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-646e739121134fd1ac76394d8ef6bda5 | C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F.ClI>>O=Cc1c(Cl)cc(F)c(I)c1F | ClC1=CC(=C(C(=C1C=O)F)[Si](C)(C)C)F.ICl.ICl>>ClC1=CC(=C(C(=C1C=O)F)I)F | C[Si](C)(C)[c:9]1[c:7]([F:8])[cH:6][c:4]([Cl:5])[c:3]([CH:2]=[O:1])[c:11]1[F:12].Cl[I:10]>>[O:1]=[CH:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([F:8])[c:9]([I:10])[c:11]1[F:12] | C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F.ClI | O=Cc1c(Cl)cc(F)c(I)c1F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 047d69fb062d430b3c4234f4d9dc2362ad3d5bebae7ca0b8684377a133bdc02a | 63283061f326a2fecd25d450c5b0c90ce007113b9f07907c978145ca0609298a | c1ccccc1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]-[C:5]=[O;D1;H0:6]):[c:7](-[F;D1;H0:8]):[c:9].Cl-[I;H0;D1;+0:10]>>[F;D1;H0:3]-[c:2](:[c:4]-[C:5]=[O;D1;H0:6]):[c;H0;D3;+0:1](-[I;H0;D1;+0:10]):[c:7](-[F;D1;H0:8]):[c:9] | 162.5 | [{"value": 162.5, "product": "ClC1=CC(=C(C(=C1C=O)F)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 6-chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde (600 mg, 2.4 mmol) in methylene chloride (7 mL) was cooled to 0° C. and treated with solution of iodochloride (780 mg, 4.8 mmol) in methylene chloride (10 mL) and stirred at ambient temperature for 2 hours. Additional iodochloride (900 mg) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | null | 2 | C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F.ClI>C(Cl)Cl>O=Cc1c(Cl)cc(F)c(I)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4361ce868eb4e1192e46ad2039e578f | CC(=O)OO.CI.Fc1cc(F)c(Br)cc1Br>>COc1cc(Br)c(F)cc1F | C(C)(=O)OO.C([O-])([O-])=O.[K+].[K+].IC.BrC1=CC(=C(C=C1F)F)Br.C(C)(C)[Mg]Cl.COB(OC)OC>>BrC1=C(C=C(C(=C1)OC)F)F | CC(=O)O[OH:2].I[CH3:1].Br[c:3]1[cH:4][c:5]([Br:6])[c:7]([F:8])[cH:9][c:10]1[F:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]([F:8])[cH:9][c:10]1[F:11] | CC(=O)OO.CI.Fc1cc(F)c(Br)cc1Br | COc1cc(Br)c(F)cc1F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 35323bfc0b79a9b61c75d6aea2581c259b70e6e672b32672029e6a3625d5929f | c40ffbbc3249442e5ee39aaa69a55be7ac2fa45f48637395e415c565c1288454 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].C-C(=O)-O-[OH;D1;+0:7].I-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 23.2 | [{"value": 23.2, "product": "BrC1=C(C=C(C(=C1)OC)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 1,3 dibromo-4,6-difluorobenzene (10.0 g, 37 mmol) in THF (50 mL) at −20° C. was added isopropyl magnesium chloride (2.0M in THF, 42 mmol) and the resulting solution warm to 0° C. and stirred for 30 minutes. Trimethylborate (4.7 g, 45 mmol) was added and the mixture stirred at ambient temperature for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.I- | C1CCOC1 | 0 | 0.5 | CC(=O)OO.CI.Fc1cc(F)c(Br)cc1Br>C1CCOC1>COc1cc(Br)c(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d5521e78560442b906e15943c2ba77c | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1cc(B2OCCCO2)c(F)cc1Cl>>COC(=O)c1nc(-c2cc(OC)c(Cl)cc2F)cc(NC(C)=O)c1Cl | COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)Cl.ClC1=CC(=C(C=C1OC)B1OCCCO1)F.[F-].[Cs+].C1(=CC=CC=C1)P(CCCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>>COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C=C(C(=C1)OC)Cl)F | Cl[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]([Cl:25])[c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:18]1.C1COB([c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([Cl:14])[cH:15][c:16]2[F:17])OC1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([Cl:14])[cH:15][c:16]2[F:17])[cH:18][c:19]([NH:2... | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1cc(B2OCCCO2)c(F)cc1Cl | COC(=O)c1nc(-c2cc(OC)c(Cl)cc2F)cc(NC(C)=O)c1Cl | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C(C)#N | C-C Coupling | Suzuki coupling with boronic esters | 24090aed37a48c66cce36a374df588b856a5a96d58744799fd5f32d2bb560bf0 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[F;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-B1-O-C-C-C-O-1):[c:13]:[c:14]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](-[F;D1;H0:9]):[c:11]):[c:7]:[c:8] | 75 | [{"value": 75.0, "product": "COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C=C(C(=C1)OC)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-acetylamino-3,6-dichloropyridine carboxylic acid methyl ester (4.3 g, 0.016 mol), 2-(4-chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane (4.5 g, 0.018 mol), cesium fluoride (3.5 g, 0.025 mol), and 1,4-bis(diphenylphosphino)butane (0.360 g, 0.0016 mol) in acetonitrile (100 mL) was degassed with nitr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.B1OCCCO1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HCl.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C(C)#N | null | null | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1cc(B2OCCCO2)c(F)cc1Cl>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C(C)#N>COC(=O)c1nc(-c2cc(OC)c(Cl)cc2F)cc(NC(C)=O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-100bc78c6db840f1b52b9e256a480b2c | COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl.Cc1c(F)ccc(Br)c1F>>COC(=O)c1nc(-c2ccc(F)c(C)c2F)cc(NC(C)=O)c1Cl | BrC1=C(C(=C(C=C1)F)C)F.COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)[Sn](C)(C)C.C1(=CC=CC=C1)P(CCCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.[F-].[Cs+]>>COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C(=C(C=C1)F)C)F | [CH3][Sn]([CH3])([CH3])[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:23]([Cl:24])[c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:17]1.Br[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([CH3:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([CH3:14])[c:15]2[F:16])[cH:17][c:18]([NH:19... | COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl.Cc1c(F)ccc(Br)c1F | COC(=O)c1nc(-c2ccc(F)c(C)c2F)cc(NC(C)=O)c1Cl | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)#N | C-C Coupling | Stille reaction_aryl | ce918bbb171f9e7bd99035931c043f0f33f636d165d8c0e73629d8717d6c595a | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[Sn](-[CH3])(-[CH3])-[CH3]):[c:13]:[c:14]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]):[c:13]:[c:14] | 20 | [{"value": 20.0, "product": "COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C(=C(C=C1)F)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-bromo-2,4-difluoro-3-methylbenzene (2.10 g, 0.09 mol), 4-acetylamino-3-chloro-6-trimethylstannylpyridine-2-carboxylic acid methyl ester (4.00 g, 0.01 mol), 1,4-bis(diphenylphosphino)butane (0.140 g, 0.0003 mol) and cesium fluoride (4.5 g, 0.03 mol) in acetonitrile (100 mL) was degassed with nitrogen. Pa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.Sn | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N | null | null | COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl.Cc1c(F)ccc(Br)c1F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N>COC(=O)c1nc(-c2ccc(F)c(C)c2F)cc(NC(C)=O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef88bfceac19452d82b5de6467be35e3 | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1c(C(F)(F)F)cc[c]([Sn]([CH3])([CH3])[CH3])c1F>>COC(=O)c1nc(-c2ccc(C(F)(F)F)c(OC)c2F)cc(NC(C)=O)c1Cl | COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)Cl.FC1=C(C=CC(=C1OC)C(F)(F)F)[Sn](C)(C)C.[F-].[Cs+].C1(=CC=CC=C1)P(CCCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>>COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C(=C(C=C1)C(F)(F)F)OC)F | Cl[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]([Cl:28])[c:22]([NH:23][C:24]([CH3:25])=[O:26])[cH:21]1.[CH3][Sn]([CH3])([CH3])[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]([O:17][CH3:18])[c:19]1[F:20]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])... | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1c(C(F)(F)F)cc[c]([Sn]([CH3])([CH3])[CH3])c1F | COC(=O)c1nc(-c2ccc(C(F)(F)F)c(OC)c2F)cc(NC(C)=O)c1Cl | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)#N | C-C Coupling | Stille reaction_aryl | ce918bbb171f9e7bd99035931c043f0f33f636d165d8c0e73629d8717d6c595a | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].[CH3]-[Sn](-[CH3])(-[CH3])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[F;D1;H0:13]):[c:14]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[F;D1;H0:13]):[c:14]):[c:7]:[c:8] | 10 | [{"value": 10.0, "product": "COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C(=C(C=C1)C(F)(F)F)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In an oven dried, nitrogen flushed 100 mL 3 neck flask equipped with a condenser and a magnetic stirbar was dissolved methyl-4-acetamido-3,6-dichloropyridine-2-carboxylate (1.2 g, 4.6 mmol) and (2-fluoro-3-methoxy-4-trifluoromethylphenyl)trimethyl stannane (1.7 g, 4.6 mmol) in acetonitrile (15 mL) and the resulting sol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HCl.Sn | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N | null | null | COC(=O)c1nc(Cl)cc(NC(C)=O)c1Cl.COc1c(C(F)(F)F)cc[c]([Sn]([CH3])([CH3])[CH3])c1F>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N>COC(=O)c1nc(-c2ccc(C(F)(F)F)c(OC)c2F)cc(NC(C)=O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eeadaa8ae94740c897fe9c4f5f77ce63 | COC(=O)c1nc(-c2ccc(Cl)cc2F)cc(N)c1Cl.O=[N+]([O-])[O-]>>COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl | NC1=C(C(=NC(=C1)C1=C(C=C(C=C1)Cl)F)C(=O)OC)Cl.S(O)(O)(=O)=O.[N+](=O)([O-])[O-].[Na+]>>COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C=C(C(=C1)[N+](=O)[O-])Cl)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:14]([Cl:15])[cH:16][c:17]2[F:18])[cH:19][c:20]([NH2:21])[c:22]1[Cl:23].[O-][N+:11](=[O:12])[O-:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[cH:16][c:17]2[F:18])[cH:19][c:20]([NH2:21])[c:22]1[Cl... | COC(=O)c1nc(-c2ccc(Cl)cc2F)cc(N)c1Cl.O=[N+]([O-])[O-] | COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl | null | null | null | Functional Group Addition | Aromatic nitration with NO3 salt | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccccn2)cc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[O-]-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[c:5]:[c:6] | 84.4 | [{"value": 84.4, "product": "COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C=C(C(=C1)[N+](=O)[O-])Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | Methyl 4-amino-3-chloro-6-(4-chloro-2-fluorophenyl)pyridine-2-carboxylate (1.0 g, 3.2 mmol) was added as a solid to well stirred concentrated sulfuric acid (16 mL) at 0° C. Sodium nitrate (0.29 g, 3.5 mmol) was added to the mixture and the resulting yellow solution was stirred at 0° C. for 1.5 hours then diluted with a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HO- | null | 0 | 1.5 | COC(=O)c1nc(-c2ccc(Cl)cc2F)cc(N)c1Cl.O=[N+]([O-])[O-]>>COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5cfacbfd659408caba2c0154e739c11 | COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl>>COC(=O)c1nc(-c2cc(N)c(Cl)cc2F)cc(N)c1Cl | NC1=C(C(=NC(=C1)C1=C(C=C(C(=C1)[N+](=O)[O-])Cl)F)C(=O)OC)Cl>>COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C=C(C(=C1)N)Cl)F | O=[N+:11]([O-])[c:10]1[cH:9][c:8](-[c:7]2[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:20]([Cl:21])[c:18]([NH2:19])[cH:17]2)[c:15]([F:16])[cH:14][c:12]1[Cl:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][c:10]([NH2:11])[c:12]([Cl:13])[cH:14][c:15]2[F:16])[cH:17][c:18]([NH2:19])[c:20]1[Cl:21] | COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl | COC(=O)c1nc(-c2cc(N)c(Cl)cc2F)cc(N)c1Cl | null | [Fe] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.7 | [{"value": 95.7, "product": "COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C=C(C(=C1)N)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Iron powder (0.78 g, 13.9 mmol) was added to a slurry of methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-5-nitrophenyl)pyridine-2-carboxylate (0.5 g, 1.39 mmol) in acetic acid (20 mL) in a 100 mL round bottomed flask. The mixture was heated to 85° C. for 15 minutes. then cooled to room temperature and filtered through cel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Fe].C(C)(=O)O | 85 | null | COC(=O)c1nc(-c2cc([N+](=O)[O-])c(Cl)cc2F)cc(N)c1Cl>[Fe].C(C)(=O)O>COC(=O)c1nc(-c2cc(N)c(Cl)cc2F)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-934967c86b6e4b24b3451998f1aebc3d | COC(=O)c1nc(I)cc(NC(C)=O)c1Cl>>COC(=O)c1nc(I)cc(N)c1Cl | O.C(C)(=O)NC1=C(C(=NC(=C1)I)C(=O)OC)Cl.C(C)(=O)Cl>>NC1=C(C(=NC(=C1)I)C(=O)OC)Cl | CC(=O)[NH:11][c:10]1[cH:9][c:7]([I:8])[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:12]1[Cl:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([I:8])[cH:9][c:10]([NH2:11])[c:12]1[Cl:13] | COC(=O)c1nc(I)cc(NC(C)=O)c1Cl | COC(=O)c1nc(I)cc(N)c1Cl | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccncc1 | C-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 78.6 | [{"value": 78.6, "product": "NC1=C(C(=NC(=C1)I)C(=O)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To solution of 4-acetylamino-3-chloro-6-iodopyridine-2-carboxylic acid, methyl ester (5.0 g, 14 mmol) in methanol (25 mL) was added acetyl chloride (1 mL) and the solution heated under reflux for 1 hour. The solution was cooled and water (25 mL) added and the precipitate was collected. Recrystallization from methanol g... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccncc1 | HO- | CO | null | null | COC(=O)c1nc(I)cc(NC(C)=O)c1Cl>CO>COC(=O)c1nc(I)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee79c5f4860c4f2f8025c67255b0b577 | COC(=O)c1nc(I)cc(N)c1Cl.COc1c(Br)ccc(B(O)O)c1F>>COC(=O)c1nc(-c2ccc(Br)c(OC)c2F)cc(NC(C)=O)c1Cl | NC1=C(C(=NC(=C1)I)C(=O)OC)Cl.BrC1=C(C(=C(C=C1)B(O)O)F)OC.[F-].[Cs+].C(OC)COC>>C(C)(=O)NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Br)OC)F)C(=O)OC)Cl | I[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]([Cl:25])[c:19]([NH2:20])[cH:18]1.OB([c:8]1[cH:9][cH:10][c:11]([Br:12])[c:13]([O:14][CH3:15])[c:16]1[F:17])[OH:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Br:12])[c:13]([O:14][CH3:15])[c:16]2[F:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:... | COC(=O)c1nc(I)cc(N)c1Cl.COc1c(Br)ccc(B(O)O)c1F | COC(=O)c1nc(-c2ccc(Br)c(OC)c2F)cc(NC(C)=O)c1Cl | null | null | O | Acylation | OtherReaction | 358e91ad2921a0b16e42cfb733731c0f0542fcb580c0e968be351aabcc6bc332 | 6ec000fb720526e36b2afdf13966b1f2a2c19b6625dec262e485ab5539e0008b | c1ccc(-c2ccccn2)cc1 | I-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]:1.O-B(-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[F;D1;H0:16]):[c:17]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[F;D1;H0:16]):[c:17]):[c:10]:[c:8](-[NH;... | null | [] | 85 | CELSIUS | null | null | A solution of 4-amino-3-chloro-6-iodopyridine-2-carboxylic acid, methyl ester (1.1 g, 3.0 mmol), 4-bromo-2-fluoro-3-methoxyphenyl boronic acid (1.3 g, 4.5 mmol) and cesium fluoride (0.60 g, 4.0 mmole) in dimethoxyethane (2 mL) and water (2 mL) was de-aerated with a stream of nitrogen for 15 minutes before adding dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Boronic acid | Secondary amide | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | I-.B | O | 85 | null | COC(=O)c1nc(I)cc(N)c1Cl.COc1c(Br)ccc(B(O)O)c1F>O>COC(=O)c1nc(-c2ccc(Br)c(OC)c2F)cc(NC(C)=O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b47ea4588ed34879940d3ad59339d2ce | CC(F)c1c(Cl)ccc(Br)c1Cl.COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl>>COC(=O)c1nc(-c2ccc(Cl)c(C(C)F)c2Cl)cc(NC(C)=O)c1Cl | O.ClC1=C(C=CC(=C1C(C)F)Cl)Br.C(C)(=O)NC1=C(C(=NC(=C1)[Sn](C)(C)C)C(=O)OC)Cl.[F-].[Cs+]>>C(C)(=O)NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Cl)C(C)F)Cl)C(=O)OC)Cl | Br[c:8]1[cH:9][cH:10][c:11]([Cl:12])[c:13]([CH:14]([CH3:15])[F:16])[c:17]1[Cl:18].[CH3][Sn]([CH3])([CH3])[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:25]([Cl:26])[c:20]([NH:21][C:22]([CH3:23])=[O:24])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Cl:12])[c:13]([CH:14]([CH3:15])[F:16])[... | CC(F)c1c(Cl)ccc(Br)c1Cl.COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl | COC(=O)c1nc(-c2ccc(Cl)c(C(C)F)c2Cl)cc(NC(C)=O)c1Cl | null | [Cu](I)I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Stille reaction_aryl | ce918bbb171f9e7bd99035931c043f0f33f636d165d8c0e73629d8717d6c595a | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(-c2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[Sn](-[CH3])(-[CH3])-[CH3]):[c:13]:[c:14]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[#7;a:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6]):[c:13]:[c:14] | null | [] | null | null | null | null | A solution of 2,4 dichloro-3-(1-fluoroethyl)-bromobenzene (3.4 g, 12.5 mmol), 4-acetylamino-3-chloro-6-trimethylstannyl-pyridine-2-carboxylic acid, methyl ester (4.7 g, 12.5 mmol), copper iodide (0.4 g, 2.1 mmol), cesium fluoride (3.6 g, 25 mmol) and dichlorobis(triphenylphosphine)palladium (0.14 g, 2 mmol) in DMF (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccccc1.c1ccncc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.Sn | [Cu](I)I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | null | null | CC(F)c1c(Cl)ccc(Br)c1Cl.COC(=O)c1n[c]([Sn]([CH3])([CH3])[CH3])cc(NC(C)=O)c1Cl>[Cu](I)I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>COC(=O)c1nc(-c2ccc(Cl)c(C(C)F)c2Cl)cc(NC(C)=O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b6cfb7fb9434e5596bf36d9d9ffccdf | COC(=O)c1nc(Cl)cc(N)c1Cl.COc1c(C)ccc(B(O)O)c1F>>COC(=O)c1nc(-c2ccc(C)c(OC)c2F)cc(N)c1Cl | NC1=C(C(=NC(=C1)Cl)C(=O)OC)Cl.FC1=C(C=CC(=C1OC)C)B(O)O.[F-].[Cs+]>>NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)C)OC)F)C(=O)OC)Cl | Cl[c:7]1[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:21]([Cl:22])[c:19]([NH2:20])[cH:18]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([CH3:12])[c:13]([O:14][CH3:15])[c:16]1[F:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([CH3:12])[c:13]([O:14][CH3:15])[c:16]2[F:17])[cH:18][c:19]([NH2:20])[c:21]1[Cl:22] | COC(=O)c1nc(Cl)cc(N)c1Cl.COc1c(C)ccc(B(O)O)c1F | COC(=O)c1nc(-c2ccc(C)c(OC)c2F)cc(N)c1Cl | null | null | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[c:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[F;D1;H0:13]):[c:14]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[F;D1;H0:13]):[c:14]):[c:7]:[c:8] | 18.2 | [{"value": 18.2, "product": "NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)C)OC)F)C(=O)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A solution of 4-amino-3,6-dichloropyridine-2-carboxylic acid, methyl ester (0.24 g, 1.1 mmol), 2-fluoro-3-methoxy-4-methylphenyl boronic acid (0.30 g, 1.63 mmol) and cesium fluoride (3.0 g, 3.26 mmole) in dimethoxyethane (2 mL) and water (2 mL) was purged with a stream of nitrogen for 15 minutes before adding dichlorob... