dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a37d7ea76d24ecaac385eef012c4fbe | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1>>Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl.ClC(C)OC(=O)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1 | c1ccc(C(c2ccccc2)[N:10]2[CH2:9][CH:8]([O:7][CH:6]([c:5]3[cH:4][cH:3][c:2]([Cl:1])[cH:20][cH:19]3)[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]3)[CH2:11]2)cc1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:11]2)[c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1 | Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 | null | null | ClCCl | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | 83.4 | [{"value": 74.0, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.4, "product": "ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 1-benzhydryl-3-(4,4′-dichlorobenzhydryloxy)azetidine (35) (8.4 mmol) in dichloromethane (50 mL) was added 1-chloroethylchloroformate (16.9 mmol) dropwise at 0° C. and the reaction mixture was stirred at reflux for 6 hours. The reaction mixture was cooled to room temperature, concentrated in vac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | ClCCl | null | null | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1>ClCCl>Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0d1dbcdd8e2e4617aeb7f8af0ec02294 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=C1 | Cl[c:26]1[c:20]([CH:12]([O:11][CH:10]2[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27]2)[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[cH:21][cH:22][c:23]([Cl:24])[cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6]>>[C:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5) (53.0 mg, 45%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a5b7c4b2fa44f2eb5ea7d3add9360e7 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC2CCCCC2)C=C1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2Cl)[c:4]2[cH:5][cH:6][c:7](Cl)[cH:8][cH:9]2)C1.[NH:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[CH2:29]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O | O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | null | null | null | Acylation | OtherReaction | a4317b937b002e8283608a8c4a0a065ff4f8d2c6eca65fe51dee1344993b2497 | 159c2f88a469ac65e290fb98d1864f3c1f10c3ad6cf9d44aadb3070c2be72939 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-C-C(-O-C(-[c;H0;D3;+0:1]2:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-Cl):[cH;D2;+0:5]:[cH;D2;+0:6]:2)-c2:c:c:c(-Cl):c:c:2-Cl)-C-1.[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1.[N-;H0;D1:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:13]=[C;H0;D3;+0:12](-[NH;D2;+0:11]-[CH;D3;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH... | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | C1CCCCC1.C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c77280c60ea431ca4c1b5e47e57c7b0 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>Cc1cccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)c1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC2=CC(=CC=C2)C)C=C1 | C[C:7](C)([CH3:1])[NH:8][C:9](=[O:10])[N:11]1[CH2:12][CH:13]([O:14][CH:15]([c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]2Cl)[CH2:30]1.Clc1ccc(C(OC2CNC2)[c:5]2[cH:4][cH:3][c:2](Cl)[cH:31][cH:6]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][NH:8][C:9](=[O:10])[... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 | Cc1cccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)c1 | null | null | null | C-C Coupling | OtherReaction | 90c084e005b63c9ddb53d8757fd429adf6bce59e2e2f7c38a5dae90849d7fa45 | 187e3752fd71c6cd074eb319e3fa549053e3a410454e27a932d847572d13186d | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[#7:3]-[C:4](-[#7:5])=[O;D1;H0:6].Cl-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C:11]):[c:12].Cl-[c;H0;D3;+0:13]1:[c:14]:[cH;D2;+0:15]:[c;H0;D3;+0:16](-C(-O-C2-C-N-C-2)-c2:c:c:c(-Cl):c:c:2):[c:17]:[c:18]:1>>[#7:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[CH2;D2;+0:1]-[c;H0;D3;+0:15]1:[c:14]:[c;H0;D3;... | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Secondary amine | null | c1ccccc1.c1ccccc1.C1CNC1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>Cc1cccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b19cf3a039c946078d866d279c55c09d | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>Cc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC2=CC=C(C=C2)C)C=C1 | CC(C)([CH3:1])[NH:7][C:8](=[O:9])[N:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][c:28]2Cl)[CH2:29]1.Clc1ccc([CH:6](OC2CNC2)[c:5]2[cH:4][cH:3][c:2](Cl)[cH:31][cH:30]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[N:10]2... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 | Cc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | adb0675eae0870c87c763744e63541ee686dbe95ca6ae56668dec607d4f0d75b | 7bdc2ef428047aacea125f351356d09c7dcd203fc43b8673df5efd9ca061958d | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-[CH3;D1;+0:1])-[NH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6])-[C:7].Cl-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C:12]):[c:13].Cl-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17](-[CH;D3;+0:18](-O-C2-C-N-C-2)-c2:c:c:c(-Cl):c:c:2):[c:19]:[c:20]:1>>[C:6]-[#7:5](-[C:3](=[O;D1;H0:4])-[NH;D2;+0:2]-[CH2;D2;+0:18]-[c:17]1:[c:16]:... | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | c1ccccc1.c1ccccc1.C1CNC1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>Cc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e223a82346f4250829716df2fd26b68 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NCc1ccc(Cl)cc1Cl)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC2=C(C=C(C=C2)Cl)Cl)C=C1 | CC(C)(C)NC(=O)N1CC(O[CH:4](c2ccc(Cl)cc2)[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[Cl:12])C1.[NH:13]1[CH2:14][CH:15]([O:16][CH:17]([c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[CH2:32]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Cl... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O | O=C(NCc1ccc(Cl)cc1Cl)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | null | null | null | Acylation | OtherReaction | 4d3961f4618426c19119df10b3b239018b4e71c71ae983c0a731976737a83d20 | 8b329017329bf85f36d0764464e508d4f4b0f3b85890cf5a91ca89b81be3bdf2 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-C-C(-O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-c2:c:c:c(-Cl):c:c:2)-C-1.[C:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-1.[N-;H0;D1:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[N;H0;D3;+0:8]1-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NCc1ccc(Cl)cc1Cl)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15fc2f8659ec4a458b3042b4e20c5f49 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NCCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCCC2=CC=CC=C2)C=C1 | CC(C)(C)NC(=O)N1CC(O[CH:5]([c:4]2ccc(Cl)cc2Cl)[c:6]2[cH:7][cH:8][c:9](Cl)[cH:10][cH:11]2)C1.[NH:12]1[CH2:13][CH:14]([O:15][CH:16]([c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[CH2:31]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9]... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O | O=C(NCCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 | null | null | null | Acylation | OtherReaction | 6c9c2479f3fa4d34a0be1d0eac0c161c35c3ea82b3e54eaf2f35a0e7069bfe96 | 159c2f88a469ac65e290fb98d1864f3c1f10c3ad6cf9d44aadb3070c2be72939 | O=C(NCCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-C-C(-O-[CH;D3;+0:1](-[c:2]2:[c:3]:[c:4]:[c;H0;D3;+0:5](-Cl):[c:6]:[c:7]:2)-[c;H0;D3;+0:8]2:c:c:c(-Cl):c:c:2-Cl)-C-1.[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-1.[N-;H0;D1:13]=[C;H0;D2;+0:14]=[O;D1;H0:15]>>[O;D1;H0:15]=[C;H0;D3;+0:14](-[NH;D2;+0:13]-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[cH;D2;+0... | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1.[N-]=C=O>>O=C(NCCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42eecf57f25544aea3951e9fcf79ab27 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>COc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 | ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=C1.[N-]=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>ClC1=CC=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC2=CC=C(C=C2)OC)C=C1 | CC(C)(C)[NH:8][C:9](=[O:10])[N:11]1[CH2:12][CH:13]([O:14][CH:15]([c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]2Cl)[CH2:30]1.Clc1ccc([CH:7](OC2CNC2)[c:6]2[cH:5][cH:4][c:3](Cl)[cH:32][cH:31]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][C:9](=[O:10])[N:11]... | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1 | COc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d1f733c644150d48b24395d0ad4125f44148d94be141c0bd7d5b3bed8421ed9d | d6cc0f744ed47a28fbc05e382559d5aae1f90c806793e4454d215f2e91c1045f | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].Cl-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[C:11]):[c:12].Cl-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16](-[CH;D3;+0:17](-O-C2-C-N-C-2)-c2:c:c:c(-Cl):c:c:2):[c:18]:[c:19]:1>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[NH;D2;+0:1]-[CH2;D2;+0:17]-[c:16]1:[c:15]:[c:14]:[c;H0;... | null | [] | null | null | null | null | This material was prepared from 3-(4,4′-dichlorobenzhydryloxy)azetidine (36) and the corresponding commercially available isocyanate, using the procedure described for compound (5).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Ether.Urea | c1ccccc1.c1ccccc1.C1CNC1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)cc1>>COc1ccc(CNC(=O)N2CC(OC(c3ccc(Cl)cc3)c3ccc(Cl)cc3)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bae93a7e0ae2414885048767655150a1 | O=C(c1ccccc1Cl)c1ccccc1Cl.OC(c1ccc(Cl)cc1)c1ccccc1Cl>>OC(c1ccccc1Cl)c1ccccc1Cl | ClC1=C(C(=O)C2=C(C=CC=C2)Cl)C=CC=C1.ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)O)C=CC=C1 | O=C(c1ccccc1Cl)c1ccccc1[Cl:9].Cl[c:6]1[cH:5][cH:4][c:3]([CH:2]([OH:1])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[cH:8][cH:7]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[Cl:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16] | O=C(c1ccccc1Cl)c1ccccc1Cl.OC(c1ccc(Cl)cc1)c1ccccc1Cl | OC(c1ccccc1Cl)c1ccccc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | f9410038cb44f4faeeec506a5296c7b4252a9bb33bc5b412cebf2c491be34201 | ee4dfb36bd00c899664a35a3af3db4b96456f985804aad51fde651ac76198bb2 | c1ccc(Cc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5]):[cH;D2;+0:6]:[c:7]:1.Cl-c1:c:c:c:c:c:1-C(=O)-c1:c:c:c:c:c:1-[Cl;H0;D1;+0:8]>>[C:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:7]:[c;H0;D3;+0:6]:1-[Cl;H0;D1;+0:8] | null | [] | null | null | null | null | This material was prepared from 2,2′-dichlorobenzophenone using the procedure described for compound (7) (8.96 g, 89%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ketone | Aromatic halide | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | null | O=C(c1ccccc1Cl)c1ccccc1Cl.OC(c1ccc(Cl)cc1)c1ccccc1Cl>>OC(c1ccccc1Cl)c1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-988f5476f69b4b66bb74ad3a905820c9 | Clc1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1Cl>>Clc1ccccc1C(OC1CNC1)c1ccccc1Cl | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)Cl)C1=C(C=CC=C1)Cl.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1 | c1ccc(C(c2ccccc2)[N:13]2[CH2:12][CH:11]([O:10][CH:9]([c:8]3[c:3]([Cl:2])[cH:4][cH:5][cH:6][cH:7]3)[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[Cl:21])[CH2:14]2)cc1>>[Cl:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]([O:10][CH:11]1[CH2:12][NH:13][CH2:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[Cl:21] | Clc1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1Cl | Clc1ccccc1C(OC1CNC1)c1ccccc1Cl | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | This material was prepared from compound (67) (12.7 mmol) using the procedure described for compound (9) (1.58 g, 48%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Clc1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1Cl>>Clc1ccccc1C(OC1CNC1)c1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30fb082b0b2e449a9dd68e4718af7da1 | CC(C)(C)N=C=O.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl>>CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.C(C)(C)(C)N=C=O.C(C)N(CC)CC>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]... | CC(C)(C)N=C=O.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | 44 | [{"value": 44.0, "product": "ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) (0.29 mmol), tert-butyl isocyanate (0.29 mmol) and triethylamine (0.58 mmol) in dichloromethane (3 mL) was shaken at room temperature overnight, quenched with water, filtered through a PTFE phase separator cartridge and reduced in vacuo to yield a... