Ethyl Acetate → N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-hydrazinocarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

HRID 2353986Notes

Reaction equation

HRID 2353986 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].O.[NH2:36][NH2:37].CCOC(C)=O>CO>[F:33][C:31]([F:32])([F:34])[C:23]1[CH:22]=[C:21]([CH:26]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:24]=1)[CH2:20][N:4]([CH:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([NH:36][NH2:37])=[O:13])[C:7]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:6]1=2)[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 866160835-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-8-chloro-2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl chloride

Product 1

HCID 86616087N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-hydrazinocarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (1.0 mmol, 0.52 g) and hydrazine hydrate (50.0 mmol, 1.56 mL) in MeOH (5 mL) was refluxed at 70° C. for 12 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 white solid; Rf 0.2 (EtOAc); MS (ES+): 523 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-d59ba0a716304775b32b987ee97cb0f1
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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