Triethylamine → HCID 121393717, compound

Participants

Reaction Steps

4-(5-{5-Methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (107 mg, 0.262 mmol) was stirred in DCM (3 mL) and triethylamine (0.109 mL, 0.786 mmol) with N,N-dimethylaminopyridine (2 mg). To this mixture was added 4-nitrophenyl chloroformate (106 mg, 0.524 mmol) and the resulting mixture stirred at RT for 1 h. N-methylethylamine (93 mg, 1.57 mmol) in DCM (1 mL) was then added and stirring was continued for a further 2 h. The mixture was diluted with more DCM, washed with water, the organic phase separated, dried over Na2SO4 and evaporated. The product was purified by chromatography on a 12 g silica gel column, eluting with a gradient of 20% to 60% EtOAc in cyclohexane. The gum thus obtained was dissolved in a small quantity (<1 mL) of EtOAc and diluted with cyclohexane resulting in a formation of a white solid which was filtered off and dried. (65 mg, 50%).

Provenance & Evidence