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | ClCCl | null | null | CC(C)(C)N=C=O.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl>ClCCl>CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4a49ae44be140198b6b2207e7401369 | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)C)C=CC=C1 | C[C:2]([CH3:1])([CH3:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[Cl:25])[CH2:26]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]2... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | CC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[#7:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[#7:4]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f397704ad47411c95b75c324b6141df | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CCC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1 | [CH3:1][C:3]([CH3:2])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[CH2:27]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | CCC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH3;D1;+0:7])-[CH3;D1;+0:8]>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0:8]-[CH3;D1;+0:7] | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CCC(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8462cd8199c4073b3e3b558ceeca07d | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NCCC)C=CC=C1 | C[C:3](C)([CH3:2])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[Cl:25])[CH2:26]1>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]2[cH:20]... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | CCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-[#7:3]-[C:4](-[#7:5])=[O;D1;H0:6]>>[#7:5]-[C:4](=[O;D1;H0:6])-[#7:3]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C;D1;H3:7] | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1>>CCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b213e1dff57421886c3cf511d31249d | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>C=CCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NCC=C)C=CC=C1 | C[C:3](C)(NC(=O)[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[Cl:25])[CH2:26]1)[CH3:2].Clc1ccccc1C(OC1CNC1)c1c(Cl)ccc[cH:1]1.[N-:4]=[C:5]=[O:6]>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O | C=CCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | cf55a6e95b5627fc762bdfcf8d770e816e103439addbfce1750840253ce1fc09 | 462903fb7084d7018191dcf28a5c53f9ff0e5790d5abdd012274194aae4cf8ab | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-[C;H0;D4;+0:1](-C)(-[CH3;D1;+0:2])-N-C(=O)-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-1.Cl-c1:c:c:c:[cH;D2;+0:7]:c:1-C(-O-C1-C-N-C-1)-c1:c:c:c:c:c:1-Cl.[N-;H0;D1:8]=[C;H0;D2;+0:9]=[O;D1;H0:10]>>[CH2;D1;+0:7]=[CH;D2;+0:2]-[CH2;D2;+0:1]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[N;H0;D3;+0:3]1-[C:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea.Allyl | C1C[NH]C1.c1ccccc1.C1CNC1.c1ccccc1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>C=CCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06874ff964f844e1a71d2e3005b235af | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>CCCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NCCCC)C=CC=C1 | C[C:3](NC(=O)N1CC(OC(c2ccccc2Cl)c2c[cH:1]ccc2Cl)C1)([CH3:2])[CH3:4].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])[CH2:27]1.[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:1... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O | CCCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | 80a680129569f0365b83e9d1de17f67f0419d860666ce2818cb9f5c61c5a7659 | ca77462d48e3a86118a3b78c4f8fc614c00426bcb4595897b73a2298a2e3d235 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-N-C(=O)-N1-C-C(-O-C(-c2:c:[cH;D2;+0:4]:c:c:c:2-Cl)-c2:c:c:c:c:c:2-Cl)-C-1.[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-1.[N-;H0;D1:9]=[C;H0;D2;+0:10]=[O;D1;H0:11]>>[CH3;D1;+0:4]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[N;H0;D3;+0:7]1-[C:6... | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>CCCCNC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13ca9276c5ec4767812276ff7320523a | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NC1CCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC2CCCC2)C=CC=C1 | CC(C)(C)NC(=O)N1[CH2:5][CH:4](OC(c2ccccc2Cl)c2cc[cH:6][cH:7]c2Cl)[CH2:8]1.[NH:9]1[CH2:10][CH:11]([O:12][CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[Cl:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[CH2:28]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[N:9]1[CH2:10][CH:11]([O... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O | O=C(NC1CCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | 07aab6c7ea5f9335db2dcf8a71210ee57c7468ee638354cc26d830e74f440e2e | ca77462d48e3a86118a3b78c4f8fc614c00426bcb4595897b73a2298a2e3d235 | O=C(NC1CCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-[CH2;D2;+0:1]-[CH;D3;+0:2](-O-C(-c2:c:c:[cH;D2;+0:3]:[cH;D2;+0:4]:c:2-Cl)-c2:c:c:c:c:c:2-Cl)-[CH2;D2;+0:5]-1.[C:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-1.[N-;H0;D1:10]=[C;H0;D2;+0:11]=[O;D1;H0:12]>>[O;D1;H0:12]=[C;H0;D3;+0:11](-[NH;D2;+0:10]-[CH;D3;+0:2]1-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0... | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | C1CCCC1.C1C[NH]C1 | C1CCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NC1CCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2704fbe56e5642e49c0766e1efa94ec5 | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1 | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2Cl)C1.[NH:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[Cl:28])[CH2:29]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10]1[CH2:11]... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | f23f7a1758fa43ade702948df8d500522084815adf00f28224963fe154b1ebf0 | ca77462d48e3a86118a3b78c4f8fc614c00426bcb4595897b73a2298a2e3d235 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-C-C(-O-C(-[c;H0;D3;+0:1]2:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6]:2-Cl)-c2:c:c:c:c:c:2-Cl)-C-1.[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1.[N-;H0;D1:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:13]=[C;H0;D3;+0:12](-[NH;D2;+0:11]-[CH;D3;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0... | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | C1CCCCC1.C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98d3025dca7644a78f511bf7143608a9 | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NCCc1ccccc1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O.ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1>>ClC1=C(C(C2=C(C=CC=C2)Cl)OC2CN(C2)C(=O)NCCC2=CC=CC=C2)C=CC=C1 | CC(C)(C)NC(=O)N1CC(OC(c2c(Cl)[cH:10][cH:9][cH:8][cH:7]2)[c:5]2[cH:4]cc[cH:11][c:6]2Cl)C1.[NH:12]1[CH2:13][CH:14]([O:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[Cl:30])[CH2:31]1.[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10]... | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O | O=C(NCCc1ccccc1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | a008a0743ef6b5c04c36d803df97f716f5eb95f21ae2ecccc5b8e897dcbaa034 | ca77462d48e3a86118a3b78c4f8fc614c00426bcb4595897b73a2298a2e3d235 | O=C(NCCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | C-C(-C)(-C)-N-C(=O)-N1-C-C(-O-C(-[c;H0;D3;+0:1]2:[cH;D2;+0:2]:c:c:[cH;D2;+0:3]:[c;H0;D3;+0:4]:2-Cl)-c2:[cH;D2;+0:5]:[c:6]:[c:7]:[cH;D2;+0:8]:c:2-Cl)-C-1.[C:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-1.[N-;H0;D1:13]=[C;H0;D2;+0:14]=[O;D1;H0:15]>>[O;D1;H0:15]=[C;H0;D3;+0:14](-[NH;D2;+0:13]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:4]... | null | [] | null | null | null | null | This material was prepared from 3-(2,2′-dichlorobenzhydryloxy)azetidine hydrochloride (68) and the corresponding commercially available isocyanate using the procedure described for compound (69).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Urea.Secondary amine | Urea | C1CNC1.c1ccccc1.c1ccccc1.C1CNC1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1.Clc1ccccc1C(OC1CNC1)c1ccccc1Cl.[N-]=C=O>>O=C(NCCc1ccccc1)N1CC(OC(c2ccccc2Cl)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ba873777d1249af93eaab92c2fe4664 | O=C(c1ccc(Br)cc1)c1ccc(Br)cc1>>OC(c1ccc(Br)cc1)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)C2=CC=C(C=C2)Br)C=C1.ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1>>BrC1=CC=C(C(C2=CC=C(C=C2)Br)O)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1 | O=C(c1ccc(Br)cc1)c1ccc(Br)cc1 | OC(c1ccc(Br)cc1)c1ccc(Br)cc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | This material was prepared from 4,4′-dibromobenzophenone using the procedure described for compound (7) (9.67 g, 96%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | null | null | null | O=C(c1ccc(Br)cc1)c1ccc(Br)cc1>>OC(c1ccc(Br)cc1)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63317e50170b4c3bac2106b7073199d5 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1.OC(c1ccc(Br)cc1)c1ccc(Br)cc1>>Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1 | BrC1=CC=C(C(C2=CC=C(C=C2)Br)O)C=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br | Cl[c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]([CH:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24]2)[c:25]2[cH:26]ccc[c:31]2Cl)[cH:32][cH:33]1.OC(c1ccc([Br:1])cc1)c1c[cH:27][c:28]([Br:29])[cH:30]c1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9]... | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1.OC(c1ccc(Br)cc1)c1ccc(Br)cc1 | Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 8412cf147da96682885cb172b2f55377e65b76ed37634b04576be52881f0b46d | 8c596e850164065c56906ff13f761c93ea17794aa84f98d3ca18669a86cde10e | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Cl-[c;H0;D3;+0:6]1:c:c:c:[cH;D2;+0:7]:[c:8]:1-[C:9].O-C(-c1:c:[cH;D2;+0:10]:[c:11](-[Br;D1;H0:12]):[cH;D2;+0:13]:c:1)-c1:c:c:c(-[Br;H0;D1;+0:14]):c:c:1>>[Br;D1;H0:12]-[c:11]1:[cH;D2;+0:10]:[cH;D2;+0:7]:[c:8](-[C:9]):[cH;D2;+0:6]:[cH;D2;+0:13]:1.[Br;H0;D1;+0:14]-[c;H0;D3;+0:1]... | null | [] | null | null | null | null | This material was prepared from 4,4′-dibromobenzhydrol (84) using the procedure described for compound (8) (6.15 g, 66%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Secondary alcohol | Aromatic halide | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1.OC(c1ccc(Br)cc1)c1ccc(Br)cc1>>Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5acc3dc7ffe14abaaf8949ae68ceaac1 | Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1>>Brc1ccc(C(OC2CNC2)c2ccc(Br)cc2)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=CC=C(C=C1)Br)C1=CC=C(C=C1)Br.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.BrC1=CC=C(C(C2=CC=C(C=C2)Br)OC2CNC2)C=C1 | c1ccc(C(c2ccccc2)[N:10]2[CH2:9][CH:8]([O:7][CH:6]([c:5]3[cH:4][cH:3][c:2]([Br:1])[cH:20][cH:19]3)[c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]3)[CH2:11]2)cc1>>[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:11]2)[c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]2)[cH:19][cH:20]1 | Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1 | Brc1ccc(C(OC2CNC2)c2ccc(Br)cc2)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-(4,4′-dibromobenzhydryloxy)azetidine (85) using the procedure described for compound (9) (1.15 mg, 30%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Brc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Br)cc2)cc1>>Brc1ccc(C(OC2CNC2)c2ccc(Br)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7926ca6fc3d9498facf261d4dc6ee5a1 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)Cl | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2cc[c:33]([Cl:34])[cH:32]c2)c(Cl)c1.Cl[c:7]1[cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[c:10]([CH:11]([OH:12])[c:30]2[cH:31]cc[cH:35][cH:36]2)[cH:9][cH:8]1.O[CH:13]1[CH2:14][N:15]([CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29]1>... | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f9f67a918b44a82cdae5042c534412ebd832da6cfa786f4a76a30f27354bd763 | 94748db0eac2e8ad8384ed6daaface4e20bb474c6a9fbc0fd109ddfcca7a7c00 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](-[OH;D1;+0:6])-[c:7]2:[c:8]:[cH;D2;+0:9]:c:c:[cH;D2;+0:10]:2):[c:11]:[c:12]:1.Cl-c1:c:c:c(-C(-O-C2-C-N(-C(-c3:c:c:c:c:c:3)-c3:c:c:c:c:c:3)-C-2)-c2:c:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[Cl;D1;H0:15]):c:c:2):c(-Cl):c:1.O-[CH;D3;+0:16]1-[C:17]-[#7:18](-[C:19])-[C:20]-1>>[C:19]-[#7:1... | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (40.1 mmol) and 2-(trifluoromethyl)-4-chlorobenzhydrol (96) (80.2 mmol) using the procedure described for compound (3) (13.5 g, 66%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ether.Secondary alcohol.Secondary alcohol.Tertiary amine | Aromatic halide.Ether | c1ccccc1.C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5a456fbf37b41c096141755c7d05d50 | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1>>FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)Cl.