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HCl.B | O.C(OC)COC | 85 | null | COC(=O)c1nc(Cl)cc(N)c1Cl.COc1c(C)ccc(B(O)O)c1F>O.C(OC)COC>COC(=O)c1nc(-c2ccc(C)c(OC)c2F)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6562d5666814b609b1d0aee0b8f25c4 | CCOc1c(Cl)ccc(-c2cc(NC(C)=O)c(Cl)c(C(=O)OC)n2)c1F>>CCOc1c(Cl)ccc(-c2cc(N)c(Cl)c(C(=O)OC)n2)c1F | O.COC(=O)C1=NC(=CC(=C1Cl)NC(C)=O)C1=C(C(=C(C=C1)Cl)OCC)F.C(C)(=O)Cl>>COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C(=C(C=C1)Cl)OCC)F | CC(=O)[NH:13][c:12]1[cH:11][c:10](-[c:9]2[cH:8][cH:7][c:5]([Cl:6])[c:4]([O:3][CH2:2][CH3:1])[c:22]2[F:23])[n:21][c:16]([C:17](=[O:18])[O:19][CH3:20])[c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9](-[c:10]2[cH:11][c:12]([NH2:13])[c:14]([Cl:15])[c:16]([C:17](=[O:18])[O:19][CH3:20])[n:21]2)[c:22]1[... | CCOc1c(Cl)ccc(-c2cc(NC(C)=O)c(Cl)c(C(=O)OC)n2)c1F | CCOc1c(Cl)ccc(-c2cc(N)c(Cl)c(C(=O)OC)n2)c1F | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(-c2ccccn2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | null | null | To a solution of 4-acetylamino-3-chloro-6-(4-chloro-2-fluoro-3-ethoxyphenyl)pyridine-2-carboxylic acid methyl ester (0.5 g, 0.0013 mol) in methanol (10 mL) was added acetyl chloride (1 mL) and the solution heated under reflux for 1 hour. Water (2 mL) was added and resulting solid collected and dried to give 4-amino-3-c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1ccncc1 | HO- | CO | null | null | CCOc1c(Cl)ccc(-c2cc(NC(C)=O)c(Cl)c(C(=O)OC)n2)c1F>CO>CCOc1c(Cl)ccc(-c2cc(N)c(Cl)c(C(=O)OC)n2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a872daf99c7d4d28a236b7ecc55a65c9 | CCO.COC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl>>CCOC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl | NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Cl)OC)F)C(=O)OC)Cl.C(C)O>>NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Cl)OC)F)C(=O)OCC)Cl | [CH3:1][CH2:2][OH:3].CO[C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[c:14]([O:15][CH3:16])[c:17]2[F:18])[cH:19][c:20]([NH2:21])[c:22]1[Cl:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[c:14]([O:15][CH3:16])[c:17]2[F:18])[cH:19][c:20]([NH2:21])[c:22]1[Cl:2... | CCO.COC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl | CCOC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | null | Acylation | C-methylation | c42e047d71ad2593a6d29093d1fe2ca16ccfd6db7b15eecf1eab340181aef83e | cb08be6428b0a3737df44d00995165c06a05fb7dec4fab744c09315c4f7771d4 | c1ccc(-c2ccccn2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | To a solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, methyl ester (200 mg, 0.9 mmol) in ethanol (5 mL) was added a catalytic amount of titanium tetraisopropoxide and the solution heated under reflux for 2 hours. The solution was cooled and partitioned between ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary alcohol | Ester | null | null | c1ccncc1.c1ccccc1 | HO- | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | null | null | CCO.COC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>CCOC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17d8536a6d734624ab5d441efbf51b62 | COc1c(C#N)cc(F)c(-c2cc(NC(C)=O)c(Cl)cn2)c1F.[OH-]>>COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F | Cl.C(C)(=O)NC1=C(C=NC(=C1)C1=C(C(=C(C=C1F)C#N)OC)F)Cl.[OH-].[Na+].CO>>NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1F)C#N)OC)F)C(=O)O)Cl | C[C:18]([NH:14][c:13]1[cH:12][c:11](-[c:10]2[c:8]([F:9])[cH:7][c:4]([C:5]#[N:6])[c:3]([O:2][CH3:1])[c:22]2[F:23])[n:21][cH:17][c:15]1[Cl:16])=[O:19].[OH-:20]>>[CH3:1][O:2][c:3]1[c:4]([C:5]#[N:6])[cH:7][c:8]([F:9])[c:10](-[c:11]2[cH:12][c:13]([NH2:14])[c:15]([Cl:16])[c:17]([C:18](=[O:19])[OH:20])[n:21]2)[c:22]1[F:23] | COc1c(C#N)cc(F)c(-c2cc(NC(C)=O)c(Cl)cn2)c1F.[OH-] | COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F | null | null | O | Acylation | OtherReaction | a0000c18848ee93d6075d39c5138acbfb275189abc9fd6c7fafccbadcd149854 | 31b5c2cecdfb3a75e2cec361b135ff00b6a7e3073224bb1da24cc9c0c7780530 | c1ccc(-c2ccccn2)cc1 | C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:[c:9]:1-[Cl;D1;H0:10].[OH-;D0:11]>>[Cl;D1;H0:10]-[c:9]1:[c:4](-[NH2;D1;+0:3]):[c:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:8]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:11] | null | [] | null | null | 1 | HOUR | A slurry of 4-acetylamino-3-chloro-6-(4-cyano-2,6-difluoro-3-methoxyphenyl)pyridine (0.13 g, 0.33 mmol) in methanol (5 mL) was treated with 1N sodium hydroxide (1.7 mL) and stirred at ambient temperature for 1 hour. The solution was diluted with water (15 mL) and acidified with 1N hydrochloric acid (1.7 mL) and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Carboxylic acid.Primary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Other | O | null | 1 | COc1c(C#N)cc(F)c(-c2cc(NC(C)=O)c(Cl)cn2)c1F.[OH-]>O>COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6978c7a509c241098730825100bbf3f8 | COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)c1nc(-c2c(F)cc(C#N)c(OC)c2F)cc(N)c1Cl | NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1F)C#N)OC)F)C(=O)O)Cl.C[Si](C)(C)C=[N+]=[N-]>>NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1F)C#N)OC)F)C(=O)OC)Cl | [OH:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12]([C:13]#[N:14])[c:15]([O:16][CH3:17])[c:18]2[F:19])[cH:20][c:21]([NH2:22])[c:23]1[Cl:24].C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7](-[c:8]2[c:9]([F:10])[cH:11][c:12]([C:13]#[N:14])[c:15]([O:16][CH3:17])[c:18]2[F:19])[cH:20]... | COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F.C[Si](C)(C)C=[N+]=[N-] | COC(=O)c1nc(-c2c(F)cc(C#N)c(OC)c2F)cc(N)c1Cl | null | null | O1CCCC1.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccc(-c2ccccn2)cc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[#7;a:2]:[c:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7;a:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | null | null | null | null | A slurry of 4-amino-3-chloro-6-(4-cyano-2,6-difluoro-3-methoxyphenyl)pyridine-2-carboxlic acid in tetrahydrofuran (10 mL) and methanol (3 mL) was treated with trimethylsilyldiazomethane (0.64 g, 0.28 mL of a 2M solution in hexanes) at ambient temperature. After 1 hour the reaction mixture was quenched with acetic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccncc1.c1ccccc1 | Other | O1CCCC1.CO | null | null | COc1c(C#N)cc(F)c(-c2cc(N)c(Cl)c(C(=O)O)n2)c1F.C[Si](C)(C)C=[N+]=[N-]>O1CCCC1.CO>COC(=O)c1nc(-c2c(F)cc(C#N)c(OC)c2F)cc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93931ac2dfd44665925ad34be5a32c56 | COC(=O)c1nc(-c2ccc(Cl)c(OCC(F)F)c2F)cc(N)c1Cl>>Nc1cc(-c2ccc(Cl)c(OCC(F)F)c2F)nc(C(=O)O)c1Cl | COC(=O)C1=NC(=CC(=C1Cl)N)C1=C(C(=C(C=C1)Cl)OCC(F)F)F.Cl>>NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Cl)OCC(F)F)F)C(=O)O)Cl | C[O:22][C:20]([c:19]1[n:18][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[c:10]([O:11][CH2:12][CH:13]([F:14])[F:15])[c:16]2[F:17])[cH:3][c:2]([NH2:1])[c:23]1[Cl:24])=[O:21]>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[c:10]([O:11][CH2:12][CH:13]([F:14])[F:15])[c:16]2[F:17])[n:18][c:19]([C:20](=[O:21])[OH:22])[c:2... | COC(=O)c1nc(-c2ccc(Cl)c(OCC(F)F)c2F)cc(N)c1Cl | Nc1cc(-c2ccc(Cl)c(OCC(F)F)c2F)nc(C(=O)O)c1Cl | null | null | CO.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 87.5 | [{"value": 87.5, "product": "NC1=C(C(=NC(=C1)C1=C(C(=C(C=C1)Cl)OCC(F)F)F)C(=O)O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-(2,2-difluoroethoxy)phenyl)pyridine-2-carboxylic acid methyl ester (0.300 g, 0.0008 mol) in methanol (5 mL) and sodium hydroxide (1N, 2 mL) was heated to reflux 1 hour and then acidified to pH 3 (concentrated hydrochloric acid) and allowed to cool. The resulting sol... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccccc1 | Other | CO.[OH-].[Na+] | null | null | COC(=O)c1nc(-c2ccc(Cl)c(OCC(F)F)c2F)cc(N)c1Cl>CO.[OH-].[Na+]>Nc1cc(-c2ccc(Cl)c(OCC(F)F)c2F)nc(C(=O)O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6668a3df1d294ec299f9a537d7d1fb2d | Brc1ccc(I)cc1.OB(O)c1cccc2c1oc1ccccc12>>Brc1ccc(-c2cccc3c2oc2ccccc23)cc1 | C1=CC=C(C=2OC3=C(C21)C=CC=C3)B(O)O.BrC1=CC=C(C=C1)I.C([O-])([O-])=O.[Na+].[Na+]>>BrC1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | I[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:20][cH:19]1.OB(O)[c:6]1[cH:7][cH:8][cH:9][c:10]2[c:11]1[o:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]21>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10]3[c:11]2[o:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][cH:20]1 | Brc1ccc(I)cc1.OB(O)c1cccc2c1oc1ccccc12 | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | a34fd3f8e97b635d120df300575865eab1505627afd99c75ec2034d5929796bd | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2oc2ccccc23)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#8;a:11]:[c:12]>>[c:10]:[c:9](:[#8;a:11]:[c:12]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | 90 | CELSIUS | null | null | A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 mL) was added to a stirred solution of 1-bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (271 mg, 5 mol %) in toluene (40 mL). 2 N sodium carbonate (4.7 mL, 9.4 mmol) was added and then the reaction was heat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HI.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)O | 90 | null | Brc1ccc(I)cc1.OB(O)c1cccc2c1oc1ccccc12>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)O>Brc1ccc(-c2cccc3c2oc2ccccc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c107263d2030456a86346d5540e75258 | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1>>O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C([O-])([O-])=O.[Na+].[Na+].C(=O)C1=CC=C(C=C1)B(O)O.BrC1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)C=O | Br[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]2[o:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:27][cH:26]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[o:17][c:18]3[cH:19]... | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1 | O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4-(4-bromophenyl)-dibenzofuran (from the previous reaction) in toluene (40 mL). Tetrakis-(Triphenylphosphine)-palladium(0) (270 mg, 5 mol %) and 2 N sodium carbonate (4.7 mL, 9.4 mmol) were added ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)O | 100 | null | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)O>O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b8c4540df4745e2b8c12305d363a39d | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | [OH-].[Na+].COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.CO.Cl>>C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | C[O:39][C:37]([CH:8](N[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH2:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]4[c:25]3[o:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]43)[cH:33][cH:34]2)[cH:35][cH:36]1)=[O:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | O1CCCC1.O | Miscellaneous | OtherReaction | 4db8e1a49fb6f0bcc9ee9f32b36a5f4a173f45727a0b6ffb6ccaf6e3e1f4602b | 67ba51d9ece8d51253e171fb304ba5fff35ed9a0dd60b78a97bb1cfca9faa562 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4](-N-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-[#16:13]>>[#16:13]-[C:12]-[C@H;D3;+0:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | null | [] | null | null | null | null | 2 N Sodium hydroxide solution (1.32 mL, 2.64 mmol) was added dropwise to a stirred solution of methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)propionate (500 mg, 0.88 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL). The clear reaction mixture was stirred at room temperature u... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester | Carboxylic acid.Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | Other | O1CCCC1.O | null | null | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>O1CCCC1.O>CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c2207eb52b04a02af89969c315ff374 | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C([O-])(O)=O.[Na+].[Si](C)(C)(C)I.COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.C(Cl)Cl>>COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)N)=O | CC(C)(C)OC(=O)[NH:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:7][S:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]4[c:23]3[o:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]43)[cH:31][cH:32]2)[cH:33][cH:34]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH2:6])[CH2:7][S:8][CH2:9][c:10]... | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | null | null | O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | 25 | MINUTE | TMS-I (290 mg, 0.21 mL, 1.45 mmol) was added dropwise to a stirred solution of methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionate (748 mg, 1.32 mmol) in anhyd methylene chloride (20 mL). The reaction mixture was stirred at room temperature for 20-30 min (TLC control), and... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HO- | O | null | 0.416667 | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>O>COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5642754eba5c41788b001474b44a80fb | COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1.O=C(O)c1cc(C(F)(F)F)ccc1F>>COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F | FC1=C(C(=O)O)C=C(C=C1)C(F)(F)F.COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)N)=O.CCN=C=NCCCN(C)C.C(C)N(CC)CC>>COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(C1=C(C=CC(=C1)C(F)(F)F)F)=O)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]4[c:22]3[o:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]43)[cH:30][cH:31]2)[cH:32][cH:33]1)[NH2:34].O[C:35](=[O:36])[c:37]1[cH:38][c:39]([C:40]([F:41])([F:42])[F:43])[cH:44][cH:45... | COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1.O=C(O)c1cc(C(F)(F)F)ccc1F | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F | null | null | O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | 5 | HOUR | 2-Fluoro-5-trifluoromethylbenzoic acid (49 mg, 0.24 mmol) was added to a stirred solution of methyl-2-amino-3-(4′-dibenzofuran-4-ylbipheny-4-ylmethylsulfanyl)-propionate (92 mg, 0.2 mmol), EDCI (58 mg, 0.3 mmol) and triethylamine (404 mg, 0.56 mL, 0.4 mmol) in anhyd methylene chloride (5 mL). The reaction mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12.c1ccccc1 | HO- | O.C(Cl)Cl | null | 5 | COC(=O)C(N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1.O=C(O)c1cc(C(F)(F)F)ccc1F>O.C(Cl)Cl>COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0661e5a39dd14691ab85ae8c07e99e14 | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F>>O=C(NC(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O)c1cc(C(F)(F)F)ccc1F | [OH-].[Na+].COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(C1=C(C=CC(=C1)C(F)(F)F)F)=O)=O.Cl>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C2=CC=C(C=C2)CSCC(C(=O)O)NC(C2=C(C=CC(=C2)C(F)(F)F)F)=O)C=C3 | C[O:35][C:33]([CH:4]([NH:3][C:2](=[O:1])[c:36]1[cH:37][c:38]([C:39]([F:40])([F:41])[F:42])[cH:43][cH:44][c:45]1[F:46])[CH2:5][S:6][CH2:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][c:20]4[c:21]3[o:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]43)[cH:29][cH:30]2)[cH:31][cH:32]1)=[O... | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F | O=C(NC(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O)c1cc(C(F)(F)F)ccc1F | null | null | O1CCCC1.O.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)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] | null | [] | null | null | null | null | 2 N Sodium hydroxide solution (0.25 mL, 0.5 mmol) was added dropwise to a stirred solution of methyl-3-(4′-dibenzofuran-4-yl-biphen-4ylmethylsulfanyl)-2(2-fluoro-5-trifluoromethylbenzoylamino)-propionate (110 mg, 0.17 mmol) in tetrahydrofuran (5 mL) and methanol (1 mL). The clear reaction mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12.c1ccccc1 | Other | O1CCCC1.O.CO | null | null | COC(=O)C(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)c1cc(C(F)(F)F)ccc1F>O1CCCC1.O.CO>O=C(NC(CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O)c1cc(C(F)(F)F)ccc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-113365e68b154ac1a705d59bf018c6dc | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-]>>CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | [OH-].[Na+].C[C@@](C(=O)[O-])(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12)NC(=O)OC(C)(C)C.Cl>>C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12 | C[C@:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH2:10][S:11][CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20](-[n:21]3[cH:22][cH:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]34)[cH:30][cH:31]2)[cH:32][cH:33]1)[C:34](=[O:35])[O-:36]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][... | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-] | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | null | null | O1CCCC1.O.CO | Miscellaneous | OtherReaction | a6b8ab131e7f70f6daa606d152ad1c80317c30ce07f436c723a799e222d8098f | d003579d88c8e6390ed4fac608b8ce68d334559ff02e2f3d9c9936750b60a874 | c1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | C-[C@;H0;D4;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9])(-[C:10]-[#16:11])-[C:12](-[O-;H0;D1:13])=[O;D1;H0:14]>>[#16:11]-[C:10]-[C@H;D3;+0:1](-[#7:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9])-[C:12](=[O;D1;H0:14])-[OH;D1;+0:13] | null | [] | null | null | null | null | 1N Sodium hydroxide solution (2.14 mL, 2.14 mmol) was added dropwise to a stirred solution of (2R)-Methyl-tert-butoxycarbonylamino-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-propionate (552 mg, 1.07 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL). The clear reaction mixture was stirred at room temperature until th... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | Other | O1CCCC1.O.CO | null | null | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-]>O1CCCC1.O.CO>CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c6a5b69c8124acf806461d03a805065 | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12>>C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CS(=O)CC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][S:11][CH2:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21](-[n:22]3[cH:23][cH:24][c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]34)[cH:31][cH:32]2)[cH:33][cH:34]1)[C:35](=[O:36])[OH:37]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C... | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:9]=[S;H0;D3;+0:6](-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[C:7]-[c:8] | null | [] | 40 | CELSIUS | 2 | HOUR | Sodium perborate tetrahydrate (151 mg, 0.95 mmol) was added as a solid to a stirred solution of (2R)-tert-Butoxycarbonylamino-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-propionic acid (380 mg, 0.76 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then diluted wit... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 2 | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6d87d33e4204defae757acd759b3761 | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-]>>COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | [Si](C)(C)(C)I.C[C@@](C(=O)[O-])(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12)NC(=O)OC(C)(C)C.C([O-])(O)=O.[Na+]>>COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12)N)=O | CC(C)(C)OC(=O)[NH:6][C@:5](C)([C:3]([O-:2])=[O:4])[CH2:7][S:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17](-[n:18]3[cH:19][cH:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][S:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14... | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-] | COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 47e29fef19aa31584b7fe52e994859163ada510d2b35acbed20cc1771c93a6f0 | 59f513d0431a3c0eec75fc6904881dfd8f6bfaabbb8014f6d2acaff8b29e8c08 | c1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C@@;H0;D4;+0:2](-C)(-[C:3]-[#16:4])-[C:5](-[O-;H0;D1:6])=[O;D1;H0:7]>>[#16:4]-[C:3]-[C@H;D3;+0:2](-[NH2;D1;+0:1])-[C:5](=[O;D1;H0:7])-[O;H0;D2;+0:6]-[C;D1;H3:8] | 95 | [{"value": 95.0, "product": "COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)N1C=CC2=CC=CC=C12)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | TMSI (1.56 mL, 10.63 mmol) was added dropwise to a stirred solution of (2R)-methyl-tert-butoxycarbonylamino-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-propionate (4.47 g, 8.66 mmol) in anhydrous methylene chloride (50 mL). The reaction was stirred for 10 mins. and then poured into 1N sodium bicarbonate solution (50 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Ester.