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-0387783899c642a8b7eb4ba379bcdf5d | ord-e2e6007ce93047669f9a428003aa1d63 | CCOC(=O)CCCCBr.COC(=O)c1ccc(CNCCc2ccccc2OCc2ccc(Br)cc2)cc1>>CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)Cc1ccc(C(=O)OC)cc1 | BrC1=CC=C(COC2=C(CCNCC3=CC=C(C(=O)OC)C=C3)C=CC=C2)C=C1.BrCCCCC(=O)OCC.C([O-])(O)=O.[Na+].O>>BrC1=CC=C(COC2=C(CCN(CCCCC(=O)OCC)CC3=CC=C(C(=O)OC)C=C3)C=CC=C2)C=C1 | Br[CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:10]([CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([Br:25])[cH:26][cH:27]1)[CH2:28][c:29]1[cH:30][cH:31][c:32]([C:33](=[O:34])[O:35][CH3:36])[cH:37][cH:38]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH... | CCOC(=O)CCCCBr.COC(=O)c1ccc(CNCCc2ccccc2OCc2ccc(Br)cc2)cc1 | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)Cc1ccc(C(=O)OC)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CNCCc2ccccc2OCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[c:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C:7]-[c:8])-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | 5.00 g (11.0 mmol) of methyl 4-[({2-[(4-bromobenzyl)oxy]phenethyl}amino)-methyl]benzoate from Ex. VIII, 2.30 g (11.0 mmol) of ethyl 5-bromovalerate and 1.109 g (13.21 mmol) of sodium bicarbonate in 30 ml of acetonitrile are heated at reflux for 18 hours. The reaction mixture is admixed with water and extracted with met... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(C)#N | null | null | CCOC(=O)CCCCBr.COC(=O)c1ccc(CNCCc2ccccc2OCc2ccc(Br)cc2)cc1>C(C)#N>CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d34544f0aa64138a4ebdecdb4794fce | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)COC(=O)c1ccccc1.OB(O)c1ccc(Cl)cc1>>CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(-c2ccc(Cl)cc2)cc1)Cc1ccc(C(=O)OC)cc1 | C(C)(=O)OCC.BrC1=CC=C(COC2=C(CCN(CCCCC(=O)OCC)COC(C3=CC=CC=C3)=O)C=CC=C2)C=C1.ClC1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=CC=C(C=C1)C1=CC=C(C=C1)COC1=C(CCN(CCCCC(=O)OCC)CC2=CC=C(C(=O)OC)C=C2)C=CC=C1 | Br[c:24]1[cH:23][cH:22][c:21]([CH2:20][O:19][c:18]2[c:13]([CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:34][O:41][C:39]([c:38]3[cH:37][cH:36][cH:35][cH:44][cH:43]3)=[O:40])[cH:14][cH:15][cH:16][cH:17]2)[cH:33][cH:32]1.OB(O)[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]1>>[... | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)COC(=O)c1ccccc1.OB(O)c1ccc(Cl)cc1 | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(-c2ccc(Cl)cc2)cc1)Cc1ccc(C(=O)OC)cc1 | null | 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 | C(OC)COC | Heteroatom Alkylation and Arylation | OtherReaction | 2a6108bec29a2813caa35a6c98d74eae0f17d9f98aa2130a0d7e18c4496fd1ca | 856922498de4416ebfdb2d129f3f2e86df04a385efa221a5841fc7056a7b076d | c1ccc(CNCCc2ccccc2OCc2ccc(-c3ccccc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#7:7](-[C:8])-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[c:18]:1.O-B(-O)-[c;H0;D3;+0:19](:[c:20]:[c:21]):[c:22]:[c:23]>>[C:6]-[#7:7](-[C:8])-[CH2;D2;+0:9]-[c;H0;D3;+0:16]1:[c:15]:[c:14]:[c:13](-[C:11](=[O;D1;H0:12])-... | null | [] | null | null | null | null | 300.0 mg (0.51 mmol) of methyl 4-({[{2-[(4-bromobenzyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 4 are initially charged in 3 ml of dimethoxyethane and admixed successively with 101.7 mg (0.62 mmol) of 4-chlorophenylboronic acid and 0.57 ml of 2M sodium carbonate solution. 10.0 mg of dichlorobi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | 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.C(OC)COC | null | null | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(Br)cc1)COC(=O)c1ccccc1.OB(O)c1ccc(Cl)cc1>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.C(OC)COC>CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(-c2ccc(Cl)cc2)cc1)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed15b91395d4451ea25ac2df9e79a8c9 | COC(=O)CCCCN(CCc1ccccc1O)Cc1ccc(C(=O)OC)cc1.ClCc1ccc(C=Cc2ccccc2)cc1>>COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 | OC1=C(CCN(CCCCC(=O)OC)CC2=CC=C(C(=O)OC)C=C2)C=CC=C1.ClCC1=CC=C(C=C1)C=CC1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>COC(CCCCN(CCC1=C(C=CC=C1)OCC1=CC=C(C=C1)\C=C\C1=CC=CC=C1)CC1=CC=C(C(=O)OC)C=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[OH:18])[CH2:34][c:35]1[cH:36][cH:37][c:38]([C:39](=[O:40])[O:41][CH3:42])[cH:43][cH:44]1.Cl[CH2:19][c:20]1[cH:21][cH:22][c:23]([CH:24]=[CH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][cH:33]1>... | COC(=O)CCCCN(CCc1ccccc1O)Cc1ccc(C(=O)OC)cc1.ClCc1ccc(C=Cc2ccccc2)cc1 | COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | C(=C/c1ccc(COc2ccccc2CCNCc2ccccc2)cc1)\c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | 1.0 g (2.50 mmol) of methyl 4-{[(2-hydroxyphenethyl)-(5-methoxy-5-oxopentyl)-amino]methyl}benzoate from Ex. 1, 0.687 g (3.00 mmol) of 4-(chloromethyl)stilbene and 0.520 g (3.75 mmol) of potassium carbonate in 10.0 ml of acetonitrile are heated at reflux for 18 hours. The solution is filtered and the solvent is distille... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(C)#N | null | null | COC(=O)CCCCN(CCc1ccccc1O)Cc1ccc(C(=O)OC)cc1.ClCc1ccc(C=Cc2ccccc2)cc1>C(C)#N>COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5d48ccf9ccf43208e15e96550ba9523 | COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1>>COC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 | COC(CCCCN(CCC1=C(C=CC=C1)OCC1=CC=C(C=C1)\C=C\C1=CC=CC=C1)CC1=CC=C(C(=O)OC)C=C1)=O.[H][H]>>COC(CCCCN(CCC1=C(C=CC=C1)OCC1=CC=C(C=C1)CCC1=CC=CC=C1)CC1=CC=C(C(=O)OC)C=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[O:18][CH2:19][c:20]1[cH:21][cH:22][c:23](/[CH:24]=[CH:25]/[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][cH:33]1)[CH2:34][c:35]1[cH:36][cH:37][c:38]([C:39](=[O:40])[O:41][CH3:42])[cH:43][cH:44]1>>[... | COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 | COC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2ccc(COc3ccccc3CCNCc3ccccc3)cc2)cc1 | [c:1]:[c:2](/[CH;D2;+0:3]=[CH;D2;+0:4]/[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | 781.8 mg (1.34 mmol) of methyl 4-({(5-methoxy-5-oxopentyl)[2-({4-[(E)-2-phenyl-ethenyl]benzyl}oxy)phenethyl]amino)methyl)benzoate from Ex. 6 and 80.0 mg of 10% palladium on activated carbon in 10 ml of ethyl acetate are hydrogenated under atmospheric pressure. After 1 hour, the calculated amount of hydrogen has been ta... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | 1 | COC(=O)CCCCN(CCc1ccccc1OCc1ccc(/C=C/c2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1>[Pd].C(C)(=O)OCC>COC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccccc2)cc1)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-501d7d3e9d7d4a4780d07b70281abad3 | COC(=O)CCCCN(CCc1cc(F)ccc1OCc1ccc(-c2ccc(C)cc2)cc1)Cc1ccc(C(=O)OC)cc1>>Cc1ccc(-c2ccc(COc3ccc(F)cc3CCN(CCCCC(=O)O)Cc3ccc(C(=O)O)cc3)cc2)cc1 | FC=1C=CC(=C(C1)CCN(CCCCC(=O)OC)CC1=CC=C(C(=O)OC)C=C1)OCC1=CC=C(C=C1)C1=CC=C(C=C1)C.[OH-].[Na+].ClCCl>>C(=O)(O)CCCCN(CCC1=C(C=CC(=C1)F)OCC1=CC=C(C=C1)C1=CC=C(C=C1)C)CC1=CC=C(C(=O)O)C=C1 | C[O:28][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:20][CH2:19][c:18]1[c:12]([O:11][CH2:10][c:9]2[cH:8][cH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:42][cH:41]3)[cH:40][cH:39]2)[cH:13][cH:14][c:15]([F:16])[cH:17]1)[CH2:29][c:30]1[cH:31][cH:32][c:33]([C:34](=[O:35])[O:36]C)[cH:37][cH:38]1)=[O:27]>>[CH3:1][c:2]1... | COC(=O)CCCCN(CCc1cc(F)ccc1OCc1ccc(-c2ccc(C)cc2)cc1)Cc1ccc(C(=O)OC)cc1 | Cc1ccc(-c2ccc(COc3ccc(F)cc3CCN(CCCCC(=O)O)Cc3ccc(C(=O)O)cc3)cc2)cc1 | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(CNCCc2ccccc2OCc2ccc(-c3ccccc3)cc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | null | [] | null | null | 8 | HOUR | 0.45 g (0.69 mmol) of methyl 4-{[(2-{5-fluoro-2-[(4′-methyl-1,1′-biphenyl-4-yl)methoxy]phenyl}ethyl)(5-methoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 185 is dissolved in 8ml of methanol. 0.5 ml of aqueous sodium hydroxide solution (45%) and 1.5 ml of dichloromethane are added, and the solution is stirred at RT for ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | CO | null | 8 | COC(=O)CCCCN(CCc1cc(F)ccc1OCc1ccc(-c2ccc(C)cc2)cc1)Cc1ccc(C(=O)OC)cc1>CO>Cc1ccc(-c2ccc(COc3ccc(F)cc3CCN(CCCCC(=O)O)Cc3ccc(C(=O)O)cc3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e62791e523bc48a79da21cd90562ab8c | CCOC(=O)CCCCN(CCc1ccccc1OCCCCCBr)Cc1ccc(C(=O)OC)cc1.c1ccc(N2CCNCC2)cc1>>CCOC(=O)CCCCN(CCc1ccccc1OCCCCCN1CCN(c2ccccc2)CC1)Cc1ccc(C(=O)OC)cc1 | BrCCCCCOC1=C(CCN(CCCCC(=O)OCC)CC2=CC=C(C(=O)OC)C=C2)C=CC=C1.C1(=CC=CC=C1)N1CCNCC1.C(C)N(CC)CC>>C(C)OC(CCCCN(CCC1=C(C=CC=C1)OCCCCCN1CCN(CC1)C1=CC=CC=C1)CC1=CC=C(C(=O)OC)C=C1)=O | Br[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][c:18]1[c:13]([CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:37][c:38]2[cH:39][cH:40][c:41]([C:42](=[O:43])[O:44][CH3:45])[cH:46][cH:47]2)[cH:14][cH:15][cH:16][cH:17]1.[NH:25]1[CH2:26][CH2:27][N:28]([c:29]2[cH:30][cH:31][cH:32][cH... | CCOC(=O)CCCCN(CCc1ccccc1OCCCCCBr)Cc1ccc(C(=O)OC)cc1.c1ccc(N2CCNCC2)cc1 | CCOC(=O)CCCCN(CCc1ccccc1OCCCCCN1CCN(c2ccccc2)CC1)Cc1ccc(C(=O)OC)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CNCCc2ccccc2OCCCCCN2CCN(c3ccccc3)CC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | null | null | 200.0 mg (0.355 mmol) of methyl 4-{[{2-[(5-bromopentyl)oxy]phenethyl}(5-ethoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 107, 69.21 mg of N-phenylpiperazine and 71.95 mg (0.711 mmol) of triethylamine in 2 ml of tetrahydrofuran are heated at reflux for 18 hours. The reaction solution is washed with water, concentrated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | null | null | CCOC(=O)CCCCN(CCc1ccccc1OCCCCCBr)Cc1ccc(C(=O)OC)cc1.c1ccc(N2CCNCC2)cc1>O1CCCC1>CCOC(=O)CCCCN(CCc1ccccc1OCCCCCN1CCN(c2ccccc2)CC1)Cc1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3350d545ae14418b8df6f55ce8d0020d | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1)Cc1ccc(C(=O)OC)cc1>>O=C(O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O)cc2)cc1)Cc1ccc(C(=O)O)cc1 | C(C)(C)(C)[Si](OC1=CC=C(C=C1)CCC1=CC=C(COC2=C(C=CC=C2)CCN(CCCCC(=O)OCC)CC2=CC=C(C(=O)OC)C=C2)C=C1)(C)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(=O)(O)CCCCN(CCC1=C(C=CC=C1)OCC1=CC=C(C=C1)CCC1=CC=C(C=C1)O)CC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][CH2:24][c:25]2[cH:26][cH:27][c:28]([O:29][Si](C)(C)C(C)(C)C)[cH:30][cH:31]2)[cH:32][cH:33]1)[CH2:34][c:35]1[cH:36][cH:37][c:38]([C:39](=[O:40])[O:41]C)[cH:42]... | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1)Cc1ccc(C(=O)OC)cc1 | O=C(O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O)cc2)cc1)Cc1ccc(C(=O)O)cc1 | null | null | C1CCOC1 | Deprotection | OtherReaction | d560bfcb270d82124149d3f51a4694375c022c670e33fde0dca76eee6afaeb6a | 203d3585efadd2a224ba51f3095a9bcc9405d220fce28f962510cdae6f7340dc | c1ccc(CCc2ccc(COc3ccccc3CCNCc3ccccc3)cc2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8].C-[O;H0;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5].[O;D1;H0:11]=[C:10](-[OH;D1;+0:9])-[c:12].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | 27 mg (0.037 mmol) of methyl 4-{[{2-[2-({4-[2-(4-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)ethyl]benzyl}oxy)phenyl]ethyl}(5-ethoxy-5-oxopentyl)amino]-methyl}benzoate from XXI are dissolved in 10 ml of THF. 0.03 ml of tetrabutylammonium fluoride (IM solution in THF) are added, and the solution is stirred at RT for 1 hour.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.TMS ether protective group | Carboxylic acid.Carboxylic acid.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 1 | CCOC(=O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O[Si](C)(C)C(C)(C)C)cc2)cc1)Cc1ccc(C(=O)OC)cc1>C1CCOC1>O=C(O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccc(O)cc2)cc1)Cc1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ab80e1ebfc347c382d0c4a31e189f35 | CC(C)C(=O)Cl.OO>>CC(C)C(=O)OOC(=O)C(C)C | C(C(C)C)(=O)Cl.OO>>C(C(C)C)(=O)OOC(C(C)C)=O | Cl[C:8]([CH:2]([CH3:1])[CH3:3])=[O:9].[OH:5][OH:6]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][O:7][C:8](=[O:9])[CH:10]([CH3:11])[CH3:12] | CC(C)C(=O)Cl.OO | CC(C)C(=O)OOC(=O)C(C)C | null | null | O | Acylation | OtherReaction | 1139e670527183451f4470bd96ef89a08287a1fdc0143a9908b3edd5c8d747b0 | 8fa2c09b803fb2345ec5ede68d914737d73081cd80ecf2244f388313e98ae4fc | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[OH;D1;+0:7]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:11]-[O;H0;D2;+0:7]-[C:12](=[O;H0;D1;+0:6])-[CH;D3;+0:3](-[C;D1;H3:4])-[C;D1;H3:5] | null | [] | null | null | null | null | In Example A, the procedure of WO 01/32613 was repeated. First, a solution of Na2O2 was prepared by combining 108.3 g of demineralized water, 18.5 g of NaOH-33 solution, and 3.7 g of the aqueous H2O2. A second reactor was charged with 33.3 g of demineralized water, 27.7 g of the PVA solution, and 16.3 g of isobutanoyl ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Peroxide | Peroxide | null | null | null | null | O | null | null | CC(C)C(=O)Cl.OO>O>CC(C)C(=O)OOC(=O)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff4c7be6474a4df4bc8cc7292c566b1d | O=Cc1cccc(Br)n1.OB(O)c1cccc2ccccc12>>O=Cc1cccc(-c2cccc3ccccc23)n1 | C1(=CC=CC2=CC=CC=C12)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].BrC1=NC(=CC=C1)C=O>>C(=O)C1=NC(=CC=C1)C1=CC=CC2=CC=CC=C12 | Br[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[O:1])[n:18]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[n:18]1 | O=Cc1cccc(Br)n1.OB(O)c1cccc2ccccc12 | O=Cc1cccc(-c2cccc3ccccc23)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | cc7b6546c43ae6dc4b9bf5c56c03385a5aaa3d7e8a3c63cb3d09ccb8ae48e364 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3ccccc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](:[c:12]):[c:13]>>[O;D1;H0:5]=[C:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](:[c:12]):[c:13]):[c:6]:[c:7] | null | [] | 70 | CELSIUS | null | null | Naphthylboronic acid (2.06 g, 12 mmol) and Na2CO3 (2.65 g, 25 mmol) were dissolved in 60 mL of degassed 4:1 H2O/MeOH. This solution was added via cannula to a solution of 1.86 g (10 mmol) of 2-bromo-6-formylpyridine and I 16 mg (0.10 mmol) of Pd(PPh3)4 in 50 mL of degassed toluene. The biphasic solution was vigorously ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccc2ccccc2c1 | c1ccncc1.c1ccc2ccccc2c1 | c1ccncc1.c1ccc2ccccc2c1 | 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 | 70 | null | O=Cc1cccc(Br)n1.OB(O)c1cccc2ccccc12>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>O=Cc1cccc(-c2cccc3ccccc23)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-302209980d6547c5afc3a3106403db72 | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(N2CCOCC2)c(F)c1>>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCOCC2)c(F)c1 | ClC(COC(=O)NC1=NOC=C1)(Cl)Cl.OC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1CCOCC1)F.C(CCC)P(CCCC)CCCC.C1CCN(CC1)C(=O)/N=N/C(=O)N2CCCCC2>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1CCOCC1)F | O=C(OCC(Cl)(Cl)Cl)[NH:6][c:7]1[cH:8][cH:9][o:10][n:11]1.O[CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:13]([c:14]2[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[c:24]([F:25])[cH:26]2)[CH2:12]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][o:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17]... | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(N2CCOCC2)c(F)c1 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCOCC2)c(F)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e0e13d8136562ab3a4402091675fa6c04121a11d3fdb7ee25e9b6032261dafdb | 10b7052cc0efeccb39d072f8152672671d4c2ab3cc682ff8244c949613b56722 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCOCC2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#8;a:4]:[c:5]:[c:6]:1.O-[CH2;D2;+0:7]-[C:8]1-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13]-1>>[O;D1;H0:11]=[C:10]1-[#7:12]-[C:13]-[C:8](-[CH2;D2;+0:7]-[NH;D2;+0:1]-[c:2]2:[#7;a:3]:[#8;a:4]:[c:5]:[c:6]:2)-[#8:9]-1 | 331.2 | [{"value": 331.2, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1CCOCC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (260 mg, 1.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (see WO 95/07271; 293 mg, 1 mmol) and tributylphosphine (303 mg, 1.5 mmol) in dry tetrahydrofuran (10 ml) at 0° C. under a nitrogen atmosphere, was added 1,1-... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary alcohol | Secondary amine | null | null | C1COC[NH]1.c1cnoc1.c1ccccc1.C1COCC[NH]1 | HCl | O1CCCC1 | null | 96 | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(N2CCOCC2)c(F)c1>O1CCCC1>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCOCC2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7bfe60b6bfc454e99c08ce2d8fbae0f | O=CN1CC=C(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)CC1>>O=CN1CC=C(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)CC1 | O1N=C(C=C1)N(C(=O)OCC(Cl)(Cl)Cl)C[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C1=CCN(CC1)C=O)F>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C1=CCN(CC1)C=O)F | O=C(OCC(Cl)(Cl)Cl)[N:15]([CH2:14][C@H:13]1[CH2:12][N:11]([c:10]2[cH:9][cH:8][c:7]([C:6]3=[CH:5][CH2:4][N:3]([CH:2]=[O:1])[CH2:28][CH2:27]3)[c:25]([F:26])[cH:24]2)[C:22](=[O:23])[O:21]1)[c:16]1[cH:17][cH:18][o:19][n:20]1>>[O:1]=[CH:2][N:3]1[CH2:4][CH:5]=[C:6]([c:7]2[cH:8][cH:9][c:10]([N:11]3[CH2:12][C@H:13]([CH2:14][NH:... | O=CN1CC=C(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)CC1 | O=CN1CC=C(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)CC1 | null | [Zn] | C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | a049294b02f92114ceaf236099274f4d9678902bbcae42ac105bc5655cd312b0 | bbcae62ba0795429ef75cdf3032894b1bfb636fffd4d1d9ae253b856ebe17489 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(C2=CCNCC2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1 | null | [] | null | null | 10 | MINUTE | To a stirred solution of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1-formyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl]oxazolidin-2-one (110 mg, 0.2 mM) in acetic acid (3 ml) was added zinc dust (130 mg, 2.0 mM). The mixture was held in an ultrasonic bath for 10 min. and then stirre... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether | Secondary amine | null | null | C1=CC[NH]CC1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | [Zn].C(C)(=O)O | null | 0.166667 | O=CN1CC=C(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)CC1>[Zn].C(C)(=O)O>O=CN1CC=C(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4cc2a19abfb4e1aa45b5a063de7adea | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1>>O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1 | ClC(COC(=O)NC1=NOC=C1)(Cl)Cl.OC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C1=CCN(CC1)CC1=CC=CC=C1)F.C(CCC)P(CCCC)CCCC.N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1>>O1N=C(C=C1)N(C(=O)OCC(Cl)(Cl)Cl)C[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C1=CCN(CC1)CC1=CC=CC=C1)F | [NH:6]([C:7](=[O:8])[O:9][CH2:10][C:11]([Cl:12])([Cl:13])[Cl:14])[c:15]1[cH:16][cH:17][o:18][n:19]1.O[CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:21]([c:22]2[cH:23][cH:24][c:25]([C:26]3=[CH:27][CH2:28][N:29]([CH2:30][c:31]4[cH:32][cH:33][cH:34][cH:35][cH:36]4)[CH2:37][CH2:38]3)[c:39]([F:40])[cH:41]2)[CH2:20]1>>[O:1]=[C:2]1[O:3... | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1 | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 11fb674a044d8d7af31448bdb9605289d85f0eae8c5cd7382bcd4eb75801f57c | 37df4f62d621c5df4eacc80f72b83ef887737caa083adb04ff0c8b3a28bbaeec | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)cc1 | O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-1.