7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → (R)-7-chloro-6-{4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1191138Notes

Reaction equation

HRID 1191138 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@@H:28]([NH:33][C:34]([CH2:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1)=[O:35])[C:29]([F:32])([F:31])[F: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:13])([F:15])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:42][CH2:41][C:40]1[CH:39]=[CH:38][C:37]([CH2:36][C:34](=[O:35])[NH:33][C@H:28]([CH3:27])[C:29]([F:32])([F:30])[F:31])=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495445(R)-4-[(1-Methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine

Product 1

HCID 86624179(R)-7-chloro-6-{4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 45%

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 (84 mg, 0.196 mmol) and (R)-4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamine (102 mg, 0.39 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain (R)-7-chloro-6-{4-[(1-methyl-2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (47 mg, 45%). MS (ES+) m/z: 536 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-f86df82d6d69444c93840007288af64a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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