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | C(Cl)Cl | null | 0.166667 | CC(C)(C)OC(=O)N[C@@](C)(CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)[O-]>C(Cl)Cl>COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f12f4d1314d41ae89b3304c88990bfc | O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>>O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CSC[C@@H](C(=O)O)NC(CC2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1>>N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CS(=O)C[C@@H](C(=O)O)NC(CC2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1 | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12]1)[NH:13][C@@H:14]([CH2:15][S:16][CH2:18][c:19]1[cH:20][cH:21][c:22](-[c:23]2[cH:24][cH:25][c:26](-[n:27]3[cH:28][cH:29][c:30]4[cH:31][cH:32][cH:33][cH:34][c:35]34)[cH:36][cH:37]2)[cH:38][cH:39]1)[C:40](=[O:41])[OH:42]>>[O:1]=[C:2]([CH2:3][c... | O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C(Cc1ccccc1)NCCS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:9]=[S;H0;D3;+0:6](-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[C:7]-[c:8] | 61.1 | [{"value": 61.0, "product": "N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CS(=O)C[C@@H](C(=O)O)NC(CC2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CS(=O)C[C@@H](C(=O)O)NC(CC2=CC(=CC=C2)[N+](=O)[O-])=O)C=C1", "details": "... | 40 | CELSIUS | 2 | HOUR | Sodium perborate tetrahydrate (97 mg, 0.63 mmol) was added as a solid to a stirred solution of (2R)-3-(4′-Indol-1-ylbiphen-4-ylmethylsulfanyl)-2-[2-(3-nitrophenyl)-acetylamino]-propionic acid (330 mg, 0.58 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then dil... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 2 | O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>O=C(Cc1cccc([N+](=O)[O-])c1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c736471cd2749cb9d11c5a8a992e28d | O=C(Cc1ccccc1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>>O=C(Cc1ccccc1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CSC[C@@H](C(=O)O)NC(CC2=CC=CC=C2)=O)C=C1>>N1(C=CC2=CC=CC=C12)C1=CC=C(C2=CC=C(C=C2)CS(=O)C[C@@H](C(=O)O)NC(CC2=CC=CC=C2)=O)C=C1 | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[NH:10][C@@H:11]([CH2:12][S:13][CH2:15][c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][c:23](-[n:24]3[cH:25][cH:26][c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]34)[cH:33][cH:34]2)[cH:35][cH:36]1)[C:37](=[O:38])[OH:39]>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c... | O=C(Cc1ccccc1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | O=C(Cc1ccccc1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C(Cc1ccccc1)NCCS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:9]=[S;H0;D3;+0:6](-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[C:7]-[c:8] | null | [] | 40 | CELSIUS | 2 | HOUR | Sodium perborate tetrahydrate (97 mg, 0.63 mmol) was added as a solid to a stirred solution of (2R)-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-2-phenylacetylamino-propionic acid (300 mg, 0.58 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then diluted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2[nH]ccc2c1 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 2 | O=C(Cc1ccccc1)N[C@@H](CSCc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>O=C(Cc1ccccc1)N[C@@H](CS(=O)Cc1ccc(-c2ccc(-n3ccc4ccccc43)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-892c3d1426bd485caba0c509e21d7fd1 | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1>>O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C([O-])([O-])=O.[Na+].[Na+].C(=O)C1=CC=C(C=C1)B(O)O.BrC1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)C=O | Br[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]2[o:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24][cH:25]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:27][cH:26]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[o:17][c:18]3[cH:19]... | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1 | O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | null | null | C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A solution of 4-formylphenylboronic acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4-(4-bromophenyl)-dibenzofuran (from the previous reaction) in toluene (40 mL). tetrakis-(Triphenylphosphine)palladium(0) (270 mg, 5 mol %) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | C1(=CC=CC=C1)C.C(C)O | 100 | null | Brc1ccc(-c2cccc3c2oc2ccccc23)cc1.O=Cc1ccc(B(O)O)cc1>C1(=CC=CC=C1)C.C(C)O>O=Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db804fd692aa4260a1641b4997e4a7cb | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | [OH-].[Na+].COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.CO.Cl>>C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | C[O:39][C:37]([C@@H:8](N[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH2:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]4[c:25]3[o:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]43)[cH:33][cH:34]2)[cH:35][cH:36]1)=[O:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5]... | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | O1CCCC1.O | Miscellaneous | OtherReaction | 4db8e1a49fb6f0bcc9ee9f32b36a5f4a173f45727a0b6ffb6ccaf6e3e1f4602b | 67ba51d9ece8d51253e171fb304ba5fff35ed9a0dd60b78a97bb1cfca9faa562 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C@@H;D3;+0:4](-N-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-[#16:13]>>[#16:13]-[C:12]-[C@H;D3;+0:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | null | [] | null | null | null | null | 2N Sodium hydroxide solution (1.32 mL, 2.64 mmol) was added dropwise to a stirred solution of (2R)-methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)propionate (500 mg, 0.88 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL). The clear reaction mixture was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester | Carboxylic acid.Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | Other | O1CCCC1.O | null | null | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>O1CCCC1.O>CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c23e125befb4d0bb9066526dd17ea9b | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>>CC(C)(C)OC(=O)[C@H](CS(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1>>C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CS(=O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([CH2:9][S:10][CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]4[c:26]3[o:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]43)[cH:34][cH:35]2)[cH:36][cH:37]1)[C:38](=[O:39])[OH:40]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | CC(C)(C)OC(=O)[C@H](CS(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[S;H0;D3;+0:6](=[O;D1;H0:12])-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | 40 | CELSIUS | 1 | HOUR | Sodium perborate tetrahydrate (42 mg, 0.27 mmol) was added as a solid to a stirred solution of (2R)-2-tert-Butoxycarbonyl-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionic acid (150 mg, 0.27 mmol), in acetic acid (5 mL) at 40° C. This solution was stirred at 40° C. for 1 hour (HPLC control) and then dilut... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 1 | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)[C@H](CS(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa161f9f8eea4eca8b8b0897739450c4 | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>>CC(C)(C)OC(=O)[C@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1>>C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CS(=O)(=O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@H:8]([CH2:9][S:10][CH2:13][c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][c:26]4[c:27]3[o:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]43)[cH:35][cH:36]2)[cH:37][cH:38]1)[C:39](=[O:40])[OH:41]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | CC(C)(C)OC(=O)[C@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4](-[C:5]-[S;H0;D4;+0:6](=[O;D1;H0:12])(=[O;D1;H0:13])-[C:7]-[c:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | 89.6 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CS(=O)(=O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.6, "product": "C(C)(C)(C)OC(=O)[C@@H](C(=O)O)CS(=O)(=O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "CALCULATEDPE... | 40 | CELSIUS | 2 | HOUR | Sodium perborate tetrahydrate (105 mg, 0.68 mmol) was added as a solid to a stirred solution of (2R)-2-tert-Butoxycarbonyl-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionic acid (150 mg, 0.27 mmol), in acetic acid (10 mL) at 50° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then di... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 2 | CC(C)(C)OC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)[C@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a380b04f2a6540cb8354a547ad1b0d5c | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | [Si](C)(C)(C)I.COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.C([O-])(O)=O.[Na+]>>COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)N)=O | CC(C)(C)OC(=O)[NH:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:7][S:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]4[c:23]3[o:24][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]43)[cH:31][cH:32]2)[cH:33][cH:34]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][S:8][CH2:9][c:... | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | null | null | O.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | 25 | MINUTE | TMS-I (870 mg, 0.63 mL, 4.35 mmol) was added dropwise to a stirred solution of (2R)-methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionate (2.24 g, 3.96 mmol) in anhydrous methylene chloride (50 mL). The reaction mixture was stirred at room temperature for 20-30 mins (TLC con... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HO- | O.C(Cl)Cl | null | 0.416667 | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>O.C(Cl)Cl>COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-990557efc3754733aed4ec56f27a6846 | COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1>>N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | [OH-].[Na+].COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)N)=O.Cl>>N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | C[O:33][C:31]([C@@H:2]([NH2:1])[CH2:3][S:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]4[c:19]3[o:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]43)[cH:27][cH:28]2)[cH:29][cH:30]1)=[O:32]>>[NH2:1][C@@H:2]([CH2:3][S:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c... | COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | O1CCCC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)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] | 86 | [{"value": 86.0, "product": "N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2N Sodium hydroxide (0.5 mL) was added to a stirred solution of the amino methyl ester, (2R)-Methyl-2-Amino-3-(4′-dibenzofuran-4-ylbipheny-4-ylmethylsulfanyl)-propionate (100 mg) in a mixture of tetrahydrofuran (5 mL) and methanol (1 mL). The solution was stirred for 1 hour and then acidified to pH 3 with 2N hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | Other | O1CCCC1.CO | null | 1 | COC(=O)[C@@H](N)CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1>O1CCCC1.CO>N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-276b12e917a04c8181274b48fa1e325e | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>>N=C(N)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N=C(N[C@H](C(=O)O)CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)CSC[C@@H](C(=O)O)NC(=N)N | CC(C)(C)OC(=O)[N:1]=[C:2]([NH:3]C(=O)OC(C)(C)C)[NH:4][C@@H:5]([CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]4[c:22]3[o:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]43)[cH:30][cH:31]2)[cH:32][cH:33]1)[C:34](=[O:35])[OH:36]>>[NH:1]=[C:2]([NH2:3])[NH:4][C@@H:5... | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | N=C(N)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | ClCCl | Reduction | Boc amine deprotection of guanidine | 9766f6229fee762ffca87ed66a89907c51d08c86b25c0988ddb4d7c2e968882c | 8451d9ce44c8e1c8be0145c0e21ac06b9d8969460bd0e7e8568f82462587cbce | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D2;+0:1]=[C:2](-[#7:3])-[NH;D2;+0:4]-C(=O)-O-C(-C)(-C)-C>>[#7:3]-[C:2](-[NH2;D1;+0:4])=[NH;D1;+0:1] | 99 | [{"value": 99.0, "product": "C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)CSC[C@@H](C(=O)O)NC(=N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)C3=CC=C(C=C3)CSC[C@@H](C(=O)O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 4 | HOUR | Trifluoroacetic acid (2 mL) was added to a stirred solution of (2R)-2-[2,3-bis-(tert-butoxycarbonyl)guanidino]-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)-propionic acid (250 mg, 0.36 mmol) in anhydrous dichloromethane (10 mL). The reaction was stirred for 4 hours (HPLC control) and then concentrated in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HO- | ClCCl | null | 4 | CC(C)(C)OC(=O)N=C(NC(=O)OC(C)(C)C)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O>ClCCl>N=C(N)N[C@@H](CSCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4146c15b24c54bf889fefafdbcae8ab2 | O=Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1>>OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)C=O)C=CC=C2.[BH4-].[Na+].O>>C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CO)C=CC=C2 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[c:12]([CH2:13][c:14]4[cH:15][cH:16][cH:17][cH:18][cH:19]4)[o:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28]2)[cH:29][cH:30]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[c:12]([CH2:13][c:14]4[cH:15][cH:16][... | O=Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | null | null | O1CCCC1.C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(Cc2oc3ccccc3c2-c2ccc(-c3ccccc3)cc2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 99.7 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CO)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CO)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4′-(2-benzylbenzofuran-3-yl)biphenyl-4-carbaldehyde (5.0 g, 12.9 mmol) in ethanol (100 mL) and tetrahydrofuran (25 mL) was added sodium borohydride (980 mg, 25.8 mmol) as a solid in 3 portions. The reaction was stirred at room temperature for 1 hour (TLC control) and then poured into water (100 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2occc2c1 | null | O1CCCC1.C(C)O | null | 1 | O=Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1>O1CCCC1.C(C)O>OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf2c72086a0e4d198532d5ad07313887 | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1>>BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | O.C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CO)C=CC=C2.BrP(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CBr)C=CC=C2 | BrP(c1ccccc1)(c1ccccc1)(c1ccccc1)[Br:1].O[CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[c:12]([CH2:13][c:14]4[cH:15][cH:16][cH:17][cH:18][cH:19]4)[o:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[cH:27][cH:28]2)[cH:29][cH:30]1>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[... | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 8872f2fae3cc46ec19a3bd8f9f9484c21a537e6d42617740a795333c61c3afc4 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(Cc2oc3ccccc3c2-c2ccc(-c3ccccc3)cc2)cc1 | Br-P(-[Br;H0;D1;+0:1])(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 87 | [{"value": 87.0, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CBr)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CBr)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4′-(2-benzylbenzofuran-3-yl)biphenyl-4-methanol (5.01 g, 12.7 mmol) in anhydrous acetonitrile (75 mL) was added dibromotriphenylphosphorane (5.45 g, 12.7 mmol) as a solid portionwise over 15 mins. The reaction was stirred for 2 hours (TLC control) and then poured into water (100 mL) and extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2occc2c1 | HBr | C(C)#N | null | 2 | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1>C(C)#N>BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0d70d242b6649fd8d306f20012c629b | BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C>>COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | O.COC([C@@H](NC(=O)OC(C)(C)C)CS)=O.C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C=C1)C1=CC=C(C=C1)CBr)C=CC=C2.C([O-])([O-])=O.[Cs+].[Cs+]>>COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(OC2=C1C=CC=C2)CC2=CC=CC=C2)NC(=O)OC(C)(C)C)=O | Br[CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16](-[c:17]3[c:18]([CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[o:26][c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]34)[cH:33][cH:34]2)[cH:35][cH:36]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][SH:7])[NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:... | BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccc(Cc2oc3ccccc3c2-c2ccc(-c3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[SH;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 92.7 | [{"value": 92.0, "product": "COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(OC2=C1C=CC=C2)CC2=CC=CC=C2)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(OC2=C1C=CC=C2)CC2=CC=CC=C2)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTY... | null | null | 2 | HOUR | N-Boc-L-Cysteine methyl ester (260 mg, 0.23 mL, 1.1 mmol) was added dropwise to a stirred suspension of 2-Benzyl-3-(4′-bromomethylbiphen-4-yl)benzofuran (500 mg, 1.1 mmol) and cesium carbonate (720 mg, 2.21 mmol) in anhydrous dimethylformamide (20 mL). The reaction was stirred at room temperature for 2 hrs (TLC control... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2occc2c1 | HBr | CN(C=O)C | null | 2 | BrCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C>CN(C=O)C>COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d8b9ee1091948778ebfa982fa423205 | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)O[C@](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)(N=C=O)C(=O)O | [OH-].