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:16]2[CH2:15][CH:14]([O:13][CH:12]([c:11]3[c:6]([C:3]([F:2])([F:4])[F:5])[cH:7][cH:8][cH:9][cH:10]3)[c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]3)[CH2:17]2)cc1>>[F:2][C:3]([F:4])([F:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH:12]([O:13][CH:14]1[CH2:15][NH:16][CH2:17]1)[c:18]1[cH:19][cH:20][c:2... | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine (97) (25.6 mmol) using the procedure described for compound (9) (8.2 g, 85%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccc(Cl)cc1>>FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-410c892c623047be80bc50bf5cc8f433 | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[CH2:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:... | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) (1.32 mmol) and tert-butyl isocyanate (1.32 mmol) using the procedure described for compound (10) (474 mg, 81%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d043ec7f960a4ff8a350b3128f95096d | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>CCCCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCCCC)C=CC=C1)(F)F | [CH2:1]1[NH:8][CH2:30][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O | CCCCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10]-[C:11]-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>CCCCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e8613b69e7e43e0941ec43ef6a238b3 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH2:1]1[NH:8][CH2:30][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1)[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1[C:26]([F:27])([F:28])[F:29].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O | CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10](-[C;D1;H3:11])-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b640dd79e454835b4b48cb47c3df42b | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>C[C@H](NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)N[C@H](C2=CC=CC=C2)C)C=CC=C1)(F)F | [CH2:1]1[NH:6][CH2:31][CH:8]1[O:9][CH:10]([c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[C:24]([F:25])([F:26])[F:27].[N-:3]=[C:4]=[O:5]>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[N:6]1[CH2:7][CH:8]([O:9][CH:10]([c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[c:18]2[cH:19][c... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O | C[C@H](NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57922983eae574c7b0bea07ba4e195d652d95429b9ffc3272d794db0a110e791 | d8ab96e5172872e309963bcfbf38e99b612cf39492274dcd4a822c945c7980c6 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:11](-[CH3;D1;+0:4])-[c:12]:[c:13]:[cH;D2;+0:6]:[c:14]:[c:15])-[C:16]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1.c1ccccc1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.[N-]=C=O>>C[C@H](NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc5b01b877184e6bab67a1995351836d | Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1.[N-]=C=O>>CCC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2Cl)C1 | Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1.[N-]=C=O>>ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(CC)C)C=CC=C1 | [CH2:1]1[NH:9][CH2:2][CH:11]1[O:12][CH:13]([c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[Cl:27].[N-:6]=[C:7]=[O:8]>>[CH3:1][CH2:2][C:3]([CH3:4])([CH3:5])[NH:6][C:7](=[O:8])[N:9]1[CH2:10][CH:11]([O:12][CH:13]([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[c:21]2[cH:... | Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1.[N-]=C=O | CCC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2Cl)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[CH2;D2;+0:6]-[CH3;D1;+0:4])-[C:14]-1 | null | [] | null | null | null | null | This material was prepared from 3-(2,4′-dichlorobenzhydryloxy)azetidine hydrochloride (9) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1.[N-]=C=O>>CCC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc45ad6a8f53427ba076493717fa957c | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(Br)cc1F>>OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.BrC1=CC(=C(C=O)C=C1)F.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=C(C=C(C=C2)Br)F)O)C=CC=C1)(F)F | [Br][Mg][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[F:20].[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[F:10]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][c:9]1[F:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[F:20] | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(Br)cc1F | OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (60 mmol) and 4-bromo-2-fluorobenzaldehyde (54 mmol) using the procedure described for compound (96) (12.3 g, 74%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(Br)cc1F>>OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd7aadbfffaf4ab4ad169f7e87f3e4f5 | OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=C(C=C(C=C2)Br)F)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=C(C=C(C=C1)Br)F | [F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[CH:9]([OH:10])[c:28]1[cH:29][cH:30][cH:31][cH:32][c:33]1[C:34]([F:35])([F:36])[F:37].O[CH:11]1[CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1>>[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][c:8]1[CH:9](... | OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (23.0 mmol) and 2-(trifluoromethyl)-2′-fluoro-4′-bromobenzhydrol (112) (34.0 mmol) using the procedure described for compound (3) (8.84 g, 67%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | OC(c1ccc(Br)cc1F)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2def2ccb294148af8422d036be79e969 | Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F>>Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=C(C=C(C=C1)Br)F.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=C(C=C(C=C2)Br)F)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:14]2[CH2:13][CH:12]([O:11][CH:10]([c:9]3[c:3]([F:2])[cH:4][c:5]([Br:6])[cH:7][cH:8]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C:22]([F:23])([F:24])[F:25])[CH2:15]2)cc1>>[F:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]1[CH:10]([O:11][CH:12]1[CH2:13][NH:14][CH2:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20... | Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F | Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-2′-fluoro-4′-bromobenzhydryloxy]azetidine (113) (15 mmol) using the procedure described for compound (9) (2.26 g, 51%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Fc1cc(Br)ccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1C(F)(F)F>>Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f26d2ec1e7e443488ecf86396c09bc3 | CC(C)(C)N=C=O.Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=C(C=C(C=C2)Br)F)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl>>FC(C1=C(C(C2=C(C=C(C=C2)Br)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[F:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14... | CC(C)(C)N=C=O.Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-2′-fluoro-4′-bromobenzhydryloxy]azetidine hydrochloride (114) and tert-butyl isocyanate (4.54 mmol) using the procedure described for compound (5) (1.33 g, 58%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Fc1cc(Br)ccc1C(OC1CNC1)c1ccccc1C(F)(F)F>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f98a6e397b64cbb9a2ba9d641d66853 | CSc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.CSC1=CC=C(C=O)C=C1.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)SC)O)C=CC=C1)(F)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:19][cH:20]1.[Br][Mg][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | CSc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br] | CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (32 mmol) and 4-(methylthio)benzaldehyde (30 mmol) using the procedure described for compound (96) (9.4 g, 100%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | CSc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b028d06a76648998b6390e0ce260e03 | CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)SC)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)SC | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]1.O[CH:9]1[CH2:10][N:11]([CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9... | CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1 | CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (15 mmol) and 2-(trifluoromethyl)-4′-(methylthio)benzhydrol (116) (30 mmol) using the procedure described for compound (3) (4.68 g, 60%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CSc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c59e34abcd84451390d37be085dee1e1 | CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)SC.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:11]2[CH2:10][CH:9]([O:8][CH:7]([c:6]3[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:24][cH:23]3)[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[C:19]([F:20])([F:21])[F:22])[CH2:12]2)cc1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]([... | CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine (117) (8.7 mmol) using the procedure described for compound (9) (2.29 g, 68%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | CSc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec99783b1061463da6c8fc80e83e44c7 | CC(C)(C)N=C=O.CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CSc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O.C([O-])([O-])=O>>FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [C:12](=[O:13])=[N:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][N:11]([C:12](=[O:13])[NH:14][C:... | CC(C)(C)N=C=O.CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CSc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-trifluoromethyl-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (1.28 mmol), tert-butyl isocyanate (1.28 mmol) and mp-carbonate (2.62 mmol/g, 3.85 mmol) using the procedure described for compound (10) (433 mg, 75%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CSc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ca1af8c1c7d481fa55baff37c9d67a2 | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(SC)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH2:1]1[NH:8][CH2:31][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][c:16]([S:17][CH3:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([S:17][CH3:18])... | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O | CCC(C)NC(=O)N1CC(OC(c2ccc(SC)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10](-[C;D1;H3:11])-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-trifluoromethyl-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(SC)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a4b1738bee54d4ea5525b7f8764cae7 | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CSc1ccc(C(OC2CN(C(=O)NCc3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CN(C2)C(=O)NCC2=CC=CC=C2)C=CC=C1)(F)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:21]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]([F:30])([F:31])[F:32])[cH:33][cH:34]1.[C:12](=[O:13])=[N-:14]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][N:11]([C:12](=[O:13])[NH:14][CH2:15][c:16]3[cH:17][cH:18][cH:19]... | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O | CSc1ccc(C(OC2CN(C(=O)NCc3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57922983eae574c7b0bea07ba4e195d652d95429b9ffc3272d794db0a110e791 | d8ab96e5172872e309963bcfbf38e99b612cf39492274dcd4a822c945c7980c6 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10]-[c:11](:[c:12]):[cH;D2;+0:6]:[c:13]:[c:14])-[C:15]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-trifluoromethyl-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1.c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CSc1ccc(C(OC2CN(C(=O)NCc3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49b4dd7ebec8402a9268ee21bc27c2de | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(F)cc1C(F)(F)F>>OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F | ClC1=CC=C(C=C1)[Mg]Br.FC1=CC(=C(C=O)C=C1)C(F)(F)F.ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)Cl>>FC(C1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)F)(F)F | [Br][Mg][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1.