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

HRID 2353991Notes

Reaction equation

HRID 2353991 reaction equation
[C:1]([N:4]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[CH:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12](Cl)=[O:13])[C:7]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:6]1=2)(=[O:3])[CH3:2].[NH3:35]>CCOC(C)=O>[C:1]([N:4]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:33])([F:32])[F:34])[CH:22]=1)[CH:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([NH2:35])=[O:13])[C:7]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:6]1=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866160835-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl chloride

Product 1

HCID 866160915-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl chloride (0.1 mmol, 50.0 mg) and ammonia (1.0 mmol, 1.0 mL, 1M in MeOH) was refluxed at 70° C. for 6 h with vigorous stirring. The solvent was removed in vacuo and the crude product was purified by crystallization using EtOAc. The product was obtained as a white solid; Rf 0.1 (EtOAc); MS (ES+): 508 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by crystallization
  3. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-564178ec30cc4a2db56da17385c00dd8
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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