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[c:13]1:[#7;a:14]:[#8;a:15]:[c:16]:[c:17]:1>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-1)-[c:13]1:[#7;a:14]:[#8;a:15]:[c:16]:[c:17]:1 | 52 | [{"value": 52.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (1.30 g, 5.0 mmol), 5(R)-hydroxymethyl-3-(3-fluoro-4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one (WO 97/30995; 1.91 g, 5.0 mmol) and tributylphosphine (1.52 g, 7.5 mmol) in dry tetrahydrofuran (50 ml) under a nitrogen atmosphe... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Primary alcohol | Carbamic ester | null | null | C1COC[NH]1.c1cnoc1.c1ccccc1.C1=CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1 | 0 | 0.5 | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1>O1CCCC1>O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(C2=CCN(Cc3ccccc3)CC2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a773cec767284af9a5ce45a2ddd1fe40 | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(N2CC=CCC2)c(F)c1.c1ccncc1>>CCCC(C)C.CCOC(C)=O | O1N=C(C=C1)N(C(=O)OCC(Cl)(Cl)Cl)C[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1CC=CCC1)F.N1=CC=CC=C1>>C(C)(=O)OCC.CCCC(C)C | O=C(OCC(Cl)(Cl)Cl)N(C[C@H:8]1[CH2:6]N(c2ccc(N3CCC=C[CH2:5]3)c(F)c2)[C:10](=[O:12])[O:9]1)c1c[cH:7]on1.n1[cH:2][cH:1][cH:11][cH:4][cH:3]1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6].[CH3:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(N2CC=CCC2)c(F)c1.c1ccncc1 | CCCC(C)C.CCOC(C)=O | null | null | ClCCl | C-C Coupling | OtherReaction | ab230edaac127c63e24ba9e64f667949681bb1defc5694e221c767356100b5a0 | 9309b76579fd5b67f50601e36c9437272ef585e92cd29e7fa52f73dc364114a4 | null | Cl-C(-Cl)(-Cl)-C-O-C(=O)-N(-C-[C@@H;D3;+0:1]1-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-N(-c2:c:c:c(-N3-C-C-C=C-[CH2;D2;+0:5]-3):c(-F):c:2)-[CH2;D2;+0:6]-1)-c1:c:[cH;D2;+0:7]:o:n:1.[cH;D2;+0:8]1:[cH;D2;+0:9]:[cH;D2;+0:10]:n:[cH;D2;+0:11]:[cH;D2;+0:12]:1>>[CH3;D1;+0:8]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:2]-[CH2;D2;+0:1]-[CH3;D1... | 60 | [{"value": 60.0, "product": "C(C)(=O)OCC.CCCC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a stirred solution of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid yl)phenyl]oxazolidin-2-one (228 mg, 0.4 mM) in dry dichloromethane (5 ml) at 0–4° C., was added pyridine (158 mg, 2.0 mM) followed by dropwise addition of a solution of (S)-(+)-2,3,0-is... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Aromatic halide.Carbamic ester.Carbamic ester.Ether.Ether.Tertiary amine | Ester | C1COCN1.c1ccccc1.C1=CCNCC1.c1cnoc1.c1ccncc1 | null | null | HF | ClCCl | null | 0.166667 | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(N2CC=CCC2)c(F)c1.c1ccncc1>ClCCl>CCCC(C)C.CCOC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b8013c42c714262b5beb18cb83eabd9 | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1>>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 | ClC(COC(=O)N(C1=NOC=C1)C[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC=C1)F)(Cl)Cl>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC=C1)F | O=C(OCC(Cl)(Cl)Cl)[N:6]([CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:13]([c:14]2[cH:15][cH:16][c:17](-[n:18]3[cH:19][cH:20][n:21][cH:22]3)[c:23]([F:24])[cH:25]2)[CH2:12]1)[c:7]1[cH:8][cH:9][o:10][n:11]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][o:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17](-[n:18]2[c... | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 | null | [Zn].[Zn] | O.C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | a049294b02f92114ceaf236099274f4d9678902bbcae42ac105bc5655cd312b0 | bbcae62ba0795429ef75cdf3032894b1bfb636fffd4d1d9ae253b856ebe17489 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1 | 41.8 | [{"value": 41.8, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 5(R)—(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one (crude, 1.7 g, ˜2.5 mM), was stirred in a mixture of acetic acid (40 ml) and water (18 ml) under nitrogen at ambient temperature. Zinc dust (824 mg, 12.5 mM) was added, the mixture stirred 20 minutes, ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether | Secondary amine | null | null | C1COC[NH]1.c1cnoc1.c1ccccc1.c1c[nH]cn1 | HCl | [Zn].[Zn].O.C(C)(=O)O | null | 0.333333 | O=C1O[C@@H](CN(C(=O)OCC(Cl)(Cl)Cl)c2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1>[Zn].[Zn].O.C(C)(=O)O>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a99a9a93cf9f400f97f0c5d45b51636c | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(-n2ccnc2)c(F)c1>>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 | N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.N1(C=NC=C1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CO)=O)F.ClC(COC(=O)NC1=NOC=C1)(Cl)Cl.C(CCC)P(CCCC)CCCC>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC=C1)F | O=C(OCC(Cl)(Cl)Cl)[NH:6][c:7]1[cH:8][cH:9][o:10][n:11]1.O[CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:13]([c:14]2[cH:15][cH:16][c:17](-[n:18]3[cH:19][cH:20][n:21][cH:22]3)[c:23]([F:24])[cH:25]2)[CH2:12]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][o:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17](-[n:18]2[... | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(-n2ccnc2)c(F)c1 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e0e13d8136562ab3a4402091675fa6c04121a11d3fdb7ee25e9b6032261dafdb | 10b7052cc0efeccb39d072f8152672671d4c2ab3cc682ff8244c949613b56722 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[#8;a:4]:[c:5]:[c:6]:1.O-[CH2;D2;+0:7]-[C:8]1-[#8:9]-[C:10](=[O;D1;H0:11])-[#7:12]-[C:13]-1>>[O;D1;H0:11]=[C:10]1-[#7:12]-[C:13]-[C:8](-[CH2;D2;+0:7]-[NH;D2;+0:1]-[c:2]2:[#7;a:3]:[#8;a:4]:[c:5]:[c:6]:2)-[#8:9]-1 | 158.5 | [{"value": 158.5, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 3-(4-Imidazol-1-yl-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (693 mg, 2.5 mM, see WO 96-23788) and 3-(2,2,2-trichloroethyloxycarbonylamino)isoxazole (649 mg, 2.5 mM) were suspended by stirring in dry tetrahydrofuran (25 ml) under nitrogen in an ice-bath. Tributylphosphine (808 mg, 4 mM) was added followed by 1... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary alcohol | Secondary amine | null | null | C1COC[NH]1.c1cnoc1.c1ccccc1.c1c[nH]cn1 | HCl | O1CCCC1 | null | 18 | O=C(Nc1ccon1)OCC(Cl)(Cl)Cl.O=C1O[C@@H](CO)CN1c1ccc(-n2ccnc2)c(F)c1>O1CCCC1>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0a6c4dccdde4393b6c140e0b62c2cd2 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(-n3cnc(CO)c3)c(F)c2)C(=O)O1)c1ccon1>>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 | OCC=1N=CN(C1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1)=O)F.FC(C(=O)O)(F)F>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC(=C1)CO)F | CC(C)(C)OC(=O)[N:6]([CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:13]([c:14]2[cH:15][cH:16][c:17](-[n:18]3[cH:19][n:20][c:21]([CH2:22][OH:23])[cH:24]3)[c:25]([F:26])[cH:27]2)[CH2:12]1)[c:7]1[cH:8][cH:9][o:10][n:11]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][o:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17... | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(-n3cnc(CO)c3)c(F)c2)C(=O)O1)c1ccon1 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 | null | null | ClCCl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1 | 66.9 | [{"value": 66.9, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC(=C1)CO)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3-(4-(4-Hydroxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (360 mg, 0.76 mM) was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (10 ml). After stirring for 30 minutes solvent was evaporated, the residue repeatedly evaporated to dry... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | C1COC[NH]1.c1cnoc1.c1ccccc1.c1c[nH]cn1 | HO- | ClCCl | null | 0.5 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(-n3cnc(CO)c3)c(F)c2)C(=O)O1)c1ccon1>ClCCl>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f117782d22684c3b8f592482d3de22f8 | CC(C)(C)OC(=O)Nc1ccon1.CC1[C@H](O)OC(=O)N1c1ccc(-n2cnc(CO[Si](C)(C)C(C)(C)C)c2)c(F)c1>>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 | N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.[Si](C)(C)(C(C)(C)C)OCC=1N=CN(C1)C1=C(C=C(C=C1)N1C(O[C@H](C1C)O)=O)F.C(C)(C)(C)OC(=O)NC1=NOC=C1.C(CCC)P(CCCC)CCCC>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC(=C1)CO)F | CC(C)(C)O[C:5](=O)[NH:6][c:7]1[cH:8][cH:9][o:10][n:11]1.CC(C)(C)[Si](C)(C)[O:23][CH2:22][c:21]1[n:20][cH:19][n:18](-[c:17]2[cH:16][cH:15][c:14]([N:13]3[C:2](=[O:1])[O:3][C@@H:4](O)[CH:12]3C)[cH:27][c:25]2[F:26])[cH:24]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[cH:8][cH:9][o:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15... | CC(C)(C)OC(=O)Nc1ccon1.CC1[C@H](O)OC(=O)N1c1ccc(-n2cnc(CO[Si](C)(C)C(C)(C)C)c2)c(F)c1 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 6c0ebf30257d466761dd59c00fc89fc3b8c6dc0b79a079d9ca286fa69b6e4969 | b077ddc606c926825b26433f5d2e8bfdb9141185e0e8e12eecae457425ad70fc | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2]-[c:3]:[#7;a:4]:[#8;a:5].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:6]-[C:7]-[c:8](:[#7;a:9]):[c:10]:[#7;a:11].C-[CH;D3;+0:12]1-[#7:13](-[c:14])-[C:15](=[O;D1;H0:16])-[#8:17]-[C@H;D3;+0:18]-1-O>>[#7;a:11]:[c:10]:[c:8](-[C:7]-[OH;D1;+0:6]):[#7;a:9].[#8;a:5]:[#7;a:4]:[c:3]-[#7:2]-[CH2;D2;... | 13.9 | [{"value": 13.9, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C=NC(=C1)CO)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5(R)-hydroxy-methyloxazolidin-2-one (842 mg, 2 mM, see WO 97-31917) and 3-(t-butoxycarbonyl-amino)isoxazole (405 mg, 2.2 mM) were suspended by stirring in dry tetrahydrofuran (15 ml) under nitrogen in an ice-bath. Tributylphosphine (444 mg, 2.2 mM) fol... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Secondary alcohol.TMS ether protective group.Boc | Ether.Primary alcohol | C1COC[NH]1 | C1COC[NH]1 | C1COC[NH]1.c1cnoc1.c1ccccc1.c1c[nH]cn1 | HO- | O1CCCC1 | null | 18 | CC(C)(C)OC(=O)Nc1ccon1.CC1[C@H](O)OC(=O)N1c1ccc(-n2cnc(CO[Si](C)(C)C(C)(C)C)c2)c(F)c1>O1CCCC1>O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2cnc(CO)c2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20a119f7c3384c64958acee5a71e6e1a | Cc1nccn1-c1ccc(N2C[C@H](CN(C(=O)OC(C)(C)C)c3ccon3)OC2=O)cc1F>>Cc1nccn1-c1ccc(N2C[C@H](CNc3ccon3)OC2=O)cc1F | CC=1N(C=CN1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1)=O)F>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C(=NC=C1)C)F | CC(C)(C)OC(=O)[N:15]([CH2:14][C@H:13]1[CH2:12][N:11]([c:10]2[cH:9][cH:8][c:7](-[n:6]3[c:2]([CH3:1])[n:3][cH:4][cH:5]3)[c:25]([F:26])[cH:24]2)[C:22](=[O:23])[O:21]1)[c:16]1[cH:17][cH:18][o:19][n:20]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][C@H:13]([CH2:14][NH:15][c:16]3[cH:17][cH:1... | Cc1nccn1-c1ccc(N2C[C@H](CN(C(=O)OC(C)(C)C)c3ccon3)OC2=O)cc1F | Cc1nccn1-c1ccc(N2C[C@H](CNc3ccon3)OC2=O)cc1F | null | null | ClCCl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(-n2ccnc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1 | 89.9 | [{"value": 89.9, "product": "O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C(=NC=C1)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using essentially the technique of Example 8, but starting from 3-(4-(2-methylimidazol-1-yl)-3-fluorophenyl)-5(R)—(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (510 mg, 1.12 mM), and isolating finally by extraction into dichloromethane gave title product (358 mg).
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ncc[nH]1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HO- | ClCCl | null | null | Cc1nccn1-c1ccc(N2C[C@H](CN(C(=O)OC(C)(C)C)c3ccon3)OC2=O)cc1F>ClCCl>Cc1nccn1-c1ccc(N2C[C@H](CNc3ccon3)OC2=O)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29e51974d6614de39e82ca9826379728 | Cc1ncc[nH]1.O=[N+]([O-])c1ccc(F)c(F)c1>>Cc1nccn1-c1ccc([N+](=O)[O-])cc1F | CC=1NC=CN1.C(C)(C)N(C(C)C)CC.FC=1C=C(C=CC1F)[N+](=O)[O-]>>FC=1C=C(C=CC1N1C(=NC=C1)C)[N+](=O)[O-] | [CH3:1][c:2]1[n:3][cH:4][cH:5][nH:6]1.F[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[F:16]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[F:16] | Cc1ncc[nH]1.O=[N+]([O-])c1ccc(F)c(F)c1 | Cc1nccn1-c1ccc([N+](=O)[O-])cc1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 03854e27c36c357a72ea8df438000a0731263e0929d803025abb25baf2816b5b | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 52 | [{"value": 52.0, "product": "FC=1C=C(C=CC1N1C(=NC=C1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Methylimidazole (9.02 g, 0.11 M) and N,N-diisopropylethylamine (32.2 g, 0.25 M) were dissolved in acetonitrile (160 ml), and 3,4-difluoronitrobenzene (15.9 g, 0.1 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (300 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1ncc[nH]1.c1ccccc1 | c1ncc[nH]1.c1ccccc1 | HF | C(C)#N | null | null | Cc1ncc[nH]1.O=[N+]([O-])c1ccc(F)c(F)c1>C(C)#N>Cc1nccn1-c1ccc([N+](=O)[O-])cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f65b8e12b144f6f95b7f3ce346cb7c1 | Cc1nccn1-c1ccc([N+](=O)[O-])cc1F>>Cc1nccn1-c1ccc(N)cc1F | FC=1C=C(C=CC1N1C(=NC=C1)C)[N+](=O)[O-].C(=O)[O-].[NH4+]>>NC=1C=CC(=C(C1)F)N1C(=NC=C1)C | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7](-[n:6]2[c:2]([CH3:1])[n:3][cH:4][cH:5]2)[c:13]([F:14])[cH:12]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]1[F:14] | Cc1nccn1-c1ccc([N+](=O)[O-])cc1F | Cc1nccn1-c1ccc(N)cc1F | null | [Pd] | CO.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.1 | [{"value": 100.1, "product": "NC=1C=CC(=C(C1)F)N1C(=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 3-Fluoro-4-(2-methylimidazol-1-yl)nitrobenzene (40 g, 0.181 M) was dissolved in a mixture of methanol (200 ml) and tetrahydrofuran (800 ml), cooled to 0° under nitrogen, and treated with ammonium formate (57 g, 0.905 M) followed by palladium on charcoal (10%, 2 g). The mixture was stirred at ambient temperature for 18 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ncc[nH]1.c1ccccc1 | Other | [Pd].CO.O1CCCC1 | null | 18 | Cc1nccn1-c1ccc([N+](=O)[O-])cc1F>[Pd].CO.O1CCCC1>Cc1nccn1-c1ccc(N)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9bb5586c23743ebb695b08c565f0db1 | Cc1nccn1-c1ccc(N)cc1F.O=C(Cl)OCc1ccccc1>>Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F | C([O-])(O)=O.[Na+].N1=CC=CC=C1.NC=1C=CC(=C(C1)F)N1C(=NC=C1)C.ClC(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C(=NC=C1)C | [CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:22][c:23]1[F:24].Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][c:... | Cc1nccn1-c1ccc(N)cc1F.O=C(Cl)OCc1ccccc1 | Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccc(-n2ccnc2)cc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 93.5 | [{"value": 93.5, "product": "C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C(=NC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene (34.25 g, 0.179 M) was dissolved in dry dichloromethane (600 ml) under nitrogen, and cooled to −5°. Pyridine (17.7 g, 0.224 M) was added, followed by benzyl chloroformate (33.7 g, 0.197 M) over 20 minutes. The mixture was stirred and the temperature allowed to rise to ambi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ncc[nH]1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 16 | Cc1nccn1-c1ccc(N)cc1F.O=C(Cl)OCc1ccccc1>ClCCl>Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa26d458b5ff4db1a0e567ab41a29afd | CCCC(=O)OC[C@H]1CO1.Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F>>Cc1nccn1-c1ccc(N2C[C@H](CO)OC2=O)cc1F | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C(=NC=C1)C.C(CCC)[Li].C([C@H]1CO1)OC(CCC)=O>>FC=1C=C(C=CC1N1C(=NC=C1)C)N1C(O[C@H](C1)CO)=O | CCCC(=O)[O:15][CH2:14][C@H:13]1[CH2:12][O:16]1.c1ccc(CO[C:17]([NH:11][c:10]2[cH:9][cH:8][c:7](-[n:6]3[c:2]([CH3:1])[n:3][cH:4][cH:5]3)[c:20]([F:21])[cH:19]2)=[O:18])cc1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][C@H:13]([CH2:14][OH:15])[O:16][C:17]2=[O:18])[cH:19][c:20]1[F:21] | CCCC(=O)OC[C@H]1CO1.Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F | Cc1nccn1-c1ccc(N2C[C@H](CO)OC2=O)cc1F | null | null | CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1 | Protection | OtherReaction | d1ed30032b11013f1920a6a085fa231d8e8ec1012a0450f5d18ac8754f532e37 | 50e808a6fd4bcd271ad07d519e8f6a040c4f51cfbbeb82b3b04cb4f71c7c4a4c | O=C1OCCN1c1ccc(-n2ccnc2)cc1 | C-C-C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[O;D1;H0:6]=[C;H0;D3;+0:7](-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:7]1-[O;H0;D2;+0:5]-[C@@H;D3;+0:3](-[C:2]-[OH;D1;+0:1])-[CH2;D2;+0:4]-[N;H0;D3;+0:8]-1-[c:9](:[c:10]):[c:11] | 44.5 | [{"value": 44.5, "product": "FC=1C=C(C=CC1N1C(=NC=C1)C)N1C(O[C@H](C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 114 ml), over 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Ether | Carbamic ester.Ether.Primary alcohol | C1CO1.c1ccccc1 | C1COC[NH]1 | c1ncc[nH]1.c1ccccc1.C1COC[NH]1 | HO- | CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1 | null | 0.5 | CCCC(=O)OC[C@H]1CO1.Cc1nccn1-c1ccc(NC(=O)OCc2ccccc2)cc1F>CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1>Cc1nccn1-c1ccc(N2C[C@H](CO)OC2=O)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc7b9a5830914572958c7fec79e92c2d | Cc1c[nH]cn1.O=[N+]([O-])c1ccc(F)c(F)c1>>Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1 | CC=1N=CNC1.C(C)(C)N(C(C)C)CC.FC=1C=C(C=CC1F)[N+](=O)[O-]>>FC=1C=C(C=CC1N1C=NC(=C1)C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][nH:4][cH:15][n:16]1.F[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[F:14]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]2[F:14])[cH:15][n:16]1 | Cc1c[nH]cn1.O=[N+]([O-])c1ccc(F)c(F)c1 | Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1>>[C;D1;H3:7]-[c:8]1:[#7;a:9]:[c:10]:[n;H0;D3;+0:11](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]):[c:12]:1 | null | [] | null | null | null | null | 4-Methylimidazole (45.1 g, 0.55 M) and N,N-diisopropylethylamine (161 g, 1.25 M) were dissolved in acetonitrile (800 ml), and 3,4-difluoronitrobenzene (79.5 g, 0.5 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (800 ml),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HF | C(C)#N | null | null | Cc1c[nH]cn1.O=[N+]([O-])c1ccc(F)c(F)c1>C(C)#N>Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00bddb52efa04079bd2ef516bbbdea34 | Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1>>Cc1cn(-c2ccc(N)cc2F)cn1 | FC=1C=C(C=CC1N1C=NC(=C1)C)[N+](=O)[O-].C(=O)[O-].[NH4+]>>NC=1C=CC(=C(C1)F)N1C=NC(=C1)C | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5](-[n:4]2[cH:3][c:2]([CH3:1])[n:14][cH:13]2)[c:11]([F:12])[cH:10]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]2[F:12])[cH:13][n:14]1 | Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1 | Cc1cn(-c2ccc(N)cc2F)cn1 | null | [Pd] | CO.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-n2ccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90.5 | [{"value": 90.5, "product": "NC=1C=CC(=C(C1)F)N1C=NC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 3-Fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g, 0.293 M) was dissolved in a mixture of methanol (200 ml) and tetrahydrofuran (800 ml), cooled to 0° under nitrogen, and treated with ammonium formate (99.3 g, 1.46 M) followed by palladium on charcoal (10%, 2.5 g). The mixture was stirred at ambient temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1c[nH]cn1.c1ccccc1 | Other | [Pd].CO.O1CCCC1 | null | 48 | Cc1cn(-c2ccc([N+](=O)[O-])cc2F)cn1>[Pd].CO.O1CCCC1>Cc1cn(-c2ccc(N)cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f57646be41af44fcb4ffc0a07957ff78 | Cc1cn(-c2ccc(N)cc2F)cn1.O=C(Cl)OCc1ccccc1>>Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1 | C([O-])(O)=O.