[O:1]=[CH:2][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]1[C:17]([F:18])([F:19])[F:20]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]1[C:17]([F:18])([F:19])[F:20] | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(F)cc1C(F)(F)F | OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | This material was prepared from 4-chlorophenylmagnesium bromide (28.6 mmol) and 4-fluoro-2-(trifluoromethyl)benzaldehyde (26.0 mmol) using the procedure described for compound (2) (6.04 g, 76%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(F)cc1C(F)(F)F>>OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-240228535b35445996cf1f04636144d4 | OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)F)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)F)C(F)(F)F)C1=CC=C(C=C1)Cl | [F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]2)[c:32]([C:33]([F:34])([F:35])[F:36])[cH:37]1.O[CH:8]1[CH2:9][N:10]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH... | OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (9.8 mmol) and 2-(trifluoromethyl)-4-fluoro-4′-chlorobenzhydrol (123) (19.7 mmol) using the procedure described for compound (3) (2.31 g, 45%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | OC(c1ccc(Cl)cc1)c1ccc(F)cc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c98931b763da4f8aaff60b5608364577 | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1>>Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)F)C(F)(F)F)C1=CC=C(C=C1)Cl.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)F)(F)F | c1ccc(C(c2ccccc2)[N:11]2[CH2:10][CH:9]([O:8][CH:7]([c:6]3[cH:5][cH:4][c:3]([F:2])[cH:25][c:20]3[C:21]([F:22])([F:23])[F:24])[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]3)[CH2:12]2)cc1>>[F:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[c:2... | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4-fluoro-4′-chlorobenzhydryloxy]azetidine (124) (3.8 mmol) using the procedure described for compound (9) (1.45 g, 97%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)c(C(F)(F)F)c1>>Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89b555ee2c0b4710adba10803bc09f10 | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)F)(F)F.C(C)(C)(C)N=C=O.C([O-])([O-])=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)F)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]2[C:27]([F:28])([F:29])[F:30])[CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:... | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4-fluoro-4′-chlorobenzhydryloxy]azetidine hydrochloride (125) (0.25 mmol), tert-butyl isocyanate (0.25 mmol) and MP-carbonate (2.62 mmol/g, 0.76 mmol) using the procedure described for compound (10) (72.4 mg, 63%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a40b45926f204b24833fc1ab68c20bc7 | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)F)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)CC)C=CC(=C1)F)(F)F | [CH2:1]1[NH:8][CH2:31][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1)[c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]1[C:27]([F:28])([F:29])[F:30].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18]... | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O | CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10](-[C;D1;H3:11])-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)-4-fluoro-4′-chlorobenzhydryloxy]azetidine hydrochloride (125) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2c7814042774eb5a59fdec7aea59ae3 | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)F)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC2CCCCC2)C=CC(=C1)F)(F)F | [CH2:4]1[NH:10][CH2:5][CH:12]1[O:13][CH:14]([c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]1[C:29]([F:30])([F:31])[F:32].[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]... | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O | O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 6f220288e27a433c524e51e8cbc778e39292302ccf6b9caadd9b3fd6c36c8e27 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[CH;D3;+0:4]2-[C:11]-[C:12]-[C:13]-[C:14]-[CH2;D2;+0:6]-2)-[C:15]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)-4-fluoro-4′-chlorobenzhydryloxy]azetidine hydrochloride (125) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1CCCCC1.C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79eabd33bc1948d7a4fec8762ba70161 | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)F)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC2=CC=CC=C2)C=CC(=C1)F)(F)F | [CH2:4]1[NH:11][CH2:10][CH:13]1[O:14][CH:15]([c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]1[C:30]([F:31])([F:32])[F:33].[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([O:14][CH:15]([c:16]2[cH:17][cH:18][c:... | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O | O=C(NCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57922983eae574c7b0bea07ba4e195d652d95429b9ffc3272d794db0a110e791 | d8ab96e5172872e309963bcfbf38e99b612cf39492274dcd4a822c945c7980c6 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[CH2;D2;+0:6]-[c:11](:[c:12]):[cH;D2;+0:4]:[c:13]:[c:14])-[C:15]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)-4-fluoro-4′-chlorobenzydryloxy]azetidine hydrochloride (125) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | Fc1ccc(C(OC2CNC2)c2ccc(Cl)cc2)c(C(F)(F)F)c1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccc(Cl)cc2)c2ccc(F)cc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db6a438c9bdf4143a6b901f9fb01f42c | FC(F)(F)c1cccc[c]1[Mg][Br].OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F>>OC(c1ccccc1)c1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.C(C1=CC=CC=C1)=O.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=CC=C2)O)C=CC=C1)(F)F | [Br][Mg][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18].FC(F)(F)c1cc(Cl)ccc1[CH:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | FC(F)(F)c1cccc[c]1[Mg][Br].OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F | OC(c1ccccc1)c1ccccc1C(F)(F)F | null | null | null | C-C Coupling | OtherReaction | 9453d4540cf87aff3409ce0b5a60b9cdfd9017d2d51f2559d5157b31ea34686b | 275679a0e4a563c3612953fcc9783343f8a900674e91162d9f16fa6902ebc315 | c1ccc(Cc2ccccc2)cc1 | Cl-c1:c:c:c(-[CH;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]):c(-C(-F)(-F)-F):c:1.[Br]-[Mg]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[C:10](-[F;D1;H0:11])(-[F;D1;H0:12])-[F;D1;H0:13]):[c:14]>>[F;D1;H0:11]-[C:10](-[F;D1;H0:12])(-[F;D1;H0:13])-[c:9](:[c:14]):[c;H0;D3;+0:6](-[CH;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]):[c:7]... | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (16 mmol) and benzaldehyde (15 mmol) using the procedure described for compound (96) (3.7 g, 98%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Trifluoro group.Aromatic halide.Secondary alcohol | Secondary alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF.Br-.Mg | null | null | null | FC(F)(F)c1cccc[c]1[Mg][Br].OC(c1ccccc1)c1ccc(Cl)cc1C(F)(F)F>>OC(c1ccccc1)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ae82d8e4ec14b779d70ea3b11630b2b | OC(c1ccccc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=CC=C2)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=CC=C1 | [F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]([OH:12])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.O[CH:13]1[CH2:14][N:15]([CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[CH2:29]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]... | OC(c1ccccc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydrol-3-azetidinol (1) (7.5 mmol) and 2-(trifluoromethyl)benzhydrol (131) (15 mmol) using the procedure described for compound (3) (1.81 g, 51%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | OC(c1ccccc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b518b97ca1b0445db7ff24f2477fb50c | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1>>FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=CC=C1.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=CC=C2)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:16]2[CH2:15][CH:14]([O:13][CH:12]([c:11]3[c:6]([C:3]([F:2])([F:4])[F:5])[cH:7][cH:8][cH:9][cH:10]3)[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:17]2)cc1>>[F:2][C:3]([F:4])([F:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH:12]([O:13][CH:14]1[CH2:15][NH:16][CH2:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:2... | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-benzhydryloxy]azetidine (132) (3.8 mmol) using the procedure described for compound (9) (0.70 g, 60%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | FC(F)(F)c1ccccc1C(OC1CN(C(c2ccccc2)c2ccccc2)C1)c1ccccc1>>FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-123aacc6a11444e495e5ac92cd1cec67 | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=CC=C2)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O.C([O-])([O-])=O>>FC(C1=C(C(C2=CC=CC=C2)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]([F:26])([F:27])[F:28])[CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:1... | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)benzhydryloxy]azetidine hydrochloride (133) (0.33 mmol), tert-butyl isocyanate (0.33 mmol) and MP-carbonate (2.62 mmol/g, 0.98 mmol) using the procedure described for compound (10) (99.5 mg, 75%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31d2a83b537b46c9b9d7bf7672808b50 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=CC=C2)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=CC=C2)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH2:1]1[NH:8][CH2:29][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[C:25]([F:26])([F:27])[F:28].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20]... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O | CCC(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10](-[C;D1;H3:11])-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)benzhydryloxy]azetidine hydrochloride (133) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-023fad67112846cea8d2c709df9e6d49 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=CC=C2)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=CC=C2)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [CH2:4]1[NH:10][CH2:9][CH:12]1[O:13][CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[C:27]([F:28])([F:29])[F:30].[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 6f220288e27a433c524e51e8cbc778e39292302ccf6b9caadd9b3fd6c36c8e27 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[CH;D3;+0:4]2-[C:11]-[C:12]-[C:13]-[C:14]-[CH2;D2;+0:6]-2)-[C:15]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)benzhydryloxy]azetidine hydrochloride (133) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1CCCCC1.C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e18581b150cc4ec295dc489669d5b9dd | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=CC=C2)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=CC=C2)OC2CN(C2)C(=O)NCC2=CC=CC=C2)C=CC=C1)(F)F | [CH2:4]1[NH:11][CH2:10][CH:13]1[O:14][CH:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28]([F:29])([F:30])[F:31].[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([O:14][CH:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57922983eae574c7b0bea07ba4e195d652d95429b9ffc3272d794db0a110e791 | d8ab96e5172872e309963bcfbf38e99b612cf39492274dcd4a822c945c7980c6 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[CH2;D2;+0:6]-[c:11](:[c:12]):[cH;D2;+0:4]:[c:13]:[c:14])-[C:15]-1 | null | [] | null | null | null | null | This material was prepared 3-[2-(trifluoromethyl)benzhydryloxy]azetidine hydrochloride (133) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccccc1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83a51bcc1d6c4d789ba4a0c17d02517c | FC(F)(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)OC(F)(F)F.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:15]2[CH2:14][CH:13]([O:12][CH:11]([c:10]3[cH:9][cH:8][c:7]([O:6][C:3]([F:2])([F:4])[F:5])[cH:28][cH:27]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]3[C:23]([F:24])([F:25])[F:26])[CH2:16]2)cc1>>[F:2][C:3]([F:4])([F:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([O:12][CH:13]2[CH2:14][NH:15][CH2:16]2)[c:17]2[... | FC(F)(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(trifluoromethoxy)benzyhydryloxy]azetidine (140) (4.8 mmol) using the procedure described for compound (9) (1.32 g, 65%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | FC(F)(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24bf1fc2193b4aaf96bdacfbe9eaa3ab | CC(C)(C)N=C=O.FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O.C([O-])([O-])=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[C:30]([F:31])([F:32])[F:33])[CH2:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11... | CC(C)(C)N=C=O.FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-(trifluoro-methoxy)benzhydryloxy]azetidine hydrochloride (141) (0.234 mmol), tert-butyl isocyanate (0.234 mmol) and MP-carbonate (2.62 mmol/g, 0.702 mmol) using the procedure described for compound (10) (78.7 mg, 69%).
