Isopropylamine → 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropylamide

HRID 2353973Notes

Reaction equation

HRID 2353973 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5]([N:8]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][N:12]([C:16](Cl)=[O:17])[C:11]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:10]1=2)(=[O:7])[CH3:6]>ClCCl>[CH:1]([NH:4][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:9]([N:8]([C:5](=[O:7])[CH3:6])[CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[C:27]([C:35]([F:36])([F:37])[F:38])[CH:26]=2)[C:10]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:11]1=2)=[O:17])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 866160835-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl chloride

Product 1

HCID 590031155-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropylamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl amine (0.3 mmol) to a dichloromethane solution of 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl chloride (0.050 g, 0.11 mmol) at room temperature under nitrogen. After stirring for 1 h remove solvent under vacuum and chromatograph the crude product over silica gel using ethyl acetate/hexane (30-40%) to elute. This provides the title compound (0.052 g, 87%) as a colorless solid: MS (ES+): 550 (M+H).

Workup

  1. customremove solvent under vacuum and chromatograph the crude product over silica gel
  2. washto elute

Sources & evidence

ORD record
ord-417611cde6ab4be48cd27643b46d5cb2
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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