Trifluoroacetic acid methylene chloride → N-(3,5-Bis-trifluoromethyl-benzyl)-N-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

HRID 2353915Notes

Reaction equation

HRID 2353915 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([N:15]([C:31](=[O:33])[CH3:32])[CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)[C:10]2[CH:34]=[C:35]([CH3:42])[C:36]([C:38]([F:41])([F:40])[F:39])=[CH:37][C:9]1=2)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=1)[CH2:16][N:15]([CH:11]1[CH2:12][CH2:13][CH2:14][NH:8][C:9]2[CH:37]=[C:36]([C:38]([F:39])([F:40])[F:41])[C:35]([CH3:42])=[CH:34][C:10]1=2)[C:31](=[O:33])[CH3:32]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86616071HCID 86616071, compound

Product 1

HCID 86616070N-(3,5-Bis-trifluoromethyl-benzyl)-N-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamideYield 96%

Procedure

A solution of (S)-5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid tert-butyl ester (0.920 g, 1.50 mmol) (Example 110) in 1:1 TFA/DCM (10.0 ml) was stirred at room temperature for 2 hours. The solvents were evaporated on a (rotary evaporation). Purification by silica gel chromatography (gradient eluent, 0-30% ethyl acetate in hexane) provided the titled compound (0.736 g, 96%) as white solid. MS (ES+): 513 (M+H).

Workup

  1. customThe solvents were evaporated on a (rotary evaporation)
  2. customPurification by silica gel chromatography (gradient eluent, 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bbc403dc0ebc4b5b82dd536fe27c1d91
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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