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24e79ee9e9614a91ae4da13176e2007c | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH2:1]1[NH:8][CH2:34][CH:10]1[O:11][CH:12]([c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[C:30]([F:31])([F:32])[F:33].[N-:5]=[C:6]=[O:7]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c... | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O | CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | OtherReaction | 3bd5ba555f0732d1354d0c3fda8a7242328c41e5ab0beefdd40557e07d5fdbd7 | 895076a135e88a4e53bbe0884de769040991ba3aec70376814a14556858102dc | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:4]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[C:10](-[C;D1;H3:11])-[C:12]-[CH3;D1;+0:6])-[C:13]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-(trifluoro-methoxy)benzyloxy]azetidine hydrochloride (141) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a57622721f94871b78cbeb723f2fc01 | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CNC2)C=CC=C1)(F)F.[N-]=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)(F)F)OC2CN(C2)C(=O)NCC2=CC=CC=C2)C=CC=C1)(F)F | [CH2:4]1[NH:11][CH2:10][CH:13]1[O:14][CH:15]([c:16]1[cH:17][cH:18][c:19]([O:20][C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][c:32]1[C:33]([F:34])([F:35])[F:36].[O:1]=[C:2]=[N-:3]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH:13]([O:14][CH:15]([c:1... | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O | O=C(NCc1ccccc1)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57922983eae574c7b0bea07ba4e195d652d95429b9ffc3272d794db0a110e791 | d8ab96e5172872e309963bcfbf38e99b612cf39492274dcd4a822c945c7980c6 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[NH;D2;+0:5]-[CH2;D2;+0:6]-1.[N-;H0;D1:7]=[C;H0;D2;+0:8]=[O;D1;H0:9]>>[C:1]-[#8:2]-[CH;D3;+0:3]1-[C:10]-[N;H0;D3;+0:5](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:7]-[CH2;D2;+0:6]-[c:11](:[c:12]):[cH;D2;+0:4]:[c:13]:[c:14])-[C:15]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-(trifluoro-methoxy)benzyloxy]azetidine hydrochloride (141) and the corresponding isocyanate using the procedure described for compound (10).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Ether.Urea | C1CNC1 | c1ccccc1.C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.[N-]=C=O>>O=C(NCc1ccccc1)N1CC(OC(c2ccc(OC(F)(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88aa605bfaa34ffaa7e065fa82d621b9 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.C12(CC3CC(CC(C1)C3)C2)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F | [NH:14]1[CH2:15][CH:16]([O:17][CH:18]([c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]([F:33])([F:34])[F:35])[CH2:36]1.[O:1]=[C:2]=[N:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:12]1)[CH2:13]2>>[O:1]=[C:2]([NH:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC12CC3CC(CC(C3)C1)C2 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])(-[C:6])-[C:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1)(-[C:6])-[C:7] | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) (0.55 mmol) and 1-adamantyl isocyanate (0.55 mmol) using the procedure described for compound (10) (229 mg, 83%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c04728cdfe2a4e1d948b3505171e4992 | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC1CCCCC1>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.C1(CCCCC1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [NH:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32]1.[O:1]=[C:2]=[N:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10]1[CH2:11][CH:12]([O... | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC1CCCCC1 | O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1)-[C:6] | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) (0.55 mmol) and cyclohexyl isocyanate (0.55 mmol) using the procedure described for compound (10) (146 mg, 59%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | null | null | FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1.O=C=NC1CCCCC1>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d05f8651193c4d94b238cc07cd1ed39b | Cc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.C1(=CC=C(C=C1)C=O)C.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)C)O)C=CC=C1)(F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[cH:18][cH:19]1.[Br][Mg][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]([F:15])([F:16])[F:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1 | Cc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br] | Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (16 mmol) and p-tolualdehyde (1.82 mL, 15 mmol) using the procedure described for compound (96) (4.28 g, 100%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | Cc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dcf7beab60df4f599652a6124e74a62a | Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CCCC(C)C.CCOC(C)=O | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)C)O)C=CC=C1)(F)F>>C(C)(=O)OCC.CCCC(C)C | FC(F)(F)c1cccc[c:11]1[CH:10]([c:5]1c[cH:6][c:2]([CH3:1])[cH:3][cH:4]1)[OH:12].c1ccc(C(c2ccccc2)N2C[CH:8]([OH:9])[CH2:7]2)cc1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6].[CH3:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1 | CCCC(C)C.CCOC(C)=O | null | null | null | Acylation | OtherReaction | e7ed4b7687cdf0cc974f235678951e61b0fee7950b3c9459292d08592b77412b | 1cb4740ab75a04ad2d56a2f0700c4a64fc26420940b21f9dbb9cac9fea4951bd | null | F-C(-F)(-F)-c1:c:c:c:c:[c;H0;D3;+0:1]:1-[CH;D3;+0:2](-[OH;D1;+0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[cH;D2;+0:9]:c:1.[OH;D1;+0:10]-[CH;D3;+0:11]1-C-N(-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[CH2;D2;+0:12]-1>>[C;D1;H3:8]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[CH;D3;+0:5](-[CH3;D1;+0:4])-[CH3;D1;... | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (7.5 mmol) and 2-(trifluoromethyl)-4′-methylbenzhydrol (149) (15 mmol) using the procedure described for compound (3). Flash column chromatography [SiO2; ethyl acetate-iso-hexane (5:95)] afforded a yellow gum (4.41 g) which was used in the next step without ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary alcohol.Secondary alcohol.Tertiary amine | Ester | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CNC1 | null | null | HF | null | null | null | Cc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CCCC(C)C.CCOC(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b00438cd9bdf473fada28fa3acf5d291 | Cc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)C.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)C)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:10]2[CH2:9][CH:8]([O:7][CH:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]3)[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]([F:19])([F:20])[F:21])[CH2:11]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]([F:19])([F:20... | Cc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | 54 | [{"value": 54.0, "product": "Cl.FC(C1=C(C(C2=CC=C(C=C2)C)OC2CNC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-methylbenzyloxy]azetidine (150) (7.5 mmol) using the procedure described for compound (9). Crystallisation from DIPE-MeOH afforded the product as a white solid (1.39 g, 54%).
Conditions: See reaction.notes.procedure_details.
Workup: Crystallisation ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Cc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d43547790faa43d19f3e126deec83131 | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>Cc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)C)OC2CNC2)C=CC=C1)(F)F.C12(CC3CC(CC(C1)C3)C2)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)C)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]1.[C:11](=[O:12])=[N:13][C:14]12[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:21]3)[CH2:22]1)[CH2:23]2>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2... | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2 | Cc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])(-[C:6])-[C:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1)(-[C:6])-[C:7] | 94 | [{"value": 94.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-methylbenzhydryloxy]azetidine hydrochloride (151) (0.56 mmol) and 1-adamantyl isocyanate (0.56 mmol) using the procedure described for compound (10). The desired product was obtained as a white foam (264 mg, 94%).
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | null | null | null | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>Cc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a2a00d17af747b1afc4cf57ac1add84 | CC(C)(C)N=C=O.Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>Cc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)C)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)C)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [C:11](=[O:12])=[N:13][C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]([C:11](=[O:12])[NH:13][C:14]([CH3:15]... | CC(C)(C)N=C=O.Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | Cc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1 | null | [] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-methylbenzhydryloxy]azetidine hydrochloride (151) (0.56 mmol) and tert-butyl isocyanate (0.56 mmol) using the procedure described for compound (10). The desired product was obtained as a colourless glass which gave a white solid on scratching (232 mg, 98%).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | null | null | null | null | CC(C)(C)N=C=O.Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>Cc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f98df0d88a7b4901896dc65308b2eb5a | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>>Cc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)C)OC2CNC2)C=CC=C1)(F)F.C1(CCCCC1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)C)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][NH:10][CH2:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]1.[C:11](=[O:12])=[N:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]([C:11](=[O:12])[NH:13]... | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1 | Cc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1)-[C:6] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 3-[2-(trifluoromethyl)-4′-methylbenzhydryloxy]azetidine hydrochloride (151) (0.56 mmol) and cyclohexyl isocyanate (0.56 mmol) using the procedure described for compound (10). The desired product was obtained as a white foam (230 mg, 91%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.C1CCCCC1.c1ccccc1 | null | null | null | null | Cc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>>Cc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5308aabd61c14dc5bd84e5dde926ff29 | COc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.C(C1=CC=C(C=C1)OC)=O.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)OC)O)C=CC=C1)(F)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:19][cH:20]1.[Br][Mg][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | COc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br] | COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (16 mmol) and p-anisaldehyde (1.86 mL, 15 mmol) using the procedure described for compound (96) (4.34 g, 100%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | COc1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08d6b79edd824fb482fa241695c35012 | COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CCCC(C)C.CCOC(C)=O | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)OC)O)C=CC=C1)(F)F>>C(C)(=O)OCC.CCCC(C)C | FC(F)(F)c1ccccc1[CH:10]([c:11]1c[cH:5][c:4](O[CH3:1])[cH:6]c1)[OH:12].Clc1ccc(C(OC2CN(C(c3ccccc3)c3cc[cH:3][cH:2]c3)C2)c2ccc(Cl)cc2Cl)cc1.c1ccc(C(c2ccccc2)N2C[CH:8]([OH:9])[CH2:7]2)cc1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6].[CH3:7][CH2:8][O:9][C:10]([CH3:11])=[O:12] | COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1 | CCCC(C)C.CCOC(C)=O | null | null | null | Acylation | OtherReaction | 83e53efc5f3bd56e1cf107abe2d0d85c7268a7c99e619bc0298c2aa78a1f8072 | 6950c97fee6238e4c3c12b252c08df61e68be43e9f45d9c96574244f30a724b1 | null | Cl-c1:c:c:c(-C(-O-C2-C-N(-C(-c3:c:[cH;D2;+0:1]:[cH;D2;+0:2]:c:c:3)-c3:c:c:c:c:c:3)-C-2)-c2:c:c:c(-Cl):c:c:2-Cl):c:c:1.F-C(-F)(-F)-c1:c:c:c:c:c:1-[CH;D3;+0:3](-[OH;D1;+0:4])-[c;H0;D3;+0:5]1:c:[cH;D2;+0:6]:[c;H0;D3;+0:7](-O-[CH3;D1;+0:8]):[cH;D2;+0:9]:c:1.[OH;D1;+0:10]-[CH;D3;+0:11]1-C-N(-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:... | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (7.5 mmol) and 2-(trifluoromethyl)-4′-methoxybenzhydrol (155) (15 mmol) using the procedure described for compound (3). Flash column chromatography [SiO2; ethyl acetate-iso-hexane (10:90→20:80)] afforded a pale yellow gum (2.73 g) which was used in the next ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Aromatic halide.Ether.Ether.Secondary alcohol.Secondary alcohol.Tertiary amine.Tertiary amine | Ester | c1ccccc1.c1ccccc1.c1ccccc1.C1CNC1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CNC1 | null | null | HF | null | null | null | COc1ccc(C(O)c2ccccc2C(F)(F)F)cc1.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CCCC(C)C.CCOC(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29fbae571dc042378fa8c5b38c6fe6b3 | COc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)OC.