Trifluoroacetic acid → N-Methyl-N-[1-(tetrahydro-2H-pyran-4-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl]acetamide

HRID 1987204Notes

Reaction equation

HRID 1987204 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([N:17]([CH3:21])[C:18](=[O:20])[CH3:19])[CH:6]=[CH:7][C:8]=1[NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[F:22][C:23]([F:28])([F:27])[C:24](O)=O>>[CH3:21][N:17]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:10][CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[C:24]([C:23]([F:28])([F:27])[F:22])=[N:2][C:3]=2[CH:4]=1)[C:18](=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57441083HCID 57441083, compound

Product 1

HCID 57723217N-Methyl-N-[1-(tetrahydro-2H-pyran-4-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazol-5-yl]acetamideYield 90%

Procedure

A solution of N-{3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}-N-methylacetamide hydrochloride (2.77 g, 10 mmol) in trifluoroacetic acid (60 mL) was heated to reflux for 18 h. After evaporation of the solvent, the residue was dissolved in EtOAc (200 mL), washed with 2N NaOH (2×10 mL) and dried over Na2SO4. The crude product was purified by MPLC using EtOAc on silica gel to give 3.18 g (90%) of a white solid as the title compound. MS (ESI) (M+H)+=356.02.

Workup

  1. temperatureto reflux for 18 h
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washwashed with 2N NaOH (2×10 mL)
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-55358127a78f43d8ac383f82c420b358
Source dataset
uspto-grants-2009_06
Patent number
US07550495B2

Reaction notes

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