-5-bromo-N4-[2-(3H-imidazol-4-yl)-ethyl]-pyrimidine-2,4-diamine (100 mg, 0.26 mmole, prepared accordin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cncnc1.c1c[nH]cn1 | HO- | CC(=O)N(C)C | null | 8 | CS(=O)(=O)c1ccc(C(=O)O)cc1[N+](=O)[O-].Nc1ccc(Nc2ncc(Br)c(NCCc3cnc[nH]3)n2)cc1>CC(=O)N(C)C>CS(=O)(=O)c1ccc(C(=O)Nc2ccc(Nc3ncc(Br)c(NCCc4cnc[nH]4)n3)cc2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed114cfebe3847bd91204ad2ff5a44c3 | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCCCOC(=O)Cl>>C#CCNc1nc(Nc2ccc(NC(=O)OCCCC)cc2)ncc1Br | O.C(C)N(CC)CC.ClC(=O)OCCCC.NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br>>C(CCC)OC(NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br)=O | [CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:21][cH:22]2)[n:23][cH:24][c:25]1[Br:26].Cl[C:14](=[O:15])[O:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[O:16][CH2:17][CH2:18][CH2:19][CH3:20]... | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCCCOC(=O)Cl | C#CCNc1nc(Nc2ccc(NC(=O)OCCCC)cc2)ncc1Br | null | null | C1CCOC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc(Nc2ncccn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (0.31 mmol, prepared in analogy to procedure 21) was dissolved in THF (20 ml), triethyl amine (0.33 mmole) and butyl chloroformate (0.33 mmole) were added at room temperature and the reaction was stirred at this temperature until the starting material di... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | null | null | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCCCOC(=O)Cl>C1CCOC1>C#CCNc1nc(Nc2ccc(NC(=O)OCCCC)cc2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69dd0512a0984eb9a6ff0183a16df756 | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.C=CCN=C=S>>C#CCNc1nc(Nc2ccc(NC(=S)NCC=C)cc2)ncc1Br | NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br.C(C=C)N=C=S>>C(C=C)NC(=S)NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br | [CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:20][cH:21]2)[n:22][cH:23][c:24]1[Br:25].[C:14](=[S:15])=[N:16][CH2:17][CH:18]=[CH2:19]>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[S:15])[NH:16][CH2:17][CH:18]=[CH2:19])[cH:20][cH:21]2... | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.C=CCN=C=S | C#CCNc1nc(Nc2ccc(NC(=S)NCC=C)cc2)ncc1Br | null | null | C(C)#N | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | c1ccc(Nc2ncccn2)cc1 | [C;D1;H2:1]=[C:2]-[C:3]-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[S;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H2:1]=[C:2]-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[S;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (100 mg, 0.3 mmole, prepared in analogy procedure 21) was dissolved in acetonitrile (10 ml) and allyl isothiocyanate (1 ml) was added at room temperature. The reaction mixture was heated under reflux for 3 hours, the solvent removed under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1cncnc1.c1ccccc1 | null | C(C)#N | null | null | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.C=CCN=C=S>C(C)#N>C#CCNc1nc(Nc2ccc(NC(=S)NCC=C)cc2)ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df8f8c45311f487e95201ed0c4a018c1 | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCN=C=O>>C#CCNc1nc(Nc2ccc(NC(=O)NCC)cc2)ncc1Br | NC1=CC=C(C=C1)NC1=NC=C(C(=N1)NCC#C)Br.C(C)N=C=O>>BrC=1C(=NC(=NC1)NC1=CC=C(C=C1)NC(=O)NCC)NCC#C | [CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:19][cH:20]2)[n:21][cH:22][c:23]1[Br:24].[C:14](=[O:15])=[N:16][CH2:17][CH3:18]>>[CH:1]#[C:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[NH:16][CH2:17][CH3:18])[cH:19][cH:20]2)[n:21][cH:22][c... | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCN=C=O | C#CCNc1nc(Nc2ccc(NC(=O)NCC)cc2)ncc1Br | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc(Nc2ncccn2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | N2-(4-Amino-phenyl)-5-bromo-N4-prop-2-ynyl-pyrimidine-2,4-diamine (100 mg, 0.3 mmole, prepared in analogy to procedure 21) was dissolved in acetonitrile (10 ml) and ethyl isocyanate (0.5 ml) was added at room temperature. The reaction mixture was heated under reflux for 5 hours and then cooled to room temperature and s... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1cncnc1.c1ccccc1 | null | C(C)#N | null | 8 | C#CCNc1nc(Nc2ccc(N)cc2)ncc1Br.CCN=C=O>C(C)#N>C#CCNc1nc(Nc2ccc(NC(=O)NCC)cc2)ncc1Br |
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