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:11]2[CH2:10][CH:9]([O:8][CH:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]3)[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[C:19]([F:20])([F:21])[F:22])[CH2:12]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]([... | COc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | 29 | [{"value": 29.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CNC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CNC2)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The corresponding hydrochloride salt was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-methoxybenzyloxy]azetidine (156) (7.5 mmol) using the procedure described for compound (9). Due to the presence of impurities, the salt was partitioned between aqueous base and an organic solvent, the organic phase dried (MgSO... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | COc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4155ee157044c5eba604188c42dd85b | COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>COc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C12(CC3CC(CC(C1)C3)C2)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]1.[C:12](=[O:13])=[N:14][C:15]12[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH2:23]1)[CH2:24]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([... | COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2 | COc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])(-[C:6])-[C:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1)(-[C:6])-[C:7] | 92 | [{"value": 92.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-methoxybenzhydryloxy]azetidine (157) (100 mg, 0.30 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (3.01 mmol/g; 100 mg, 0.30 mmol) and 1-adamantyl isocyanate (55 mg, 0.30 mmol). The resultant mixture was shaken at ambient temperature for 5 h, after which time it was pour... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | C(Cl)Cl | null | null | COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>C(Cl)Cl>COc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-976cb1e249184975b23b28ec16e2c9db | CC(C)(C)N=C=O.COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>COc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [C:12](=[O:13])=[N:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][N:11]([C:12](=[O:13])[NH:14][C:... | CC(C)(C)N=C=O.COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | COc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1 | 70 | [{"value": 70.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-methoxybenzhydryloxy]azetidine (157) (100 mg, 0.30 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (3.01 mmol/g; 100 mg, 0.30 mmol) and tert-butyl isocyanate (35 μL, 0.30 mmol). The resultant mixture was shaken at ambient temperature for 5 h, after which time it was poure... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)(C)N=C=O.COc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>COc1ccc(C(OC2CN(C(=O)NC(C)(C)C)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37829da8c28c4383bf0640fbec818027 | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(F)cc1>>OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.FC1=CC=C(C=O)C=C1.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)F)O)C=CC=C1)(F)F | [Br][Mg][c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]([F:17])([F:18])[F:19].[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[C:16]([F:17])([F:18])[F:19] | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(F)cc1 | OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (16 mmol) and 4-fluorobenzaldehyde (1.64 mL, 15 mmol) using the procedure described for compound (96) (4.27 g, 100%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(F)cc1>>OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62fbb1e06dcc4cf48b8456677bf4b467 | OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)F)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)F | [F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]([F:32])([F:33])[F:34])[cH:35][cH:36]1.O[CH:8]1[CH2:9][N:10]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]... | OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (7.5 mmol) and 2-(trifluoromethyl)-4′-fluorobenzhydrol (160) (15 mmol) using the procedure described for compound (3). After basic aqueous workup, the crude product was used in the next step without further purification.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | OC(c1ccc(F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94e76d7f07a041e5a96f6a5d1cb7a590 | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)F.Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1>>Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:11]2[CH2:10][CH:9]([O:8][CH:7]([c:6]3[cH:5][cH:4][c:3]([F:2])[cH:24][cH:23]3)[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[C:19]([F:20])([F:21])[F:22])[CH2:12]2)cc1>>[F:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]([F:20])([F:21])... | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[C:3]-[N;H0;D3;+0:4]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-1 | 55 | [{"value": 55.0, "product": "Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-fluorobenzyloxy]azetidine (161) (7.5 mmol) using the procedure described for compound (9). Crystallisation from DIPE-MeOH afforded the product as a white solid (1.49 g, 55%).
Conditions: See reaction.notes.procedure_details.
Workup: Crystallisation ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | Fc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-246f692f99e441b79d3a712b87bb1bee | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C12(CC3CC(CC(C1)C3)C2)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F | [NH:14]1[CH2:15][CH:16]([O:17][CH:18]([c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]([F:33])([F:34])[F:35])[CH2:36]1.[O:1]=[C:2]=[N:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][CH:10]([CH2:11]3)[CH2:12]1)[CH2:13]2>>[O:1]=[C:2]([NH:3][C:4]12[CH2:5][CH:6]3[CH2:7][CH:8]... | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])(-[C:6])-[C:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1)(-[C:6])-[C:7] | 93 | [{"value": 92.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (200 mg, 0.55 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.01 mmol/g; 550 mg, 1.65 mmol) and 1-adamantyl isocyanate (101 mg, 0.55 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | C(Cl)Cl | null | null | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>C(Cl)Cl>O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9aa2e174e0da4f2fabc23ebe7036b4b0 | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[CH2:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:1... | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | 87.4 | [{"value": 87.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.4, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (200 mg, 0.55 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.01 mmol/g; 550 mg, 1.65 mmol) and tert-butyl isocyanate (65 μL, 0.55 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which tim... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CC(C)(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95fd3190ab70495497f761ac3b49cfda | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C1(CCCCC1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [NH:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32]1.[O:1]=[C:2]=[N:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10]1[CH2:11][CH:12]([O:... | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1 | O=C(NC1CCCCC1)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1)-[C:6] | 78.3 | [{"value": 78.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (200 mg, 0.55 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.01 mmol/g; 550 mg, 1.65 mmol) and cyclohexyl isocyanate (72 μL, 0.55 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which tim... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>C(Cl)Cl>O=C(NC1CCCCC1)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbbe158230a44abcad8b7d125cde9f22 | C=CCN=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1>>C=CCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C=C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F | [CH2:1]=[CH:2][CH2:3][N:4]=[C:5]=[O:6].[NH:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]([F:26])([F:27])[F:28])[CH2:29]1>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[c... | C=CCN=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1 | C=CCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H2:1]=[C:2]-[C:3]-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H2:1]=[C:2]-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | 61 | [{"value": 61.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.5, "product": "FC(C1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-chlorobenzhydryloxy]azetidine hydrochloride (98) (100 mg, 0.28 mmol) in anhydrous DCM (3 mL) was added MP-carbonate (3.01 mmol/g; 275 mg, 0.84 mmol) and allyl isocyanate (25 μL, 0.28 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after which time it w... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | C=CCN=C=O.FC(F)(F)c1ccccc1C(OC1CNC1)c1ccc(Cl)cc1>C(Cl)Cl>C=CCNC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61bc58caa2094760bb0a142c93d4357d | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>>CSc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C12(CC3CC(CC(C1)C3)C2)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CN(C2)C(=O)NC23CC4CC(CC(C2)C4)C3)C=CC=C1)(F)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[C:32]([F:33])([F:34])[F:35])[cH:36][cH:37]1.[C:12](=[O:13])=[N:14][C:15]12[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH2:23]1)[CH2:24]2>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([... | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2 | CSc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC12CC3CC(CC(C3)C1)C2)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])(-[C:6])-[C:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:11]1-[C:8]-[C:9]-[C:10]-1)(-[C:6])-[C:7] | 51 | [{"value": 51.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (100 mg, 0.26 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.10 mmol/g; 250 mg, 0.84 mmol) and 1-adamantyl isocyanate (47 mg, 0.26 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after wh... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1C2CC3CC1CC(C2)C3 | null | C(Cl)Cl | null | null | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC12CC3CC(CC(C3)C1)C2>C(Cl)Cl>CSc1ccc(C(OC2CN(C(=O)NC34CC5CC(CC(C5)C3)C4)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b882c3fe42704152805daba2a81e1922 | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>>CSc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C1(CCCCC1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)SC)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]1.[C:12](=[O:13])=[N:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][N:11]([C:12](=[O... | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1 | CSc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1)-[C:6] | 52 | [{"value": 52.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-(methylthio)benzhydryloxy]azetidine hydrochloride (118) (100 mg, 0.26 mmol) in anhydrous DCM (5 mL) was added MP-carbonate (3.10 mmol/g; 250 mg, 0.84 mmol) and cyclohexyl isocyanate (33 μL, 0.26 mmol). The resultant mixture was shaken at ambient temperature for 16 h, after whi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.C1CCCCC1.c1ccccc1 | null | C(Cl)Cl | null | null | CSc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>C(Cl)Cl>CSc1ccc(C(OC2CN(C(=O)NC3CCCCC3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dde7f526db1f4046aa203d05de1beca4 | CS(=O)(=O)c1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.CS(=O)(=O)C1=CC=C(C=O)C=C1.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)O)C=CC=C1)(F)F | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:21][cH:22]1.[Br][Mg][c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[C:17]([F:18])([F:19])[F:20]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1 | CS(=O)(=O)c1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br] | CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1 | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | 108.6 | [{"value": 100.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)O)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.6, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)O)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (14.5 mmol) and 4-(methylsulfonyl)benzaldehyde (2.68 g, 13.8 mmol) using the procedure described for compound (96). The product was obtained as an amber gum (4.95 g, 100%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | CS(=O)(=O)c1ccc(C=O)cc1.FC(F)(F)c1cccc[c]1[Mg][Br]>>CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-634ac4484cfe4f599103e9afa830d46a | CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)S(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([OH:10])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]([F:35])([F:36])[F:37])[cH:38][cH:39]1.O[CH:11]1[CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[... | CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1 | CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | 44.4 | [{"value": 44.4, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (6.9 mmol) and 2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydrol (169) (13.8 mmol) using the procedure described for compound (3). After basic aqueous workup, the crude product was partially purified by flash column chromatography [SiO2; ethyl acetate-iso-he... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CS(=O)(=O)c1ccc(C(O)c2ccccc2C(F)(F)F)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60b0a6d711754491a673488e4c8ca64b | CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)S(=O)(=O)C.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)Cl>>FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CNC2)C=CC=C1)(F)F | c1ccc(C(c2ccccc2)[N:13]2[CH2:12][CH:11]([O:10][CH:9]([c:8]3[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:26][cH:25]3)[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[C:21]([F:22])([F:23])[F:24])[CH2:14]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([O:10][CH:11]2[CH2:12][NH:13][CH2:14]2)[c:15]2[cH:16]... | CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Deprotection | Hydrogenolysis of tertiary amines | b1d315bef48d6a81e10fb4eab17bea03d13eb9363139421badf3e724cd9c125a | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]1-[C:2]-[N;H0;D3;+0:3](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:4]-1>>[C:1]1-[C:2]-[NH;D2;+0:3]-[C:4]-1 | 9 | [{"value": 9.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CNC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.8, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CNC2)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydryloxy]azetidine (170) (6.9 mmol) using the procedure described for compound (4). After basic aqueous workup, purification by flash column chromatography [SiO2; ethyl acetate-methanol (90:10)→ethyl acetate-methanol—ammonium hy... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | Other | null | null | null | CS(=O)(=O)c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71c8e3b4d941402b88d00224e36b95b8 | CC(C)(C)N=C=O.CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(S(C)(=O)=O)cc2)c2ccccc2C(F)(F)F)C1 | FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CNC2)C=CC=C1)(F)F.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]([F:30])([F:31])[F:32])[CH2:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][... | CC(C)(C)N=C=O.CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(S(C)(=O)=O)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | 67 | [{"value": 67.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.9, "product": "FC(C1=C(C(C2=CC=C(C=C2)S(=O)(=O)C)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(methylsulfonyl)benzhydryloxy]azetidine (171) (222 mg, 0.58 mmol) in anhydrous DCM (7 mL) was added molecular sieves and tert-butyl isocyanate (68 μL, 0.58 mmol). After shaking at ambient temperature for 16 h, the mixture was poured onto a DCM-wet SCX-2 cartridge (2 g). Elutio... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 16 | CC(C)(C)N=C=O.CS(=O)(=O)c1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CC(C)(C)NC(=O)N1CC(OC(c2ccc(S(C)(=O)=O)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6218bdcc60e6473797af67e748ba2783 | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(OC(F)F)cc1>>OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)[Mg]Br)(F)F.FC(OC1=CC=C(C=O)C=C1)F.FC(C1=C(C(C2=CC=CC=C2)O)C=CC(=C1)Cl)(F)F>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)O)C=CC=C1)(F)F | [Br][Mg][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22].[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[cH:11][cH:12]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[cH:11][cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(OC(F)F)cc1 | OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F | null | null | null | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH;D3;+0:11](-[OH;D1;+0:10])-[c:12](:[c:13]):[c:14]):[c:2]:[c:3] | 64 | [{"value": 64.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)O)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.9, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)O)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 2-(trifluoromethyl)phenylmagnesium bromide (16 mmol) and 4-(difluoromethoxy)benzaldehyde (2.09 mL, 15 mmol) using the procedure described for compound (96). The product was obtained as an amber gum (3.05 g, 64%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | null | null | null | FC(F)(F)c1cccc[c]1[Mg][Br].O=Cc1ccc(OC(F)F)cc1>>OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74ca3a7ed76e4f6a81781521e817cd43 | OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)O)C=CC=C1)(F)F.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)OC(F)F | [F:1][CH:2]([F:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH:9]([OH:10])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]([F:35])([F:36])[F:37])[cH:38][cH:39]1.O[CH:11]1[CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27]1>>[F:1][CH:2]([F:3])[O:4][c:5]1[cH:6][cH:7... | OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1 | FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | 111.6 | [{"value": 111.6, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)OC(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (1.12 g, 4.7 mmol) and 2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydrol (173) (3.0 g, 9.4 mmol) using the procedure described for compound (3). After basic aqueous workup, the crude product was partially purified by flash column chromatography [SiO2; ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | OC(c1ccc(OC(F)F)cc1)c1ccccc1C(F)(F)F.OC1CN(C(c2ccccc2)c2ccccc2)C1>>FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50c20bd30b5747c1b945b789e9d83ef9 | CC(Cl)OC(=O)Cl.FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>>Cl.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)C(F)(F)F)C1=CC=C(C=C1)OC(F)F.ClC(=O)OC(C)Cl>>Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F | CC(Cl)OC(=O)[Cl:1].c1ccc(C(c2ccccc2)[N:14]2[CH2:13][CH:12]([O:11][CH:10]([c:9]3[cH:8][cH:7][c:6]([O:5][CH:3]([F:2])[F:4])[cH:27][cH:26]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[C:22]([F:23])([F:24])[F:25])[CH2:15]2)cc1>>[ClH:1].[F:2][CH:3]([F:4])[O:5][c:6]1[cH:7][cH:8][c:9]([CH:10]([O:11][CH:12]2[CH2:13][NH:14][CH2:... | CC(Cl)OC(=O)Cl.FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1 | Cl.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 89a5abfed04083d8a577adf1e6b601d847582832e04d2c8e6d772c9562443319 | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].[C:2]1-[C:3]-[N;H0;D3;+0:4](-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:5]-1>>[C:2]1-[C:3]-[NH;D2;+0:4]-[C:5]-1.[ClH;D0;+0:1] | null | [] | null | null | 1 | HOUR | To a stirred solution of 1-benzhydryl-3-[2-(trifluoromethyl)-4′-(difluoro-methoxy)benzhydryloxy]azetidine (174) (2.73 g from previous step-assumed 4.7 mmol) in DCM (40 mL), cooled in ice-water bath, was added 1-chloroethyl chloroformate (1 mL, 9.4 mmol). After 1 h, the mixture was allowed to warm to ambient temperature... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | HCl | C(Cl)Cl | null | 1 | CC(Cl)OC(=O)Cl.FC(F)Oc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>Cl.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c41b24adb1f7401da5c430bf650698cc | CC(C)(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]([F:30])([F:31])[F:32])[CH2:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12... | CC(C)(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | 79.4 | [{"value": 78.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.4, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and tert-butyl isocyanate (29 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | CC(C)(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CC(C)(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47d7f310c62e4a03b070e27ca4584c84 | CCC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(CC)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH3:1][CH2:2][CH:3]([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([O:17][CH:18]([F:19])[F:20])[cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[C:29]([F:30])([F:31])[F:32])[CH2:33]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12](... | CCC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-1>>[C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:10]-1 | 71.4 | [{"value": 70.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.4, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and sec-butyl isocyanate (29 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mix... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | CCC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CCC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8eb88c272e2244d2bf0d985b28d29265 | CC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)C)C=CC=C1)(F)F | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][c... | CC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | 67.3 | [{"value": 66.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC(C)C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and iso-propyl isocyanate (25 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | CC(C)N=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CC(C)NC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a9223888b274104b8d56e1f6709704e | FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>>O=C(NC1CCCCC1)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C1(CCCCC1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F | [NH:10]1[CH2:11][CH:12]([O:13][CH:14]([c:15]2[cH:16][cH:17][c:18]([O:19][CH:20]([F:21])[F:22])[cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]([F:32])([F:33])[F:34])[CH2:35]1.[O:1]=[C:2]=[N:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[N:10... | FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1 | O=C(NC1CCCCC1)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NC1CCCCC1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5])-[C:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1)-[C:6] | 76.1 | [{"value": 75.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NC2CCCCC2)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and cyclohexyl isocyanate (32 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1CCCCC1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1.O=C=NC1CCCCC1>C(Cl)Cl>O=C(NC1CCCCC1)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33c04908f03e448ea4d26c7f14b073b1 | C=CCN=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>C=CCNC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C=C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F | [CH2:1]=[CH:2][CH2:3][N:4]=[C:5]=[O:6].[NH:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([O:16][CH:17]([F:18])[F:19])[cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]([F:29])([F:30])[F:31])[CH2:32]1>>[CH2:1]=[CH:2][CH2:3][NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:... | C=CCN=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C=CCNC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H2:1]=[C:2]-[C:3]-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H2:1]=[C:2]-[C:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | 62.1 | [{"value": 61.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "FC(C1=C(C(C2=CC=C(C=C2)OC(F)F)OC2CN(C2)C(=O)NCC=C)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[2-(trifluoromethyl)-4′-(difluoromethoxy)benzhydryloxy]azetidine hydrochloride (175) (100 mg, 0.24 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 280 mg, 0.72 mmol), molecular sieves and allyl isocyanate (22 μL, 0.24 mmol). After shaking at ambient temperature for 2 h, the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 2 | C=CCN=C=O.FC(F)Oc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>C=CCNC(=O)N1CC(OC(c2ccc(OC(F)F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82b9ec978d6e4ce1ad73097fdf97948d | CCC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CCC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(CC)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F | [CH3:1][CH2:2][CH:3]([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]([F:27])([F:28])[F:29])[CH2:30]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15]... | CCC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CCC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[NH;D2;+0:9]-[C:10]-1>>[C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:10]-1 | 77 | [{"value": 77.0, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.7, "product": "FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)CC)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (150 mg, 0.42 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 475 mg, 1.26 mmol), molecular sieves and sec-butyl isocyanate (49 μL, 0.42 mmol). The resultant mixture was shaken at ambient temperature for 16 b... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | CCC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CCC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bd225598cb54d33a95dd01bf1b64ce3 | CC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>CC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C(C)(C)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)NC(C)C)C=CC=C1)(F)F | [CH3:1][CH:2]([CH3:3])[N:4]=[C:5]=[O:6].