[Na+].COC([C@H](CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(OC2=C1C=CC=C2)CC2=CC=CC=C2)NC(=O)OC(C)(C)C)=O.Cl>>C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CSC[C@@](C(=O)O)(OC(C)(C)C)N=C=O)C=C1)C=CC=C2 | C[O:43][C:41]([C@H:6]([CH2:7][S:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17](-[c:18]3[c:19]([CH2:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[o:27][c:28]4[cH:29][cH:30][cH:31][cH:32][c:33]34)[cH:34][cH:35]2)[cH:36][cH:37]1)[NH:38][C:39]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:40])=[O:42]>>[CH3:1... | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)O[C@](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)(N=C=O)C(=O)O | null | null | O1CCCC1.CO | Miscellaneous | OtherReaction | bddd03b924038931273bed81e8862363f2f3e48dd28556c3a68c5d8c7a1d08f8 | cc5b0328a1c3fc37b615ae32d720dd8bdc1cf4d0986d2062548d49debb17cf49 | c1ccc(Cc2oc3ccccc3c2-c2ccc(-c3ccccc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C@H;D3;+0:4](-[C:5]-[#16:6])-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[#16:6]-[C:5]-[C@;H0;D4;+0:4](-[N;H0;D2;+0:7]=[C;H0;D2;+0:8]=[O;D1;H0:9])(-[O;H0;D2;+0:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[C... | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CSC[C@@](C(=O)O)(OC(C)(C)C)N=C=O)C=C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1N Sodium hydroxide (2 mL) was added to a stirred solution of (2R)-methyl-3-[4′-(2-benzylbenzofuran-3-yl)biphen-4-ylmethylsulfanyl]-2-tert-butoxycarbonylamino-propionate (100 mg) in a mixture of tetrahydrofuran (6 mL) and methanol (2 mL). The solution was stirred for 1 hour and then acidified to pH 3 with 1N hydrochlor... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester | Carboxylic acid.Ether.Isocyanate | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2occc2c1 | Other | O1CCCC1.CO | null | 1 | COC(=O)[C@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>O1CCCC1.CO>CC(C)(C)O[C@](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)(N=C=O)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-baf9dffcf2204eb8856112afb74bef5b | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O | B1(OO1)[O-].O.O.O.O.[Na+].C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CSC[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C=C1)C=CC=C2>>C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CS(=O)(=O)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C=C1)C=CC=C2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][S:11][CH2:14][c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22](-[c:23]3[c:24]([CH2:25][c:26]4[cH:27][cH:28][cH:29][cH:30][cH:31]4)[o:32][c:33]4[cH:34][cH:35][cH:36][cH:37][c:38]34)[cH:39][cH:40]2)[cH:41][cH:42]1)[C:43](=[O:44])[OH:45]>>[CH3:... | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O | CC(C)(C)OC(=O)N[C@@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O | null | null | C(C)(=O)O.C(C)(=O)OCC | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(Cc2oc3ccccc3c2-c2ccc(-c3ccccc3)cc2)cc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:9]=[S;H0;D4;+0:6](=[O;D1;H0:10])(-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[C:7]-[c:8] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CS(=O)(=O)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C=C1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "C(C1=CC=CC=C1)C=1OC2=C(C1C1=CC=C(C3=CC=C(C=C3)CS(=O)(=O)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C=C1)C=CC=C2", "details":... | 40 | CELSIUS | 2 | HOUR | Sodium perborate tetrahydrate (320 mg, 2.1 mmol) was added as a solid to a stirred solution of (2R)-3-[4′-(2-benzylbenzofuran-3-yl)biphen-4-ylmethylsulfanyl]-2-tert-butoxycarbonylamino-propionic acid (440 mg, 0.74 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2occc2c1 | null | C(C)(=O)O.C(C)(=O)OCC | 40 | 2 | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O>C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@@H](CS(=O)(=O)Cc1ccc(-c2ccc(-c3c(Cc4ccccc4)oc4ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9e0f04e7b404f6dbea27116ba7ebe2e | CS(=O)(=O)Cl.OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1>>CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1 | C1(=CC=CC=C1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=C(C=C1)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>C1(=CC=CC=C1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=C(COS(=O)(=O)C)C=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[n:28]2)[cH:29][cH:30]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[n:12][c:13](-[c:14]3[cH:15]... | CS(=O)(=O)Cl.OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1 | CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(-c2cc(-c3ccccc3)nc(-c3ccccc3)n2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C:6]-[c:7] | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of [4-(4,6-diphenylpyrimidin-2-yl)-phenyl]methanol, 0.38 g (1.11 mmol), triethylamine, 0.34 mL (2.45 mmol), and 6 mL of methylene chloride was cooled to 0° C. via ice-water bath. Methanesulfonyl chloride, 0.10 mL (1.23 mmol) was added dropwise over minutes. The solution stirred for 2 h at 0° C. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 2 | CS(=O)(=O)Cl.OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1>C(Cl)Cl>CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d421daf3a5f455eb4058ba1413d1e40 | COC(=O)[C@H](CS)NC(=O)OC(C)(C)C.CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1>>COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C | C1(=CC=CC=C1)C1=NC(=NC(=C1)C1=CC=CC=C1)C1=CC=C(COS(=O)(=O)C)C=C1.COC([C@@H](NC(=O)OC(C)(C)C)CS)=O.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>COC(C(CSCC1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=CC=C1)C1=CC=CC=C1)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][SH:7])[NH:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40].CS(=O)(=O)O[CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[n:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[n:30]2)[cH:31][cH:32]1>>[CH3:1][O:2][C:... | COC(=O)[C@H](CS)NC(=O)OC(C)(C)C.CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1 | COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 5ef6153311053d1fb9aeb0863ac740df1693ec5dc2fd63b54be9bba291d50d91 | 5d51471fb107f265fe2b725316ea74298d6b5b18b8910d02b969c8ad6fbd6b39 | c1ccc(-c2cc(-c3ccccc3)nc(-c3ccccc3)n2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[SH;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | HOUR | A mixture of Methanesulfonic acid 4-(4,6-diphenylpyrimidin-2-yl)-benzyl ester, 0.15 g (0.36 mmol), N-(tert-Butoxycarbonyl)-L-cysteine methyl ester, 0.08 mL (0.36 mmol), cesium carbonate, 235 mg (0.72 mmol), and 10 mL of N,N-dimethylformamide was stirred at room temperature for 4 h. The mixture was diluted with 10 mL of... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | MsOH.HO- | O | null | 4 | COC(=O)[C@H](CS)NC(=O)OC(C)(C)C.CS(=O)(=O)OCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1>O>COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d07a2c718bb74917ab2d64f61b49b0ea | COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)C(=O)O | COC(C(CSCC1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=CC=C1)C1=CC=CC=C1)NC(=O)OC(C)(C)C)=O.CO.[OH-].[K+]>>C(C)(C)(C)OC(=O)NC(C(=O)O)CSCC1=CC=C(C=C1)C1=NC(=CC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 | C[O:39][C:37]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][S:11][CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26][c:27](-[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[n:34]2)[cH:35][cH:36]1)=[O:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][... | COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)C(=O)O | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cc(-c3ccccc3)nc(-c3ccccc3)n2)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 | 1 | HOUR | To a solution of 2-tert-Butoxy carbonylamino-3-[4-(4,6-diphenylpyrimidin-2-yl)-benzylsulfanyl]-propionic acid methyl ester, 0.18 g (0.32 mmol) in 10 mL of tetrahydrofuran and 5 mL of methanol was added 1.62 mL of 1.0M aq. KOH. The solution was stirred for 1 h at room temperature. The solution was diluted with 10 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.O | null | 1 | COC(=O)C(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C>O1CCCC1.O>CC(C)(C)OC(=O)NC(CSCc1ccc(-c2nc(-c3ccccc3)cc(-c3ccccc3)n2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8b428ec23fd4237a150471823319346 | COC(=O)c1ccc(I)cc1.OB(O)c1ccc(Br)cc1>>COC(=O)c1ccc(-c2ccc(Br)cc2)cc1 | C(=O)([O-])[O-].[Na+].[Na+].C(C)O.IC1=CC=C(C(=O)OC)C=C1.BrC1=CC=C(C=C1)B(O)O>>COC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)Br | I[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1.OB(O)[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[cH:16][cH:17]1 | COC(=O)c1ccc(I)cc1.OB(O)c1ccc(Br)cc1 | COC(=O)c1ccc(-c2ccc(Br)cc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | null | [] | 80 | CELSIUS | null | null | A mixture of methyl 4-iodobenzoate, 9.38 g (35.8 mmol), 4-bromophenylboronic acid 7.18 g (35.8 mmol), Pd(PPh3)4, 2.07 g (1.79 mmol), in 180 mL of toluene and 100 mL of ethanol was heated to obtain a clear solution. To the solution was added 30 mL of 4.0M aq. Na2CO3. The reaction mixture refluxed for 4 h at 80° C. The m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC | 80 | null | COC(=O)c1ccc(I)cc1.OB(O)c1ccc(Br)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC>COC(=O)c1ccc(-c2ccc(Br)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d8b78dd1e8e4d319a4cdeb5fdbd1fab | COC(=O)c1ccc(-c2ccc(Br)cc2)cc1>>OCc1ccc(-c2ccc(Br)cc2)cc1 | COC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)Br.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>BrC1=CC=C(C=C1)C1=CC=C(C=C1)CO | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[cH:14][cH:15]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[cH:14][cH:15]1 | COC(=O)c1ccc(-c2ccc(Br)cc2)cc1 | OCc1ccc(-c2ccc(Br)cc2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | A solution of 4′-Bromo-biphenyl-4-carboxylic acid methyl ester, 7.8 g (27.9 mmol) in 150 mL of tetrahydrofuran was cooled to 0° C. via ice-water bath. Lithium aluminum hydride, 1.1 g (27.9 mmol) was added to the solution in one portion. The reaction mixture stirred at 0° C. for 1 h. The mixture was slowly quenched with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1 | 0 | 1 | COC(=O)c1ccc(-c2ccc(Br)cc2)cc1>O1CCCC1>OCc1ccc(-c2ccc(Br)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b21c13c0f3b44b3bddb7e6cd4e61e8f | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(Br)cc2)cc1>>BrCc1ccc(-c2ccc(Br)cc2)cc1 | BrC1=CC=C(C=C1)C1=CC=C(C=C1)CO.BrP(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)Br>>BrC1=CC=C(C=C1)C1=CC=C(C=C1)CBr | BrP(c1ccccc1)(c1ccccc1)(c1ccccc1)[Br:1].O[CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[cH:14][cH:15]1>>[Br:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[cH:14][cH:15]1 | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(Br)cc2)cc1 | BrCc1ccc(-c2ccc(Br)cc2)cc1 | null | null | O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 8872f2fae3cc46ec19a3bd8f9f9484c21a537e6d42617740a795333c61c3afc4 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc(-c2ccccc2)cc1 | Br-P(-[Br;H0;D1;+0:1])(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of (4′-bromo-biphenyl-4-yl)-methanol, 7.01 g (27.9 mmol) and dibromo-triphenylphosphorane 11.8 g (27.9 mmol) in 150 mL of methylene chloride stirred at room temperature for 2 h. The solution was diluted with 100 mL of water and extracted with 2×200 mL portions of diethyl ether. The organic layers were combin... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HBr | O.C(Cl)Cl | null | null | BrP(Br)(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1ccc(-c2ccc(Br)cc2)cc1>O.C(Cl)Cl>BrCc1ccc(-c2ccc(Br)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a5c271ada4a460a91ac4613c6188126 | BrCc1ccc(-c2ccc(Br)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C>>COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C | BrC1=CC=C(C=C1)C1=CC=C(C=C1)CBr.COC([C@@H](NC(=O)OC(C)(C)C)CS)=O.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O | Br[CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]2)[cH:20][cH:21]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][SH:7])[NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][c:1... | BrCc1ccc(-c2ccc(Br)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C | COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C | null | null | O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccc(-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[SH;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | HOUR | A mixture of 4′-Bromo-4-bromomethyl-biphenyl, 9.1 g (27.9 mmol), N-(tert-Butoxy-carbonyl)-L-cysteine methyl ester, 5.74 mL (27.9 mmol), cesium carbonate, 18.2 g (55.8 mmol), and 100 mL of N,N-dimethylformamide was stirred at room temperature for 4 h. The mixture was diluted with 200 mL of water and extracted with 2×200... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1 | HBr | O | null | 4 | BrCc1ccc(-c2ccc(Br)cc2)cc1.COC(=O)[C@H](CS)NC(=O)OC(C)(C)C>O>COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-924209de829f46698e0c5472ddea0acc | COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc2c(c1)OCO2>>COC(=O)C(N)(CSCc1ccc(-c2ccc(-c3ccc4c(c3)OCO4)cc2)cc1)C(=O)OC(C)(C)C | C(=O)([O-])[O-].[Na+].[Na+].C(C)O.C1(=CC=CC=C1)C.COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O.C1OC=2C=C(C=CC2O1)B(O)O>>COC(C(CSCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC2=C(OCO2)C=C1)(C(=O)OC(C)(C)C)N)=O | Br[c:17]1[cH:16][cH:15][c:14](-[c:13]2[cH:12][cH:11][c:10]([CH2:9][S:8][CH2:7][CH:5]([C:3]([O:2][CH3:1])=[O:4])[NH:6][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:30][cH:29]2)[cH:28][cH:27]1.OB(O)[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2>>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH2:6])([CH... | COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc2c(c1)OCO2 | COC(=O)C(N)(CSCc1ccc(-c2ccc(-c3ccc4c(c3)OCO4)cc2)cc1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)(=O)OCC | C-C Coupling | OtherReaction | 8bfdeabe353177261302af58ff5d125f7cc327422930bad1cf6fd6e991251f27 | e5c3d9302fdfa5543f6fae69ac941917f16ef75f0b4c9bd17dbd8e8ddd91a4bb | c1ccc(-c2ccc(-c3ccc4c(c3)OCO4)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16:6]-[C:7]-[CH;D3;+0:8](-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;H3:20].O-B(-O)-[c;H0;D3;+0:21](:[c:22]:[c:23]):[c:24]:[c:25]-[#8:26]>>[#16:6]-[C:7]-[C;H0;D4;+0:8](-[NH2;D1;+... | null | [] | 80 | CELSIUS | null | null | A mixture of 3-(4′-bromobiphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester, 0.26 g (0.54 mmol), 3,4-methylenedioxyphenylboronic acid, 90 mg (0.54 mmol), Pd(PPh3)4, 63 mg (0.054 mmol), in 5 mL of toluene and 3 mL of ethanol was heated to obtain a clear solution. To the solution was added... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ester.Ether.Boronic acid | Ester.Ester.Primary amine.Boc | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)OCO2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC | 80 | null | COC(=O)C(CSCc1ccc(-c2ccc(Br)cc2)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc2c(c1)OCO2>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.C(C)(=O)OCC>COC(=O)C(N)(CSCc1ccc(-c2ccc(-c3ccc4c(c3)OCO4)cc2)cc1)C(=O)OC(C)(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e0ced95fa914006b48b49eb33157ff9 | COC(=O)C(CS)NC(=O)OC(C)(C)C.O=[N+]([O-])c1ccc(CBr)cc1>>COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C | BrCC1=CC=C(C=C1)[N+](=O)[O-].C([O-])([O-])=O.[Cs+].[Cs+].COC(C(CS)NC(=O)OC(C)(C)C)=O.C(C)(=O)OCC>>COC([C@H](CSCC1=CC=C(C=C1)N)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][SH:7])[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([CH2:8]Br)[cH:15][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1)[NH:16][C:17](=[O:18])[O:19][C:20]([CH... | COC(=O)C(CS)NC(=O)OC(C)(C)C.O=[N+]([O-])c1ccc(CBr)cc1 | COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C | null | null | CCCCCCC.CN(C)C=O | Functional Group Interconversion | OtherReaction | 553deca63c3a8c4d19c0ad505165c3556b3a45eedc28fd1d37d79d0ef5f89b4b | e4ebb23b210d1b6420aef2681cd46eddaa6b419e415077c98e81572b75a5dacb | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]:[c:8]:1.[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]-[C:13]-[SH;D1;+0:14]>>[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]-[C:13]-[S;H0;D2;+0:14]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7]:[c:8]:1 | null | [] | null | null | null | null | A mixture of 1-bromomethyl-4-nitro-benzene (2.15 g, 9.95 mmol), cesium carbonate (6.49 g, 19.9 mmol) and 2-tert-butoxycarbonylamino-3-mercapto-propionic acid methyl ester (2.46 g, 10.5 mmol) in DMF (25 mL) was stirred at room temperature. Upon completion of the reaction (TLC control: 30% ethyl acetate in heptane), the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitro group.Aliphatic thiol | Primary amine.Monosulfide | null | null | c1ccccc1 | Br- | CCCCCCC.CN(C)C=O | null | null | COC(=O)C(CS)NC(=O)OC(C)(C)C.O=[N+]([O-])c1ccc(CBr)cc1>CCCCCCC.CN(C)C=O>COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1c8218e96c0429f89ef8054ddc0d591 | COC(=O)[C@H](CSCc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C>>COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C | COC([C@H](CSCC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C)=O.[Sn](Cl)Cl>>COC([C@H](CSCC1=CC=C(C=C1)N)NC(=O)OC(C)(C)C)=O | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([CH2:8][S:7][CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:15][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][S:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1)[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:... | COC(=O)[C@H](CSCc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C | COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C | null | null | ClCCl.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 | [] | 50 | CELSIUS | null | null | A mixture of (2R)-methyl-2-tert-butoxycarbonylamino-3-(4-nitro-benzylsulfanyl)-propionate (3.75 g, 10.1 mmol) and tin (II) chloride (5.76 g, 30.0 mmol) in methanol (50 mL) was stirred at 50° C. Upon completion (TLC: 5% methanol in dichloromethane), the mixture was cooled to room temperature, quenched with saturated pot... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | ClCCl.CO | 50 | null | COC(=O)[C@H](CSCc1ccc([N+](=O)[O-])cc1)NC(=O)OC(C)(C)C>ClCCl.CO>COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9bc9c368d9240b2aab2a92d59f507ce | CCOC(=O)Cn1ccc2ccccc21>>O=C(O)Cn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.[H-].[Na+].Cl.C(C)OC(CN1C=CC2=CC=CC=C12)=O.[OH-].[Na+].C(C)OC(CBr)=O>>N1(C=CC2=CC=CC=C12)CC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]([OH:3])[CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | CCOC(=O)Cn1ccc2ccccc21 | O=C(O)Cn1ccc2ccccc21 | null | null | ClCCl.CO.CN(C)C=O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2[nH]ccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 70 | CELSIUS | null | null | 1H-indole (5.0 g, 42.7 mmol) in anhydrous DMF (10 mL) was added to a suspension of sodium hydride (1.13 g, 46.9 mmol) in anhydrous DMF (20 mL) in a flame dried flask at 0° C. stirred under nitrogen atmosphere. Fifteen minutes after gas evolution had ceased, bromo-acetic acid ethyl ester (5.7 mL, 51.2 mmol) was added an... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]ccc2c1 | Other | ClCCl.CO.CN(C)C=O.C1CCOC1 | 70 | null | CCOC(=O)Cn1ccc2ccccc21>ClCCl.CO.CN(C)C=O.C1CCOC1>O=C(O)Cn1ccc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccde56c91db340b7b0fea8969f019ce6 | COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C.O=C(O)Cn1ccc2ccccc21>>CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3ccccc32)cc1)C(=O)O | [OH-].[Na+].Cl.COC([C@H](CSCC1=CC=C(C=C1)NC(CN1C=CC2=CC=CC=C12)=O)NC(=O)OC(C)(C)C)=O.N1(C=CC2=CC=CC=C12)CC(=O)O.COC([C@H](CSCC1=CC=C(C=C1)N)NC(=O)OC(C)(C)C)=O.C(CCl)Cl.