7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624177, compound

HRID 1191136Notes

Reaction equation

HRID 1191136 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][C:28]([CH3:43])([CH3:42])[C:29]([NH:31][CH2:32][CH2:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=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:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([CH2:33][CH2:32][NH:31][C:29](=[O:30])[C:28]([CH3:42])([CH3:27])[CH3:43])=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495507HCID 58495507, compound

Product 1

HCID 86624177HCID 86624177, compoundYield 70.3%

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 (106 mg, 0.251 mmol) and 4-[2-(2,2-dimethyl-propionylamino)-ethyl]-benzylamine (110 mg, 0.427 mmol). Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (6:4) to obtain 7-chloro-6-{4-[2-(2,2-dimethyl-propionylamino)-ethyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (90 mg, 70%). MS (ES+) m/z: 510 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (6:4)

Sources & evidence

ORD record
ord-9ce35b625cf44072a6a35e94ba2df6f2
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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