[Na+].N1=CC=CC=C1.NC=1C=CC(=C(C1)F)N1C=NC(=C1)C.ClC(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C=NC(=C1)C | [CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:20][c:21]2[F:22])[cH:23][n:24]1.Cl[C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]2[F:22])... | Cc1cn(-c2ccc(N)cc2F)cn1.O=C(Cl)OCc1ccccc1 | Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1 | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccc(-n2ccnc2)cc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 92.9 | [{"value": 92.9, "product": "C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C=NC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 5-Amino-2-(4-methylimidazol-1-yl)fluorobenzene (50.6 g, 0.265 M) was dissolved in dry dichloromethane (800 ml) under nitrogen, and cooled to −5°. Pyridine (26.1 g, 0.33 M) was added, followed by benzyl chloroformate (49.9 g, 0.292 M) over 30 minutes. The mixture was stirred and the temperature allowed to rise to ambien... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 16 | Cc1cn(-c2ccc(N)cc2F)cn1.O=C(Cl)OCc1ccccc1>ClCCl>Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d11bd3e8708b472f9e50678f20eb8f7e | CCCC(=O)OC[C@H]1CO1.Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1>>Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC(=O)NC=1C=CC(=C(C1)F)N1C=NC(=C1)C.C(CCC)[Li].C([C@H]1CO1)OC(CCC)=O>>FC=1C=C(C=CC1N1C=NC(=C1)C)N1C(O[C@H](C1)CO)=O | CCCC(=O)[O:13][CH2:12][C@H:11]1[CH2:10][O:14]1.c1ccc(CO[C:15]([NH:9][c:8]2[cH:7][cH:6][c:5](-[n:4]3[cH:3][c:2]([CH3:1])[n:21][cH:20]3)[c:18]([F:19])[cH:17]2)=[O:16])cc1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([N:9]3[CH2:10][C@H:11]([CH2:12][OH:13])[O:14][C:15]3=[O:16])[cH:17][c:18]2[F:19])[cH:20][n:21]1 | CCCC(=O)OC[C@H]1CO1.Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1 | Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1 | null | null | CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1 | Protection | OtherReaction | d1ed30032b11013f1920a6a085fa231d8e8ec1012a0450f5d18ac8754f532e37 | 50e808a6fd4bcd271ad07d519e8f6a040c4f51cfbbeb82b3b04cb4f71c7c4a4c | O=C1OCCN1c1ccc(-n2ccnc2)cc1 | C-C-C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C@H;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[O;D1;H0:6]=[C;H0;D3;+0:7](-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:7]1-[O;H0;D2;+0:5]-[C@@H;D3;+0:3](-[C:2]-[OH;D1;+0:1])-[CH2;D2;+0:4]-[N;H0;D3;+0:8]-1-[c:9](:[c:10]):[c:11] | 33.7 | [{"value": 33.7, "product": "FC=1C=C(C=CC1N1C=NC(=C1)C)N1C(O[C@H](C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 114 ml), over 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Ether | Carbamic ester.Ether.Primary alcohol | C1CO1.c1ccccc1 | C1COC[NH]1 | c1c[nH]cn1.c1ccccc1.C1COC[NH]1 | HO- | CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1 | null | 0.5 | CCCC(=O)OC[C@H]1CO1.Cc1cn(-c2ccc(NC(=O)OCc3ccccc3)cc2F)cn1>CN1C(N(CCC1)C)=O.C(C)(=O)OCC.O1CCCC1>Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f379275646448efaafdb55402752361 | CS(=O)(=O)Cl.Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1>>Cc1cn(-c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)cn1 | FC=1C=C(C=CC1N1C=NC(=C1)C)N1C(O[C@H](C1)CO)=O.CS(=O)(=O)Cl>>FC=1C=C(C=CC1N1C=NC(=C1)C)N1C(O[C@H](C1)COS(=O)(=O)C)=O | Cl[S:14]([CH3:15])(=[O:16])=[O:17].[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([N:9]3[CH2:10][C@H:11]([CH2:12][OH:13])[O:18][C:19]3=[O:20])[cH:21][c:22]2[F:23])[cH:24][n:25]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([N:9]3[CH2:10][C@H:11]([CH2:12][O:13][S:14]([CH3:15])(=[O:16])=[O:17])[O:18][C:19]3=[O:2... | CS(=O)(=O)Cl.Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1 | Cc1cn(-c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)cn1 | null | null | C(C)N(CC)CC.N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C1OCCN1c1ccc(-n2ccnc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 78.2 | [{"value": 78.2, "product": "FC=1C=C(C=CC1N1C=NC(=C1)C)N1C(O[C@H](C1)COS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (11.8 g, 40.5 mM) was stirred in a mixture of pyridine (200 ml) and triethylamine (4.86 g, 48.2 mM) under nitrogen in an ice-bath. Methanesulfonyl chloride (5.16 g, 45 mM) was added dropwise, and the mixture stirrd for 2 hours, allowing the... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1c[nH]cn1.c1ccccc1.C1COC[NH]1 | HCl | C(C)N(CC)CC.N1=CC=CC=C1 | null | 2 | CS(=O)(=O)Cl.Cc1cn(-c2ccc(N3C[C@H](CO)OC3=O)cc2F)cn1>C(C)N(CC)CC.N1=CC=CC=C1>Cc1cn(-c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-922c46907e9948e5a0588459ece71f2f | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1>>CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1 | FC=1C=C(C=CC1N1C[C@H](CC1)NC(=O)OC(C)(C)C)[N+](=O)[O-]>>NC=1C=CC(=C(C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][c:13]([N:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:21]2)[c:19]([F:20])[cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:18][c:19]2[F:20])[CH2:21]1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1 | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCC2)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 | 3-Fluoro-4-(3(S)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)nitrobenzene (33.5 g, 0.103 M) was dissolved in ethyl acetate (500 ml) treated with palladium catalyst (10% on carbon, 5 g) and hydrogenated at atmospheric pressure until the theoretical uptake of gas. After filtration through celite and evaporation, the required ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]C1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1>[Pd].C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7fabcc4ef964da58ab368502f8f1aa2 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl>>CCOC(=O)Nc1ccc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1 | NC=1C=CC(=C(C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C.ClC(=O)OCC>>C(C)OC(=O)NC=1C=CC(=C(C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C | [NH2:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]([F:25])[cH:26]1.Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][... | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl | CCOC(=O)Nc1ccc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1 | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc(N2CCCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | 5-Amino-2-(3(S)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)fluorobenzene (30.4 g, 0.103 M) was dissolved in dry pyridine (150 ml) and cooled under nitrogen with stirring to 0°. Ethyl chloroformate (12.3, 0.113 M) was added dropwise, and the mixture stirred 1 hour at the same temperature. Ice-water (250 ml) was added, and s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]C1 | HCl | N1=CC=CC=C1 | null | 1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl>N1=CC=CC=C1>CCOC(=O)Nc1ccc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7291f44eacd4e79aaeaf6bbf1321c22 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | Cl.C(C)(C)(C)OC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F>>N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F | CC(C)(C)OC(=O)[NH:1][C@H:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][C@H:12]([CH2:13][N:14]([C:15](=[O:16])[O:17][CH2:18][C:19]([Cl:20])([Cl:21])[Cl:22])[c:23]4[cH:24][cH:25][o:26][n:27]4)[O:28][C:29]3=[O:30])[cH:31][c:32]2[F:33])[CH2:34]1>>[NH2:1][C@H:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([... | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | null | null | ClCCl.C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[NH2;D1;+0:1])-[C:3] | 110.8 | [{"value": 110.8, "product": "N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 3-(4-(3(S)-(t-Butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (1.03 g, 1.62 mM) was dissolved in dichloromethane (5 ml) under nitrogen and treated with a solution of hydrogen chloride in ethanol (3.8 M, 25 ml). After stirring 5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HO- | ClCCl.C(C)O | null | 5 | CC(C)(C)OC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>ClCCl.C(C)O>N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-193fe8c4c29b49618063ab36b76ee128 | CC(=O)OC(C)=O.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | C(C)(=O)OC(C)=O.C([O-])(O)=O.[Na+].ClCCl.Cl.N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F.C(C)(=O)OC(C)=O>>C(C)(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][C@H:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][C@H:15]([CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][C:22]([Cl:23])([Cl:24])[Cl:25])[c:26]4[cH:27][cH:28][o:29][n:30]4)[O:31][C:32]3=[O:33])[cH:34][c:35]2[F:36])[CH2:37]1>>[CH3:1][C:2](=[O:3])[NH:4][C@H:5]1[CH2:6][... | CC(=O)OC(C)=O.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | null | null | O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]-[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[#7:4]-[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:8] | 83.7 | [{"value": 83.7, "product": "C(C)(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.74 mM) was dissolved in water (5 ml) and treated with aqueous sodium bicarbonate solution (5 ml) and dichloromethane (10 ml) in an ice-bath. Acetic anhydride... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HO- | O | null | 18 | CC(=O)OC(C)=O.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>O>CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-341b1e2140474ab1a8223849066386e1 | CS(=O)(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>CS(=O)(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C[C@H](CC1)NC(C)=O)F.Cl.N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F.CS(=O)(=O)Cl>>O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C[C@H](CC1)NS(=O)(=O)C)F | Cl[S:2]([CH3:1])(=[O:3])=[O:4].O=C(OCC(Cl)(Cl)Cl)[N:18]([CH2:17][C@H:16]1[CH2:15][N:14]([c:13]2[cH:12][cH:11][c:10]([N:9]3[CH2:8][CH2:7][C@H:6]([NH2:5])[CH2:30]3)[c:28]([F:29])[cH:27]2)[C:25](=[O:26])[O:24]1)[c:19]1[cH:20][cH:21][o:22][n:23]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][C@H:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11]... | CS(=O)(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | CS(=O)(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | null | null | null | Acylation | OtherReaction | bbd18e6fb49a4bc559c23899ae8635a47071e4eb7c9b618fccd4bd4a4f7a8f1e | 40a9b929fd63eebd0cf3adef126c0ea99c6f7d1806b409978918ca12654859fb | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1.[#7:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14].Cl-[S;H0;D4;+0:15](-[C;D1;H3:16])(=[O;D1;H0:17])=[O;D1;H0:18]>>[#7:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[S;H0;D4;+0:15](-[C;D1;H3:16])(=[O;D1;H0:17])=[O;D1;H0:18])-[C:14].[#8:4]-... | null | [] | null | null | null | null | Using essentially the method for the intermediate of Example 12, starting from 3-(4-(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.74 mM) and methanesulfonyl chloride gave the desired product (361 mg).
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether.Primary amine.Sulfonyl halide | Sulfonamide.Secondary amine | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | null | null | null | CS(=O)(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>CS(=O)(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83164a6e6ec64b3992c252649b011b55 | COC(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>COC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C[C@H](CC1)NC(C)=O)F.Cl.N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F.ClC(=O)OC>>COC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F | Cl[C:3]([O:2][CH3:1])=[O:4].O=C(OCC(Cl)(Cl)Cl)[N:18]([CH2:17][C@H:16]1[CH2:15][N:14]([c:13]2[cH:12][cH:11][c:10]([N:9]3[CH2:8][CH2:7][C@H:6]([NH2:5])[CH2:30]3)[c:28]([F:29])[cH:27]2)[C:25](=[O:26])[O:24]1)[c:19]1[cH:20][cH:21][o:22][n:23]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12... | COC(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | COC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | null | null | null | Protection | OtherReaction | c90caf5438ce604b4a3914d30fa30c38615ee7c7c05a7f393121859ef03a8294 | 46c446ef4253fff9fa97aadfb88e30d11a8aa0371309af97c90cdf3c762dbff9 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1.[#7:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14].Cl-[C;H0;D3;+0:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18]>>[#7:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[C;H0;D3;+0:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18])-[C:14].[#8:4]-[C:3]-[C:2]-[N... | null | [] | null | null | null | null | Using essentially the method for the intermediate of Example 12, starting from 3-(4-(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (360 mg, 0.63 mM) and methyl chloroformate gave the desired product (280 mg).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Carbamic ester.Ether.Ether.Primary amine | Carbamic ester.Ether.Secondary amine | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | null | null | null | COC(=O)Cl.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>COC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4da7f0e9e12b4595a727327cc42d2122 | CC(=O)OCC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1>>O=C(CO)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | C(C)(=O)OCC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F.C([O-])([O-])=O.[K+].[K+]>>OCC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F | CC(=O)[O:4][CH2:3][C:2](=[O:1])[NH:5][C@H:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][NH:18][c:19]4[cH:20][cH:21][o:22][n:23]4)[O:24][C:25]3=[O:26])[cH:27][c:28]2[F:29])[CH2:30]1>>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][C@H:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([N:14]3[CH2:... | CC(=O)OCC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | O=C(CO)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]>>[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[OH;D1;+0:1] | 8.1 | [{"value": 8.1, "product": "OCC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-(3(S)-Acetoxyacetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(3-isoxazolylamino-methyl)oxazolidin-2-one (1051 mg, 0.23 mM) and potassium carbonate (300 mg, 2.2 mM) were stirred at ambient temperature under nitrogen in methanol (20 ml) for 20 minutes. The mixture was evaporated to dryness and triturated with water (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HO- | CO | null | null | CC(=O)OCC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1>CO>O=C(CO)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8438e2094b024065b29bce8406738a13 | CC1(C)OC[C@@H](C(=O)Cl)O1.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>O=C([C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1)[C@@H](O)CO | Cl.N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F.CC1(OC[C@H](O1)C(=O)Cl)C>>O[C@H](C(=O)[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F)CO | CC1(C)[O:29][C@H:28]([C:2](Cl)=[O:1])[CH2:30][O:31]1.N[C@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([N:11]3[CH2:12][C@H:13]([CH2:14][N:15](C(=O)OCC(Cl)(Cl)Cl)[c:16]4[cH:17][cH:18][o:19][n:20]4)[O:21][C:22]3=[O:23])[cH:24][c:25]2[F:26])[CH2:27]1>>[O:1]=[C:2]([C@H:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([N... | CC1(C)OC[C@@H](C(=O)Cl)O1.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | O=C([C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1)[C@@H](O)CO | null | null | ClCCl.O.C(C)(=O)OCC.N1=CC=CC=C1 | C-C Coupling | OtherReaction | 13de2f752491f1f90ab3d47f800dc535c12ae9454c8347547636104d36ef988d | e9f3a72c11918a5ea0a2f664201765690c42711e718c78cb9dc173f844744960 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4])-[C:5]-[O;H0;D2;+0:6]-1.Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:7](-[C:8]-[C:9]-[#8:10])-[c:11]1:[#7;a:12]:[#8;a:13]:[c:14]:[c:15]:1.N-[C@@H;D3;+0:16]1-[C:17]-[#7:18](-[c:19])-[C:20]-[C:21]-1>>[#8:10]-[C:9]-[C:8]-[NH;D2;+0:7]-[c:11]1:[#7;a:12]:[#8;a:13]:[c:14]... | 143.5 | [{"value": 143.5, "product": "O[C@H](C(=O)[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.698 mM) in pyridine (5 ml) was treated dropwise with a solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (200 mg, 1.2 mM) in dichloromethane (2 ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Carbamic ester.Ether.Ether.Ether.Primary amine | Ketone.Primary alcohol.Secondary alcohol.Secondary amine | C1COCO1.C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | ClCCl.O.C(C)(=O)OCC.N1=CC=CC=C1 | null | 3 | CC1(C)OC[C@@H](C(=O)Cl)O1.N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>ClCCl.O.C(C)(=O)OCC.N1=CC=CC=C1>O=C([C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1)[C@@H](O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d6e3d9e1bbd4dc7b675038819d674a7 | COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | COCCOC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F>>COCCOC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F | O=C(OCC(Cl)(Cl)Cl)[N:21]([CH2:20][C@H:19]1[CH2:18][N:17]([c:16]2[cH:15][cH:14][c:13]([N:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])[CH2:33]3)[c:31]([F:32])[cH:30]2)[C:28](=[O:29])[O:27]1)[c:22]1[cH:23][cH:24][o:25][n:26]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH... | COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | null | [Zn] | O.C(C)(=O)O | Reduction | Hydrogenolysis of tertiary amines | a049294b02f92114ceaf236099274f4d9678902bbcae42ac105bc5655cd312b0 | bbcae62ba0795429ef75cdf3032894b1bfb636fffd4d1d9ae253b856ebe17489 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | Cl-C(-Cl)(-Cl)-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#8;a:7]:[c:8]:[c:9]:1 | 48.6 | [{"value": 48.6, "product": "COCCOC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3-(4-(3(S)-(2-Methoxyethoxycarbonylamino)pyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one (400 mg, 0.5 mM) was stirred in a mixture of acetic acid (10 ml) and water (2 ml). Zinc dust (203 mg, 3.1 mM) was added, and the mixture stirred 30 minutes at ambi... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Carbamic ester.Ether | Secondary amine | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | [Zn].O.C(C)(=O)O | null | 0.5 | COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>[Zn].O.C(C)(=O)O>COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23028e4a040e4c08b0b8bcec767ce4a0 | CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1.COCCOC(=O)Cl>>COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C[C@H](CC1)NC(C)=O)F.Cl.O1C(NCC1)=O.ClC(=O)OCCOC>>COCCOC(=O)N[C@@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NOC=C1)=O)F | CC(=O)[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][C@H:19]([CH2:20][NH:21][c:22]4[cH:23][cH:24][o:25][n:26]4)[O:27][C:28]3=[O:29])[cH:30][c:31]2[F:32])[CH2:33]1.Cl[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][... | CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1.COCCOC(=O)Cl | COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 | null | null | null | Protection | OtherReaction | e22c5dd7a91378b0f864a608026f7ca9dbe6de6e35b14b4321ab84a7ebb2d59d | 76db93014d141d40094d77040ae6ee87abae0748bc6fac225e4ba0f878a6fa51 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | C-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[#7:5]-[C:4]-[C:2](-[NH;D2;+0:1]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:3] | null | [] | null | null | null | null | Using essentially the method for the intermediate of Example 12, starting from 3-(4(3(S)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (419 mg, 0.73 mM) and 2-methoxyethyl chloroformate (450 mg, 3.27 mM) gave the title compound... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amide | Carbamic ester | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | null | null | null | CC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1.COCCOC(=O)Cl>>COCCOC(=O)N[C@H]1CCN(c2ccc(N3C[C@H](CNc4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a870c76f4f7a49d2b266d70d50a35915 | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1>>CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1 | FC=1C=C(C=CC1N1C[C@@H](CC1)NC(=O)OC(C)(C)C)[N+](=O)[O-]>>NC=1C=CC(=C(C1)F)N1C[C@@H](CC1)NC(=O)OC(C)(C)C | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][c:13]([N:12]2[CH2:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:21]2)[c:19]([F:20])[cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:18][c:19]2[F:20])[CH2:21]1 | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1 | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1 | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCCC2)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 | 3-Fluoro-4-(3(R)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)nitrobenzene (32.7 g, 0.101 M) was dissolved in ethyl acetate (500 ml) treated with palladium catalyst (10% on carbon, 7.5 g) and hydrogenated at atmospheric pressure until the theoretical uptake of gas. After filtration through celite and evaporation, the require... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]C1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc([N+](=O)[O-])cc2F)C1>[Pd].C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db8d6f655da64d2d908ee0e7543d2edf | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl>>CCOC(=O)Nc1ccc(N2CC[C@@H](NC(=O)OC(C)(C)C)C2)c(F)c1 | NC=1C=CC(=C(C1)F)N1C[C@@H](CC1)NC(=O)OC(C)(C)C.ClC(=O)OCC>>C(C)OC(=O)NC=1C=CC(=C(C1)F)N1C[C@@H](CC1)NC(=O)OC(C)(C)C | [NH2:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]([F:25])[cH:26]1.Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@@H:14]([NH:15][C:16](=[O:17])[O:18... | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl | CCOC(=O)Nc1ccc(N2CC[C@@H](NC(=O)OC(C)(C)C)C2)c(F)c1 | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc(N2CCCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | 5-Amino-2-(3(R)-(t-butoxycarbonyl)aminopyrrolidin-1-yl)fluorobenzene (27.33 g, 0.093 M) was dissolved in dry pyridine (150 ml) and cooled under nitrogen with stirring to 0°. Ethyl chloroformate (11.01, 0.102 M) was added dropwise, and the mixture stirred 30 minutes at the same temperature. Ice-water (250 ml) was added,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]C1 | HCl | N1=CC=CC=C1 | null | 1 | CC(C)(C)OC(=O)N[C@@H]1CCN(c2ccc(N)cc2F)C1.CCOC(=O)Cl>N1=CC=CC=C1>CCOC(=O)Nc1ccc(N2CC[C@@H](NC(=O)OC(C)(C)C)C2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9c26683fe6c4386af383530af265d04 | COC(=O)Cl.N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>COC(=O)N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | O1N=C(C=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)N1C[C@H](CC1)NC(C)=O)F.Cl.N[C@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F.ClC(=O)OC>>COC(=O)N[C@H]1CN(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OCC(Cl)(Cl)Cl)C1=NOC=C1)=O)F | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][C@@H:6]1[CH2:7][CH2:8][N:9]([c:10]2[cH:11][cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][N:18]([C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])[c:27]4[cH:28][cH:29][o:30][n:31]4)[O:32][C:33]3=[O:34])[cH:35][c:36]2[F:37])[CH2:38]1>>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@@H:6]1... | COC(=O)Cl.N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | COC(=O)N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 | null | null | null | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(N2CCCC2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[#7:5]-[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[#7:5]-[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4])-[C:9] | null | [] | null | null | null | null | Using essentially the method for the intermediate of Example 12, starting from 3-(4-(3(R)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (1.61 g, 2.81 mM) and methyl chloroformate gave the desired product (1.61 g).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | C1CC[NH]C1.c1ccccc1.C1COC[NH]1.c1cnoc1 | HCl | null | null | null | COC(=O)Cl.N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1>>COC(=O)N[C@@H]1CCN(c2ccc(N3C[C@H](CN(C(=O)OCC(Cl)(Cl)Cl)c4ccon4)OC3=O)cc2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c9980eebe4241d8beb60ce8c9ed9491 | Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1>>Cc1cc(NC[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H](O)CO)CC4)c(F)c3)C(=O)O2)on1 | CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=CC(=NO1)C)=O)F)C.FC(C(=O)O)(F)F.O>>O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=CC(=NO1)C)=O)F)CO | CC(C)(C)OC(=O)[N:5]([c:4]1[cH:3][c:2]([CH3:1])[n:34][o:33]1)[CH2:6][C@H:7]1[CH2:8][N:9]([c:10]2[cH:11][c:12]([F:13])[c:14]([C:15]3=[CH:16][CH2:17][N:18]([C:19](=[O:20])[C@H:21]4[O:22]C(C)(C)[O:24][CH2:23]4)[CH2:25][CH2:26]3)[c:27]([F:28])[cH:29]2)[C:30](=[O:31])[O:32]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][C@H:7]2[CH... | Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1 | Cc1cc(NC[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H](O)CO)CC4)c(F)c3)C(=O)O2)on1 | null | null | ClCCl | Reduction | OtherReaction | 21805618214ccb41a25d3034b12a6fd79a6d9d8a6037af10492407dcf33cacf7 | ffa6253082d9dbf6cf19ebffce6d492731bc65d4c853366f501d6ae12d0c7ff0 | O=C1O[C@@H](CNc2ccno2)CN1c1ccc(C2=CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#8;a:6]:[#7;a:7]:[c:8]:[c:9]:1.C-C1(-C)-[O;H0;D2;+0:10]-[C:11](-[C:12](=[O;D1;H0:13])-[#7:14](-[C:15])-[C:16]-[C:17]=[C:18])-[C:19]-[O;H0;D2;+0:20]-1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#8;a:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:18]=[C:17]-[C:16]-[#7:14](-[C:1... | 58.5 | [{"value": 58.5, "product": "O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=CC(=NO1)C)=O)F)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxycarbonyl)-3-methylisoxazol-5-ylaminomethyl)oxazolidin-2-one (400 mg, 0.65 mM) was dissolved in dichloromethane (6 ml) and treated with trifluoroacetic acid (6 ml) at 0°. After stirring for 30 minutes at... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Boc | Primary alcohol.Secondary alcohol.Secondary amine | C1COCO1 | null | c1cnoc1.C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1 | HO- | ClCCl | null | 0.5 | Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1>ClCCl>Cc1cc(NC[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H](O)CO)CC4)c(F)c3)C(=O)O2)on1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b05ae7b448e84b5da1a807abc403583a | CC(=O)OC(C)=O.CC1[C@H](O)OC(=O)N1c1cc(F)c(C2=CCN(Cc3ccccc3)CC2)c(F)c1>>CC(=O)O[C@@H]1OC(=O)N(c2cc(F)c(C3=CCN(Cc4ccccc4)CC3)c(F)c2)C1C | C(C1=CC=CC=C1)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1C)O)=O)F.C(C)(=O)OC(C)=O.C([O-])(O)=O.[Na+].C(=O)=O>>C(C1=CC=CC=C1)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1C)OC(C)=O)=O)F | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][C@@H:5]1[O:6][C:7](=[O:8])[N:9]([c:10]2[cH:11][c:12]([F:13])[c:14]([C:15]3=[CH:16][CH2:17][N:18]([CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[CH2:26][CH2:27]3)[c:28]([F:29])[cH:30]2)[CH:31]1[CH3:32]>>[CH3:1][C:2](=[O:3])[O:4][C@@H:5]1[O:6][C:7](=[O:8])[N:9]([c:10]2[cH:11][c:12... | CC(=O)OC(C)=O.CC1[C@H](O)OC(=O)N1c1cc(F)c(C2=CCN(Cc3ccccc3)CC2)c(F)c1 | CC(=O)O[C@@H]1OC(=O)N(c2cc(F)c(C3=CCN(Cc4ccccc4)CC3)c(F)c2)C1C | null | CN(C1=CC=NC=C1)C | ClCCl.C(C)N(CC)CC | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | O=C1OCCN1c1ccc(C2=CCN(Cc3ccccc3)CC2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[#8:10]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:9]-[C:8]1-[#8:10]-[C:5](=[O;D1;H0:4])-[#7:6]-[C:7]-1 | null | [] | null | null | 1 | HOUR | 3-(4-(1-Benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxy-methyloxazolidin-2-one (20 g, 50 mM, see WO 97-30995) was suspended by stirring in dry dichloromethane (400 ml) under nitrogen at 0°, and treated with triethylamine (5.5 g, 54.4 mM) and 4-dimethylaminopyridine (0.3 g, 2.7 mM). Acetic anhydrid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.C(C)N(CC)CC | null | 1 | CC(=O)OC(C)=O.CC1[C@H](O)OC(=O)N1c1cc(F)c(C2=CCN(Cc3ccccc3)CC2)c(F)c1>CN(C1=CC=NC=C1)C.ClCCl.C(C)N(CC)CC>CC(=O)O[C@@H]1OC(=O)N(c2cc(F)c(C3=CCN(Cc4ccccc4)CC3)c(F)c2)C1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22258999a9794eeb9e7c66c8a3b3f6bc | CC(=O)OC[C@H]1CN(c2cc(F)c(N3CC=CCC3)c(F)c2)C(=O)O1.CC1(C)OC[C@@H](C(=O)Cl)O1>>CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1 | C([O-])(O)=O.[Na+].Cl.N1(CC=CCC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COC(C)=O)=O)F.N1=CC=CC=C1.CC1(OC[C@H](O1)C(=O)Cl)C>>CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COC(C)=O)=O)F)C | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([N:17]3[CH2:16][CH:15]=[CH:14][CH2:28][CH2:27]3)[c:29]([F:30])[cH:31]2)[C:32](=[O:33])[O:34]1.Cl[C:18](=[O:19])[C@@H:20]1[CH2:21][O:22][C:23]([CH3:24])([CH3:25])[O:26]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:... | CC(=O)OC[C@H]1CN(c2cc(F)c(N3CC=CCC3)c(F)c2)C(=O)O1.CC1(C)OC[C@@H](C(=O)Cl)O1 | CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1 | null | null | ClCCl | Acylation | OtherReaction | 115011b272b81985dd093f7f56502b57120f8c4356c62cbf5171001e0928c74a | 7da20c2e2c34d1dd982a91b3333ed3c480165fa1ae9d2aa385b5b9d2065f54c9 | O=C([C@@H]1COCO1)N1CC=C(c2ccc(N3CCOC3=O)cc2)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[#8:4]-[C:5]-[#8:6]-[C:7]-1.[F;D1;H0:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[N;H0;D3;+0:12]1-[C:13]-[C:14]=[CH;D2;+0:15]-[C:16]-[C:17]-1):[c:18](-[F;D1;H0:19]):[c:20]>>[F;D1;H0:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[C;H0;D3;+0:15]1=[C:14]-[C:13]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:... | 97.7 | [{"value": 97.7, "product": "CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COC(C)=O)=O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride (14.5 g, 37.3 mM) was suspended in dry dichloromethane (300 ml) under nitrogen at 0°, and treated with pyridine (9.78 g, 0.12 M). A solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (9.59 g, 75.6 mM) in di... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amine | Tertiary amide | c1ccccc1.C1=CC[NH]CC1 | c1ccccc1.C1=CC[NH]CC1 | C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1.C1COCO1 | HCl | ClCCl | null | 3 | CC(=O)OC[C@H]1CN(c2cc(F)c(N3CC=CCC3)c(F)c2)C(=O)O1.CC1(C)OC[C@@H](C(=O)Cl)O1>ClCCl>CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1d02d975dd644069dccecc38e8a3752 | CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1>>CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1 | C([O-])(O)=O.[Na+].CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COC(C)=O)=O)F)C.C([O-])([O-])=O.[K+].[K+].C(C)(=O)O>>CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CO)=O)F)C | CC(=O)[O:22][CH2:21][C@H:20]1[CH2:19][N:18]([c:17]2[cH:16][c:14]([F:15])[c:13]([C:12]3=[CH:11][CH2:10][N:9]([C:7]([C@@H:6]4[CH2:5][O:4][C:2]([CH3:1])([CH3:3])[O:31]4)=[O:8])[CH2:30][CH2:29]3)[c:27]([F:28])[cH:26]2)[C:24](=[O:25])[O:23]1>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([C:7](=[O:8])[N:9]2[CH2:10][CH:11]=[C:1... | CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1 | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C([C@@H]1COCO1)N1CC=C(c2ccc(N3CCOC3=O)cc2)CC1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 92.6 | [{"value": 92.6, "product": "CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CO)=O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one (8.64 g, 18 mM) was suspended in methanol (350 ml) and stirred at ambient temperature under nitrogen. Potassium carbonate (3.73 g, 27 mM) was added, and the mixture stirred for 20 min... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COCO1.C1=CC[NH]CC1.c1ccccc1.C1COC[NH]1 | HO- | CO | null | null | CC(=O)OC[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1>CO>CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a4596b4ef68147ca86a0a4abc61ea774 | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1.CS(=O)(=O)Cl>>CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1 | C([O-])(O)=O.[Na+].C(C)N(CC)CC.CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CO)=O)F)C.CS(=O)(=O)Cl>>CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COS(=O)(=O)C)=O)F)C | [CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([C:7](=[O:8])[N:9]2[CH2:10][CH:11]=[C:12]([c:13]3[c:14]([F:15])[cH:16][c:17]([N:18]4[CH2:19][C@H:20]([CH2:21][OH:22])[O:27][C:28]4=[O:29])[cH:30][c:31]3[F:32])[CH2:33][CH2:34]2)[O:35]1.Cl[S:23]([CH3:24])(=[O:25])=[O:26]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([C:7](=[O:8])... | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1.CS(=O)(=O)Cl | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C([C@@H]1COCO1)N1CC=C(c2ccc(N3CCOC3=O)cc2)CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 93 | [{"value": 93.0, "product": "CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COS(=O)(=O)C)=O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (2.19 g, 5 mM) was dissolved in dry dichloromethane (40 ml) under nitrogen at 0°, and treated with triethylamine (0.81 g, 8 mM). Methanesulfonyl chloride (0.687 g, 6 mM) was added, an... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1COCO1.C1=CC[NH]CC1.c1ccccc1.C1COC[NH]1 | HCl | ClCCl | null | 2 | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](CO)OC4=O)cc3F)CC2)O1.CS(=O)(=O)Cl>ClCCl>CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69112d76987b4639bb687f96e5828388 | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1.Cc1cc(NC(=O)OC(C)(C)C)on1>>Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1 | O.[H-].[Na+].CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)COS(=O)(=O)C)=O)F)C.C(C)(C)(C)OC(=O)NC1=CC(=NO1)C>>CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=CC(=NO1)C)=O)F)C | CS(=O)(=O)O[CH2:6][C@H:7]1[CH2:8][N:9]([c:10]2[cH:11][c:12]([F:13])[c:14]([C:15]3=[CH:16][CH2:17][N:18]([C:19](=[O:20])[C@@H:21]4[CH2:22][O:23][C:24]([CH3:25])([CH3:26])[O:27]4)[CH2:28][CH2:29]3)[c:30]([F:31])[cH:32]2)[C:33](=[O:34])[O:35]1.[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[... | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1.Cc1cc(NC(=O)OC(C)(C)C)on1 | Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 265ef1e08e67559db2c6466ec57d49384021675b5ee5915b78896cc146e360fe | 79c8a28d011f5aa01e3d0ecfb27300b52e98d06fe0c13860d213baa12603b24a | O=C([C@@H]1COCO1)N1CC=C(c2ccc(N3C[C@H](CNc4ccno4)OC3=O)cc2)CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-1.[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[NH;D2;+0:15]-[c:16]1:[#8;a:17]:[#7;a:18]:[c:19]:[c:20]:1>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:12]-[C:13](=[O;D1;H0:14])-[N;H0;D3;+0:15](-[CH2;D2;+0:... | 68 | [{"value": 68.0, "product": "CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=CC(=NO1)C)=O)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Sodium hydride (60% in oil, 72 mg, 1.8 mM) was suspended in dry N,N-dimethylformamide (3 ml), cooled to 0° under nitrogen, and a solution of 5-(t-butoxycarbonylamino)-3-methylisoxazole (356 mg, 1.8 mM) in N,N-dimethylformamide (3 ml) added. After stirring for 10 minutes, a solution of 3-(4(1-(2,2-dimethyl-1,3-dioxolan-... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Carbamic ester | Carbamic ester | null | null | c1cnoc1.C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1.C1COCO1 | MsOH.HO- | CN(C=O)C | null | 0.166667 | CC1(C)OC[C@@H](C(=O)N2CC=C(c3c(F)cc(N4C[C@H](COS(C)(=O)=O)OC4=O)cc3F)CC2)O1.Cc1cc(NC(=O)OC(C)(C)C)on1>CN(C=O)C>Cc1cc(N(C[C@H]2CN(c3cc(F)c(C4=CCN(C(=O)[C@@H]5COC(C)(C)O5)CC4)c(F)c3)C(=O)O2)C(=O)OC(C)(C)C)on1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49445dd07c0c488a8eefec53cc2c09c9 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnccn1>>O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1 | CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NC=CN=C1)=O)F)C.FC(C(=O)O)(F)F.O>>O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=NC=CN=C1)=O)F)CO | CC(C)(C)OC(=O)[N:20]([CH2:19][C@H:18]1[CH2:17][N:16]([c:15]2[cH:14][c:12]([F:13])[c:11]([C:10]3=[CH:9][CH2:8][N:7]([C:2](=[O:1])[C@H:3]4[O:4]C(C)(C)[O:6][CH2:5]4)[CH2:34][CH2:33]3)[c:31]([F:32])[cH:30]2)[C:28](=[O:29])[O:27]1)[c:21]1[cH:22][n:23][cH:24][cH:25][n:26]1>>[O:1]=[C:2]([C@@H:3]([OH:4])[CH2:5][OH:6])[N:7]1[CH... | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnccn1 | O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1 | null | null | ClCCl | Reduction | OtherReaction | 21805618214ccb41a25d3034b12a6fd79a6d9d8a6037af10492407dcf33cacf7 | ffa6253082d9dbf6cf19ebffce6d492731bc65d4c853366f501d6ae12d0c7ff0 | O=C1O[C@@H](CNc2cnccn2)CN1c1ccc(C2=CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1.C-C1(-C)-[O;H0;D2;+0:11]-[C:12](-[C:13](=[O;D1;H0:14])-[#7:15](-[C:16])-[C:17]-[C:18]=[C:19])-[C:20]-[O;H0;D2;+0:21]-1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c:10]:1.[C:19]=[C:18]-[C:17]... | 102 | [{"value": 102.0, "product": "O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=NC=CN=C1)=O)F)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)pyrazin-2-ylaminomethyl)oxazolidin-2-one (400 mg, 0.65 mM) was dissolved in dichloromethane (4 ml) and treated with trifluoroacetic acid (4 ml) at ambient temperature. After stirring for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Boc | Primary alcohol.Secondary alcohol.Secondary amine | C1COCO1 | null | C1=CC[NH]CC1.c1ccccc1.C1COC[NH]1.c1cnccn1 | HO- | ClCCl | null | 0.5 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnccn1>ClCCl>O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ffcee3aef244c46ad73a59445cc6d99 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cnccn1>>CC(C)(C)OC(=O)Nc1cnccn1 | O.C(=O)=O.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=CN=C1.[OH-].[Na+]>>C(C)(C)(C)OC(=O)NC1=NC=CN=C1 | CC(C)(C)OC(=O)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]1[cH:10][n:11][cH:12][cH:13][n:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][n:11][cH:12][cH:13][n:14]1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cnccn1 | CC(C)(C)OC(=O)Nc1cnccn1 | null | null | CO | Reduction | Boc amine deprotection | bcc011127fa718807e0d7b0a671a01c099e47bed90492c043e6bf345999375d4 | aa4c6868eefa4924ddc45fff3928b49191d6faed20391b19e19c13cdcb9fcecf | c1cnccn1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1 | 74.2 | [{"value": 74.2, "product": "C(C)(C)(C)OC(=O)NC1=NC=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Di-(t-butoxycarbonyl)aminopyrazine (2.1 g, 7.1 mM) in methanol (50 ml) under nitrogen, was treated with aqueous sodium hydroxide (2.5 M, 2.84 ml, 7.1 mM), and stirred at ambient temperature for 2 hours. The mixture was neutralised by the addition of water (25 ml) and solid carbon dioxide, then methanol evaporated. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Substituted dicarboximide.Boc | Carbamic ester | null | null | c1cnccn1 | HO- | CO | null | 2 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cnccn1>CO>CC(C)(C)OC(=O)Nc1cnccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de80b7472ee04bd9950c8d3bee94cb3e | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncccn1>>CC(C)(C)OC(=O)Nc1ncccn1 | C(C)(C)(C)OC(=O)N(C1=NC=CC=N1)C(=O)OC(C)(C)C.O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=NC=CN=C1)=O)F)CO>>C(C)(C)(C)OC(=O)NC1=NC=CC=N1 | CC(C)(C)OC(=O)[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]1[n:10][cH:11][cH:12][cH:13][n:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[n:10][cH:11][cH:12][cH:13][n:14]1 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncccn1 | CC(C)(C)OC(=O)Nc1ncccn1 | null | null | null | Reduction | Boc amine deprotection | bcc011127fa718807e0d7b0a671a01c099e47bed90492c043e6bf345999375d4 | aa4c6868eefa4924ddc45fff3928b49191d6faed20391b19e19c13cdcb9fcecf | c1cncnc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8])-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]:[c:13] | 93.1 | [{"value": 93.1, "product": "C(C)(C)(C)OC(=O)NC1=NC=CC=N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(Di-(t-butoxycarbonyl)amino)pyrimidine (5.2 g, 17.6 mM) was hydrolysed by essentially the technique for the appropriate intermediate of Example 22 to give the title product as a white solid (3.2 g). NMR (DMSO-d6) δ: 1.43 (s, 9H); 7.08 (t, 1H); 8.57 (d, 2H); 9.91 (s, 1H). MS (ESP): 196 (MH+) for C9H13N3O2