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CSCC1=CC=C(C=C1)NC(CN1C=CC2=CC=CC=C12)=O | C[O:34][C:32]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][S:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[cH:30][cH:31]1)=[O:33].O[C:18](=[O:19])[CH2:20][n:21]1[cH:22][cH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:1... | COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C.O=C(O)Cn1ccc2ccccc21 | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3ccccc32)cc1)C(=O)O | null | CN(C)C=1C=CN=CC1 | C(C)(=O)OCC.CCCCCCC.CO.C(Cl)Cl.ClCCl.C1CCOC1 | Acylation | OtherReaction | 2f4be8b14ede2d52c920d439e5f741d97aa4249f4c57807152c62994aca84307 | 87a69d5ad38be49e96448ab38c6e7071a2232ada5542b6b62a2f1e1b1e6e076f | O=C(Cn1ccc2ccccc21)Nc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[C:11]-[#7;a:12]>>[#7;a:12]-[C:11]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of indol-1-yl-acetic acid (1.25 g, 7.14 mmol), (2R)-3-(4-amino-benzylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (2.67 g, 7.85 mmol), EDC (1.71 g, 8.93 mmol), triethylamine (2.48 mL, 17.85 mmol) and DMAP (87 mg, 0.714 mmol) in DCM (50 mL) was stirred at ambient temperature. Upon completi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | HO- | CN(C)C=1C=CN=CC1.C(C)(=O)OCC.CCCCCCC.CO.C(Cl)Cl.ClCCl.C1CCOC1 | null | null | COC(=O)[C@H](CSCc1ccc(N)cc1)NC(=O)OC(C)(C)C.O=C(O)Cn1ccc2ccccc21>CN(C)C=1C=CN=CC1.C(C)(=O)OCC.CCCCCCC.CO.C(Cl)Cl.ClCCl.C1CCOC1>CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3ccccc32)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5ab36560acc4cb5812d92c3f885bfc0 | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O>>CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O | CO.C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CSCC1=CC=C(C=C1)NC(CN1C=CC2=CC(=CC=C12)F)=O.B1(OO1)[O-].O.O.O.O.[Na+]>>C(C)(C)(C)OC(=O)N[C@H](C(=O)O)CS(=O)CC1=CC=C(C=C1)NC(CN1C=CC2=CC(=CC=C12)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][S:11][CH2:13][c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[CH2:21][n:22]2[cH:23][cH:24][c:25]3[cH:26][c:27]([F:28])[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[C:34](=[O:35])[OH:36]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]([C... | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O | CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O | null | null | ClCCl.C(C)(=O)O.C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=C(Cn1ccc2ccccc21)Nc1ccccc1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-[C:7]-[c:8]>>[O;D1;H0:9]=[S;H0;D3;+0:6](-[C:5]-[C:4]-[C:2](=[O;D1;H0:1])-[O;D1;H1:3])-[C:7]-[c:8] | null | [] | null | null | null | null | To a stirred solution of (2R)-2-tert-butoxycarbonylamino-3-{4-[2-(5-fluoro-indol-1-yl)-acetylamino]-benzylsulfanyl}-propionic acid (460 mg, 0.917 mmol) in acetic acid (20 mL) was added sodium perborate tetrahydrate (148 mg, 0.963 mmol). This solution was stirred at 40° C. until complete (TLC: 20% methanol in dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1ccc2[nH]ccc2c1 | null | ClCCl.C(C)(=O)O.C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N[C@@H](CSCc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O>ClCCl.C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@@H](CS(=O)Cc1ccc(NC(=O)Cn2ccc3cc(F)ccc32)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58f58401393a45d59b85a43a7bd85fc0 | CCCCc1cc2ccccc2o1.O=C(Cl)c1ccc(Br)cc1>>CCCCc1oc2ccccc2c1C(=O)c1ccc(Br)cc1 | C(CCC)C=1OC2=C(C1)C=CC=C2.BrC1=CC=C(C(=O)Cl)C=C1.[Al+3].[Cl-].[Cl-].[Cl-]>>BrC1=CC=C(C=C1)C(=O)C1=C(OC2=C1C=CC=C2)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[o:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1.Cl[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[o:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1 | CCCCc1cc2ccccc2o1.O=C(Cl)c1ccc(Br)cc1 | CCCCc1oc2ccccc2c1C(=O)c1ccc(Br)cc1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | b92ea6a688e6ba35d387a21fbedc1e5690fb4da234146ba469a67b2fc1ec6714 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1coc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[c:7]1:[#8;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[cH;D2;+0:13]:1>>[C:6]-[c:7]1:[#8;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 36 | [{"value": 36.0, "product": "BrC1=CC=C(C=C1)C(=O)C1=C(OC2=C1C=CC=C2)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.8, "product": "BrC1=CC=C(C=C1)C(=O)C1=C(OC2=C1C=CC=C2)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 2-n-butylbenzofurane (19.8 g, 114 mmol) and 4-bromobenzoyl chloride (25.0 g, 114 mmol) in dry dichloromethane (300 mL, 0.4 M) was cooled to 0° C. and treated with AlCl3 (16.6 g, 1.1 equiv., 125.4 mmol) in 3 portions. After the additions were complete, the solution was stirred for 3 h and carefully added t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1 | HCl | ClCCl | null | 3 | CCCCc1cc2ccccc2o1.O=C(Cl)c1ccc(Br)cc1>ClCCl>CCCCc1oc2ccccc2c1C(=O)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4268f2ef6eb48fa95d250d115fed018 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c([N+](=O)[O-])c2)cc1>>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1 | C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)[N+](=O)[O-])C=CC=C2>>C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)N)C=CC=C2 | O=[N+:34]([O-])[c:33]1[c:22]([O:23][CH2:24][CH2:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:21][cH:20][c:19](-[c:18]2[cH:17][cH:16][c:15]([CH2:14][c:13]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[o:6][c:7]4[cH:8][cH:9][cH:10][cH:11][c:12]43)[cH:37][cH:36]2)[cH:35]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[o:6][c:7]2... | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c([N+](=O)[O-])c2)cc1 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1 | null | [Fe] | C(C)(=O)O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCCOc2ccc(-c3ccc(Cc4coc5ccccc45)cc3)cc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 29 | [{"value": 29.0, "product": "C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)N)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.2, "product": "C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)N)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 2-butyl-3-[3′-nitro-4′-(3-phenyl-propoxy)-biphenyl-4-ylmethyl]-benzofuran (53 mg, 0.105 mmol) in ethanol (1 mL) and acetic acid (1 mL) was treated with Fe (26.4 mg, 4.5 equiv., 0.472 mmol) and heated to 120° C. for 3 h. After cooling to room temperature, the solution was poured into a 20% aq NaOH/ice wate... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2occc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Fe].C(C)(=O)O.C(C)O | 120 | null | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c([N+](=O)[O-])c2)cc1>[Fe].C(C)(=O)O.C(C)O>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08c148bcbf344169864e17a15718c071 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1.CCOC(=O)C(=O)Cl>>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1 | C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)N)C=CC=C2.C(C)(C)N(CC)C(C)C.ClC(C(=O)OCC)=O>>C(C)OC(C(=O)NC=1C=C(C=CC1OCCCC1=CC=CC=C1)C1=CC=C(C=C1)CC1=C(OC2=C1C=CC=C2)CCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[o:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1[CH2:14][c:15]1[cH:16][cH:17][c:18](-[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][CH2:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[c:33]([NH2:34])[cH:42]2)[cH:43][cH:44]1.Cl[C:35](=[O:36])[C:37](=[O:38])[O:39][CH2:40][CH3:41]>... | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1.CCOC(=O)C(=O)Cl | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1 | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | a0f509c51b80cfca9aa6355468af6f3d901b4a3653602f32ee5994157ced49f8 | 41a2c91a94881e86389ce33bb44cfd1f3b3dc1b8c84cd64ddc8a356ca8fd86c3 | c1ccc(CCCOc2ccc(-c3ccc(Cc4coc5ccccc45)cc3)cc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 77.1 | [{"value": 77.0, "product": "C(C)OC(C(=O)NC=1C=C(C=CC1OCCCC1=CC=CC=C1)C1=CC=C(C=C1)CC1=C(OC2=C1C=CC=C2)CCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "C(C)OC(C(=O)NC=1C=C(C=CC1OCCCC1=CC=CC=C1)C1=CC=C(C=C1)CC1=C(OC2=C1C=CC=C2)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 2 | HOUR | A solution of 4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-ylamine (129 mg, 0.264 mmol) and diisopropylethylamine (0.115 mL, 2.5 equiv., 0.66 mmol) in dichloromethane (5 mL) was treated with a solution of ethyl chlorooxoacetate (44 mg, 1.2 equiv., 0.317 mmol) in dichloromethane (1 mL). After stirr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Ester.Secondary amide | null | null | c1ccc2occc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl.O | null | 2 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(N)c2)cc1.CCOC(=O)C(=O)Cl>ClCCl.O>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66a338ee4d88413c8f774dee44584a97 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1>>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)O)c2)cc1 | Cl.C(C)OC(C(=O)NC=1C=C(C=CC1OCCCC1=CC=CC=C1)C1=CC=C(C=C1)CC1=C(OC2=C1C=CC=C2)CCCC)=O.[OH-].[Na+]>>C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)NC(C(=O)O)=O)C=CC=C2 | CC[O:39][C:37]([C:35]([NH:34][c:33]1[c:22]([O:23][CH2:24][CH2:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:21][cH:20][c:19](-[c:18]2[cH:17][cH:16][c:15]([CH2:14][c:13]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[o:6][c:7]4[cH:8][cH:9][cH:10][cH:11][c:12]43)[cH:42][cH:41]2)[cH:40]1)=[O:36])=[O:38]>>[CH3:1][CH2:2][... | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1 | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)O)c2)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCCOc2ccc(-c3ccc(Cc4coc5ccccc45)cc3)cc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[c:7]>>[O;D1;H0:5]=[C:4](-[#7:6]-[c:7])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 28 | [{"value": 28.0, "product": "C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)NC(C(=O)O)=O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.9, "product": "C(CCC)C=1OC2=C(C1CC1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC1=CC=CC=C1)NC(C(=O)O)=O)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | null | null | A solution of N-[4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid ethyl ester (120 mg, 0.204 mmol) in ethanol (3 mL) was treated with aq 1 N NaOH (0.3 mL, 1.5 equiv., 0.306 mmol) and stirred at room temperature. After stirring 1 h, the solution was acidified to pH<4 with 10% HCl, con... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2occc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)O | null | null | CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)OCC)c2)cc1>C(C)O>CCCCc1oc2ccccc2c1Cc1ccc(-c2ccc(OCCCc3ccccc3)c(NC(=O)C(=O)O)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-101023113fe040809a5c82f0e36ff349 | C[Si](C)(C)c1ccc(Br)cc1.OB(O)c1cccc2c1oc1ccccc12>>C[Si](C)(C)c1ccc(-c2cccc3c2oc2ccccc23)cc1 | C1=CC=C(C=2OC3=C(C21)C=CC=C3)B(O)O.BrC1=CC=C(C=C1)[Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+]>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)[Si](C)(C)C | Br[c:8]1[cH:7][cH:6][c:5]([Si:2]([CH3:1])([CH3:3])[CH3:4])[cH:23][cH:22]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[o:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]21>>[CH3:1][Si:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[c:14]2[o:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]32)[c... | C[Si](C)(C)c1ccc(Br)cc1.OB(O)c1cccc2c1oc1ccccc12 | C[Si](C)(C)c1ccc(-c2cccc3c2oc2ccccc23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | a34fd3f8e97b635d120df300575865eab1505627afd99c75ec2034d5929796bd | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2oc2ccccc23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#8;a:11]:[c:12]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9](:[c:10]):[#8;a:11]:[c:12] | 96.8 | [{"value": 96.0, "product": "C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of dibenzofuran-4-yl-boronic acid (20.0 g, 94.3 mmol), (4-bromo-phenyl)-trimethyl-silane (21.62 g, 94.3 mmol), K2CO3 (39.1 g, 3 equiv., 283 mmol) in toluene (100 mL), ethanol (60 mL) and water (30 mL) was purged with nitrogen for 5 min (bubbled into solution) and treated with Pd(PPh3)4 (3.59 g, 2.9 mmol). Af... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)O | 80 | null | C[Si](C)(C)c1ccc(Br)cc1.OB(O)c1cccc2c1oc1ccccc12>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)O>C[Si](C)(C)c1ccc(-c2cccc3c2oc2ccccc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4a20bd2579a469cb008df46655d2422 | CC(C)(C)OC(=O)NC(Cc1ccc(I)cc1)C(=O)O.CI>>COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C | IC.C(C)(C)(C)OC(=O)NC(C(=O)O)CC1=CC=C(C=C1)I.C(=O)([O-])[O-].[K+].[K+]>>COC(C(CC1=CC=C(C=C1)I)NC(=O)OC(C)(C)C)=O | [OH:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].I[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([I:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21] | CC(C)(C)OC(=O)NC(Cc1ccc(I)cc1)C(=O)O.CI | COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 110.7 | [{"value": 98.0, "product": "COC(C(CC1=CC=C(C=C1)I)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.7, "product": "COC(C(CC1=CC=C(C=C1)I)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A solution of 2-tert-butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid (5.0 g, 12.8 mmol) in DMF (50 mL) was treated with K2CO3 (2.2 g, 15.4 mmol). After stirring for 15 min, the solution was cooled to 0° C. and treated with iodomethane (1.0 mL, 15.4 mmol) After the addition was complete, the reaction mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | CN(C)C=O | 0 | 0.25 | CC(C)(C)OC(=O)NC(Cc1ccc(I)cc1)C(=O)O.CI>CN(C)C=O>COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1e6650e50484852b3b264bedba24929 | COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>>COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | COC(C(CC1=CC=C(C=C1)I)NC(=O)OC(C)(C)C)=O.C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>COC(C(CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O | I[c:10]1[cH:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[NH:32][C:33](=[O:34])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[cH:31][cH:30]1.OB(O)[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]3[c:20]2[o:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]32)[cH:28][cH:29]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5](... | COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1 | COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 70.3 | [{"value": 70.0, "product": "COC(C(CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "COC(C(CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | null | null | A solution of 2-tert-Butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid methyl ester (1.22 g, 3 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (0.906 g, 3.15 mmol) and Pd(PPh3)4 (160 mg, 5 mol %) in toluene (25 mL) and ethanol (6.0 mL) was treated with 2 M K2CO3 (4.5 mL). The reaction mixture was heated to reflux for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | null | null | COC(=O)C(Cc1ccc(I)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O>COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc3... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1f2ad0e7d754a7eb8022375fb43e47c | COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | COC(C(CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.[OH-].[K+].Cl>>C(C)(C)(C)OC(=O)NC(C(=O)O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | C[O:38][C:36]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][c:23]4[c:24]3[o:25][c:26]3[cH:27][cH:28][cH:29][cH:30][c:31]43)[cH:32][cH:33]2)[cH:34][cH:35]1)=[O:37]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:... | COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | CO.C(C)(=O)OCC.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)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] | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "C(C)(C)(C)OC(=O)NC(C(=O)O)CC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 1 | HOUR | A solution of 2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-yl)-propanoic acid methyl ester (125 mg, 0.24 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | Other | CO.C(C)(=O)OCC.C1CCOC1 | null | 1 | COC(=O)C(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>CO.C(C)(=O)OCC.C1CCOC1>CC(C)(C)OC(=O)NC(Cc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4746e29d97774ab99b4403d390d1b542 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.CS(=O)(=O)Cl>>COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C | Cl.C(C)(C)(C)OC(=O)N[C@@H](CO)C(=O)O.C(C)N(CC)CC.CS(=O)(=O)Cl>>COC(C(CS(=O)(=O)C)NC(=O)OC(C)(C)C)=O | O[CH2:6][C@@H:5]([C:3]([OH:2])=[O:4])[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].Cl[S:7]([CH3:8])(=[O:9])=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][S:7]([CH3:8])(=[O:9])=[O:10])[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.CS(=O)(=O)Cl | COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C | null | null | ClCCl | Acylation | OtherReaction | f340fda5ddb0801f9d294237f8b5aa464e0f39c22881cfcbf8ee50f8e31debc0 | 59e7803dc5747eb096367d38cb340b4bd5044ddb99993781a2b4a889032ab5b2 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C@H;D3;+0:6](-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[C:15](=[O;D1;H0:16])-[OH;D1;+0:17]>>[C;D1;H3:12]-[C:11](-[C;D1;H3:13])(-[C;D1;H3:14])-[#8:10]-[C:8](=[O;D1;H0:9])-[#7:7]-[CH;D3;+0:6](-[CH2;D2;+... | 88.9 | [{"value": 84.0, "product": "COC(C(CS(=O)(=O)C)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "COC(C(CS(=O)(=O)C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of N-tert-butoxycarbonylserine (1.1 g, 5.0 mmol) and triethylamine (0.84 mL, 6.0 mmol) in dichloromethane (50 mL) was cooled to 0° C. and treated with methylsulfonyl chloride (0.44 mL, 5.8 mmol)). After stirring an additional 2 h, the reaction mixture was acidified with 2% HCl (20 mL) and extracted with dich... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Sulfonyl halide | Ester.Sulfone | null | null | null | Other | ClCCl | null | 2 | CC(C)(C)OC(=O)N[C@@H](CO)C(=O)O.CS(=O)(=O)Cl>ClCCl>COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f470bd2d0d19441fb55111aeb427b95d | COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C.Sc1ccc(Br)cc1>>COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C | Cl.COC(C(CS(=O)(=O)C)NC(=O)OC(C)(C)C)=O.BrC1=CC=C(C=C1)S.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC(C(CSC1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O | CS(=O)(=O)[CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22].[SH:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1)[NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[C... | COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C.Sc1ccc(Br)cc1 | COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4192b8e9846f9aa599819ba0483e36bc07a5d02e0fa0c81cf986e2b744c178e4 | f2e0bb31edbeb92a7317d787d4b892418ccdf9fe3a4c00c7fbe8e3075b7e8833 | c1ccccc1 | C-S(=O)(=O)-[CH2;D2;+0:1]-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14].