Dimethylformamide → HCID 22100849, compound

Participants

Reaction Steps

To 2-isopropyl-4-methoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-ylamino)benzimidazole (3.3 g) in DMF (200 mL) was added NaH (0.35 g) at ambient temperature. After stirring at ambient temperature for 30 minutes, the reaction flask was cooled to -10° C. and 7-bromomethyl-2-naphthonitrile (2.2 g) was added. The reaction was allowed to warm to ambient temperature and stirred at ambient temperature for 15 hours. The reaction was worked up between ethyl acetate and H2O. The organic layer was dried, concentrated and purified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient) to afford 1-(4-cyanonaphth-1-yl)methyl-2-isopropyl-4-methoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-ylamino)benzimidazole, and 1-(4-cyanonaphth-1-yl)methyl-2-isopropyl-7-methoxycarbonyl-5-(N-(tert-butoxycarbonyl)-piperidin-4-ylamino)benzimidazole.

Provenance & Evidence