Pyridine → HCID 68775643, compound

Participants

Reaction Steps

To a solution of 2-{4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl}butan-1-ol (60 mg, 0.129 mmol) in pyridine (0.5 mL) was added methanesulfonyl chloride (0.050 ml, 0.645 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate at 0° C. and extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting mesylate was dissolved in N,N-dimethylformamide (1 mL) and potassium carbonate (36 mg, 258 mmol) was added. The mixture was stirred at 80° C. for 15 hr. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 1-15% ethyl acetate/n-hexane gradient mixture. The desired fractions were concentrated in vacuo, and the resulting solid was recrystallized from methanol to give the title compound (23 mg, 0.0515 mmol, 40%) as a colorless crystal.

Provenance & Evidence