[NH:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]([F:26])([F:27])[F:28])[CH2:29]1>>[CH3:1][CH:2]([CH3:3])[NH:4][C:5](=[O:6])[N:7]1[CH2:8][CH:9]([O:10][CH:11]([c:12]2[cH:13][cH:14][c:15]([F:16])[c... | CC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | CC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (150 mg, 0.42 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 475 mg, 1.26 mmol), molecular sieves and iso-propyl isocyanate (42 μL, 0.42 mmol). The resultant mixture was shaken at ambient temperature for 16 ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | CC(C)N=C=O.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>CC(C)NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ad871b074964553af5f26611c5407c1 | C[C@H](N=C=O)c1ccccc1.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>>C[C@H](NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 | Cl.FC(C1=C(C(C2=CC=C(C=C2)F)OC2CNC2)C=CC=C1)(F)F.C([O-])([O-])=O.C[C@@H](C1=CC=CC=C1)N=C=O>>FC(C1=C(C(C2=CC=C(C=C2)F)OC2CN(C2)C(=O)N[C@H](C2=CC=CC=C2)C)C=CC=C1)(F)F | [CH3:1][C@H:2]([N:3]=[C:4]=[O:5])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[NH:6]1[CH2:7][CH:8]([O:9][CH:10]([c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]([F:25])([F:26])[F:27])[CH2:28]1>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[N:6]1[CH2:7][CH:8]([O:9][CH:10]([c:11]2[c... | C[C@H](N=C=O)c1ccccc1.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1 | C[C@H](NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(NCc1ccccc1)N1CC(OC(c2ccccc2)c2ccccc2)C1 | [C;D1;H3:1]-[C:2](-[c:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C;D1;H3:1]-[C:2](-[c:3])-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:10]1-[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | null | null | To a solution of 3-[2-(trifluoromethyl)-4′-fluorobenzhydryloxy]azetidine hydrochloride (162) (150 mg, 0.42 mmol) in anhydrous DCM (4 mL) was added MP-carbonate (2.62 mmol/g; 475 mg, 1.26 mmol), molecular sieves and (S)-α-methylbenzyl isocyanate (60 μL, 0.42 mmol). The resultant mixture was shaken at ambient temperature... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | null | C[C@H](N=C=O)c1ccccc1.Fc1ccc(C(OC2CNC2)c2ccccc2C(F)(F)F)cc1>C(Cl)Cl>C[C@H](NC(=O)N1CC(OC(c2ccc(F)cc2)c2ccccc2C(F)(F)F)C1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3aa7d5465d64bea8395e49a7103e3a1 | C1CCNCC1.CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(C(=O)N3CCCCC3)cc2F)c2ccccc2C(F)(F)F)C1 | FC(C1=C(C(C2=C(C=C(C=C2)Br)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F.COCCOCCOC.C(=O)([O-])[O-].[K+].[K+].N1CCCCC1>>FC(C1=C(C(C2=C(C=C(C=C2)C(N2CCCCC2)=O)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.Br[c:16]1[cH:15][cH:14][c:13]([CH:12]([O:11][CH:10]2[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:38]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]([F:35])([F:36])[F:37])[c:26]([F:27])[cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[... | C1CCNCC1.CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(C(=O)N3CCCCC3)cc2F)c2ccccc2C(F)(F)F)C1 | null | CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)O.CC(=O)O.[Pd].[Pd] | C1(=CC=CC=C1)C | Acylation | OtherReaction | 86cab999e50c19aef9cb186a18524a99fd328f3546ffb30a7f2ed8765276ab5b | ec2db6fbb5e841818165b2afa8160946861f997bac6f4f60c5dc3c5839fa5323 | O=C(c1ccc(C(OC2CNC2)c2ccccc2)cc1)N1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 12 | [{"value": 12.0, "product": "FC(C1=C(C(C2=C(C=C(C=C2)C(N2CCCCC2)=O)F)OC2CN(C2)C(=O)NC(C)(C)C)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-[2-(trifluoromethyl)-2′-fluoro-4′-bromobenzhydryloxy]-N-(tert-butyl)-azetidine-1-carboxamide (115) (106 mg, 0.21 mmol), diglyme (1 mL), 4M K2CO3 (0.2 mL), toluene (1 mL), (R/S)-BINAP (12.1 mg), Herrmann's catalyst [CAS: 172418-32-5] (7.0 mg), Mo(CO)6 (26.0 mg) and piperidine (27 μL) was irradiated, with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amide | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | C1C[NH]C1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)O.CC(=O)O.[Pd].[Pd].C1(=CC=CC=C1)C | null | null | C1CCNCC1.CC(C)(C)NC(=O)N1CC(OC(c2ccc(Br)cc2F)c2ccccc2C(F)(F)F)C1>CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3[CH2-].CC(=O)O.CC(=O)O.[Pd].[Pd].C1(=CC=CC=C1)C>CC(C)(C)NC(=O)N1CC(OC(c2ccc(C(=O)N3CCCCC3)cc2F)c2ccccc2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cd42dda05e64188b4bc8d4b43d19fc1 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.OB(O)c1cccs1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccs4)cc3)c2C(F)(F)F)C1 | IC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F.S1C(=CC=C1)B(O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])(O)=O.[Na+]>>S1C(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F | I[c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][cH:14][c:13]([CH2:12][O:11][CH:10]3[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:34]3)[c:29]2[C:30]([F:31])([F:32])[F:33])[cH:28][cH:27]1.OB(O)[c:22]1[cH:23][cH:24][cH:25][s:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:... | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.OB(O)c1cccs1 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccs4)cc3)c2C(F)(F)F)C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCCC1 | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(COC2CNC2)cc(-c2ccc(-c3cccs3)cc2)c1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 73 | [{"value": 73.0, "product": "S1C(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "S1C(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | To a solution of aryl iodide (191) (100 mg, 0.19 mmol), 2-thiopheneboronic acid (48 mg, 0.38 mmol), palladium acetate (4 mg, 0.019 mmol) and triphenylphosphine (10 mg, 0.38 mmol) in tetrahydrofuran (10 mL) was added sodium bicarbonate (10 mL, saturated aqueous). The reaction mixture was heated to reflux (65° C.) for 4 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccsc1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1 | 65 | null | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.OB(O)c1cccs1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccs4)cc3)c2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7847d0a589b14840a0668750baef4bc6 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.c1cncc(B2OCCCO2)c1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccnc4)cc3)c2C(F)(F)F)C1 | IC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F.B1(OCCCO1)C2=CN=CC=C2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])(O)=O.[Na+]>>N1=CC(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F | I[c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][cH:14][c:13]([CH2:12][O:11][CH:10]3[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:35]3)[c:30]2[C:31]([F:32])([F:33])[F:34])[cH:29][cH:28]1.C1COB([c:22]2[cH:23][cH:24][cH:25][n:26][cH:27]2)OC1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]... | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.c1cncc(B2OCCCO2)c1 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccnc4)cc3)c2C(F)(F)F)C1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCCC1 | C-C Coupling | Suzuki coupling with boronic esters | 24090aed37a48c66cce36a374df588b856a5a96d58744799fd5f32d2bb560bf0 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc(-c3cccc(COC4CNC4)c3)cc2)c1 | C1-C-O-B(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-O-C-1.I-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10]:[c:11] | 8.5 | [{"value": 8.5, "product": "N1=CC(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.4, "product": "N1=CC(=CC=C1)C1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | To a solution of aryl iodide (191) (100 mg, 0.19 mmol), pyridine-3-boronic acid 1,3-propanediol cyclic ester (61 mg, 0.38 mmol), palladium acetate (4 mg, 0.019 mmol) and triphenylphosphine (10 mg, 0.38 mmol) in tetrahydrofuran (10 mL) was added sodium bicarbonate (10 mL, saturated aqueous). The reaction mixture was hea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.B1OCCCO1.c1ccncc1 | c1ccccc1.c1ccncc1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccncc1 | HI.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1 | 65 | null | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(I)cc3)c2C(F)(F)F)C1.c1cncc(B2OCCCO2)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(-c4cccnc4)cc3)c2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2f1392018114bdfb8d2b6298aa1e4bd | C1COCCN1.CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CN4CCOCC4)cc3)c2C(F)(F)F)C1 | ClCC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F.N1CCOCC1>>N1(CCOCC1)CC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F | [NH:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1.Cl[CH2:22][c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][cH:14][c:13]([CH2:12][O:11][CH:10]3[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36]3)[c:31]2[C:32]([F:33])([F:34])[F:35])[cH:30][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[... | C1COCCN1.CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CN4CCOCC4)cc3)c2C(F)(F)F)C1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(COC2CNC2)cc(-c2ccc(CN3CCOCC3)cc2)c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1):[c:4] | 70 | [{"value": 70.0, "product": "N1(CCOCC1)CC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "N1(CCOCC1)CC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The benzyl chloride (195) (40 mg, 0.088 mmol) and morpholine (3 mL, 31 mmol) were heated to 50° C. for 18 h. The reaction mixture was cooled, excess amine was removed under reduced pressure and the residue partitioned between ethyl acetate and sodium hydroxide (1M). The organic phase was washed with water (2×20 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1C[NH]C1.c1ccccc1.c1ccccc1.C1COCC[NH]1 | HCl | null | null | null | C1COCCN1.CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CN4CCOCC4)cc3)c2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95d2b18bc88b41818ace71d5bb059c8e | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1.NCC1CC1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CNCC4CC4)cc3)c2C(F)(F)F)C1 | ClCC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F.C1(CC1)CN>>C1(CC1)CNCC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F | Cl[CH2:22][c:21]1[cH:20][cH:19][c:18](-[c:17]2[cH:16][cH:15][cH:14][c:13]([CH2:12][O:11][CH:10]3[CH2:9][N:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:35]3)[c:30]2[C:31]([F:32])([F:33])[F:34])[cH:29][cH:28]1.[NH2:23][CH2:24][CH:25]1[CH2:26][CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[... | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1.NCC1CC1 | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CNCC4CC4)cc3)c2C(F)(F)F)C1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1cc(COC2CNC2)cc(-c2ccc(CNCC3CC3)cc2)c1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "C1(CC1)CNCC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "C1(CC1)CNCC1=CC=C(C=C1)C=1C(=C(C=CC1)COC1CN(C1)C(=O)NC(C)(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The benzyl chloride (195) (34 mg, 0.075 mmol) and cyclopropylmethylamine (1 mL, 12 mmol) were heated to 50° C. for 18 h. The reaction mixture was cooled, excess amine was removed under reduced pressure and the residue partitioned between ethyl acetate and sodium hydroxide (1M). The organic phase was washed with water (... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1.C1CC1 | HCl | null | null | null | CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CCl)cc3)c2C(F)(F)F)C1.NCC1CC1>>CC(C)(C)NC(=O)N1CC(OCc2cccc(-c3ccc(CNCC4CC4)cc3)c2C(F)(F)F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d641a6ce846447a866203aa6b991174 | O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-]>>O=C(O)[C@@H](O)[C@H](O)C(=O)O | C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-].C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-].C(C)(C)(C)NC(=O)N>>C(C)(C)(C)NC(=O)N.C([C@@H](O)[C@H](O)C(=O)O)(=O)O | [O:9]=[C:10]([O-:11])[C@@H:12]([OH:13])[C@H:14]([OH:15])[C:16](=[O:17])[O-:18]>>[O:9]=[C:10]([OH:11])[C@@H:12]([OH:13])[C@H:14]([OH:15])[C:16](=[O:17])[OH:18] | O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] | O=C(O)[C@@H](O)[C@H](O)C(=O)O | null | null | null | Reduction | OtherReaction | 3b3d485bc5c30e363af0f73a916e2e04c81f73cf1897f856fd2936b9219ffa7a | c73219abf332cf4c9f2a915b45ea4e3750da12c7d0c441b84d0af067a1278a90 | null | [O-;H0;D1:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[O;D1;H0:8]=[C:6](-[OH;D1;+0:7])-[C:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | The batch 1 D-tartrate of (208), was reconverted to the free base (a necessary part of the chiral assay procedure) using the procedure given above (to give 3.49 g), and the D-tartrate formation procedure was repeated as described to give the batch 2 salt of (208), 4.41 g (92% from D-tartaric acid) (chiral LC: 1.7% at 8... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid.Carboxylic acid | null | null | null | null | null | null | null | O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-]>>O=C(O)[C@@H](O)[C@H](O)C(=O)O |
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