7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 58495608, compound

HRID 1191062Notes

Reaction equation

HRID 1191062 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.[CH3:27][N:28]([CH3:40])[C:29]([S:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1)=[O:30]>>[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:14])([F:15])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:37][CH2:36][C:35]1[CH:34]=[CH:33][C:32]([S:31][C:29](=[O:30])[N:28]([CH3:27])[CH3:40])=[CH:39][CH:38]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 59828901HCID 59828901, compound

Product 1

HCID 58495608HCID 58495608, compoundYield 43.7%

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 (348 mg, 0.8 mmol) with 4-dimethylcarbamoylthio-benzylamine (345 mg, 1.6 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate (170 mg, 43%).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-485e9effc9dc46f39939f51da04368ce
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…