7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624175, compound

HRID 1191133Notes

Reaction equation

HRID 1191133 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]([CH3:42])([CH3:41])[C:29]([NH:31][CH2:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=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:38][CH2:37][C:36]1[CH:39]=[CH:40][C:33]([CH2:32][NH:31][C:29](=[O:30])[C:28]([CH3:41])([CH3:27])[CH3:42])=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 59828903HCID 59828903, compound

Product 1

HCID 86624175HCID 86624175, compoundYield 76%

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 (299 mg, 0.704 mmol) and 4-[(2,2-dimethyl-propionylamino)-methyl]-benzylamine (310 mg, 1.41 mmol). Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (3:2) to obtain 7-chloro-6-{4-[(2,2-dimethyl-propionylamino)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (265 mg, 76%). MS (ES+) m/z: 496 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (3:2)

Sources & evidence

ORD record
ord-c340ca378d194cf18a57c29cb6c22373
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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