[SH;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[C:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;... | 76 | [{"value": 76.0, "product": "COC(C(CSC1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.0, "product": "COC(C(CSC1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Solution of 2-tert-Butoxycarbonylamino-3-methylsulfonylpropanoic acid methyl ester (0.86 g, 2.89 mmol) and 4-bromobenzenthiol (0.56 g, 2.89 mmol) in DMF (10 mL) was cooled to at 0° C. and treated with Cs2CO3 (1.1 g, 3.2 mmol). After stirring at room temperature for 2 h, the reaction was acidified with 5% HCl (15 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Sulfone | Monosulfide | null | null | c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 2 | COC(=O)C(CS(C)(=O)=O)NC(=O)OC(C)(C)C.Sc1ccc(Br)cc1>CN(C)C=O.C(C)(=O)OCC>COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea35a83fce73409183c02a33f4f806f0 | COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>>COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | COC(C(CSC1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O.C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>COC(C(CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O | Br[c:11]1[cH:10][cH:9][c:8]([S:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[NH:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[cH:32][cH:31]1.OB(O)[c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]3[c:21]2[o:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]32)[cH:29][cH:30]1>>[CH3:1][O:2][C:3](=[O:4])... | COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1 | COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 72 | [{"value": 72.0, "product": "COC(C(CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "COC(C(CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | A solution of 2-tert-Butoxycarbonylamino-3-(4-bromophenylsulfanyl)-propanoic acid methyl ester (0.55 g, 1.41 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (0.44 g, 1.52 mmol) and Pd(PPh3)4 (0.073 g, 5 mol %) in toluene (15 mL) and ethanol (3.0 mL) was treated with 2 M K2CO3 (2.2 mL). The reaction mixture was heated to... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | null | null | COC(=O)C(CSc1ccc(Br)cc1)NC(=O)OC(C)(C)C.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O>COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccc... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-435cf321ee11435b869150c33a1c4555 | COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | COC(C(CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OC(C)(C)C)=O.[OH-].[K+].Cl>>C(C)(C)(C)OC(=O)NC(C(=O)O)CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1 | C[O:39][C:37]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][S:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]4[c:25]3[o:26][c:27]3[cH:28][cH:29][cH:30][cH:31][c:32]43)[cH:33][cH:34]2)[cH:35][cH:36]1)=[O:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6... | COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O | null | null | CO.C(C)(=O)OCC.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)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] | 75.5 | [{"value": 75.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)O)CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.5, "product": "C(C)(C)(C)OC(=O)NC(C(=O)O)CSC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 1 | HOUR | A solution of 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester (0.150 g, 0.27 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | Other | CO.C(C)(=O)OCC.C1CCOC1 | null | 1 | COC(=O)C(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)NC(=O)OC(C)(C)C>CO.C(C)(=O)OCC.C1CCOC1>CC(C)(C)OC(=O)NC(CSc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9aa82c76c054259a0a3ebc54c17fbf5 | COC(=O)C(NC(=O)OC(C)(C)C)C(C)(C)SCc1ccc(Br)cc1.Cc1ccccc1.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>>CCCCOC(=O)NC(C(=O)OC)C(C)(C)SCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | COC(C(C(C)(C)SCC1=CC=C(C=C1)Br)NC(=O)OC(C)(C)C)=O.C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(C=C3)B(O)O.C(=O)([O-])[O-].[K+].[K+].C1(=CC=CC=C1)C>>COC(C(C(C)(C)SCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OCCCC)=O | C[C:4](C)([CH3:3])[O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:11])[O:12][CH3:13])[C:14]([CH3:15])([CH3:16])[S:17][CH2:18][c:19]1[cH:20][cH:21][c:22](Br)[cH:42][cH:43]1.Cc1ccc[cH:2][cH:1]1.OB(O)[c:23]1[cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][cH:30][c:31]3[c:32]2[o:33][c:34]2[cH:35][cH:36][cH:37][cH:38][c:39]32)[cH:40][... | COC(=O)C(NC(=O)OC(C)(C)C)C(C)(C)SCc1ccc(Br)cc1.Cc1ccccc1.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1 | CCCCOC(=O)NC(C(=O)OC)C(C)(C)SCc1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)(=O)OCC.C(C)O | C-C Coupling | OtherReaction | 5e550543c7c565dfa80df90145ddb8fa53a35e733978f9e0c5f360f8b3b8f5e3 | 9fc696656adfb7f4ae6a873f93ff0ac2e287a4da8334f055d43ea90269917e79 | c1ccc(-c2ccc(-c3cccc4c3oc3ccccc34)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[C;H0;D4;+0:6](-C)(-[CH3;D1;+0:7])-[#8:8]-[C:9](-[#7:10])=[O;D1;H0:11].C-c1:[cH;D2;+0:12]:[cH;D2;+0:13]:c:c:c:1.O-B(-O)-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[#7:10]-[C:9](=[O;D1;H0:11])-[#8:8]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:13]-[CH3;D1;+0:12].[c:3]:[c:2]:[... | 72 | [{"value": 72.0, "product": "COC(C(C(C)(C)SCC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC2=C1OC1=C2C=CC=C1)NC(=O)OCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-tert-butoxycarbonylamino-3-(4-bromophenylmethylsulfanyl)-3,3-dimethylpropanoic acid methyl ester (0.432 g, 1 mmol), 4-(4-dibenzofuranyl)benzeneboronic acid (0.305 g, 1.05 mmol) and Pd(PPh3)4 (0.052 g, 5 mol %) in toluene (10 mL) and ethanol (3.0 mL) was treated with 2 M K2CO3 (1.5 mL). The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Boronic acid.Boc | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C(C)O | null | null | COC(=O)C(NC(=O)OC(C)(C)C)C(C)(C)SCc1ccc(Br)cc1.Cc1ccccc1.OB(O)c1ccc(-c2cccc3c2oc2ccccc23)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C(C)O>CCCCOC(=O)NC(C(=O)OC)C(C)(C)SCc1ccc(-c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cedbaf4b2594034ab946f7c953de0a0 | Brc1cccc(I)c1.OB(O)c1cccc2c1oc1ccccc12>>Brc1cccc(-c2cccc3c2oc2ccccc23)c1 | C1=CC=C(C=2OC3=C(C21)C=CC=C3)B(O)O.BrC1=CC(=CC=C1)I.C(=O)([O-])[O-].[Na+].[Na+]>>BrC=1C=C(C=CC1)C1=CC=CC2=C1OC1=C2C=CC=C1 | I[c:6]1[cH:5][cH:4][cH:3][c:2]([Br:1])[cH:20]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[o:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]21>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[o:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]32)[cH:20]1 | Brc1cccc(I)c1.OB(O)c1cccc2c1oc1ccccc12 | Brc1cccc(-c2cccc3c2oc2ccccc23)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 | O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | a34fd3f8e97b635d120df300575865eab1505627afd99c75ec2034d5929796bd | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3c2oc2ccccc23)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[#8;a:11]:[c:12]>>[c:10]:[c:9](:[#8;a:11]:[c:12]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | null | [] | 80 | CELSIUS | null | null | A mixture of 4-dibenzofuranboronic acid (51 mmol), 1-Bromo-3-iodo-benzene (51 mmol), and Pd(PPh3)4, (4 mmol) in 250 mL of toluene and 150 mL of ethanol was heated to obtain a clear solution, then Na2CO3 (155 mmol) in 250 mL water was added. The reaction mixture refluxed for 4 h at 80° C. The mixture was cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | 80 | null | Brc1cccc(I)c1.OB(O)c1cccc2c1oc1ccccc12>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O>Brc1cccc(-c2cccc3c2oc2ccccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-601a9a85a17547e6be9054fa64ff6c66 | Brc1cccc(-c2cccc3c2oc2ccccc23)c1.OB(O)c1ccc(O)cc1>>Oc1ccc(-c2cccc(-c3cccc4c3oc3ccccc34)c2)cc1 | Cl.C(=O)([O-])[O-].[Na+].[Na+].BrC=1C=C(C=CC1)C1=CC=CC2=C1OC1=C2C=CC=C1.OC1=CC=C(C=C1)B(O)O>>C1=CC=C(C=2OC3=C(C21)C=CC=C3)C=3C=C(C=CC3)C3=CC=C(C=C3)O | Br[c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]2[o:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]32)[cH:24]1.OB(O)[c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:26][cH:25]1>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[o:17][c:18]3[cH:19][cH:20]... | Brc1cccc(-c2cccc3c2oc2ccccc23)c1.OB(O)c1ccc(O)cc1 | Oc1ccc(-c2cccc(-c3cccc4c3oc3ccccc34)c2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(-c3cccc4c3oc3ccccc34)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | A mixture of 4-(3-bromo-phenyl)-dibenzofuran (0.62 mmol), 4-hydroxyphenyl boronic acid (0.62 mmol), and Pd(PPh3)4, (0.05 mmol) in 2 mL of toluene and 1 mL ethanol was heated to obtain a clear solution, then Na2CO3 (1.9 mmol) in 2 mL water was added. The reaction mixture refluxed for 5 h at 80° C. The mixture was cooled... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)oc1ccccc12 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O | 80 | null | Brc1cccc(-c2cccc3c2oc2ccccc23)c1.OB(O)c1ccc(O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C1(=CC=CC=C1)C.C(C)(=O)OCC.C(C)O>Oc1ccc(-c2cccc(-c3cccc4c3oc3ccccc34)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2cd2207d0084987a974d1c5932b137e | BrCc1cccc(Br)c1.FC(F)(F)c1ccc2c(c1)NCCC2>>FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2 | BrC1=CC(=CC=C1)CBr.FC(C1=CC=C2CCCNC2=C1)(F)F.C(C)(=O)[O-].[Na+]>>BrC=1C=C(CN2CCCC3=CC=C(C=C23)C(F)(F)F)C=CC1 | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]1.[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[NH:11][CH2:20][CH2:21][CH2:22]2>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[N:11]([CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]1)[CH2:20][CH2:21][CH2:22]2 | BrCc1cccc(Br)c1.FC(F)(F)c1ccc2c(c1)NCCC2 | FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 219d202b93cb5a235df7e6646f3b9409e60d3c325f1ec37d9b75eb0c3554d20f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCCc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:8](:[c:9]):[c:10] | 82 | [{"value": 82.0, "product": "BrC=1C=C(CN2CCCC3=CC=C(C=C23)C(F)(F)F)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "BrC=1C=C(CN2CCCC3=CC=C(C=C23)C(F)(F)F)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | Under a nitrogen atmosphere, a solution of bromo-3-bromomethyl-benzene (3.47 g, 13.p mmol) and 7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (2.93 g, 14.6 mmol) in ethanol (15 mL, 1 M) was treated with sodium acetate (5.69 g, 69.3 mmol) and heated to 80° C. After stirring 2 h, the solution was cooled to room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr | O.C(C)O | 80 | 2 | BrCc1cccc(Br)c1.FC(F)(F)c1ccc2c(c1)NCCC2>O.C(C)O>FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a49809f6e49547d4830ecc1868c240e0 | FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2.OCc1ccc(B(O)O)cc1>>OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1 | BrC=1C=C(CN2CCCC3=CC=C(C=C23)C(F)(F)F)C=CC1.OCC1=CC=C(C=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>FC(C1=CC=C2CCCN(C2=C1)CC=1C=C(C=CC1)C1=CC=C(C=C1)CO)(F)F | Br[c:7]1[cH:8][cH:9][cH:10][c:11]([CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][c:26]32)[cH:27]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:29][cH:28]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH2:12][N:13]3[CH2:14][CH2:15][CH2... | FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2.OCc1ccc(B(O)O)cc1 | OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1 | null | null | C1(=CC=CC=C1)C.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc(CN3CCCc4ccccc43)c2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | Under a nitrogen atmosphere, a solution of 1-(3-bromo-benzyl)-7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (2.36 g, 6.37 mmol), 4-(hydroxymethyl)phenyl boronic acid (1.07 g, 7.01 mmol), and 2 M Na2CO3 (7 mL, 12.7 mmol) in 16 mL of toluene and 4 mL ethanol (0.3 M) was treated with tetrakistriphenylphosphine palladium ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HBr.B | C1(=CC=CC=C1)C.C(C)O | 80 | null | FC(F)(F)c1ccc2c(c1)N(Cc1cccc(Br)c1)CCC2.OCc1ccc(B(O)O)cc1>C1(=CC=CC=C1)C.C(C)O>OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-167f9e071d6e41f2b5c42031809a40b8 | COC(=O)C(CS)NC(=O)OC(C)(C)C.OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1>>COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C | FC(C1=CC=C2CCCN(C2=C1)CC=1C=C(C=CC1)C1=CC=C(C=C1)CO)(F)F.COC(C(CS)NC(=O)OC(C)(C)C)=O.N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.N1C=NC=C1.CP(C)C>>COC(C(CSCC1=CC=C(C=C1)C1=CC(=CC=C1)CN1CCCC2=CC=C(C=C12)C(F)(F)F)NC(=O)OC(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][SH:7])[NH:36][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43].O[CH2:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][c:17]([CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][c:23]4[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][c:32]43)[cH:33]2)[cH:34][cH:35]1>>[C... | COC(=O)C(CS)NC(=O)OC(C)(C)C.OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1 | COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C | null | null | ClCCl.CCCCCCC | Heteroatom Alkylation and Arylation | OtherReaction | 94a14d3014f7fdb5c4fa6f9f37d523bd85860ea21497647c55ba9393bbc36835 | f8355ba7e68f7d5b10019904f32df628ca7b7bc14adae6579e7d0de9afb40579 | c1ccc(-c2cccc(CN3CCCc4ccccc43)c2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[SH;D1;+0:10]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | Under a nitrogen atmosphere, a solution of [3′-(7-trifluoromethyl-3,4-dihydro-2H-quinolin-1-ylmethyl)-biphenyl-4-yl]-methanol (0.257 g, 0.65 mmol), 2-tert-butoxycarbonylamino-3-mercapto-propionic acid methyl ester (0.304 g, 1.29 mmol), 1,1′-(azodicarbonyl)dipiperidine (0.343 g, 1.36 mmol), and imidazole (0.92 g, 1.36 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | HO- | ClCCl.CCCCCCC | null | 1 | COC(=O)C(CS)NC(=O)OC(C)(C)C.OCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1>ClCCl.CCCCCCC>COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a561daa93bc41678b94a936453b3b2f | COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NC(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)C(=O)O | COC(C(CSCC1=CC=C(C=C1)C1=CC(=CC=C1)CN1CCCC2=CC=C(C=C12)C(F)(F)F)NC(=O)OC(C)(C)C)=O.[OH-].[Na+].Cl>>C(C)(C)(C)OC(=O)NC(C(=O)O)CSCC1=CC=C(C=C1)C1=CC(=CC=C1)CN1CCCC2=CC=C(C=C12)C(F)(F)F | C[O:42][C:40]([CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][S:11][CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]([CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][c:27]4[cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35][c:36]43)[cH:37]2)[cH:38][cH:39]1)=[O:41]>>[CH3:1][C:2]... | COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NC(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)C(=O)O | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cccc(CN3CCCc4ccccc43)c2)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 | 3 | HOUR | Under a nitrogen atmosphere, a solution of 2-tert-butoxycarbonylamino-3-[3′-(7-trifluoromethyl-3,4-dihydro-2H-quinolin-1-ylmethyl)-biphenyl-4-ylmethylsulfanyl]-propionic acid methyl ester (0.173 g, 0.281 mmol) in 4 mL of THF and 1 mL of methanol was treated with 2 N NaOH (1.5 mL, 2.81 mmol). After stirring at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCC[NH]2 | Other | CO.C1CCOC1 | null | 3 | COC(=O)C(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)NC(=O)OC(C)(C)C>CO.C1CCOC1>CC(C)(C)OC(=O)NC(CSCc1ccc(-c2cccc(CN3CCCc4ccc(C(F)(F)F)cc43)c2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70823f437a944b05a91f156fe600ec4b | CC(C)(C)OC(=O)NN.O=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>>CC(C)(C)OC(=O)NN=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N1CCC(CC1)=O.N(N)C(=O)OC(C)(C)C>>CC(C)(OC(=O)NN=C1CCN(CC1)C(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9].O=[C:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][CH2:17][CH:18]2[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3-[c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)[CH2:31][CH2:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][N:9]=[C:10]1[CH2:11][CH2:12]... | CC(C)(C)OC(=O)NN.O=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | CC(C)(C)OC(=O)NN=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | c65f0bc70664fcfce830ed71426d33f4ad8e3395c2675dbe7ef04b365fe00b18 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | N=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[NH2;D1;+0:15]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[N;H0;D2;+0:15]=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | A mixture of 16.0 g (0.05 mol) of 1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinone, 7.25 g (0.055 mol) of tert. butyl hydrazinoformate and 250 ml of ethanol was refluxed for 1 hour. The solvent was distilled off in vacuo, the oily residue remaining was triturated with diethylether. The crystalline precipitate thus for... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)Cc1ccccc12 | HO- | C(C)O | null | null | CC(C)(C)OC(=O)NN.O=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>C(C)O>CC(C)(C)OC(=O)NN=C1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c53bb0e510fb4a73be010faee4a6d4a9 | CC(C)(C)OC(=O)NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>>NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | CC(C)(OC(=O)NNC1CCN(CC1)C(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)C.Cl.Cl>>Cl.C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N1CCC(CC1)NN | CC(C)(C)OC(=O)[NH:2][NH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][CH:12]2[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3-[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]32)[CH2:25][CH2:26]1>>[NH2:2][NH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][CH:12]2[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3-[c:19]3[... | CC(C)(C)OC(=O)NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | null | null | FC(C(=O)O)(F)F.C(C)(=O)OCC | Reduction | Reduction of primary amides to amines | 39e11744340ea5c8f4187a9034f8b9800b3b6ccbfd7b2876214303dc07bb979f | 2249bb4c64fe4943bfcef5de0ada6c23bea6dec24992f87f55d0785b30b30b5a | O=C(OCC1c2ccccc2-c2ccccc21)N1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[#7:2]-[C:3]>>[C:3]-[#7:2]-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | 21.8 g (0.0498 mol) of N-(1,1-dimethylethoxycarbonyl)-N′-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-hydrazine were dissolved in 100 ml of trifluoroacetic acid and stirred for 1 hour at room temperature. The excess trifluoroacetic acid was removed in vacuo, the residue was dissolved in 50 ml of water and made al... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Ether.Boc | Hydrazine | null | null | C1CC[NH]CC1.c1ccc2c(c1)Cc1ccccc12 | HO- | FC(C(=O)O)(F)F.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>FC(C(=O)O)(F)F.C(C)(=O)OCC>NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcb9f893e85643fa826eef35bcb0e1ab | C1CCOC1.C1CCOC1.NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>>O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1 | O1CCCC1.C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N1CCC(CC1)NN.S.O1CCCC1>>C1(=CC=CC=C1)C=1NC(N(N1)C1CCN(CC1)C(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)=O | [CH2:25]1[CH2:26][CH2:27][O:33][CH2:32]1.O1[CH2:24][CH2:28][CH2:29][CH2:30]1.[O:1]=[C:2]([O:3][CH2:4][CH:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21)[N:18]1[CH2:19][CH2:20][CH:21]([NH:22][NH2:23])[CH2:34][CH2:35]1>>[O:1]=[C:2]([O:3][CH2:4][CH:5]1[c:6]2[cH:7][cH:8][cH:9][cH:10][... | C1CCOC1.C1CCOC1.NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1 | O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 55694136454ea5ff34e514d0cb673e9c4e0c5e49262f03f99def3591d5f64421 | 698ca8f9fc42fbe71c5a41554d6cf45f43ec89e80787604700bb38bda168cae4 | O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[CH2;D2;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-1.