Sodium hydride → N, N-dicyclopentyl-4-(1H-imidazo[4,5-b]pyridin-1-ylmethyl)-3-methoxybenzamide

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To a stirred solution of imidazo[4,5-b]pyridine (350 mg, 2.94 mmol) in N,N-dimethylformamide (25 mL), sodium hydride (118 mg, 60% dispersion in mineral oil, 2.94 mmol) was added. After stirring for 2 hr, 4-bromomethyl-3-methoxy-N,N-dicyclopentyl benzamide (1.4 g, 3.57 mmol) was added in small installments over 10 min. The reaction mixture was stirred under argon at 25° C. After 18 h, the reaction was quenched by adding acetic acid (0.5 mL) and the solvent was removed under reduced pressure at <45° C. The crude mixture (2 g) was chromatographed (silica gel, CH2Cl2 -MeOH-NH4OH 90-10-1) to give the title compound. (160 mg, 13%) DSC 198° C.; Anal calcd. for C25H30N4O2 ·0.7H2O: C, 69.65; H, 7.34; N, 12.99. Found C, 69.72; H, 7.39; N, 12.63.

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