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

HRID 2353987Notes

Reaction equation

HRID 2353987 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([NH:20][NH2:21])=[O:19])[C:13]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:12]1=2)[C:8](=[O:10])[CH3:9].Cl[C:37]([O:39][CH2:40][CH3:41])=O>CO.CCOC(C)=O>[F:33][C:30]([F:31])([F:32])[C:28]1[CH:27]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:34])[F:35])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[O:19][C:37]([O:39][CH2:40][CH3:41])=[N:21][N:20]=2)[C:13]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:12]1=2)[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 86616087N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-hydrazinocarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Product 1

HCID 59003105N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-(5-ethoxy-[1,3,4]oxadiazol-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-hydrazinocarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.13 mmol, 73 mg) in MeOH (1 mL) was added ethyl chloroformate (0.41 mmol, 45.0 μL) and the reaction mixture was refluxed for 12 h. After completion (by TLC), the mixture was cooled, diluted with EtOAc (20 mL), washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the crude product as viscous oil. Purification by flash silica gel column chromatography gave the title compound as colorless foam; Rf 0.40 (EtOAc/Hexane, 1:1, v/v); MS (ES+): 599 (M+Na+).

Workup

  1. temperaturethe reaction mixture was refluxed for 12 h
  2. temperatureAfter completion (by TLC), the mixture was cooled
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product as viscous oil
  7. customPurification by flash silica gel column chromatography

Sources & evidence

ORD record
ord-27889d956803454d94e6c7370ac52548
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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