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Substituted dicarboximide.Boc | Carbamic ester | null | null | c1cncnc1 | HO- | null | null | null | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncccn1>>CC(C)(C)OC(=O)Nc1ncccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6b7e39aa88a417b83bfa4edaf24c448 | CC(C)(C)OC(=O)Nc1cccnn1.CCOC(C)=O.O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1>>CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cccnn1 | C(C)(=O)OCC.O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CNC1=NC=CN=C1)=O)F)CO.C(C)(C)(C)OC(=O)NC=1N=NC=CC1.N1=CC=NC=C1>>CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C=1N=NC=CC1)=O)F)C | c1c(N[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])n[n:43][cH:42][cH:41]1.O=[C:27](OC[CH3:29])[CH3:28].c1c[n:44][c:39]([NH:8][CH2:9][C@H:10]2[CH2:11][N:12]([c:13]3[cH:14][c:15]([F:16])[c:17]([C:18]4=[CH:19][CH2:20][N:21]([C:22](=[O:23])[C@H:24]([CH2:25][OH:26])[OH:30])[CH2:31][CH2:32]4)[c:33]([F:34])[cH:35]3)[C:36](... | CC(C)(C)OC(=O)Nc1cccnn1.CCOC(C)=O.O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cccnn1 | null | null | ClCCl | C-C Coupling | OtherReaction | c5ba0f7e15d8e3a3b5b98fcc455712de80b9c2b2a09075c666bfe4b570a053a7 | 86941341f8f073d628e0b5cb6e9e80aa617b5da7369c36c9025ccca7468c35bd | O=C([C@@H]1COCO1)N1CC=C(c2ccc(N3C[C@H](CNc4cccnn4)OC3=O)cc2)CC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-O-C-[CH3;D1;+0:3].[#8:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[c:8]1:[cH;D2;+0:9]:n:c:c:[n;H0;D2;+0:10]:1.[C:11]=[C:12]-[C:13]-[#7:14](-[C:15](=[O;D1;H0:16])-[C:17](-[OH;D1;+0:18])-[C:19]-[OH;D1;+0:20])-[C:21].[C;D1;H3:22]-[C:23](-[C;D1;H3:24])(-[C;D1;H3:25])-[#8:26]-[C;H0;D3;+0:27](=[O;D1;H0:28])-N-... | null | [] | null | null | null | null | Essentially the technique for the appropriate intermediate of Example 22 was used, but substituting 3-(t-butoxycarbonylamino)pyridazine (293 mg, 1.5 mM) for the pyrazine analogue. The reaction was carried out by heating at 45° for 4 hour, and the chromatography was carried out with a gradient from 0% to 100% ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Primary alcohol.Secondary alcohol.Secondary amine.Boc | Carbamic ester.Ether.Ether.Ether.Boc | c1ccnnc1.c1cnccn1 | C1COCO1.c1ccnnc1 | C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1.C1COCO1.c1ccnnc1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)Nc1cccnn1.CCOC(C)=O.O=C([C@@H](O)CO)N1CC=C(c2c(F)cc(N3C[C@H](CNc4cnccn4)OC3=O)cc2F)CC1>ClCCl>CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cccnn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-113e2b98e3cf49ecb1df7262ef21fec9 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnsn1>>O=C([C@@H](O)CO)N1CC=C(c2ccc(N3C[C@H](CNc4cnsn4)OC3=O)cc2F)CC1 | CC1(OC[C@H](O1)C(=O)N1CC=C(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NSN=C1)=O)F)C.N.C(C)OCC>>O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NSN=C1)=O)F)CO | CC(C)(C)OC(=O)[N:19]([CH2:18][C@H:17]1[CH2:16][N:15]([c:14]2[cH:13][cH:12][c:11]([C:10]3=[CH:9][CH2:8][N:7]([C:2](=[O:1])[C@H:3]4[O:4]C(C)(C)[O:6][CH2:5]4)[CH2:32][CH2:31]3)[c:29]([F:30])[cH:28]2)[C:26](=[O:27])[O:25]1)[c:20]1[cH:21][n:22][s:23][n:24]1>>[O:1]=[C:2]([C@@H:3]([OH:4])[CH2:5][OH:6])[N:7]1[CH2:8][CH:9]=[C:1... | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnsn1 | O=C([C@@H](O)CO)N1CC=C(c2ccc(N3C[C@H](CNc4cnsn4)OC3=O)cc2F)CC1 | null | null | O.FC(C(=O)O)(F)F | Reduction | OtherReaction | 21805618214ccb41a25d3034b12a6fd79a6d9d8a6037af10492407dcf33cacf7 | ffa6253082d9dbf6cf19ebffce6d492731bc65d4c853366f501d6ae12d0c7ff0 | O=C1O[C@@H](CNc2cnsn2)CN1c1ccc(C2=CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5]1:[#7;a:6]:[#16;a:7]:[#7;a:8]:[c:9]:1.C-C1(-C)-[O;H0;D2;+0:10]-[C:11](-[C:12](=[O;D1;H0:13])-[#7:14](-[C:15])-[C:16]-[C:17]=[C:18])-[C:19]-[O;H0;D2;+0:20]-1>>[#8:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[c:5]1:[#7;a:6]:[#16;a:7]:[#7;a:8]:[c:9]:1.[C:18]=[C:17]-[C:16]-[#7:1... | 46 | [{"value": 46.0, "product": "O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NSN=C1)=O)F)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.6, "product": "O[C@H](C(=O)N1CC=C(CC1)C1=C(C=C(C=C1)N1C(O[C@H](C1)CNC1=NSN=C1)=O)F)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 3-(4(1-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)-5(R)-(N-(t-butoxycarbonyl)-1,2,5-thiadiazol-3-ylamino-methyl)oxazolidin-2-one (580 mg, 0.96 mM) in trifluoroacetic acid (2 ml) was warmed at 60° for 2 minutes and then kept at ambient temperature for 10 minute... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Boc | Primary alcohol.Secondary alcohol.Secondary amine | C1COCO1 | null | C1=CC[NH]CC1.c1ccccc1.C1COC[NH]1.c1cnsn1 | HO- | O.FC(C(=O)O)(F)F | null | 0.166667 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2ccc(C3=CCN(C(=O)[C@@H]4COC(C)(C)O4)CC3)c(F)c2)C(=O)O1)c1cnsn1>O.FC(C(=O)O)(F)F>O=C([C@@H](O)CO)N1CC=C(c2ccc(N3C[C@H](CNc4cnsn4)OC3=O)cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d36e2869281c45db888da5180557e81a | CS(=O)(=O)OC[C@H]1CN(c2ccc(C3=CCOCC3)c(F)c2)C(=O)O1.Nc1ncco1>>O=C1O[C@@H](CNc2ncco2)CN1c1ccc(C2=CCOCC2)c(F)c1 | NC=1OC=CN1.[Li]CCCC.CS(=O)(=O)OC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C=1CCOCC1)F>>O1C(=NC=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C=1CCOCC1)F | CS(=O)(=O)O[CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:13]([c:14]2[cH:15][cH:16][c:17]([C:18]3=[CH:19][CH2:20][O:21][CH2:22][CH2:23]3)[c:24]([F:25])[cH:26]2)[CH2:12]1.[NH2:6][c:7]1[n:8][cH:9][cH:10][o:11]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][NH:6][c:7]2[n:8][cH:9][cH:10][o:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17]([C:18]... | CS(=O)(=O)OC[C@H]1CN(c2ccc(C3=CCOCC3)c(F)c2)C(=O)O1.Nc1ncco1 | O=C1O[C@@H](CNc2ncco2)CN1c1ccc(C2=CCOCC2)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=C1O[C@@H](CNc2ncco2)CN1c1ccc(C2=CCOCC2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-1.[NH2;D1;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:1>>[O;D1;H0:5]=[C:4]1-[#7:6]-[C:7]-[C:2](-[CH2;D2;+0:1]-[NH;D2;+0:8]-[c:9]2:[#7;a:10]:[c:11]:[c:12]:[#8;a:13]:2)-[#8:3]-1 | 4.6 | [{"value": 4.6, "product": "O1C(=NC=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C=1CCOCC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.5, "product": "O1C(=NC=C1)NC[C@H]1CN(C(O1)=O)C1=CC(=C(C=C1)C=1CCOCC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred partial solution of 2-aminooxazole (169 mg, 2.0 mmol) in dry THF (10 ml), cooled to −78° C., under argon, was added slowly n-BuLi (1.33M, 1.5 ml, 2.0 mmol), followed after 1 h by 5(R)-methylsulfonyloxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (see Example 41; 371 mg, 11.0 mo... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | C1COC[NH]1.c1cocn1.c1ccccc1.C1=CCOCC1 | MsOH.HO- | C1CCOC1 | null | null | CS(=O)(=O)OC[C@H]1CN(c2ccc(C3=CCOCC3)c(F)c2)C(=O)O1.Nc1ncco1>C1CCOC1>O=C1O[C@@H](CNc2ncco2)CN1c1ccc(C2=CCOCC2)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d74723608cfc44a6a532e662cf53482e | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCNCC3)c(F)c2)C(=O)O1)c1ccon1.O=C(O)CCO>>CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)CCO)CC3)c(F)c2)C(=O)O1)c1ccon1 | C(C)(C)N(C(C)C)CC.OCCC(=O)O.Cl.N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1)=O)F.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C>>OCCC(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1)=O)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][C@H:10]1[CH2:11][N:12]([c:13]2[cH:14][c:15]([F:16])[c:17]([C:18]3=[CH:19][CH2:20][NH:21][CH2:27][CH2:28]3)[c:29]([F:30])[cH:31]2)[C:32](=[O:33])[O:34]1)[c:35]1[cH:36][cH:37][o:38][n:39]1.O[C:22](=[O:23])[CH2:24][CH2:25][OH:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])... | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCNCC3)c(F)c2)C(=O)O1)c1ccon1.O=C(O)CCO | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)CCO)CC3)c(F)c2)C(=O)O1)c1ccon1 | null | null | CN(C=O)C.O.C(C)(=O)OCC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | d656df32b00a004c70c973d75e36f2d650ed6cd124473afe5d288b56673af478 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C1O[C@@H](CNc2ccon2)CN1c1ccc(C2=CCNCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]-[C:6]1=[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]=[C:6](-[c:5])-[C:11]-[C:10]-1 | 74.2 | [{"value": 74.2, "product": "OCCC(=O)N1CC=C(CC1)C1=C(C=C(C=C1F)N1C(O[C@H](C1)CN(C(=O)OC(C)(C)C)C1=NOC=C1)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 3-hydroxypropionic acid (45 mg, 0.5 mM) in N,N dimethylformamide (2 ml) was added 3-(4-(1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)(N-(t-butoxy-carbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride (256 mg, 0.5 mM, reference example 10), and O-benzotriazol-1-yl-N,N,N′,N′-tetrameth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1=CCNCC1 | C1=CC[NH]CC1 | C1COC[NH]1.c1ccccc1.C1=CC[NH]CC1.c1cnoc1 | HO- | CN(C=O)C.O.C(C)(=O)OCC | null | 18 | CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCNCC3)c(F)c2)C(=O)O1)c1ccon1.O=C(O)CCO>CN(C=O)C.O.C(C)(=O)OCC>CC(C)(C)OC(=O)N(C[C@H]1CN(c2cc(F)c(C3=CCN(C(=O)CCO)CC3)c(F)c2)C(=O)O1)c1ccon1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57fb327c6424452aa0687ad11e5803ae | C=CCCC(=O)OCC.CO>>CCOC(=O)CCC(O)CO | CO.ClCCl.C(CCC=C)(=O)OCC.C[N+]1(CCOCC1)[O-].O1CCCC1>>C(C)OC(CCC(CO)O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]=[CH2:10].C[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]([OH:9])[CH2:10][OH:11] | C=CCCC(=O)OCC.CO | CCOC(=O)CCC(O)CO | null | [Os](=O)(=O)(=O)=O | O | Functional Group Addition | OtherReaction | c4a40a66274762b24d70fbc71a664366a7dd0ce72b0653bfa87fec1b71f1ada7 | 690c9d42246ffbb4581574bfdc64a18ac90793546cae2896d9fa698566b02594 | null | C-[OH;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[CH;D2;+0:7]=[CH2;D1;+0:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[CH;D3;+0:7](-[O;D1;H1:9])-[CH2;D2;+0:8]-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "C(C)OC(CCC(CO)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of ethyl pent-4-enoate (11.7 g, 91.3 mmol) in tetrahydrofuran (420 mL) and water (40 mL) is treated with osmium tetroxide (1.0 g, 4.2 mmol) and 4-methylmorpholine N-oxide (32.5 mL, 50% in water) at room temperature and stired for 3 h, at which time no more starting material is detectable by TLC (SiO2, 2% met... | 10.6084/m9.figshare.5104873.v1 | null | Allyl.Methanol | Primary alcohol.Secondary alcohol | null | null | null | null | [Os](=O)(=O)(=O)=O.O | null | 3 | C=CCCC(=O)OCC.CO>[Os](=O)(=O)(=O)=O.O>CCOC(=O)CCC(O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7d7674ad59d4f66821709f6ec79f701 | CC(C)(C)[Si](C)(C)Cl.CCOC(=O)CCC(O)CO>>CCOC(=O)CCC(O)CO[Si](C)(C)C(C)(C)C | C(C)OC(CCC(CO)O)=O.C(C)(C)(C)[Si](C)(C)Cl.C(C)N(CC)CC>>C(C)OC(CCC(CO[Si](C)(C)C(C)(C)C)O)=O | Cl[Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]([OH:9])[CH2:10][OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH:8]([OH:9])[CH2:10][O:11][Si:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)[Si](C)(C)Cl.CCOC(=O)CCC(O)CO | CCOC(=O)CCC(O)CO[Si](C)(C)C(C)(C)C | null | CN(C1=CC=NC=C1)C | ClCCl | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | 18 | HOUR | A solution of 4,5-dihydroxy-pentanoic acid ethyl ester, (7 g, 43.2 mmol) and 4-dimethylaminopyridine (0.2 g, 1.73 mmol) in dichloromethane (145 mL) at room temperature under nitrogen is treated with tert-butyl-dimethyl-silyl chloride (7.8 g, 51.85 mmol) and triethylamine (6.9 mL, 47.52 mmol) and stirred 18 h. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 18 | CC(C)(C)[Si](C)(C)Cl.CCOC(=O)CCC(O)CO>CN(C1=CC=NC=C1)C.ClCCl>CCOC(=O)CCC(O)CO[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da68cd3ff7414fb3bec916908e6cbd70 | O=CCOCc1ccccc1.[Cl][Mg][CH2]Cc1ccccc1>>OC(CCc1ccccc1)COCc1ccccc1 | C(C1=CC=CC=C1)OCC=O.C1(=CC=CC=C1)CC[Mg]Cl.Cl>>C(C1=CC=CC=C1)OCC(CCC1=CC=CC=C1)O | [O:1]=[CH:2][CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[Cl][Mg][CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[OH:1][CH:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | O=CCOCc1ccccc1.[Cl][Mg][CH2]Cc1ccccc1 | OC(CCc1ccccc1)COCc1ccccc1 | null | null | O1CCCC1 | C-C Coupling | Grignard from aldehyde to alcohol | fec51c6fbcca146daa523566f7e8d93ddaee19549cd7ca45d0ef939f0a2ea2fd | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(CCCCOCc2ccccc2)cc1 | [#8:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[Cl]-[Mg]-[CH2;D2;+0:5]-[C:6]-[c:7]>>[#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[CH2;D2;+0:5]-[C:6]-[c:7] | null | [] | -78 | CELSIUS | 1 | HOUR | Benzyloxy-acetaldehyde (3.0 g, 20 mmol) is dissolved in tetrahydrofuran (200 mL), cooled to −78° C. This solution is treated with phenylethylmagnesium chloride (1.0 M in tetrahydrofuran, 24 mL, 24 mmol), and stirred for one hour. The mixture is allowed to warm to room temperature and stirred for 4 h. The mixture is tre... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | Mg | O1CCCC1 | -78 | 1 | O=CCOCc1ccccc1.[Cl][Mg][CH2]Cc1ccccc1>O1CCCC1>OC(CCc1ccccc1)COCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16f69d03a0444212bf99c7b0fcc0694b | OC(CCc1ccccc1)COCc1ccccc1>>O=C(CCc1ccccc1)COCc1ccccc1 | C(C1=CC=CC=C1)OCC(CCC1=CC=CC=C1)O.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>C(C1=CC=CC=C1)OCC(CCC1=CC=CC=C1)=O | [OH:1][CH:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | OC(CCc1ccccc1)COCc1ccccc1 | O=C(CCc1ccccc1)COCc1ccccc1 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CCc1ccccc1)COCc1ccccc1 | [#8:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[C:6]>>[#8:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | 68.3 | [{"value": 68.0, "product": "C(C1=CC=CC=C1)OCC(CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.3, "product": "C(C1=CC=CC=C1)OCC(CCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 1-benzyloxy-4-phenyl-butan-2-ol, (8.4 g, 32.8 mmol) in dichloromethane (400 mL) is added a mixture of pyridinium chlorochromate (14.1 g, 65.6 mmol) with SiO2 (14 g) and stirred for 3 h at room temperature. The mixture is filtered through a pad of SiO2 and concentrated to provide the title compound 5.7 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1 | null | ClCCl | null | 3 | OC(CCc1ccccc1)COCc1ccccc1>ClCCl>O=C(CCc1ccccc1)COCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d0268180b8e432b931028249aef5399 | COC(=O)C=C(COC(C)=O)c1ccccc1>>COC(=O)CC(COC(C)=O)c1ccccc1 | COC(C=C(COC(C)=O)C1=CC=CC=C1)=O>>COC(CC(COC(C)=O)C1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH2:7][O:8][C:9]([CH3:10])=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([CH2:7][O:8][C:9]([CH3:10])=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | COC(=O)C=C(COC(C)=O)c1ccccc1 | COC(=O)CC(COC(C)=O)c1ccccc1 | null | [Pd] | C(C)(=O)O | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]-[C;H0;D3;+0:6](=[CH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11])-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]-[CH;D3;+0:6](-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11])-[c:12](:[c:13]):[c:14] | 92.2 | [{"value": 92.0, "product": "COC(CC(COC(C)=O)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "COC(CC(COC(C)=O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-acetoxy-3-phenyl-but-2-enoic acid methyl ester, (1.0 g, 4.27 mmol), 10 wt. % palladium on activated carbon (1.0 g), acetic acid (10 mL) is shaken under an atmosphere of hydrogen on a Parr® Shaker. The mixture is filtered through a pad of Celite® and rinsed with methanol. The solution is concentrated in v... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | null | [Pd].C(C)(=O)O | null | null | COC(=O)C=C(COC(C)=O)c1ccccc1>[Pd].C(C)(=O)O>COC(=O)CC(COC(C)=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a2ba70e58064169870e248f2da8307c | CC(=O)OC(C)=O.O=C(CO)c1ccccc1>>CC(=O)OCC(=O)c1ccccc1 | OCC(=O)C1=CC=CC=C1.N1=CC=CC=C1.C(C)(=O)OC(C)=O>>O=C(COC(C)=O)C1=CC=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CC(=O)OC(C)=O.O=C(CO)c1ccccc1 | CC(=O)OCC(=O)c1ccccc1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5](-[c:6])-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:8]-[C:7]-[C:5](=[O;D1;H0:4])-[c:6] | null | [] | null | null | 18 | HOUR | A solution of 2-hydroxyaceto-phenone (10 g, 73.4 mmol), pyridine (17.4 g, 220.2 mmol), dichloromethane (734 mL), 3 crystals of 4-dimethylaminopyridine is cooled to −78° C. To this solution is added acetic anhydride (13.9 mL, 146.9 mmol) then warmed to room temperature and stirred for 18 h. The mixture is washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 18 | CC(=O)OC(C)=O.O=C(CO)c1ccccc1>CN(C1=CC=NC=C1)C.ClCCl>CC(=O)OCC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6312909cd6b54e469cf5f87a6f5c5ccc | C1CCOC1.COc1cccc(B(O)O)c1.O=C([O-])[O-]>>COc1cccc(C2=CC(=O)OC2)c1 | COC=1C=C(C=CC1)B(O)O.O1CCCC1.C([O-])([O-])=O.[Na+].[Na+]>>COC=1C=C(C=CC1)C1=CC(OC1)=O | C1O[CH2:9][CH2:8][CH2:13]1.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14]1.[O-][C:10](=[O:11])[O-:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2=[CH:9][C:10](=[O:11])[O:12][CH2:13]2)[cH:14]1 | C1CCOC1.COc1cccc(B(O)O)c1.O=C([O-])[O-] | COc1cccc(C2=CC(=O)OC2)c1 | null | null | O.CCOCC | C-C Coupling | OtherReaction | 4a192cbea9ba043a51e841b0bf9e368987ce473b85da8b493b8d29ea84f93c7c | c99f842bfe9bb6b5968ac8d5ede8ff531166903bbd3c279723b586c2b026a58c | O=C1C=C(c2ccccc2)CO1 | C1-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-1.O-B(-O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-])=[O;D1;H0:11]>>[O;D1;H0:11]=[C;H0;D3;+0:10]1-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[CH2;D2;+0:3]-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | 3-Methoxy-phenyl-boronic acid (2.16 g, 14.2 mmol) and trifluoromethansulfonic acid 5-oxo-2,5-dihydro-furan-3-yl ester1 (3 g, 12.92 mmol) in tetrahydrofuran (110 mL) is dissolved and de-gassed for 15 min. To this solution is added sodium carbonate (3.42 g, 32.3 mmol) in water (10 mL) and tetrakis-triphenylphosphine-pall... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boronic acid | Ester | C1CCOC1.c1ccccc1 | c1ccccc1.C1=CCOC1 | c1ccccc1.C1=CCOC1 | HO-.B | O.CCOCC | null | null | C1CCOC1.COc1cccc(B(O)O)c1.O=C([O-])[O-]>O.CCOCC>COc1cccc(C2=CC(=O)OC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-538069ed8cf7470bb3d92d6da33140e4 | COc1cccc(C2=CC(=O)OC2)c1>>COc1cccc(C2COC(=O)C2)c1 | COC=1C=C(C=CC1)C1=CC(OC1)=O>>COC=1C=C(C=CC1)C1CC(OC1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2=[CH:13][C:11](=[O:12])[O:10][CH2:9]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][C:11](=[O:12])[CH2:13]2)[cH:14]1 | COc1cccc(C2=CC(=O)OC2)c1 | COc1cccc(C2COC(=O)C2)c1 | null | [Ni] | O1CCCC1 | Reduction | Hydrogenation (double to single) | 25b2459a210963b1d1bc72ac31a5797c48861107ebf4c28e1d8551120eb0174a | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | O=C1CC(c2ccccc2)CO1 | [O;D1;H0:1]=[C:2]1-[#8:3]-[C:4]-[C;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])=[CH;D2;+0:9]-1>>[O;D1;H0:1]=[C:2]1-[#8:3]-[C:4]-[CH;D3;+0:5](-[c:6](:[c:7]):[c:8])-[CH2;D2;+0:9]-1 | null | [] | null | null | 18 | HOUR | To a solution of 4-(3-methoxy-phenyl)-5H-furan-2-one, (1.9 g, 10 mmol) in tetrahydrofuran (100 mL) and is added Raney nickel (7.6 g, 50% suspension in water) the mixture is stirred under hydrogen (ambient pressure) 18 h at room temperature. The mixture is filtered through Celite® and concentrated in vacuo to yield the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | C1=CCOC1 | C1CCOC1 | c1ccccc1.C1CCOC1 | null | [Ni].O1CCCC1 | null | 18 | COc1cccc(C2=CC(=O)OC2)c1>[Ni].O1CCCC1>COc1cccc(C2COC(=O)C2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf969af1f15b46b8932210d8fa0e3faf | C=O.O=C(O)CCC(=O)c1ccccc1>>O=C1CC(C(=O)c2ccccc2)CO1 | Cl.C(C1=CC=CC=C1)(=O)CCC(=O)O.C([O-])([O-])=O.[K+].[K+].C=O>>C(C1=CC=CC=C1)(=O)C1CC(OC1)=O | O=[CH2:13].[O:1]=[C:2]([CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[OH:14]>>[O:1]=[C:2]1[CH2:3][CH:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][O:14]1 | C=O.O=C(O)CCC(=O)c1ccccc1 | O=C1CC(C(=O)c2ccccc2)CO1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 548ce3a24061a9426117acfb891ea6e22051a93a44e9d3a89018c1444cd65550 | 7a98ce1c9a86125996763be2cdbb32fd0aad9a3de06f1e4cb4bcad4d1e31a866 | O=C1CC(C(=O)c2ccccc2)CO1 | O=[CH2;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[C:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[O;D1;H0:2]=[C:3]1-[C:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[c:9])-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-1 | 84.1 | [{"value": 84.1, "product": "C(C1=CC=CC=C1)(=O)C1CC(OC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | A mixture of 3-benzoylpropionic acid (18 g, 101 mmol), potassium carbonate (10 g, 75 mmol), water (45 mL) and formaldehyde (36% in water, 7.8 mL, 101 mmol) is stirred at room temperature for 5 days, warmed to 30° C. and stirred for 3 additional days. To this mixture is added concentrated hydrochloric acid (10 mL) to pH... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Carboxylic acid.Ketone | Ketone.Ester | null | C1CCOC1 | C1CCOC1.c1ccccc1 | HO- | O | null | 120 | C=O.O=C(O)CCC(=O)c1ccccc1>O>O=C1CC(C(=O)c2ccccc2)CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b00c056f9bc46b2b56d079b375aa7cc | O=C1CC(C(=O)c2ccccc2)CO1>>O=C1CC(Cc2ccccc2)CO1 | C(C1=CC=CC=C1)(=O)C1CC(OC1)=O>>C(C1=CC=CC=C1)C1CC(OC1)=O | O=[C:5]([CH:4]1[CH2:3][C:2](=[O:1])[O:13][CH2:12]1)[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][O:13]1 | O=C1CC(C(=O)c2ccccc2)CO1 | O=C1CC(Cc2ccccc2)CO1 | null | [Pd](Cl)Cl | CO | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | O=C1CC(Cc2ccccc2)CO1 | O=[C;H0;D3;+0:1](-[C:2]1-[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[C:7]-1)-[c:8](:[c:9]):[c:10]>>[O;D1;H0:6]=[C:5]1-[#8:4]-[C:3]-[C:2](-[CH2;D2;+0:1]-[c:8](:[c:9]):[c:10])-[C:7]-1 | 54 | [{"value": 30.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.0, "product": "C(C1=CC=CC=C1)C1CC(OC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "C(C1=CC=CC=C1)C1CC(OC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 4-benzoyl-dihydro-furan-2-one (5 g) in methanol (250 mL) in a Parr® reactor is added palladium chloride (0.25 g). The mixture is shaken under hydrogen (50 PSI) for 3 h. The mixture is filtered through a pad of Celite® (40 g) and the filtrate concentrated. The residue is chromatographed on SiO2 (10% eth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | C1CCOC1.c1ccccc1 | Other | [Pd](Cl)Cl.CO | null | 3 | O=C1CC(C(=O)c2ccccc2)CO1>[Pd](Cl)Cl.CO>O=C1CC(Cc2ccccc2)CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d114d255e7104c6da67a11cdcb488991 | COC(=O)C=C(CCc1ccccc1)COCc1ccccc1>>O=C1CC(CCc2ccccc2)CO1 | COC(C=C(CCC1=CC=CC=C1)COCC1=CC=CC=C1)=O>>C(CC1=CC=CC=C1)C1CC(OC1)=O | CO[C:2](=[O:1])[CH:3]=[C:4]([CH2:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[CH2:13][O:14]Cc1ccccc1>>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][O:14]1 | COC(=O)C=C(CCc1ccccc1)COCc1ccccc1 | O=C1CC(CCc2ccccc2)CO1 | null | [Pd] | C(C)(=O)O | Miscellaneous | OtherReaction | b38b4b1c02fe272e65b2f3389d8a5d68d2583b601d44b6423f4b77a78532abbc | 116b574453683d5a4bdd21420703492a263525e2ce7c81f840c82a3ae5861983 | O=C1CC(CCc2ccccc2)CO1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C:5]-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1)-[C:7]-[C:8]>>[C:8]-[C:7]-[CH;D3;+0:4]1-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-1 | 62 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "C(CC1=CC=CC=C1)C1CC(OC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.7, "product": "C(CC1=CC=CC=C1)C1CC(OC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 3-benzyloxymethyl-5-phenyl-pent-2-enoic acid methyl ester, (3.2 g, 13.5 mmol), 10 wt. % palladium on activated carbon (3.2 g), and acetic acid (40 mL) is placed in a Parr® Shaker under hydrogen (45 PSI) and shaken 4 h. The mixture is filtered through a pad of Celite® and concentrated in vacuo. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester | c1ccccc1 | C1CCOC1 | C1CCOC1.c1ccccc1 | HO- | [Pd].C(C)(=O)O | null | 4 | COC(=O)C=C(CCc1ccccc1)COCc1ccccc1>[Pd].C(C)(=O)O>O=C1CC(CCc2ccccc2)CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c72e25f5b65a41dcba6135476c5cb717 | COC(=O)CC(COC(C)=O)c1ccccc1>>O=C1CC(c2ccccc2)CO1 | COC(CC(COC(C)=O)C1=CC=CC=C1)=O>>C1(=CC=CC=C1)C1CC(OC1)=O | CC(=O)O[CH2:11][CH:4]([CH2:3][C:2](=[O:1])[O:12]C)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]1[CH2:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][O:12]1 | COC(=O)CC(COC(C)=O)c1ccccc1 | O=C1CC(c2ccccc2)CO1 | null | null | O1CCOCC1.S(O)(O)(=O)=O | Heteroatom Alkylation and Arylation | OtherReaction | 1eb30051237b9a9c112cba40b15fc51dc9f11aa40c9ecefc25cbf35639ec14e3 | af7b9f47dc4b2fc77b69f8751f8aca252642781fb348457551bd8b9e82cb1ea1 | O=C1CC(c2ccccc2)CO1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[c:6])-[CH2;D2;+0:7]-O-C(-C)=O>>[O;D1;H0:3]=[C:2]1-[C:4]-[C:5](-[c:6])-[CH2;D2;+0:7]-[O;H0;D2;+0:1]-1 | null | [] | 45 | CELSIUS | null | null | A solution of 4-acetoxy-3-phenyl-butyric acid methyl ester, (4.5 g, 19.2 mmol) in 1,4-dioxane (29 mL) and sulfuric acid (29 mL) is stirred at room temperature for one hour then heated at 45° C. for 18 h. Volatile solvents are evaporated and the residue is extracted with toluene. The combined organic extracts are extrac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | C1CCOC1 | C1CCOC1.c1ccccc1 | HO- | O1CCOCC1.S(O)(O)(=O)=O | 45 | null | COC(=O)CC(COC(C)=O)c1ccccc1>O1CCOCC1.S(O)(O)(=O)=O>O=C1CC(c2ccccc2)CO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1c79f3c05474aeeb8f26acb075fcc5f | BrCc1ccccc1.O=C1CC[C@H](CO)O1>>O=C1CC[C@H](COCc2ccccc2)O1 | OC[C@H]1CCC(O1)=O.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC[C@H]1CCC(O1)=O | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[C:2]1[CH2:3][CH2:4][C@H:5]([CH2:6][OH:7])[O:15]1>>[O:1]=[C:2]1[CH2:3][CH2:4][C@H:5]([CH2:6][O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[O:15]1 | BrCc1ccccc1.O=C1CC[C@H](CO)O1 | O=C1CC[C@H](COCc2ccccc2)O1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | O=C1CC[C@H](COCc2ccccc2)O1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a solution of (R)-5-hydroxymethyl-dihydro-furan-2-one (5 g, 43.06 mmol) in tetrahydrofuran (130 mL) is added sodium hydride (2.58 g, 60% oil dispersion, 64.59 mmol) and tetrabutylammonium iodide (spatula) and stirred for 30 min. To the mixture is added benzyl bromide (6.18 mL, 51.67 mmol) and refluxed for 3 h. The m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CCOC1.c1ccccc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1 | null | 0.5 | BrCc1ccccc1.O=C1CC[C@H](CO)O1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.O1CCCC1>O=C1CC[C@H](COCc2ccccc2)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7582e27591542cc9b1ae12d23cd68f8 | C1=CCOC1.CCOC(=O)c1ccc(N)cc1.CO>>CCOC(=O)c1ccc(C2COC(OC)C2)cc1 | O1CC=CC1.CO.N(=O)[O-].[Na+].NC1=CC=C(C(=O)OCC)C=C1.F[B-](F)(F)F.[H+]>>C(C)OC(C1=CC=C(C=C1)C1COC(C1)OC)=O | [CH:10]1=[CH:16][CH2:13][O:12][CH2:11]1.N[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:18][cH:17]1.[OH:14][CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]2[CH2:11][O:12][CH:13]([O:14][CH3:15])[CH2:16]2)[cH:17][cH:18]1 | C1=CCOC1.CCOC(=O)c1ccc(N)cc1.CO | CCOC(=O)c1ccc(C2COC(OC)C2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O | Heteroatom Alkylation and Arylation | OtherReaction | 92bf3b05a573c5156daa7944b55a6f4a501751c1d52e64a6fe4316c5a196873f | f469fd03cbc40f6c6beb133d84759a6c97775bd51e33713e2b0a83765aaed9d6 | c1ccc(C2CCOC2)cc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[CH2;D2;+0:10]-1.[C;D1;H3:11]-[OH;D1;+0:12]>>[C;D1;H3:11]-[O;H0;D2;+0:12]-[CH;D3;+0:10]1-[#8:6]-[C:7]-[CH;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[CH2;D2;+0:9]-1 | null | [] | null | null | 30 | MINUTE | A solution of sodium nitrite (1.67 g, 24.2 mmol) in water (14 mL) is added dropwise to an ice cold mixture of ethyl 4-aminobenzoate (4.0 g, 24.2 mmol) and tetrafluoroboric acid (7.8 mL, 48%, 59.78 mmol) and stirred for 30 min. Methanol (28.5 mL), 2,5-dihydrofuran (3.66 mL, 48.4 mmol) and palladium(II) acetate (70 mg, 0... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Methanol | Ether.Ether | C1=CCOC1.c1ccccc1 | c1ccccc1.C1CCOC1 | c1ccccc1.C1CCOC1 | Other | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O | null | 0.5 | C1=CCOC1.CCOC(=O)c1ccc(N)cc1.CO>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O>CCOC(=O)c1ccc(C2COC(OC)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-533050e5611d4df3b3683b95512ad06a | CCOC(=O)c1ccc(C2COC(OC)C2)cc1>>CCOC(=O)c1ccc(C2COC(=O)C2)cc1 | B(F)(F)F.CCOCC.C(C)OC(C1=CC=C(C=C1)C1COC(C1)OC)=O.ClC1=CC(=CC=C1)C(=O)OO.S(=O)(=O)([O-])[O-].[Mg+2]>>C(C)OC(C1=CC=C(C=C1)C1COC(C1)=O)=O | C[O:14][CH:13]1[O:12][CH2:11][CH:10]([c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][cH:16]2)[CH2:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]2[CH2:11][O:12][C:13](=[O:14])[CH2:15]2)[cH:16][cH:17]1 | CCOC(=O)c1ccc(C2COC(OC)C2)cc1 | CCOC(=O)c1ccc(C2COC(=O)C2)cc1 | null | null | ClCCl.CCOCC | Miscellaneous | OtherReaction | 085d774928066e35d93cb222c267f7f821821dd755d9236646e6e48ceaf5e735 | 97b24fecaee23e50630ebc9f63250b1199fc3b89bfb58c5e3f91a716697df2a3 | O=C1CC(c2ccccc2)CO1 | C-[O;H0;D2;+0:1]-[CH;D3;+0:2]1-[#8:3]-[C:4]-[C:5]-[C:6]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[#8:3]-[C:4]-[C:5]-[C:6]-1 | null | [] | null | null | 30 | MINUTE | To a solution of 75% 3-chloroperbenzoic acid (2.7 g, 11.76 mmol) in dichloromethane (35 mL) is added magnesium sulfate (2.0 g, 16.6 mmol) and the mixture stirred for 30 min. Solids are removed by filtration and the filtrate treated with borontrifluoride etherate (0.5 mL, 3.92 mmol) and 4-(5-methoxy-tetrahydro-furan-3-y... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ester | C1CCOC1 | C1CCOC1 | c1ccccc1.C1CCOC1 | Other | ClCCl.CCOCC | null | 0.5 | CCOC(=O)c1ccc(C2COC(OC)C2)cc1>ClCCl.CCOCC>CCOC(=O)c1ccc(C2COC(=O)C2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9cd95b0817f941b7980e1a771dfd5afc | COc1cccc(C2COC(=O)C2)c1.NN=C(c1ccccc1)c1ccccc1>>COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 | [OH-].[Na+].C[Al](C)C.C(C1=CC=CC=C1)(C1=CC=CC=C1)=NN.COC=1C=C(C=CC1)C1CC(OC1)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NNC(CC(CO)C1=CC(=CC=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][O:10][C:12](=[O:13])[CH2:11]2)[cH:29]1.[NH2:14][N:15]=[C:16]([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([CH2:9][OH:10])[CH2:11][C:12](=[O:13])[NH:14][N:15]=[C:16]([c:17... | COc1cccc(C2COC(=O)C2)c1.NN=C(c1ccccc1)c1ccccc1 | COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 | null | null | ClCCl | Acylation | OtherReaction | b8a23b98df076582c6ccf65d2fa0a607c6e4a438dc08de2b74f0b8df816010b9 | 4f0ad68b197489e3f881c141fd71ea18b0259bfa9821e2e07f771c18398bca2e | O=C(CCc1ccccc1)NN=C(c1ccccc1)c1ccccc1 | [NH2;D1;+0:1]-[#7:2]=[C:3](-[c:4])-[c:5].[O;D1;H0:6]=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[O;H0;D2;+0:11]-1>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[C:8]-[C:9]-[C:10]-[OH;D1;+0:11])-[NH;D2;+0:1]-[#7:2]=[C:3](-[c:4])-[c:5] | null | [] | null | null | 30 | MINUTE | Trimethylaluminum (12 mL, 2 M in hexane, 24 mmol) is added dropwise to a solution of benzophenone hydrazone (1.57 g, 8 mmol) in dichloromethane (20 mL) at room temperature and under nitrogen. After the mixture is stirred for 30 min, 4-(3-methoxy-phenyl)-dihydro-furan-2-one, (1.54 g, 8 mmol) in dichloromethane (5 mL) is... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ester | Hydrazone amide.Primary alcohol | C1CCOC1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | ClCCl | null | 0.5 | COc1cccc(C2COC(=O)C2)c1.NN=C(c1ccccc1)c1ccccc1>ClCCl>COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f77ff8a164647918c5589fae50e5da4 | COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1.CS(=O)(=O)Cl>>COc1cccc(C(COS(C)(=O)=O)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)=NNC(CC(CO)C1=CC(=CC=C1)OC)=O.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NNC(=O)CC(COS(=O)(=O)C)C1=CC(=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([CH2:9][OH:10])[CH2:15][C:16](=[O:17])[NH:18][N:19]=[C:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:33]1.Cl[S:11]([CH3:12])(=[O:13])=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]([CH2:9][O:10][S:11]([CH3:12])(... | COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1.CS(=O)(=O)Cl | COc1cccc(C(COS(C)(=O)=O)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 | null | CN(C1=CC=NC=C1)C | ClCCl.N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C(CCc1ccccc1)NN=C(c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 18 | HOUR | A solution of 4-hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide and (1.7 g, 4.38 mmol) and 4-dimethylaminopyridine (26 mg, 0.22 mmol) in pyridine (15 mL) is cooled to 0° C. treated with methanesulfonyl chloride (0.4 mL, 5.25 mmol) and stirred 18 h at room temperature. The mixture is diluted with dic... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.ClCCl.N1=CC=CC=C1 | null | 18 | COc1cccc(C(CO)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1.CS(=O)(=O)Cl>CN(C1=CC=NC=C1)C.ClCCl.N1=CC=CC=C1>COc1cccc(C(COS(C)(=O)=O)CC(=O)NN=C(c2ccccc2)c2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea0419dad2e9469f94ef59108d4767eb | COc1cccc(C2CC(=O)N(N=C(c3ccccc3)c3ccccc3)C2)c1>>COc1cccc(C2CC(=O)N(N)C2)c1 | Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)=NN1C(CC(C1)C1=CC(=CC=C1)OC)=O>>NN1C(CC(C1)C1=CC(=CC=C1)OC)=O | c1ccc(C(c2ccccc2)=[N:13][N:12]2[C:10](=[O:11])[CH2:9][CH:8]([c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15]3)[CH2:14]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][C:10](=[O:11])[N:12]([NH2:13])[CH2:14]2)[cH:15]1 | COc1cccc(C2CC(=O)N(N=C(c3ccccc3)c3ccccc3)C2)c1 | COc1cccc(C2CC(=O)N(N)C2)c1 | null | null | O | Miscellaneous | OtherReaction | 7e1efe12b4f68485be3498906d5138c74be459dede0ebe793a15fcc1e8fcb70a | 6c88cb03fc77e3bec3cbf5390374412e6c7f2a982339fdc2958a00062af29c1d | O=C1CC(c2ccccc2)CN1 | [C:1]-[#7:2](-[N;H0;D2;+0:3]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:4](=[O;D1;H0:5])-[C:6]>>[C:1]-[#7:2](-[NH2;D1;+0:3])-[C:4](=[O;D1;H0:5])-[C:6] | null | [] | null | null | null | null | Concentrated hydrochloric acid (0.35 mL) is added to a suspension of 1-(benzhydrylidene-amino)-4-(3-methoxy-phenyl)-pyrrolidin-2-one, (0.8 g, 2.16 mmol) in water (17 mL) and refluxed for one hour. The mixture is concentrated in vacuo and water azeotroped away using ethanol and toluene. The residue is dissolved in metha... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | Acylhydrazine | c1ccccc1.c1ccccc1 | null | c1ccccc1.C1CC[NH]C1 | Other | O | null | null | COc1cccc(C2CC(=O)N(N=C(c3ccccc3)c3ccccc3)C2)c1>O>COc1cccc(C2CC(=O)N(N)C2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e9f813cdbf440e28165af869bd6f9f1 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl>>O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 | O.ClCCCC(=O)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)=NN.N1=CC=CC=C1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NNC(CCCCl)=O | [NH2:7][N:8]=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Cl:6]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[NH:7][N:8]=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl | O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e1e032c84f30f6c93cf688039f3cc62747a034583f6175d60f7a0e21b27b6064 | 863011cce7fa0c660ac34aaac93028d203ff6ffc4b5a2233660e564db26255d2 | N=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[#7:6]=[C:7](-[c:8])-[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]=[C:7](-[c:8])-[c:9] | null | [] | null | null | 0.5 | HOUR | 4-Chlorobutyryl chloride (57 mL, 510 mmol) is added to a solution of benzophenone hydrazone (100 g, 510 mmol) and pyridine (41 mL, 510 mmol) in anhydrous dichloromethane (520 mL) under nitrogen at a rate that maintains a gentle reflux throughout the addition. The mixture is stirred for 0.5 h and poured into water (1 L)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone | Hydrazone amide | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 0.5 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl>ClCCl>O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb6b605148f94f1c8e3a24b3c564aca0 | C=O.Cl.Fc1cccc2ccccc12>>Fc1ccc(CCl)c2ccccc12 | FC1=CC=CC2=CC=CC=C12.C=O.P(O)(O)(O)=O.Cl.C(C)(=O)O>>ClCC1=CC=C(C2=CC=CC=C12)F | O=[CH2:6].[ClH:7].[F:1][c:2]1[cH:3][cH:4][cH:5][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][Cl:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | C=O.Cl.Fc1cccc2ccccc12 | Fc1ccc(CCl)c2ccccc12 | null | null | O | C-C Coupling | OtherReaction | 5472b3a61cf7b7c58043a3bba014643077668571965b13c34b2141bbc7a744fc | 9040382df3c5c738c70f57f2da5c03057ad8ce8a09c32bd12c78827f9fd1b464 | c1ccc2ccccc2c1 | O=[CH2;D1;+0:1].[ClH;D0;+0:2].[c:3]:[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Cl;H0;D1;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:4](:[c:3]):[c:5] | null | [] | null | null | null | null | A solution of 1-fluoronaphthalene (5.5 g, 37.6 mmol), paraformaldehyde (2.5 g, 83 mmol), glacial acetic acid (3.5 mL), phosphoric acid (2 mL) and concentrated hydrochloric acid (5 mL) is heated at 85° C. for 15 h. The reaction mixture is poured into water and extracted three times with dichloromethane. The organic extr... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary halide | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | O | null | null | C=O.Cl.Fc1cccc2ccccc12>O>Fc1ccc(CCl)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0dd637ef9f742f487655199b8f5393a | BrCc1ccccc1.COc1ccc([N+](=O)[O-])cc1O>>COc1ccc([N+](=O)[O-])cc1OCc1ccccc1 | COC1=C(C=C(C=C1)[N+](=O)[O-])O.C(C1=CC=CC=C1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C1=CC=CC=C1)OC1=C(C=CC(=C1)[N+](=O)[O-])OC | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.COc1ccc([N+](=O)[O-])cc1O | COc1ccc([N+](=O)[O-])cc1OCc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | A solution of 2-methoxy-5-nitrophenol (54.3 g, 321 mmol), benzyl bromide (26.5 mL, 223 mmol,) and cesium carbonate (73 g, 223 mmol) is stirred in N,N-dimethylformamide (250 mL) for 24 h at room temperature. The mixture is partitioned between water and ethyl acetate. The layers are separated and the organic layer washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | null | BrCc1ccccc1.COc1ccc([N+](=O)[O-])cc1O>CN(C=O)C>COc1ccc([N+](=O)[O-])cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1453f3f499cc49b1ac8cfe210902109d | COc1ccc([N+](=O)[O-])cc1OCc1ccccc1>>COc1ccc(N)cc1OCc1ccccc1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)OC1=C(C=CC(=C1)[N+](=O)[O-])OC.C(C)(=O)OCC.O.[Sn](Cl)Cl>>C(C1=CC=CC=C1)OC=1C=C(C=CC1OC)N | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | COc1ccc([N+](=O)[O-])cc1OCc1ccccc1 | COc1ccc(N)cc1OCc1ccccc1 | null | null | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(COc2ccccc2)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 | 2 | DAY | To a solution of 2-(benzyloxy)-1-methoxy-4-nitrobenzene (35.35 g, 136 mmol) in 1:1 ethyl acetate: ethanol (640 mL) at 80° C. is added tin(II) chloride hydrate in portions over 25 minutes. The mixture is heated at this temperature for 5 h. The mixture is allowed to cool to room temperature and stirred for 2 days. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | O.C(C)O | null | 48 | COc1ccc([N+](=O)[O-])cc1OCc1ccccc1>O.C(C)O>COc1ccc(N)cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61b52ed67bce44c09e6ab3755fd6da79 | CCO.Fc1ccc(Br)nc1.[C]=O>>CCOC(=O)c1ccc(F)cn1 | C(Cl)Cl.C(C)O.BrC1=NC=C(C=C1)F.C(C)(=O)[O-].[Na+].[C]=O>>FC=1C=CC(=NC1)C(=O)OCC | [CH3:1][CH2:2][OH:3].Br[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][n:12]1.[C:4]=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][n:12]1 | CCO.Fc1ccc(Br)nc1.[C]=O | CCOC(=O)c1ccc(F)cn1 | null | Cl[Pd]Cl | null | Acylation | OtherReaction | c355c7fe6677583964bee36b8da5e775d73d0ff613788a19e0d181a38d05f627 | cb2457ddc31be6a34efcab473e76115982b4ecde38288b80cb0e3a124b5c7fdd | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8].[C;H0;D1;+0:9]=[O;D1;H0:10]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 58 | [{"value": 58.0, "product": "FC=1C=CC(=NC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 2-bromo-5-fluoropyridine (5.00 g, 28.4 mmol), sodium acetate (9.33 g, 114 mmol), and 1-1′bis(diphenylphosphino)ferrocene]dichloropalladium(II):CH2Cl2 (0.464 g, 0.57 mmol) in ethanol (80 mL) in a Parr® high pressure stainless steel reactor vessel is placed under an atmosphere of 50 psi carbon monoxide and h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ester | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | Cl[Pd]Cl | 90 | null | CCO.Fc1ccc(Br)nc1.[C]=O>Cl[Pd]Cl>CCOC(=O)c1ccc(F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6f91fd8aa044449a8fb53ad9db2adc17 | CO.Cc1cccc(C(=O)O)n1>>COC(=O)c1cccc(C)n1 | CC1=CC=CC(=N1)C(=O)O.CO.C(CCl)Cl>>COC(=O)C1=NC(=CC=C1)C | O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1 | CO.Cc1cccc(C(=O)O)n1 | COC(=O)c1cccc(C)n1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccncc1 | O-[CH3;D1;+0:1].[#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 | [] | 0 | CELSIUS | 6 | HOUR | To a suspension of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) in methylene chloride (200 mL) cooled to 0° C. is added methanol (10 mL), 4-dimethylaminopyridine (11.6 g, 94.8 mmol), and EDC (18.2 g, 94.8 mmol). The mixture is stirred at room temperature for 6 h, washed with water and brine, and dried over sod... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | 0 | 6 | CO.Cc1cccc(C(=O)O)n1>CN(C1=CC=NC=C1)C.C(Cl)Cl>COC(=O)c1cccc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07b35be662464431ac6ab56315a55875 | CO.O=C(O)c1cccc(F)c1>>COC(=O)c1cccc(F)c1 | FC=1C=C(C(=O)O)C=CC1.S(=O)(Cl)Cl.CO>>FC=1C=C(C(=O)OC)C=CC1 | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([F:10])[cH:11]1 | CO.O=C(O)c1cccc(F)c1 | COC(=O)c1cccc(F)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 2.5 | HOUR | A solution of 3-fluorobenzoic acid (3.0 g, 21.4 mmol) in methanol (71 mL) at 0° C. is treated dropwise with thionyl chloride (3.1 mL, 42.8 mmol). The solution is stirred for 15 min at 0° C., 2.5 h at room temperature, and 2 h at 50° C. The reaction is concentrated in vacuo and the residue dissolved in ethyl acetate (15... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | 0 | 2.5 | CO.O=C(O)c1cccc(F)c1>>COC(=O)c1cccc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88a28dff53a6456da92966bba8830b33 | CNOC.O=C(O)c1cnccn1>>CON(C)C(=O)c1cnccn1 | N1=C(C=NC=C1)C(=O)O.C(C(=O)Cl)(=O)Cl.CN(C=O)C.Cl.CNOC.C(C)N(CC)CC>>CON(C(=O)C1=NC=CN=C1)C | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[cH:8][n:9][cH:10][cH:11][n:12]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][n:9][cH:10][cH:11][n:12]1 | CNOC.O=C(O)c1cnccn1 | CON(C)C(=O)c1cnccn1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1cnccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1.[C;D1;H3:9]-[#8:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:9]-[#8:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | 18 | HOUR | To a solution of pyrazine-2-carboxylic acid (2.0 g, 16.1 mmol) in methylene chloride (54 mL) at 0° C. is added oxalyl chloride (7.1 mL, 80.6 mmol) and N,N-dimethylformamide (0.12 mL, 1.6 mmol). The cooling bath is removed after 10 min and the reaction mixture stirred 18 h at room temperature. The reaction mixture is co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1cnccn1 | HO- | C(Cl)Cl | null | 18 | CNOC.O=C(O)c1cnccn1>C(Cl)Cl>CON(C)C(=O)c1cnccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd8e422ad9204a379e007b50fb4602f2 | Fc1ccc(CCl)c2ccccc12.[C-]#N>>N#CCc1ccc(F)c2ccccc12 | ClCC1=CC=C(C2=CC=CC=C12)F.[C-]#N.[Na+].O>>FC1=CC=C(C2=CC=CC=C12)CC#N | Cl[CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | Fc1ccc(CCl)c2ccccc12.[C-]#N | N#CCc1ccc(F)c2ccccc12 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C-;H0;D1:5]#[N;D1;H0:6]>>[N;D1;H0:6]#[C;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | null | null | A solution of 1-chloromethyl-4-fluoronaphthalene (5.45 g, 5.66 mmol), sodium cyanide (333 mg, 6.79 mmol), and water (2 mL) in N,N-dimethylformamide (30 mL) is stirred for 8 h, then heated at 70° C. for 15 h. The mixture is cooled to room temperature and partitioned between saturated sodium bicarbonate solution and ethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1ccc2ccccc2c1 | Other | CN(C=O)C | 70 | null | Fc1ccc(CCl)c2ccccc12.[C-]#N>CN(C=O)C>N#CCc1ccc(F)c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ddafcaa7a4c4934a5f45f40641eb3de | Cc1ccc2ncccc2c1.[C-]#N>>N#CCc1ccc2ncccc2c1 | [C-]#N.[Na+].C([O-])(O)=O.[K+].CC=1C=C2C=CC=NC2=CC1.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>N1=CC=CC2=CC(=CC=C12)CC#N | [CH3:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1.[N:1]#[C-:2]>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][cH:9][cH:10][cH:11][c:12]2[cH:13]1 | Cc1ccc2ncccc2c1.[C-]#N | N#CCc1ccc2ncccc2c1 | null | null | CN(C=O)C.C(Cl)(Cl)(Cl)Cl | C-C Coupling | OtherReaction | e60c5c43322dfc46d7f6c74a9700db994e17c940f4ba384de70b2fce04697817 | b8bacb90390718f4555f6dee24489036b4f724075b0543a5a9bf8e9abad9b32c | c1ccc2ncccc2c1 | [C-;H0;D1:1]#[N;D1;H0:2].[CH3;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[N;D1;H0:2]#[C;H0;D2;+0:1]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 18.6 | [{"value": 18.0, "product": "N1=CC=CC2=CC(=CC=C12)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.6, "product": "N1=CC=CC2=CC(=CC=C12)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 6-methyl-quinoline (3.00 g, 20.6 mmol), N-bromosuccinimide (3.96 g, 22.0 mmol), and benzoyl peroxide (0.51 g, 2.10 mmol) in carbon tetrachloride (100 mL) is stirred at reflux for 2 h. The reaction is cooled to room temperature then washed with saturated aqueous sodium bisulfite (50 mL). The organic phase ... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitrile | null | null | c1ccc2ncccc2c1 | null | CN(C=O)C.C(Cl)(Cl)(Cl)Cl | null | 2 | Cc1ccc2ncccc2c1.[C-]#N>CN(C=O)C.C(Cl)(Cl)(Cl)Cl>N#CCc1ccc2ncccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24f8476f7c90486db479cc7ee0b431c1 | Cc1cccc(Br)n1>>C#Cc1cccc(C)n1 | Cl.BrC1=NC(=CC=C1)C.C[Si](C)(C)C#C.[OH-].[Na+]>>C(#C)C1=NC(=CC=C1)C | Br[c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[n:9]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:8])[n:9]1 | Cc1cccc(Br)n1 | C#Cc1cccc(C)n1 | null | [Cu]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 | CO.C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | c8c8739a85e16b31f7d4b92316f211725d1032d2b0544d94648a80ea897a9f31 | 3328c8f87c438567981cd74666102f3c9878dcf86df57abda9cd69bae6cfdc49 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[C;D1;H1:6]#[C:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 341.4 | [{"value": 24.0, "product": "C(#C)C1=NC(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 341.4, "product": "C(#C)C1=NC(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 2-bromo-6-methylpyridine (0.5 g, 2.9 mmol) and (trimethylsilyl)acetylene (0.29 g, 2.9 mmol) in triethylamine (15 mL) is purged with argon. Copper(I) iodide (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction is stirred under argon at room temperature for 2 h. The solvent is r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | [Cu]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.CO.C(C)N(CC)CC | null | 2 | Cc1cccc(Br)n1>[Cu]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.CO.C(C)N(CC)CC>C#Cc1cccc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-387ee0643a204a82b0a724a86cb806fb | C#Cc1cccc(C)n1.CCOC(=O)Cl>>CCOC(=O)C#Cc1cccc(C)n1 | ClC(=O)OCC.[Li+].CCC[CH2-].C(#C)C1=NC(=CC=C1)C>>C(C)OC(C#CC1=NC(=CC=C1)C)=O | [CH:6]#[C:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH3:13])[n:14]1.Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[C:7][c:8]1[cH:9][cH:10][cH:11][c:12]([CH3:13])[n:14]1 | C#Cc1cccc(C)n1.CCOC(=O)Cl | CCOC(=O)C#Cc1cccc(C)n1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | f0d1f729ee70f108d605628df9d2463422c892bb8c241b363d0d99a27601790a | 9a3b333eb7c664144b0fd5e443dac028970b092968aced74877492b1046e7d62 | c1ccncc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7;a:5]:[c:6]-[C:7]#[CH;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]#[C;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 83 | [{"value": 83.0, "product": "C(C)OC(C#CC1=NC(=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C(C)OC(C#CC1=NC(=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of 2-ethynyl-6-methyl-pyridine (0.5 g, 4.3 mmol) in tetrahydrofuran (20 mL) is cooled to −78° C. and treated with 1.6 M N-butyllithium in hexanes (2.9 mL, 4.7 mmol) and stirred for 0.5 h. This solution is then treated with ethyl chloroformate (2.85 mL, 30 mmol) and stirred for 3 h while the solution warms to... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Alkyne | Ester | null | null | c1ccncc1 | HCl | O1CCCC1 | null | 0.5 | C#Cc1cccc(C)n1.CCOC(=O)Cl>O1CCCC1>CCOC(=O)C#Cc1cccc(C)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a89cb4b4dfe40218f7f1ec5cf9e62e9 | O=C(Cc1ccnc2ccccc12)c1ccccn1>>C(#Cc1ccnc2ccccc12)c1ccccn1 | N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=O.C(C)N(CC)CC.FC(S(=O)(=O)OS(=O)(=O)C(F)(F)F)(F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O>>N1=C(C=CC=C1)C#CC1=CC=NC2=CC=CC=C12 | O=[C:1]([CH2:2][c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1>>[C:1](#[C:2][c:3]1[cH:4][cH:5][n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]12)[c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1 | O=C(Cc1ccnc2ccccc12)c1ccccn1 | C(#Cc1ccnc2ccccc12)c1ccccn1 | null | null | ClCCCl | Functional Group Interconversion | OtherReaction | df4f03d2116228d20bc5d8403092a8dd982f38312b775d7fadf08d78c364384d | 70d06bbe4d921df55900f4b8f7e6e878b9de0b1a93bf34dcf81c33c29d9b3281 | C(#Cc1ccnc2ccccc12)c1ccccn1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:10]:[c:9](-[C;H0;D2;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1):[#7;a:11]:[c:12] | 43.4 | [{"value": 43.4, "product": "N1=C(C=CC=C1)C#CC1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of triphenyphosphine oxide (5.56 g, 10 mmol) in 1,2-dichloroethane (30 mL) is cooled in an ice bath. Trifluoromethanesulfonic anhydride (1.57 mL, 10 mmol) is added dropwise over 15 min. To this mixture is added a solution of 1-(2-pyridyl)-2-(4-quinolyl)ethan-1-one (2.5 g, 10 mmol) in 1,2-dichloroethane (10 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Alkyne | null | null | c1ccc2ncccc2c1.c1ccncc1 | HO- | ClCCCl | null | null | O=C(Cc1ccnc2ccccc12)c1ccccn1>ClCCCl>C(#Cc1ccnc2ccccc12)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9dbb6f48418e4ea8ad11976c7e04ceca | C#Cc1ccccn1.CCOC(=O)c1cc(Br)c2ccccc2n1>>CCOC(=O)c1cc(C#Cc2ccccn2)c2ccccc2n1 | C(C)N(CC)CC.BrC1=CC(=NC2=CC=CC=C12)C(=O)OCC.C(C)N(CC)CC.C(#C)C1=NC=CC=C1>>C(C)OC(=O)C1=NC2=CC=CC=C2C(=C1)C#CC1=NC=CC=C1 | [CH:9]#[C:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1.Br[c:8]1[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:23][c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([C:9]#[C:10][c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[n:23]1 | C#Cc1ccccn1.CCOC(=O)c1cc(Br)c2ccccc2n1 | CCOC(=O)c1cc(C#Cc2ccccn2)c2ccccc2n1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I | CC#N | C-C Coupling | Sonogashira alkyne_aryl halide | 1e174391e4a252d3fd1450e5e0322e210429c2a497011bc6a30357bb5bc3eef3 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccnc2ccccc12)c1ccccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[#7;a:7]:[c:8](:[c:9]):[c:10]:1:[c:11].[#7;a:12]:[c:13]-[C:14]#[CH;D1;+0:15]>>[#7;a:12]:[c:13]-[C:14]#[C;H0;D2;+0:15]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[#7;a:7]:[c:8](:[c:9]):[c:10]:1:[c:11] | 50.3 | [{"value": 50.0, "product": "C(C)OC(=O)C1=NC2=CC=CC=C2C(=C1)C#CC1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "C(C)OC(=O)C1=NC2=CC=CC=C2C(=C1)C#CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 77.5 | CELSIUS | null | null | A mixture of ethyl 4-bromoquinoline-2-carboxylate (2.80 g, 10.0 mmol, J. Org. Chem. 1947, 12, 456), triethylamine (1.7 mL, 12 mmol), bis(triphenylphosphine)-palladium(II)chloride (0.561 g, 0.80 mmol), CuI (0.114 g, 0.60 mmol), and 2-ethynylpyridine (1.11 g, 10.8 mmol) in CH3CN (80 mL) is heated at 75-80° C. for 18 h in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccncc1.c1ccc2ncccc2c1 | HBr | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.CC#N | 77.5 | null | C#Cc1ccccn1.CCOC(=O)c1cc(Br)c2ccccc2n1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.CC#N>CCOC(=O)c1cc(C#Cc2ccccn2)c2ccccc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d9b0d77c42e4e83b987cc8dcbc78150 | Br.O=C1CC(Cc2ccccc2)CO1>>O=C(O)CC(CBr)Cc1ccccc1 | C(C1=CC=CC=C1)C1CC(OC1)=O.Br>>C(C1=CC=CC=C1)C(CC(=O)O)CBr | [BrH:7].[O:1]=[C:2]1[O:3][CH2:6][CH:5]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:4]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]([CH2:6][Br:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | Br.O=C1CC(Cc2ccccc2)CO1 | O=C(O)CC(CBr)Cc1ccccc1 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | e195582b18019269513135d0f2c64ae43826bbf04baea06338e9831623dfe759 | d3d8d635a9a7e50d7927704f488389bc47ca675447acc560d8fcaf66810055ec | c1ccccc1 | [BrH;D0;+0:1].[C:2]-[C:3]1-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH2;D2;+0:8]-1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:8]-[C:3](-[C:2])-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | 80 | CELSIUS | null | null | A mixture of 4-benzyl-dihydrofuran-2-one (1.0 g, 5.6 mmol), acetic acid (1.7 mL), HBr (33% in acetic acid, 2.0 mL) is heated at 80° C. for 4 h. The mixture is cooled to room temperature, poured into ice-water (20 mL), and extracted with chloroform (2×30 mL). The combined organic extracts are washed with water and brine... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary halide.Carboxylic acid | C1CCOC1 | null | c1ccccc1 | null | C(C)(=O)O | 80 | null | Br.O=C1CC(Cc2ccccc2)CO1>C(C)(=O)O>O=C(O)CC(CBr)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a73591ed459f4fe0b68338a627538e04 | O=C(O)CC(CBr)Cc1ccccc1.O=S(Cl)Cl>>O=C(Cl)CC(CBr)Cc1ccccc1 | C(C1=CC=CC=C1)C(CC(=O)O)CBr.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)C(CC(=O)Cl)CBr | O[C:2](=[O:1])[CH2:4][CH:5]([CH2:6][Br:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[CH2:4][CH:5]([CH2:6][Br:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | O=C(O)CC(CBr)Cc1ccccc1.O=S(Cl)Cl | O=C(Cl)CC(CBr)Cc1ccccc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | 127 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)C(CC(=O)Cl)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 127.0, "product": "C(C1=CC=CC=C1)C(CC(=O)Cl)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 3-benzyl-4-bromo-butyric acid (2.0 g, 7.78 mmol) and thionyl chloride (6.0 mmol) is heated to 80° C. for 2 h. The thionyl chloride is evaporated to yield 3-benzyl-4-bromo-butyryl chloride 2.1 g (99%), as a colorless liquid.
Conditions: See reaction.notes.procedure_details.