[C:10]-[C:11](-[NH;D2;+0:12]-[NH2;D1;+0:13])-[C:14]>>[C:10]-[C:11](-[n;H0;D3;+0:12]1:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:2]:[cH;D2;+0:3]:... | null | [] | null | null | null | null | The solutions of 5.56 g (0.0165 mol) of [1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-hydrazine in 60 ml of tetrahydrofuran and 3.7 g (0.0177 mol) of N-(ethoxycarbonyl)-benzothionamide in 30 ml of tetrahydrofuran were combined and refluxed for 1 hour, whereupon hydrogen sulphide was released. The solvent was disti... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ether.Ether | null | C1CCOC1.C1CCOC1 | c1nc[nH]n1.c1ccccc1 | C1CC[NH]CC1.c1nc[nH]n1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | null | null | null | null | C1CCOC1.C1CCOC1.NNC1CCN(C(=O)OCC2c3ccccc3-c3ccccc32)CC1>>O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ead69204b774477a7b81d6b89c7fb2e | O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1>>COc1cccc(-c2cn(C3CCNCC3)c(=O)[nH]2)c1 | C1(=CC=CC=C1)C=1NC(N(N1)C1CCN(CC1)C(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)=O.O1CCCC1.C(C)NCC>>COC=1C=C(C=CC1)C=1NC(N(C1)C1CCNCC1)=O | O=C(OCC1c2ccccc2-c2ccccc21)[N:14]1[CH2:13][CH2:12][CH:11]([n:10]2n[c:8](-[c:7]3[cH:6][cH:5][cH:4][cH:3][cH:20]3)[nH:19][c:17]2=[O:18])[CH2:16][CH2:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[c:17](=[O:18])[nH:19]2)[cH:20]1 | O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1 | COc1cccc(-c2cn(C3CCNCC3)c(=O)[nH]2)c1 | null | null | CO | Miscellaneous | OtherReaction | 3da7a02878e06cc9f6a906874197bfde22e9ae16c883b5c0220ac17f35368816 | 554d5d10a57a42367e87de6a63897338738b1766c5273ea9d2039a3c5775eef8 | O=c1[nH]c(-c2ccccc2)cn1C1CCNCC1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[n;H0;D3;+0:5]2:n:[c;H0;D3;+0:6](-[c:7]3:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[c:12]:3):[#7;a:13]:[c:14]:2=[O;D1;H0:15])-[C:16]-[C:17]-1>>[C;D1;H3:18]-[#8:19]-[c;H0;D3;+0:9]1:[c:8]:[c:7](-[c;H0;D3;+0:6]2:[#7;a:13]:[c:14](=[O;D1;H0:15]):[n;H0;D3... | null | [] | null | null | 30 | MINUTE | A mixture of 9.0 g (0.0193 mol) of 2,4-dihydro-5-phenyl-2-[1-(9H-fluoren-9-ylmethoxycarbonyl)-4-piperidinyl]-3H-1,2,4-triazol-3-one, 50 ml of tetrahydrofuran and 70 ml of diethylamine was stirred at room temperature until the end of the reaction monitored by thin layer chromatography. The solvent was removed in vacuo, ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Ether.Secondary amine | C1CC[NH]CC1.c1nc[nH]n1.c1ccccc1.c1ccc2c(c1)Cc1ccccc12 | c1ccccc1.c1c[nH]cn1.C1CCNCC1 | c1ccccc1.c1c[nH]cn1.C1CCNCC1 | HO- | CO | null | 0.5 | O=C(OCC1c2ccccc2-c2ccccc21)N1CCC(n2nc(-c3ccccc3)[nH]c2=O)CC1>CO>COc1cccc(-c2cn(C3CCNCC3)c(=O)[nH]2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff6a90c0b5fb4cd7861aa8294d016af9 | CC(C)(C)C(=O)Cl.Nc1ccccn1>>CC(C)(C)C(=O)Nc1ccccn1 | NC1=NC=CC=C1.C(C)N(CC)CC.C(C(C)(C)C)(=O)Cl>>N1=C(C=CC=C1)NC(C(C)(C)C)=O | Cl[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1 | CC(C)(C)C(=O)Cl.Nc1ccccn1 | CC(C)(C)C(=O)Nc1ccccn1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:4]-[C:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11] | null | [] | null | null | 2 | HOUR | To a solution of 94.1 g (1.0 mol) of 2-aminopyridine and 173 ml (1.25 mol) of triethylamine in 400 ml of dichloromethane were added dropwise, whilst cooling with ice water, 132.5 g (1.099 mol) of pivaloyl chloride in 150 ml of dichloromethane. The. mixture was stirred for 2 hours at room temperature and filtered to rem... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1 | HCl | ClCCl | null | 2 | CC(C)(C)C(=O)Cl.Nc1ccccn1>ClCCl>CC(C)(C)C(=O)Nc1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34c5e22bc1414db5be821d960eb43398 | CN(C)C=O.Nc1ncccc1CNC1CCN(Cc2ccccc2)CC1>>O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1 | NC1=NC=CC=C1CNC1CCN(CC1)CC1=CC=CC=C1.CN(C=O)C>>C1(=CC=CC=C1)CN1CCC(CC1)N1C(NC2=C(C1)C=CC=N2)=O | CN(C)[CH:2]=[O:1].[NH2:3][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[O:1]=[C:2]1[NH:3][c:4]2[n:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][N:11]1[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][... | CN(C)C=O.Nc1ncccc1CNC1CCN(Cc2ccccc2)CC1 | O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1 | null | null | null | Acylation | OtherReaction | afaddc71d708dfe1a0eeaab802c260059d19c88180ebdb822fd909e0afa6ced6 | eebab57e6facb6b0e9da3aa098a8e1cdfa27d9611f85f9a72fe0b16b5e461392 | O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[NH;D2;+0:5]-[C:6]-[c:7]:[c:8](-[NH2;D1;+0:9]):[#7;a:10]:[c:11])-[C:12]>>[C:3]-[C:4](-[N;H0;D3;+0:5]1-[C:6]-[c:7]:[c:8](:[#7;a:10]:[c:11])-[NH;D2;+0:9]-[C;H0;D3;+0:1]-1=[O;D1;H0:2])-[C:12] | null | [] | 100 | CELSIUS | null | null | A mixture of 4.2 g (0.0142 mol) of 2-amino-3-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-pyridine, 2.4 g (0.0148 mol) of N,N′-carbonyldiimidazole and 50 ml of dimethylformamide was heated to 100° C. for 30 minutes. The still warm mixture was stirred into 300 ml of ice water, the precipitate formed was suction filte... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Secondary amine | Urea | null | c1cnc2c(c1)C[NH]CN2 | c1cnc2c(c1)C[NH]CN2.C1CC[NH]CC1.c1ccccc1 | Other | null | 100 | null | CN(C)C=O.Nc1ncccc1CNC1CCN(Cc2ccccc2)CC1>>O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-870be06ed5314773b62b576b77a485d7 | O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1>>O=C1Nc2ncccc2CN1C1CCNCC1 | [H][H].C1(=CC=CC=C1)CN1CCC(CC1)N1C(NC2=C(C1)C=CC=N2)=O>>N1CCC(CC1)N1C(NC2=C(C1)C=CC=N2)=O | c1ccc(C[N:15]2[CH2:14][CH2:13][CH:12]([N:11]3[C:2](=[O:1])[NH:3][c:4]4[n:5][cH:6][cH:7][cH:8][c:9]4[CH2:10]3)[CH2:17][CH2:16]2)cc1>>[O:1]=[C:2]1[NH:3][c:4]2[n:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][N:11]1[CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1 | O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1 | O=C1Nc2ncccc2CN1C1CCNCC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1Nc2ncccc2CN1C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 4.7 g (0.0146 mol) of 3,4-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(1H)-pyrido[2,3-d]-pyrimidinone in 50 ml of methanol was hydrogenated at a temperature of 50° C. and in the presence of 2.0 g of 20% palladium/charcoal until the uptake of hydrogen ceased. After removal of the catalyst and solvent 3.3 g... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1cnc2c(c1)C[NH]CN2.C1CCNCC1 | Other | [Pd].CO | null | null | O=C1Nc2ncccc2CN1C1CCN(Cc2ccccc2)CC1>[Pd].CO>O=C1Nc2ncccc2CN1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2c2cf6c7ccf4edbbce9fe82df963a88 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.COC(OC)N(C)C>>COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1 | CC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-].COC(N(C)C)OC>>CN(\C=C\C1=C(C=C(C=C1)C(=O)OC)[N+](=O)[O-])C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1.CO[CH:10](OC)[N:11]([CH3:12])[CH3:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](/[CH:9]=[CH:10]/[N:11]([CH3:12])[CH3:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.COC(OC)N(C)C | COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 83af34be484ee7162f3917cbabe10b671ad3f0d9bc6950031ada8dde2656d2d8 | cd2513a82ead55986b41bf6d9bf4ca65c678444c433e242d0b640f08804ca4c6 | c1ccccc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])/[CH;D2;+0:1]=[CH;D2;+0:5]/[c:6](:[c:7]):[c:8] | null | [] | 140 | CELSIUS | null | null | A mixture of 98.3 g (0.504 mol) of methyl 4-methyl-3-nitrobenzoate, 78.0 g (0.655 mol) of N,N-dimethylformamide dimethylacetal and 1 l of dimethylformamide was heated to 140° C. for 3 hours. The solvent was distilled off in vacuo, the residue was triturated thoroughly with 1 l methanol. After drying in vacuo 119.5 g (9... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Enamine | null | null | c1ccccc1 | HO- | CN(C=O)C | 140 | null | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.COC(OC)N(C)C>CN(C=O)C>COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f43393d6a1145668204b71ffdc0ca52 | COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1.[O-][I+3]([O-])([O-])[O-]>>COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1 | CN(\C=C\C1=C(C=C(C=C1)C(=O)OC)[N+](=O)[O-])C.I(=O)(=O)(=O)[O-].[Na+]>>COC(=O)C1=CC(=C(C=O)C=C1)[N+](=O)[O-] | CN(C)/C=[CH:9]/[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][c:11]1[N+:12](=[O:13])[O-:14].[O-][I+3]([O-])([O-])[O-:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1.[O-][I+3]([O-])([O-])[O-] | COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1 | null | null | O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1bc53144aaaadfebb6804333b37b20e33a34fa620575111a961d81231c604008 | ee34f37ac54cbb3add9bb610747eeab45d01320a19fe84bf63f0866779dc68a8 | c1ccccc1 | C-N(-C)/C=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4].[O-;H0;D1:5]-[I+3](-[O-])(-[O-])-[O-]>>[O;H0;D1;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2.5 | HOUR | To a mixture of 119.5 g (0.478 mol) of (E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]-ethene and 1.3 l of water/tetrahydrofuran mixture (1/1 v/v) were added, in batches, 308.0 g (1.44 mol) of sodium metaperiodate, whilst the reaction temperature was regulated at under +30° C. by external cooling with ice w... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Aldehyde | null | null | c1ccccc1 | HI | O.O1CCCC1 | null | 2.5 | COC(=O)c1ccc(/C=C/N(C)C)c([N+](=O)[O-])c1.[O-][I+3]([O-])([O-])[O-]>O.O1CCCC1>COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4491907cb0f14f1cb199fb1f36d8dd47 | COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1.NC1CCN(Cc2ccccc2)CC1>>COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1 | NC1CCN(CC1)CC1=CC=CC=C1.COC(=O)C1=CC(=C(C=O)C=C1)[N+](=O)[O-].[BH4-].[Na+]>>C1(=CC=CC=C1)CN1CCC(CC1)NCC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-] | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:28][c:24]1[N+:25](=[O:26])[O-:27].[NH2:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:1... | COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1.NC1CCN(Cc2ccccc2)CC1 | COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1 | null | null | CO | Functional Group Addition | Reductive amination with aldehyde | d42fc338dbdae89d3c539bd9d12d3b5ac50c40ef3b87bdc4c4d930c8ee74fb7d | b4dd31b60400cab3abb24376ebe2822f4ce30c85b6d3b9ac994d7e3c5f2bfd96 | c1ccc(CNC2CCN(Cc3ccccc3)CC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | null | [] | null | null | null | null | To a solution of 41.0 g (0.215 mol) of 4-amino-1-(phenylmethyl)-piperidine and 45.0 g (0.215 mol) of 4-(methoxycarbonyl)-2-nitrobenzaldehyde in 1 l methanol were added in batches, at room temperature, 8.3 g (0.22 mol) of sodium borohydride and the mixture was then stirred for 30 minutes at the same temperature. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | CO | null | null | COC(=O)c1ccc(C=O)c([N+](=O)[O-])c1.NC1CCN(Cc2ccccc2)CC1>CO>COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-afcea6d8e8ac4fc7834c61852ba74c2f | COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1>>COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c(N)c1 | C1(=CC=CC=C1)CN1CCC(CC1)NCC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-]>>NC=1C=C(C(=O)OC)C=CC1CNC1CCN(CC1)CC1=CC=CC=C1 | O=[N+:25]([O-])[c:24]1[c:8]([CH2:9][NH:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][cH:18]... | COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1 | COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c(N)c1 | null | [Rh].C | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CNC2CCN(Cc3ccccc3)CC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 58.0 g (0.151 mol) of methyl 4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-3-nitrobenzoate in 800 ml of methanol was hydrogenated in the presence of 10 g of 5% rhodium/charcoal for 7 hours at room temperature. The catalyst was filtered off, the filtrate was evaporated down in vacuo. 50.0 g (93.7% of t... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | [Rh].C.CO | null | null | COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c([N+](=O)[O-])c1>[Rh].C.CO>COC(=O)c1ccc(CNC2CCN(Cc3ccccc3)CC2)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dee884051634d85978fb60409e5c8dd | CCOC(=O)Cl.COC(=O)c1cscc1N>>CCOC(=O)Nc1cscc1C(=O)OC | Cl.NC=1C(=CSC1)C(=O)OC.C(C)N(CC)CC.C(OCC)(=O)Cl>>C(C)OC(=O)NC=1C(=CSC1)C(=O)OC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[cH:8][s:9][cH:10][c:11]1[C:12](=[O:13])[O:14][CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][s:9][cH:10][c:11]1[C:12](=[O:13])[O:14][CH3:15] | CCOC(=O)Cl.COC(=O)c1cscc1N | CCOC(=O)Nc1cscc1C(=O)OC | null | null | C1(=CC=CC=C1)C | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccsc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#16;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#16;a:10]:[c:11]:[c:12]:1-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | null | null | null | null | A mixture of 50.0 g (0.258 mol) of methyl 4-aminothiophen-3-carboxylate-hydrochloride, 700 ml of toluene, 26 g (0.257 mol) of triethylamine and 27 ml (0.283 mol) of ethyl chlorocarbonate was refluxed for 5 hours. The insoluble matter was filtered off, the filtrate was evaporated down in vacuo and the residue was crysta... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccsc1 | HCl | C1(=CC=CC=C1)C | null | null | CCOC(=O)Cl.COC(=O)c1cscc1N>C1(=CC=CC=C1)C>CCOC(=O)Nc1cscc1C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12cfe412697a4cd0af7243a718237d05 | CCOC(=O)Nc1cscc1C(=O)OC>>CCOC(=O)Nc1cscc1C=O | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C)OC(=O)NC=1C(=CSC1)C(=O)OC.O.[OH-].[Na+].O>>C(C)OC(=O)NC=1C(=CSC1)C=O | CO[C:12]([c:11]1[c:7]([NH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:8][s:9][cH:10]1)=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][s:9][cH:10][c:11]1[CH:12]=[O:13] | CCOC(=O)Nc1cscc1C(=O)OC | CCOC(=O)Nc1cscc1C=O | null | null | C(C)(C)(C)OC | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccsc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | 1 | HOUR | Into an ice-cold suspension of 12.9 g (0.34 mol) of lithium aluminium hydride in 800 ml of tert. butyl-methylether was added dropwise, at a reaction temperature of about 0° C., a solution of 59.1 g (0.258 mol) of methyl 4-(ethoxycarbonylamino)-thiophene-3-carboxylate in 200 ml of tert. butyl-methylether, and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccsc1 | HO- | C(C)(C)(C)OC | null | 1 | CCOC(=O)Nc1cscc1C(=O)OC>C(C)(C)(C)OC>CCOC(=O)Nc1cscc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bc2df2cc74f40edba51ff4f322dc1db | CC(C)(C)OC(=O)N1CCC(N)CC1.CCOC(=O)Nc1cscc1C=O>>CCOC(=O)Nc1cscc1CNC1CCN(C(=O)OC(C)(C)C)CC1 | [BH4-].[Na+].C(C)OC(=O)NC=1C(=CSC1)C=O.NC1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)C>>CC(C)(OC(=O)N1CCC(CC1)NCC=1C(=CSC1)NC(=O)OCC)C | [NH2:13][CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1.O=[CH:12][c:11]1[c:7]([NH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:8][s:9][cH:10]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][s:9][cH:10][c:11]1[CH2:12][NH:13][CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O... | CC(C)(C)OC(=O)N1CCC(N)CC1.CCOC(=O)Nc1cscc1C=O | CCOC(=O)Nc1cscc1CNC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1cc(CNC2CCNCC2)cs1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1)-[C:10] | null | [] | null | null | null | null | A mixture of 28.2 g (0.142 mol) of 4-(ethoxycarbonyl-amino)-thiophene-3-carboxaldehyde, 28.2 g (0.141 mol) of 4-amino-1-(1,1-dimethyl-ethoxycarbonyl)piperidine and 300 ml of toluene was refluxed using a water separator until water formation had ceased. The solvent was removed in vacuo, the residue was dissolved in 300 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccsc1.C1CC[NH]CC1 | Other | O | null | null | CC(C)(C)OC(=O)N1CCC(N)CC1.CCOC(=O)Nc1cscc1C=O>O>CCOC(=O)Nc1cscc1CNC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7a875b97ebe4b8d8c79a2571fbe561e | CC(C)(C)OC(=O)N1CCC(N2Cc3cscc3NC2=O)CC1.O=C(O)C(F)(F)F>>O=C([O-])C(F)(F)F.O=C1Nc2cscc2CN1C1CCNCC1 | CC(C)(OC(=O)N1CCC(CC1)N1C(NC=2C(C1)=CSC2)=O)C.FC(C(=O)O)(F)F>>N1CCC(CC1)N1C(NC=2C(C1)=CSC2)=O.FC(C(=O)[O-])(F)F | CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][CH:18]([N:17]2[C:9](=[O:8])[NH:10][c:11]3[cH:12][s:13][cH:14][c:15]3[CH2:16]2)[CH2:23][CH2:22]1.[O:1]=[C:2]([OH:3])[C:4]([F:5])([F:6])[F:7]>>[O:1]=[C:2]([O-:3])[C:4]([F:5])([F:6])[F:7].[O:8]=[C:9]1[NH:10][c:11]2[cH:12][s:13][cH:14][c:15]2[CH2:16][N:17]1[CH:18]1[CH2:19][CH2:20][NH:2... | CC(C)(C)OC(=O)N1CCC(N2Cc3cscc3NC2=O)CC1.O=C(O)C(F)(F)F | O=C([O-])C(F)(F)F.O=C1Nc2cscc2CN1C1CCNCC1 | null | null | null | Miscellaneous | OtherReaction | 682e089fbfc4d16c974a525961e4df91784d114b83c27ef342a0481baecd0ade | 3b21d7a593211fb542228e23c12b5c46779cf3cdc7f54f93350e1b43ee65b9f4 | O=C1Nc2cscc2CN1C1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C:10](-[O-;H0;D1:12])=[O;D1;H0:11] | null | [] | null | null | 30 | MINUTE | A mixture of 10.0 g (0.0296 mol) of 3,4-dihydro-3-[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]-1H-thieno[3,4-d]pyrimidin-2-one and 50 ml of trifluoroacetic acid was stirred at room temperature for 30 minutes. The residue remaining after removal of the excess trifluoroacetic acid was triturated with diethylether and s... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1scc2c1C[NH]CN2.C1CCNCC1 | HO- | null | null | 0.5 | CC(C)(C)OC(=O)N1CCC(N2Cc3cscc3NC2=O)CC1.O=C(O)C(F)(F)F>>O=C([O-])C(F)(F)F.O=C1Nc2cscc2CN1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87cef751482546b88fce41513d644f7c | O=c1[nH]c2ccccc2cc1-c1ccncc1>>O=C1Nc2ccccc2CC1C1CCNCC1 | N1=CC=C(C=C1)C=1C(NC2=CC=CC=C2C1)=O.Cl>>Cl.N1CCC(CC1)C1C(NC2=CC=CC=C2C1)=O | [O:2]=[c:3]1[nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11][c:12]1-[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1>>[O:2]=[C:3]1[NH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][CH:12]1[CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1 | O=c1[nH]c2ccccc2cc1-c1ccncc1 | O=C1Nc2ccccc2CC1C1CCNCC1 | null | [Pt](=O)=O | C(C)O | Reduction | OtherReaction | 338a6fd42b5469849527cb5dc5a3275784c739143a9f5003b69ee45ab7cbf4b8 | 211104e8b119db7b18ca563982f63840af02165e5ca58709899a446d5754a027 | O=C1Nc2ccccc2CC1C1CCNCC1 | [O;D1;H0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](:[c:7])-[CH2;D2;+0:8]-[CH;D3;+0:9]-1-[CH;D3;+0:10]1-[CH2;D2;+0:11]-[... | null | [] | null | null | 4 | HOUR | A mixture of 1.1 g (4.949 mmol) of 3-(4-pyridinyl)-2(1H)-quinolone (D. R. Bragg and D. G. Wibberley, J. Chem. Soc. 1961, 5074-5077), 100 ml of ethanol, 5 ml (5 mmol) of 1N hydrochloric acid and 0.2 g platinum (IV) oxide was hydrogenated for 4 hours at room temperature. The catalyst was filtered off, the filtrate evapor... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amide.Secondary amine | c1cnc2ccccc2c1.c1ccncc1 | c1ccc2c(c1)CCCN2.C1CCNCC1 | c1ccc2c(c1)CCCN2.C1CCNCC1 | null | [Pt](=O)=O.C(C)O | null | 4 | O=c1[nH]c2ccccc2cc1-c1ccncc1>[Pt](=O)=O.C(C)O>O=C1Nc2ccccc2CC1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7ba1bc8ae2e46cf9c66cbd38f66d461 | O=c1[nH]c2ccccc2cc1-c1ccncc1>>O=c1cc(N2CCCCC2)c2ccccc2[nH]1 | N1=CC=C(C=C1)C=1C(NC2=CC=CC=C2C1)=O.Cl.