7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624180, compound

HRID 1191139Notes

Reaction equation

HRID 1191139 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.[C:27]([NH:31][C:32]([CH2:34][CH2:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([NH:31][C:32]([CH2:34][CH2:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:3]2[C:4]3[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6][C:5]=3[CH:17]=[CH:18][C:2]=2[Cl:1])=[CH:38][CH:37]=1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 59828846HCID 59828846, compound

Product 1

HCID 86624180HCID 86624180, compoundYield 74%

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 (85 mg, 0.2 mmol) and 4-[2-(tert-butylcarbamoyl)-ethyl]-benzylamine (80 mg, 0.34 mmol). Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (95:5 to 1:1 gradient) to obtain 6-{4-[2-(tert-butylcarbamoyl)-ethyl]benzylamino}-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (75 mg, 74%). MS (ES+) m/z: 510 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (95:5 to 1:1 gradient)

Sources & evidence

ORD record
ord-96599063bed44ce893ae08b98caca75a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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