7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624167, compound

HRID 1191122Notes

Reaction equation

HRID 1191122 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[CH:27]1([C:33](=[O:43])[CH2:34][C:35]2[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:40][CH2:39][C:38]1[CH:41]=[CH:42][C:35]([CH2:34][C:33]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:43])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495452HCID 58495452, compound

Product 1

HCID 86624167HCID 86624167, compoundYield 46.1%

Procedure

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (137 mg, 0.325 mmol) and 4-(2-cyclohexyl-2-oxo-ethyl)-benzylamine (150 mg, 0.65 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (95:5) to obtain 7-chloro-6-[4-(2-cyclohexyl-2-oxo-ethyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (76 mg, 46%). MS (ES+) m/z: 507 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (95:5)

Sources & evidence

ORD record
ord-80eec4145df64a0b9e05af7cb19d40d3
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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