Workup: The thionyl chloride is e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | 80 | null | O=C(O)CC(CBr)Cc1ccccc1.O=S(Cl)Cl>>O=C(Cl)CC(CBr)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31b2586fc45a4951aff7c78af74ea681 | NN=C(Cc1ccnc2ccccc12)c1ccccn1.O=C(Cl)CC(CBr)Cc1ccccc1>>O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1 | CO.C(C1=CC=CC=C1)C(CC(=O)Cl)CBr.N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=NN.N1=CC=CC=C1>>N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=NNC(CC(CBr)CC1=CC=CC=C1)=O | [NH2:14][N:15]=[C:16]([CH2:17][c:18]1[cH:19][cH:20][n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12)[c:28]1[cH:29][cH:30][cH:31][cH:32][n:33]1.Cl[C:2](=[O:1])[CH2:3][CH:4]([CH2:5][Br:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([CH2:3][CH:4]([CH2:5][Br:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH... | NN=C(Cc1ccnc2ccccc12)c1ccccn1.O=C(Cl)CC(CBr)Cc1ccccc1 | O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1 | null | null | ClCCl.[Cl-].[NH4+] | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e1e032c84f30f6c93cf688039f3cc62747a034583f6175d60f7a0e21b27b6064 | 863011cce7fa0c660ac34aaac93028d203ff6ffc4b5a2233660e564db26255d2 | O=C(CCCc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7](-[C:8])=[#7:9]-[NH2;D1;+0:10]>>[#7;a:5]:[c:6]-[C:7](-[C:8])=[#7:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 2 | HOUR | A solution of (1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine (2.25 g, 8.40 mmol) in anhydrous dichloromethane (100 mL) and pyridine (1.81 mL, 22.4 mmol) is cooled to −78° C., treated with a solution of 3-benzyl-4-bromo-butyryl chloride (2.1 g, 7.8 mmol) in dichloromethane (10 mL), and stirred for 2 h. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone | Hydrazone amide | null | null | c1ccccc1.c1ccc2ncccc2c1.c1ccncc1 | HCl | ClCCl.[Cl-].[NH4+] | null | 2 | NN=C(Cc1ccnc2ccccc12)c1ccccn1.O=C(Cl)CC(CBr)Cc1ccccc1>ClCCl.[Cl-].[NH4+]>O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da6e96936d2f4a35966ec382e248cadc | C=CC(C)=O.Cc1cccc(N)c1>>Cc1ccc2c(C)ccnc2c1 | CC=1C=C(C=CC1)N.S(O)(O)(=O)=O.CC(=O)C=C>>CC1=CC=C2C(=CC=NC2=C1)C | O=[C:6]([CH3:7])[CH:8]=[CH2:9].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:11]([NH2:10])[cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:7])[cH:8][cH:9][n:10][c:11]2[cH:12]1 | C=CC(C)=O.Cc1cccc(N)c1 | Cc1ccc2c(C)ccnc2c1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 7d164ccd2a961120aaa0574a88528d2776564b1fb1b3cf378b67e98287524e77 | e8439cfe055023d9132dc0595e690b94c7d2d437ab1f19554009dc0b9bd47b59 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=[CH2;D1;+0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8]:1:[c:9]:[c:10] | null | [] | 12 | CELSIUS | null | null | A solution of 3-methyl-phenylamine (1 eq), in 1,4-dioxane is stirred and cooled to approximately 12° C. Sulfuric acid (2 eq.) is slowly added and heated at reflux. Methylvinyl ketone (1.5 eq) is added dropwise into the refluxing solution. The solution is heated for 1 h after addition is complete. The reaction solution ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Vinyl | null | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | O1CCOCC1 | 12 | null | C=CC(C)=O.Cc1cccc(N)c1>O1CCOCC1>Cc1ccc2c(C)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7684deafb9754f5c9167cd490a836f8c | CCOC(=O)c1ccccn1.Cc1ccnc2ccccc12>>O=C(Cc1ccnc2ccccc12)c1ccccn1 | N1=C(C=CC=C1)C(=O)OCC.N1=C(C=CC=C1)C(=O)OCC.N1=CC=C(C)C2=CC=CC=C12.C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=O | CCO[C:2](=[O:1])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1.[CH3:3][c:4]1[cH:5][cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12)[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1 | CCOC(=O)c1ccccn1.Cc1ccnc2ccccc12 | O=C(Cc1ccnc2ccccc12)c1ccccn1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccnc2ccccc12)c1ccccn1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[CH3;D1;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:7]-[c:8]1:[c:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1)-[c:3](:[c:4]):[#7;a:5]:[c:6] | 82 | [{"value": 82.0, "product": "N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1.5 | HOUR | In a 3-neck 3-liter round bottom flask equipped with two addition funnels is dissolved lepidine (10.0 mL, 75.63 mmol) in tetrahydrofuran (200 mL). One addition funnel is charged with ethyl picolinate (20.43 mL, 151.26 mmol) and the other with 0.5 M potassium bis(trimethylsilyl)amide (166.4 mL, 83.19 mmol) in toluene. T... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | c1ccc2ncccc2c1.c1ccncc1 | HO- | O1CCCC1.C1(=CC=CC=C1)C | -78 | 1.5 | CCOC(=O)c1ccccn1.Cc1ccnc2ccccc12>O1CCCC1.C1(=CC=CC=C1)C>O=C(Cc1ccnc2ccccc12)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93bcccec9d1e4801a4fde7f976f24c31 | N#CCc1ccc(F)cc1.O=C(Sc1ccc(Cl)cc1)c1cccc(C(F)(F)F)n1>>N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.ClC1=CC=C(C=C1)SC(=O)C1=NC(=CC=C1)C(F)(F)F.FC1=CC=C(C=C1)CC#N.C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>FC1=CC=C(C=C1)C(C#N)C(C1=NC(=CC=C1)C(F)(F)F)=O | [N:1]#[C:2][CH2:3][c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1.Clc1ccc(S[C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[n:15]2)cc1>>[N:1]#[C:2][CH:3]([C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[n:15]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]1 | N#CCc1ccc(F)cc1.O=C(Sc1ccc(Cl)cc1)c1cccc(C(F)(F)F)n1 | N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1 | null | null | O1CCCC1.C(Cl)Cl | C-C Coupling | OtherReaction | 0a3c978124a46dde55d1c0fa4367d6fb4fed3218902405559392b86d04d7596f | c4fa183d1b774aa9884765178fdcac13366222551b6302f96a809868120872ff | O=C(Cc1ccccc1)c1ccccn1 | Cl-c1:c:c:c(-S-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]):c:c:1.[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[N;D1;H0:7]#[C:8]-[CH;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[c:10](:[c:11]):[c:12] | 66 | [{"value": 66.0, "product": "FC1=CC=C(C=C1)C(C#N)C(C1=NC(=CC=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 4-fluorophenylacetonitrile (0.12 mL, 1.0 mmol) in dry tetrahydrofuran (2 mL) is treated dropwise with potassium bis(trimethylsilyl)amide (0.5 M toluene, 3.0 mL, 1.5 mmol) at 0° C. under an atmosphere of nitrogen. The mixture is stirred 10 min then 6-trifluoromethyl-pyridine-2-carbothioic acid S-(4-chloro-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbo-thioester | Ketone | c1ccccc1 | null | c1ccncc1.c1ccccc1 | HCl | O1CCCC1.C(Cl)Cl | null | 0.166667 | N#CCc1ccc(F)cc1.O=C(Sc1ccc(Cl)cc1)c1cccc(C(F)(F)F)n1>O1CCCC1.C(Cl)Cl>N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a30b69e3a2e470fa2da2fd96723c11b | COC(=O)c1cccc(C)n1.N#CCc1ccc(F)c(Cl)c1>>Cc1cccc(C(=O)Cc2ccc(F)c(Cl)c2)n1 | Cl.ClC=1C=C(C=CC1F)CC#N.COC(=O)C1=NC(=CC=C1)C.[H-].[Na+]>>ClC=1C=C(C=CC1F)CC(=O)C1=NC(=CC=C1)C | CO[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:18]1)=[O:8].N#C[CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([Cl:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([Cl:16])[cH:17]2)[n:18]1 | COC(=O)c1cccc(C)n1.N#CCc1ccc(F)c(Cl)c1 | Cc1cccc(C(=O)Cc2ccc(F)c(Cl)c2)n1 | null | null | C(C)O | C-C Coupling | OtherReaction | 1b16a945c064060b9dc1d7c61be52049e6812512d56740af5e2d6fcf4eab26cc | ca44a2606496224632fe7a0faef60b003bb3c3ebed2d59f5afc836241b82d0f1 | O=C(Cc1ccccc1)c1ccccn1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].N#C-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | A dispersion of sodium hydride, (60% in mineral oil, 0.7 g, 17.7 mmol) is added to ethanol (25 mL). When gas evolution ceases, 3-chloro-4-fluorophenylacetonitrile (Fluorochemicals, 2.0 g, 11.8 mmol) and 6-methyl-pyridine-2-carboxylic acid methyl ester (1.8 g, 11.8 mmol), are added. The mixture is refluxed for 2.5 h and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Ketone | null | null | c1ccncc1.c1ccccc1 | HO- | C(C)O | null | null | COC(=O)c1cccc(C)n1.N#CCc1ccc(F)c(Cl)c1>C(C)O>Cc1cccc(C(=O)Cc2ccc(F)c(Cl)c2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bc2f7f0f41d432a9827529aae96896e | CON(C)C(=O)c1cccc(C)n1.Cc1ccc(CCl)cc1>>Cc1ccc(CC(=O)c2cccc(C)n2)cc1 | [Mg].CC1=CC=C(CCl)C=C1.CON(C(=O)C1=NC(=CC=C1)C)C.CC1=CC=C(CCl)C=C1>>CC1=CC=CC(=N1)C(CC1=CC=C(C=C1)C)=O | CON(C)[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([CH3:14])[n:15]1.Cl[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][c:13]([CH3:14])[n:15]2)[cH:16][cH:17]1 | CON(C)C(=O)c1cccc(C)n1.Cc1ccc(CCl)cc1 | Cc1ccc(CC(=O)c2cccc(C)n2)cc1 | null | BrCCBr | O1CCCC1.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 1c0aa534cb3fe7a42aaa28e25676e29933058c7a8affa796609125a1135cffe8 | 87557076a2c53e7aee3b4ed2ee06910d111f39dfea07a594aa2e5c19d7ad68e4 | O=C(Cc1ccccc1)c1ccccn1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].Cl-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | 50 | CELSIUS | 1 | HOUR | To a slurry of magnesium turnings (406 mg, 16.7 mmol) in toluene (10 mL) is added 4-methylbenzylchloride (10 mg, 0.06 mmol) dropwise in tetrahydrofuran (0.2 mL). Two drops of 1,2-dibromoethane are added, the mixture heated to 50° C., and allowed to cool to room temperature. This process is repeated until reaction initi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide | Ketone | null | null | c1ccccc1.c1ccncc1 | HCl | BrCCBr.O1CCCC1.C1(=CC=CC=C1)C | 50 | 1 | CON(C)C(=O)c1cccc(C)n1.Cc1ccc(CCl)cc1>BrCCBr.O1CCCC1.C1(=CC=CC=C1)C>Cc1ccc(CC(=O)c2cccc(C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6f40288404e4a31815604afe24316b9 | N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1>>O=C(Cc1ccc(F)cc1)c1cccc(C(F)(F)F)n1 | FC1=CC=C(C=C1)C(C#N)C(C1=NC(=CC=C1)C(F)(F)F)=O>>FC1=CC=C(C=C1)CC(=O)C1=NC(=CC=C1)C(F)(F)F | N#C[CH:3]([C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20]1)[c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20]1 | N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1 | O=C(Cc1ccc(F)cc1)c1cccc(C(F)(F)F)n1 | null | null | Br | Miscellaneous | OtherReaction | c32b33048eee920cb08b7d56a774fdcb84d9bc047d50dc2f096ad75fb3a60d28 | 1e421f64d5c920473451dd84107058fc9f90c8509b37369c398bc5938f0ae86b | O=C(Cc1ccccc1)c1ccccn1 | N#C-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5])-[c:6](:[c:7]):[c:8]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[c:6](:[c:7]):[c:8] | 65.5 | [{"value": 65.0, "product": "FC1=CC=C(C=C1)CC(=O)C1=NC(=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.5, "product": "FC1=CC=C(C=C1)CC(=O)C1=NC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A slurry of 2-(4-fluoro-phenyl)-3-oxo-3-(6-tri fluoromethyl-pyridin-2-yl)-propionitrile (1.4 g, 4.4 mmol) in 48% HBr is warmed to reflux for 8 h, allowed to stand at ambient temperature 16 h, then warmed at reflux for 8 h. The mixture is extracted with ether, treated with a small amount of sodium bicarbonate, extracted... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile | Ketone | null | null | c1ccccc1.c1ccncc1 | Other | Br | null | 16 | N#CC(C(=O)c1cccc(C(F)(F)F)n1)c1ccc(F)cc1>Br>O=C(Cc1ccc(F)cc1)c1cccc(C(F)(F)F)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a72c5d993d8b483c94f70f3134fc65f0 | NN.O=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1>>NN=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1 | N1=CC=C(C2=CC=CC=C12)CC(=O)C1=CC(=CC=C1)C(F)(F)F.NN.Cl>>N1=CC=C(C2=CC=CC=C12)CC(C1=CC(=CC=C1)C(F)(F)F)=NN | [NH2:1][NH2:2].O=[C:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[c:15]1[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1>>[NH2:1][N:2]=[C:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[c:15]1[cH:16][cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[... | NN.O=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1 | NN=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 83882590079d324612170330ec542715e8ce71411b1b2946e5f0d75ea75ad4dd | 16267fcabf9e555e6c245927fd3675c621f876db12f50a1b3e8576a12e06a1cf | N=C(Cc1ccnc2ccccc12)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6].[N;D1;H2:7]-[NH2;D1;+0:8]>>[N;D1;H2:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 2-quinolin-4-yl-1-(3-trifluoromethyl-phenyl)-ethanone (1.0 g, 3.2 mmol) in ethanol (13 mL) is cooled to 0° C. and treated with hydrazine (0.6 g, 19 mmol) and concentrated hydrochloric acid (0.13 mL, 1.6 mmol). The mixture is refluxed for 2 h and concentrated in vacuo. The residue is taken up in dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone | Hydrazone | null | null | c1ccc2ncccc2c1.c1ccccc1 | HO- | C(C)O | null | null | NN.O=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1>C(C)O>NN=C(Cc1ccnc2ccccc12)c1cccc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88fed48013e14196bee88628cda044de | O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1>>O=C1CC(Cc2ccccc2)CN1N=C(Cc1ccnc2ccccc12)c1ccccn1 | N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=NNC(CC(CBr)CC1=CC=CC=C1)=O.[H-].[Na+].[Cl-].[NH4+]>>C(C1=CC=CC=C1)C1CC(N(C1)N=C(CC1=CC=NC2=CC=CC=C12)C1=NC=CC=C1)=O | Br[CH2:12][CH:4]([CH2:3][C:2](=[O:1])[NH:13][N:14]=[C:15]([CH2:16][c:17]1[cH:18][cH:19][n:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12)[c:27]1[cH:28][cH:29][cH:30][cH:31][n:32]1)[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]1[CH2:3][CH:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][N:13]1[N:1... | O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1 | O=C1CC(Cc2ccccc2)CN1N=C(Cc1ccnc2ccccc12)c1ccccn1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0c57c37b9d37fe9a1ef797b1bc00089c49cd4a2cf7ec1d62a9592190f8bb80d6 | cc77de970ed067f9dabab413863dd0165515adfc55cf394e9afab11c189d9f55 | O=C1CC(Cc2ccccc2)CN1N=C(Cc1ccnc2ccccc12)c1ccccn1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[#7:8]=[C:9](-[C:10])-[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]-[C:9](-[C:10])=[#7:8]-[N;H0;D3;+0:7]1-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]-1=[O;D1;H0:6] | null | [] | null | null | 2 | HOUR | A mixture of 3-benzyl-4-bromo-butyric acid(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide (PREP. 70, 0.8 g, 1.6 mmol) in tetrahydrofuran (26 mL) at 0° C. is treated with NaH (60% in mineral oil, 0.086 g, 2.2 mmol). The mixture is warmed to room temperature and stirred for 2 h. Saturated ammonium chloride (2 mL) i... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Primary halide | Hydrazone amide | null | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccc2ncccc2c1.c1ccncc1 | HBr | O1CCCC1 | null | 2 | O=C(CC(CBr)Cc1ccccc1)NN=C(Cc1ccnc2ccccc12)c1ccccn1>O1CCCC1>O=C1CC(Cc2ccccc2)CN1N=C(Cc1ccnc2ccccc12)c1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b641563e84c94560b4b6dd88498fa0b5 | COc1cccc(C2CC(=O)N(N)C2)c1.O=C(Cc1ccnc2ccccc12)c1ccccn1>>COc1cccc(C2CC(=O)N(N=C(Cc3ccnc4ccccc34)c3ccccn3)C2)c1 | N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=O.N1=CC=CC=C1.NN1C(CC(C1)C1=CC(=CC=C1)OC)=O>>COC=1C=C(C=CC1)C1CC(N(C1)N=C(CC1=CC=NC2=CC=CC=C12)C1=NC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][C:10](=[O:11])[N:12]([NH2:13])[CH2:32]2)[cH:33]1.O=[C:14]([CH2:15][c:16]1[cH:17][cH:18][n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12)[c:26]1[cH:27][cH:28][cH:29][cH:30][n:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][C:10](=[O:11])[N:12]([N:1... | COc1cccc(C2CC(=O)N(N)C2)c1.O=C(Cc1ccnc2ccccc12)c1ccccn1 | COc1cccc(C2CC(=O)N(N=C(Cc3ccnc4ccccc34)c3ccccn3)C2)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | c69945ad5120b7f16dfc8592e8b603d143befb589c2a10c6f629e0efaa5d6175 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | O=C1CC(c2ccccc2)CN1N=C(Cc1ccnc2ccccc12)c1ccccn1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[#7:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[C:13]>>[C:8]-[#7:9](-[N;H0;D2;+0:10]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[C:11](=[O;D1;H0:12])-[C:13] | null | [] | null | null | 18 | HOUR | A solution of 1-pyridin-2-yl-2-quinolin-4-yl-ethanone, (0.25 g, 1 mmol) and pyridine (0.242 mL, 3 mmol) in acetic acid (2 mL) is added to 1-amino-4-(3-methoxy-phenyl)-pyrrolidin-2-one, (0.2 g, 1 mmol) at room temperature under nitrogen. The mixture is stirred 18 h and concentrated in vacuo. The residue is chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | null | null | c1ccccc1.C1CC[NH]C1.c1ccc2ncccc2c1.c1ccncc1 | HO- | C(C)(=O)O | null | 18 | COc1cccc(C2CC(=O)N(N)C2)c1.O=C(Cc1ccnc2ccccc12)c1ccccn1>C(C)(=O)O>COc1cccc(C2CC(=O)N(N=C(Cc3ccnc4ccccc34)c3ccccn3)C2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f20cb3d9c17f4dcbbbca7c8f90a35e53 | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@@H]1COCc1ccccc1>>Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@@H]2COCc2ccccc2)n1 | NN1C(CC[C@@H]1COCC1=CC=CC=C1)=O.B(F)(F)F.CCOCC.FC1=CC=C(C=C1)CC(=O)C1=NC(=CC=C1)C>>C(C1=CC=CC=C1)OC[C@H]1CCC(N1N=C(CC1=CC=C(C=C1)F)C1=NC(=CC=C1)C)=O | O=[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:32]1)[CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1.[NH2:16][N:17]1[C:18](=[O:19])[CH2:20][CH2:21][C@@H:22]1[CH2:23][O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[c... | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@@H]1COCc1ccccc1 | Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@@H]2COCc2ccccc2)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c69945ad5120b7f16dfc8592e8b603d143befb589c2a10c6f629e0efaa5d6175 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | O=C1CC[C@H](COCc2ccccc2)N1N=C(Cc1ccccc1)c1ccccn1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11](-[NH2;D1;+0:12])-[C:13]>>[C:8]-[C:9](=[O;D1;H0:10])-[#7:11](-[N;H0;D2;+0:12]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[C:13] | null | [] | null | null | 30 | MINUTE | Boron trifluoride etherate (0.25 mL, 1.98 mmol) is added to a solution of 2-(4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone (0.45 g, 1.98 mmol) in tetrahydrofuran (6.6 mL) under nitrogen and stirred for 30 min. A solution of (R)-1-amino-5-benzyloxymethyl-pyrrolidin-2-one (0.43 g, 1.98 mmol) in tetrahydrofuran (1.0... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | null | null | c1ccncc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@@H]1COCc1ccccc1>O1CCCC1>Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@@H]2COCc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-107ff0fc209646f1a567aa9737b3f702 | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@H]1COCc1ccccc1>>Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@H]2COCc2ccccc2)n1 | NN1C(CC[C@H]1COCC1=CC=CC=C1)=O.FC1=CC=C(C=C1)CC(=O)C1=NC(=CC=C1)C>>C(C1=CC=CC=C1)OC[C@@H]1CCC(N1N=C(CC1=CC=C(C=C1)F)C1=NC(=CC=C1)C)=O | O=[C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:32]1)[CH2:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1.[NH2:16][N:17]1[C:18](=[O:19])[CH2:20][CH2:21][C@H:22]1[CH2:23][O:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH... | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@H]1COCc1ccccc1 | Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@H]2COCc2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | c69945ad5120b7f16dfc8592e8b603d143befb589c2a10c6f629e0efaa5d6175 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | O=C1CC[C@@H](COCc2ccccc2)N1N=C(Cc1ccccc1)c1ccccn1 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7].[C:8]-[C:9](=[O;D1;H0:10])-[#7:11](-[NH2;D1;+0:12])-[C:13]>>[C:8]-[C:9](=[O;D1;H0:10])-[#7:11](-[N;H0;D2;+0:12]=[C;H0;D3;+0:1](-[C:2]-[c:3])-[c:4](:[c:5]):[#7;a:6]:[c:7])-[C:13] | null | [] | null | null | null | null | A mixture of (S)-1-amino-5-benzyloxymethyl-pyrrolidin-2-one (0.5 g, 2.27 mmol) and 2-(4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone (0.52 g, 2.27 mmol) in toluene (2.5 mL) in a round bottom flask equipped with a Dean-Stark apparatus is refluxed for 1 h. The mixture is concentrated in vacuo and the residue chromat... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | null | null | c1ccncc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | Cc1cccc(C(=O)Cc2ccc(F)cc2)n1.NN1C(=O)CC[C@H]1COCc1ccccc1>C1(=CC=CC=C1)C>Cc1cccc(C(Cc2ccc(F)cc2)=NN2C(=O)CC[C@H]2COCc2ccccc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3764ff29850433d878043b9dcb90022 | ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.Sc1ncccn1>>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCCCSc5ncccn5)ccc24)CCC3)nc1 | ClCCCOC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2.SC1=NC=CC=N1.[I-].[K+]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCSC2=NC=CC=N2 | Cl[CH2:20][CH2:19][CH2:18][O:17][c:16]1[cH:15][c:14]2[n:13][cH:12][cH:11][c:10](-[c:9]3[c:5](-[c:4]4[cH:3][cH:2][cH:1][cH:35][n:34]4)[n:6][n:7]4[c:8]3[CH2:31][CH2:32][CH2:33]4)[c:30]2[cH:29][cH:28]1.[SH:21][c:22]1[n:23][cH:24][cH:25][cH:26][n:27]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][... | ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.Sc1ncccn1 | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCCCSc5ncccn5)ccc24)CCC3)nc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCCCSc5ncccn5)ccc24)CCC3)nc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9] | 76 | [{"value": 76.0, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCSC2=NC=CC=N2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCSC2=NC=CC=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 7-(3-Chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (0.060 g, 0.148 mmol), 2-mercaptopyrimidine (0.033 g, 0.296 mmol, 2.0 equiv) and potassium iodide (0.010 g, 0.120 mmol, 0.80 equiv) are combined in N,N-dimethylformamide (1.0 mL) and the reaction is heated at 60° C. for 72 h. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cncnc1.c1cc2n(n1)CCC2 | HCl | CN(C=O)C | 60 | null | ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.Sc1ncccn1>CN(C=O)C>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCCCSc5ncccn5)ccc24)CCC3)nc1 |
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