Diethyl Ether → 1-{5-[10-Chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridin-2-yl}ethanone

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Reaction Steps

Under nitrogen atmosphere to a solution of 5-[10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-4-methylpyridine-2-carbonitrile (Example 59; 70.0 mg, 0.172 mmol) in tetrahydrofuran (2 mL) was added 3M methylmagnesium bromide solution in diethyl ether (0.115 mL, 0.345 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 30 min, the mixture was diluted with 0.1N hydrochloric acid (5 mL) at 0° C. After the resultant mixture was stirred at room temperature for 30 min, the mixture was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give, the title compound as a solid (59.6 mg, 0.140 mmol, 81%). Analytically pure material was obtained by recrystallization from ethyl acetate/n-hexane.

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