7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624170, compound

HRID 1191125Notes

Reaction equation

HRID 1191125 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]([O:31][C:32]([N:34]([CH2:41][C:42]1[CH:49]=[CH:48][C:45]([CH2:46][NH2:47])=[CH:44][CH:43]=1)[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32]([N:34]([CH2:41][C:42]1[CH:43]=[CH:44][C:45]([CH2:46][NH:47][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:48][CH:49]=1)[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]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 58495631HCID 58495631, compound

Product 1

HCID 86624170HCID 86624170, 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 (300 mg, 0.71 mmol) and 4-[N-(tert-butoxycarbonyl)-N-(cyclohexyl)-aminomethyl]-benzylamine (335 mg, 1.05 mmol). Purify by chromatography on silica gel (150 g) eluting with hexane/EtOAc (1:0 to 9:1 gradient) to obtain 6-{-4-[N-(tert-butoxycarbonyl)-N-(cyclohexyl)-aminomethyl]-benzylamino}-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (320 mg, 76%). MS (ES+) m/z: 494 (M-Boc+H)+.

Workup

  1. customPurify by chromatography on silica gel (150 g)
  2. washeluting with hexane/EtOAc (1:0 to 9:1 gradient)

Sources & evidence

ORD record
ord-6a984ca813bd4f15b0b50fae8ba3d27d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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