Water → 2-{4-[2-[1-(acetylamino)-1-methylethyl]-6-chloro-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate

HRID 2077819Notes

Reaction equation

HRID 2077819 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27]([NH2:30])([CH3:29])[CH3:28])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[C:31](Cl)(=[O:33])[CH3:32].O>ClCCl>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17]3[CH:18]=[C:19]([Cl:26])[C:20]([C:22]([F:24])([F:25])[F:23])=[CH:21][C:16]=3[N:15]=[C:14]2[C:27]([NH:30][C:31](=[O:33])[CH3:32])([CH3:29])[CH3:28])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 21876466HCID 21876466, compound

Product 1

HCID 218760062-{4-[2-[1-(acetylamino)-1-methylethyl]-6-chloro-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetateYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{4-[2-(1-amino-1-methylethyl)-6-chloro-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl acetate (step 3, 121 mg, 0.27 mmol) in dichloromethane (5 ml) was added acetyl chloride (0.02 ml, 0.3 mmol). The reaction mixture was stirred at room temperature for 7 h. To the reaction mixture was added water (5 ml) and the aqueous mixture was extracted with dichloromethane (30 ml). The organic layer was washed with water (5 ml) and brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with CH2Cl2/methanol (10/1) to afford 76 mg (57%) of the title compound as white amorphous.

Workup

  1. extractionthe aqueous mixture was extracted with dichloromethane (30 ml)
  2. washThe organic layer was washed with water (5 ml) and brine (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with CH2Cl2/methanol (10/1)

Sources & evidence

ORD record
ord-dbd7933bacdb48f0b22c94f1a2b7697a
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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