[H][H]>>N1(CCCCC1)C1=CC(NC2=CC=CC=C12)=O | [O:1]=[c:2]1[c:3](-[c:8]2[cH:7][cH:6][n:5][cH:9][cH:10]2)[cH:4][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[nH:17]1>>[O:1]=[c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[nH:17]1 | O=c1[nH]c2ccccc2cc1-c1ccncc1 | O=c1cc(N2CCCCC2)c2ccccc2[nH]1 | null | [Pd] | C(C)O | Miscellaneous | OtherReaction | 83903bfe79e2b2f0bc9f5438967ab0682e7e694b8433de0ac04c44b9bd87cae2 | 4c812c1c920bf53b5923291709d187e223e40a94df3acb57982c9a7523919d2a | O=c1cc(N2CCCCC2)c2ccccc2[nH]1 | [O;D1;H0:1]=[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:[c;H0;D3;+0:9]:1-[c;H0;D3;+0:10]1:[cH;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:1>>[O;D1;H0:1]=[c:2]1:[#7;a:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](-[N;H0;D3;+0:13]2-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:10]-[CH2;D2;... | null | [] | null | null | null | null | A mixture of 8.6 g (0.0387 mol) of 3-(4-pyridinyl)-2(1H)-quinolone, 1.2 l of ethanol, 39 ml (0.039 mol) of 1N hydrochloric acid and 8.0 g of 10% palladium/charcoal was hydrogenated at a temperature of 40° C. until about 0.08 mol of hydrogen had been taken up. The mixture was freed from catalyst, the filtrate was evapor... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccncc1.c1cnc2ccccc2c1 | C1CC[NH]CC1.c1ccc2ccccc2n1 | C1CC[NH]CC1.c1ccc2ccccc2n1 | null | [Pd].C(C)O | null | null | O=c1[nH]c2ccccc2cc1-c1ccncc1>[Pd].C(C)O>O=c1cc(N2CCCCC2)c2ccccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71b9ae1165ef4c35902a8fb64b852509 | O=C1Nc2cccc(Cl)c2CN1C1CCN(Cc2ccccc2)CC1>>O=C1Nc2cccc(Cl)c2CN1C1CCNCC1 | ClC1=C2CN(C(NC2=CC=C1)=O)C1CCN(CC1)CC1=CC=CC=C1.C(OC(C)Cl)(=O)Cl>>ClC1=C2CN(C(NC2=CC=C1)=O)C1CCNCC1 | c1ccc(C[N:16]2[CH2:15][CH2:14][CH:13]([N:12]3[C:2](=[O:1])[NH:3][c:4]4[cH:5][cH:6][cH:7][c:8]([Cl:9])[c:10]4[CH2:11]3)[CH2:18][CH2:17]2)cc1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([Cl:9])[c:10]2[CH2:11][N:12]1[CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1 | O=C1Nc2cccc(Cl)c2CN1C1CCN(Cc2ccccc2)CC1 | O=C1Nc2cccc(Cl)c2CN1C1CCNCC1 | null | null | ClCCl | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1Nc2ccccc2CN1C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | 0 | CELSIUS | null | null | An ice-cold solution of 6.3 g (0.0177 mol) of 5-chloro-3,4-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(1H)-quinazolinone (prepared analogously to Example A4e)) in 50 ml of dichloromethane was mixed dropwise with 3.34 g (0.0234 mol) of (α-chloroethyl chlorocarbonate whilst maintaining a reaction temperature of 0° C., a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccc2c(c1)C[NH]CN2.C1CCNCC1 | Other | ClCCl | 0 | null | O=C1Nc2cccc(Cl)c2CN1C1CCN(Cc2ccccc2)CC1>ClCCl>O=C1Nc2cccc(Cl)c2CN1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de5f82b46ecb4eeab685bf270778f146 | BrBr.O=C1Nc2ccccc2CN1C1CCNCC1>>Br.O=C1Nc2ccc(Br)cc2CN1C1CCNCC1 | C(C)(=O)[O-].[Na+].N1CCC(CC1)N1C(NC2=CC=CC=C2C1)=O.BrBr>>Br.BrC=1C=C2CN(C(NC2=CC1)=O)C1CCNCC1 | [Br:1][Br:9].[O:2]=[C:3]1[NH:4][c:5]2[cH:6][cH:7][cH:8][cH:10][c:11]2[CH2:12][N:13]1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1>>[BrH:1].[O:2]=[C:3]1[NH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][c:11]2[CH2:12][N:13]1[CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1 | BrBr.O=C1Nc2ccccc2CN1C1CCNCC1 | Br.O=C1Nc2ccc(Br)cc2CN1C1CCNCC1 | null | null | O.C(C)(=O)O | Miscellaneous | Bromination | 62ade74d96be9803b859f68bffbf6b388ebc22ac2e4b4efe0e6f817cee0cb193 | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | O=C1Nc2ccccc2CN1C1CCNCC1 | [Br;H0;D1;+0:1]-[Br;H0;D1;+0:2].[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:2]-[c;H0;D3;+0:5](:[c:4]:[c:3]):[c:6]:[c:7].[BrH;D0;+0:1] | null | [] | 14 | CELSIUS | null | null | To a solution of 6.16 g (0.075 mol) of sodium acetate and 11.565 g (0.05 mol) of 3,4-dihydro-3-(4-piperidinyl)-2(1H)-quinazolinone in a mixture of 150 ml of glacial acetic acid and 35 ml of water a solution of 8.8 g (0.055 mol) of anhydrous bromine in 20 ml of glacial acetic acid was added dropwise, with stirring and w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)C[NH]CN2 | c1ccc2c(c1)C[NH]CN2 | c1ccc2c(c1)C[NH]CN2.C1CCNCC1 | null | O.C(C)(=O)O | 14 | null | BrBr.O=C1Nc2ccccc2CN1C1CCNCC1>O.C(C)(=O)O>Br.O=C1Nc2ccc(Br)cc2CN1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6db817171436441985f094ec712656cc | NC1CCN(Cc2ccccc2)CC1.O=c1[nH]c2ccccc2c(=O)o1>>Nc1ccccc1C(=O)NC1CCN(Cc2ccccc2)CC1 | NC1CCN(CC1)CC1=CC=CC=C1.C1=2C(=O)OC(NC1=CC=CC2)=O>>NC1=C(C(=O)NC2CCN(CC2)CC2=CC=CC=C2)C=CC=C1 | [NH2:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22][CH2:23]1.O=c1o[c:8](=[O:9])[c:7]2[c:2]([nH:1]1)[cH:3][cH:4][cH:5][cH:6]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)... | NC1CCN(Cc2ccccc2)CC1.O=c1[nH]c2ccccc2c(=O)o1 | Nc1ccccc1C(=O)NC1CCN(Cc2ccccc2)CC1 | null | null | O1CCCC1.C(C)O | Acylation | OtherReaction | 05f2f4b560cbf584ccb0bd125cb5ac7db8ee3251741e8cf30be7edbfdf8b694e | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(NC1CCN(Cc2ccccc2)CC1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3])-[C:11] | 68.3 | [{"value": 68.3, "product": "NC1=C(C(=O)NC2CCN(CC2)CC2=CC=CC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice-cold solution of 28 ml (134 mmol) of 4-amino-1-(phenylmethyl)piperidine in 200 ml of tetrahydrofuran were added, batchwise, 21.9 g (134 mmol) of isatoic acid anhydride. The resulting suspension was stirred for 2½ hours at room temperature and 2½ hours at reflux temperature, then freed from solvent. The residu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ocnc2ccccc12 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1.C(C)O | null | null | NC1CCN(Cc2ccccc2)CC1.O=c1[nH]c2ccccc2c(=O)o1>O1CCCC1.C(C)O>Nc1ccccc1C(=O)NC1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87a01a56e7674e36a17dab6713efaf0a | O=C1Nc2ccccc2CN1C1CCN(C2CCN(Cc3ccccc3)CC2)CC1>>O=C1Nc2ccccc2CN1C1CCN(C2CCNCC2)CC1 | C1(=CC=CC=C1)CN1CCC(CC1)N1CCC(CC1)N1C(NC2=CC=CC=C2C1)=O.N>>N1CCC(CC1)N1CCC(CC1)N1C(NC2=CC=CC=C2C1)=O | c1ccc(C[N:19]2[CH2:18][CH2:17][CH:16]([N:15]3[CH2:14][CH2:13][CH:12]([N:11]4[C:2](=[O:1])[NH:3][c:4]5[cH:5][cH:6][cH:7][cH:8][c:9]5[CH2:10]4)[CH2:23][CH2:22]3)[CH2:21][CH2:20]2)cc1>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[CH2:10][N:11]1[CH:12]1[CH2:13][CH2:14][N:15]([CH:16]2[CH2:17][CH2:18][NH:19][CH2:20... | O=C1Nc2ccccc2CN1C1CCN(C2CCN(Cc3ccccc3)CC2)CC1 | O=C1Nc2ccccc2CN1C1CCN(C2CCNCC2)CC1 | null | [OH-].[OH-].[Pd+2] | ClCCl.CO.C1CCCCC1 | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1Nc2ccccc2CN1C1CCN(C2CCNCC2)CC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 92 | [{"value": 92.0, "product": "N1CCC(CC1)N1CCC(CC1)N1C(NC2=CC=CC=C2C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A3f) from 3,4-dihydro-3-[1-[1-(phenylmethyl)-4-piperidinyl]-4-piperidinyl]-2(1H)-quinazolinone by hydrogenolysis, but using Pearlman's catalyst, in a yield of 92% of theory. Colourless crystals, Rf=0.48 (Macherey-Nagel, POLYGRAM® SIL G/UV254ready-made films for TLC; eluant: dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccc2c(c1)C[NH]CN2.C1CC[NH]CC1.C1CCNCC1 | Other | [OH-].[OH-].[Pd+2].ClCCl.CO.C1CCCCC1 | null | null | O=C1Nc2ccccc2CN1C1CCN(C2CCN(Cc3ccccc3)CC2)CC1>[OH-].[OH-].[Pd+2].ClCCl.CO.C1CCCCC1>O=C1Nc2ccccc2CN1C1CCN(C2CCNCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c77a00f1f4914724b3abd5bbcc00f5e6 | O=C1Nc2ccccc2CN1C1CCNCC1>>O=C1NC2CCCCC2CN1C1CCNCC1 | N.[H][H].N1CCC(CC1)N1C(NC2=CC=CC=C2C1)=O.C(C)(=O)[O-].ClCCl.CO>>N1CCC(CC1)N1C(NC2CCCCC2C1)=O.C(C)(=O)[O-] | [O:5]=[C:6]1[NH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH2:14][N:15]1[CH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1>>[O:5]=[C:6]1[NH:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH2:14][N:15]1[CH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1 | O=C1Nc2ccccc2CN1C1CCNCC1 | O=C1NC2CCCCC2CN1C1CCNCC1 | null | [Rh+]=O.O.[Pt](=O)=O | CO | Reduction | Arene hydrogenation | 1246ee61807f1157c941c0c1d66e1757d2db4a83ff8514b6b86ee2a2e16cdf32 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C1NC2CCCCC2CN1C1CCNCC1 | [C:1]-[#7:2]1-[C:3]-[c;H0;D3;+0:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9]:2-[#7:10]-[C:11]-1=[O;D1;H0:12]>>[C:1]-[#7:2]1-[C:3]-[CH;D3;+0:4]2-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH;D3;+0:9]-2-[#7:10]-[C:11]-1=[O;D1;H0:12] | null | [] | null | null | null | null | A solution of 5.0 g (17.17 mmol) of 3,4-dihydro-3-(4-piperidinyl)-2(1H)-quinazolinone-acetate in 70 ml of methanol was hydrogenated at room temperature and in the presence of 1.0 g rhodium (III) oxide-platinum (IV) oxide hydrate catalyst (46.45% rhodium, 20.15% platinum) until the hydrogen uptake had ceased. The cataly... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c(c1)C[NH]CN2 | C1CCC2NC[NH]CC2C1 | C1CCC2NC[NH]CC2C1.C1CCNCC1 | null | [Rh+]=O.O.[Pt](=O)=O.CO | null | null | O=C1Nc2ccccc2CN1C1CCNCC1>[Rh+]=O.O.[Pt](=O)=O.CO>O=C1NC2CCCCC2CN1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa4bb05d0c4c4347bdb647373b5eaf41 | NC1CCN(Cc2ccccc2)CC1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 | [N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl.NC1CCN(CC1)CC1=CC=CC=C1.C(C)N(CC)CC>>[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)NC1CCN(CC1)CC1=CC=CC=C1 | [NH2:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1.Cl[S:10]([c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1)(=[O:11])=[O:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10](=[O:11])(=[O:12])[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:18... | NC1CCN(Cc2ccccc2)CC1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NC1CCN(Cc2ccccc2)CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10] | null | [] | null | null | 30 | MINUTE | Whilst carrying out external cooling with ice water a solution of 44.3 g (0.2 mol) of 2-nitrobenzenesulphonyl chloride in 250 ml of chloroform was added dropwise to a solution of 38.0 g (0.2 mol) of 4-amino-1-(phenylmethyl)piperidine and 22.0 g (0.22 mol) of triethylamine in 250 ml of chloroform. After the cooling was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 0.5 | NC1CCN(Cc2ccccc2)CC1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>C(Cl)(Cl)Cl>O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c16f0b3efb414c96b5009953046aea03 | O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1>>Nc1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 | [N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)NC1CCN(CC1)CC1=CC=CC=C1.O.O.S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>NC1=C(C=CC=C1)S(=O)(=O)NC1CCN(CC1)CC1=CC=CC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20]... | O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 | Nc1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 | null | null | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(NC1CCN(Cc2ccccc2)CC1)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 | null | null | To a solution of 75.0 g (0.2 mol) of 2-nitro-N-[1-(phenylmethyl)-4-piperidinyl]-benzenesulphonic acid amide in 2.0 l ethanol was added dropwise, at room temperature, a solution of 174.0 g ( 0.828 mol) of sodium dithionite-dihydrate in 700 ml of water. After the heat of the exothermic reaction had died away the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | O.C(C)O | null | null | O=[N+]([O-])c1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1>O.C(C)O>Nc1ccccc1S(=O)(=O)NC1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15fb64b0243f426eb0e8ea24464000af | NS(N)(=O)=O.Nc1ccccc1CNC1CCN(Cc2ccccc2)CC1>>O=S1(=O)Nc2ccccc2CN1C1CCN(Cc2ccccc2)CC1 | NC1=C(C=CC=C1)CNC1CCN(CC1)CC1=CC=CC=C1.S(=O)(=O)(N)N>>O=S1(NC2=C(CN1C1CCN(CC1)CC1=CC=CC=C1)C=CC=C2)=O | N[S:2](=[O:1])(=[O:3])[NH2:4].N[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[O:1]=[S:2]1(=[O:3])[NH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][N:12]1[CH:13]1[CH2:14][CH2:15][N:16]([CH2:17][c:18]2[cH:19][cH:... | NS(N)(=O)=O.Nc1ccccc1CNC1CCN(Cc2ccccc2)CC1 | O=S1(=O)Nc2ccccc2CN1C1CCN(Cc2ccccc2)CC1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | b6b3b5cefac03fb1305f8cf424bdaa7abe03f5a0bb5812c3475110522a1d2b02 | b397e30a6ccc587e05245a90512edc37f945dcc48b8cf6366dd21901a04fa1ba | O=S1(=O)Nc2ccccc2CN1C1CCN(Cc2ccccc2)CC1 | N-[S;H0;D4;+0:1](-[NH2;D1;+0:2])(=[O;D1;H0:3])=[O;D1;H0:4].N-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[C:9]-[NH;D2;+0:10]-[C:11](-[C:12])-[C:13]):[c:14]>>[C:12]-[C:11](-[N;H0;D3;+0:10]1-[C:9]-[c:8](:[c:14]):[c;H0;D3;+0:5](:[c:6]:[c:7])-[NH;D2;+0:2]-[S;H0;D4;+0:1]-1(=[O;D1;H0:3])=[O;D1;H0:4])-[C:13] | null | [] | null | null | null | null | A solution of 11.0 g (0.0372 mol) of 2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine in 200 ml of pyridine was added dropwise within 1.5 hours and at reflux temperature to a solution of 3.4 g (0.0354 mol) of sulphamide in 200 ml of pyridine and the mixture was then refluxed for 6 hours. The mixture was fr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Primary amine.Secondary amine | Sulfonamide.Tertiary amine | c1ccccc1 | c1ccc2c(c1)C[NH]SN2 | c1ccc2c(c1)C[NH]SN2.C1CC[NH]CC1.c1ccccc1 | Other | N1=CC=CC=C1 | null | null | NS(N)(=O)=O.Nc1ccccc1CNC1CCN(Cc2ccccc2)CC1>N1=CC=CC=C1>O=S1(=O)Nc2ccccc2CN1C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-926f7b0a23cc4338b77caa0fd2afa495 | BrBr.CC(=O)Nc1ccccc1C(C)=O>>CC(=O)Nc1ccccc1C(=O)CBr | BrBr.C(C)(=O)NC1=C(C=CC=C1)C(C)=O>>C(C)(=O)NC1=C(C=CC=C1)C(CBr)=O | Br[Br:14].[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[CH3:13]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[CH2:13][Br:14] | BrBr.CC(=O)Nc1ccccc1C(C)=O | CC(=O)Nc1ccccc1C(=O)CBr | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | 45.0 g (0.282 mol) of dry bromine were added dropwise to a boiling solution of 50.0 g (0.282 mol) of 1-[2-(acetylamino)phenyl]ethanone in 400 ml of chloroform at room temperature. The solvent was distilled off, the residue was distributed between dichloromethane and saturated ice-cold sodium hydrogen carbonate solution... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)Cl | null | null | BrBr.CC(=O)Nc1ccccc1C(C)=O>C(Cl)(Cl)Cl>CC(=O)Nc1ccccc1C(=O)CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c9ef28bfebc44cb821975586637595e | CC(=O)Nc1ccccc1C(=O)CBr.CCN(C(C)C)C(C)C.N#C[O-].NC1CCN(Cc2ccccc2)CC1>>CC(=O)Nc1ccccc1-c1cccc2c1[nH]c(=O)n2C1CCN(Cc2ccccc2)CC1 | NC1CCN(CC1)CC1=CC=CC=C1.CCN(C(C)C)C(C)C.C(C)(=O)NC1=C(C=CC=C1)C(CBr)=O.ClCCl.ClCCl.[O-]C#N.[Na+]>>C(C)(=O)NC1=C(C=CC=C1)C1=CC=CC=2N(C(NC21)=O)C2CCN(CC2)CC2=CC=CC=C2 | O=[C:11]([c:10]1[c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][cH:9]1)[CH2:16]Br.CC(C)N([CH2:14][CH3:13])[CH:15](C)C.[N:17]#[C:18][O-:19].[NH2:20][CH:21]1[CH2:22][CH2:23][N:24]([CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32][CH2:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:... | CC(=O)Nc1ccccc1C(=O)CBr.CCN(C(C)C)C(C)C.N#C[O-].NC1CCN(Cc2ccccc2)CC1 | CC(=O)Nc1ccccc1-c1cccc2c1[nH]c(=O)n2C1CCN(Cc2ccccc2)CC1 | null | null | C(C)(=O)OCC.CO.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 22e0571356f9b4546f1a6f12dd95cfce26ead01636f86f17c3d07e188843b96c | 19b234a2c18b40db1eaf3feabf89dba2808f77a81cb843547290f6bdf88c8551 | O=c1[nH]c2c(-c3ccccc3)cccc2n1C1CCN(Cc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[#7:7]-[C:8](-[C;D1;H3:9])=[O;D1;H0:10]):[c:11].C-C(-C)-N(-[CH2;D2;+0:12]-[CH3;D1;+0:13])-[CH;D3;+0:14](-C)-C.[C:15]-[C:16](-[NH2;D1;+0:17])-[C:18].[N;H0;D1;+0:19]#[C;H0;D2;+0:20]-[O-;H0;D1:21]>>[C:15]-[C:16](-[n;H0;D3;+0:17]1:[c;H0;D3;+0:14]2:[cH;... | null | [] | null | null | 2 | HOUR | To a solution of 26.3 g (0.138 mol) of 4-amino-1-(phenylmethyl)piperidine and 17.8 g (0.138 mol) of DIEA in 300 ml of dichloromethane was added dropwise a solution of 35.4 g (0.138 mol) of 1-[2-(acetylamino)phenyl]-2-bromoethanone in 150 ml of dichloromethane and the mixture was kept for a further 2 hours at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Nitrile.Primary amine.Tertiary amine | null | null | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CC[NH]CC1.c1ccccc1 | HBr | C(C)(=O)OCC.CO.C(C)(=O)O | null | 2 | CC(=O)Nc1ccccc1C(=O)CBr.CCN(C(C)C)C(C)C.N#C[O-].NC1CCN(Cc2ccccc2)CC1>C(C)(=O)OCC.CO.C(C)(=O)O>CC(=O)Nc1ccccc1-c1cccc2c1[nH]c(=O)n2C1CCN(Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bded59d75a645acb5b742b039b9008e | CC(=O)Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1>>Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1 | C(C)(=O)NC1=C(C=CC=C1)C=1NC(N(C1)C1CCN(CC1)CC1=CC=CC=C1)=O.[OH-].[Na+]>>NC1=C(C=CC=C1)C=1NC(N(C1)C1CCN(CC1)CC1=CC=CC=C1)=O | CC(=O)[NH:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[c:24](=[O:25])[nH:26]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:15][c:16]3[cH:17][cH:18][cH... | CC(=O)Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1 | Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=c1[nH]c(-c2ccccc2)cn1C1CCN(Cc2ccccc2)CC1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 3.0 g (7.68 mmol) of 4-[2-(acetylamino)phenyl]-1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-imidazol-2-one, 50 ml of 5 N sodium hydroxide solution and 25 ml of ethanol was refluxed for 3 hours. After cooling the organic phase was separated off, dried over sodium sulphate and evaporated down in vacuo. ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1c[nH]cn1.C1CC[NH]CC1.c1ccccc1 | HO- | C(C)O | null | null | CC(=O)Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1>C(C)O>Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24ab265129514a1faacd700f780a30a3 | C=O.Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1>>O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1 | NC1=C(C=CC=C1)C=1NC(N(C1)C1CCN(CC1)CC1=CC=CC=C1)=O.C=O>>C1(=CC=CC=C1)CN1CCC(CC1)N1C(NC2=C1C=NC=1C=CC=CC21)=O | O=[CH2:12].[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH2:11])[cH:13][n:14]1[CH:15]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[O:1]=[c:2]1[nH:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[n:11][cH:12][c:13]2[n:14]1[CH:15]1[CH2:16][CH2:17][N:18]([CH... | C=O.Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1 | O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 1b4fbe9ba18bc2d6b0b4c110dc5aeab38259cba7aa06bf91653c1dbde5322e8c | 2f683162edeeaf0c6befa932010538b477a0290a1dac1031381b95d746c912ec | O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1 | O=[CH2;D1;+0:1].[C:2]-[#7;a:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]):[#7;a:12]:[c:13]:1=[O;D1;H0:14]>>[C:2]-[#7;a:3]1:[c:13](=[O;D1;H0:14]):[#7;a:12]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:4]:1:[cH;D2;+0:1]:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c;H0;D3;+0:6]:2:[c:7]:[c:8] | null | [] | null | null | 1 | HOUR | A solution of 2.67 g (7.66 mmol) of 4-(2-aminophenyl)-1,3-dihydro-1-[1-(phenylmethyl)-4-piperidinyl]-2H-imidazol-2-one in 50 ml of chloroform was mixed with 3.0 g of paraformaldehyde and refluxed for 3.5 hours. The residue remaining after evaporation of the solvent was taken up in 100 ml of methanol and acidified with ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | null | c1c[nH]cn1.c1ccccc1 | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)ncc1nc[nH]c12.C1CC[NH]CC1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 1 | C=O.Nc1ccccc1-c1cn(C2CCN(Cc3ccccc3)CC2)c(=O)[nH]1>C(Cl)(Cl)Cl>O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1 |
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