Chloroacetyl chloride → HCID 69146822, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of 2-amino-4-[3-amino-4-(dimethylamino)phenyl]-6-{2-[(4-methoxybenzyl)-oxy]phenyl}nicotinonitrile (starting compound 4, 0.500 g, 1.724 mmol) in THF (7 mL) under an argon atmosphere was added chloroacetyl chloride (0.121 g, 1.074 mmol). The mixture was stirred at 0° C. for 15 minutes and then partitioned between ethyl acetate and saturated aqueous NaHCO3. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was suspended in ethyl acetate and ethanol. The resulting solid was collected by filtration, washed with ethanol, and dried under reduced pressure to give N-[5-(2-amino-3-cyano-6-{2-[(4-methoxybenzyl)oxy]-phenyl}-4-pyridinyl)-2-(dimethylamino)phenyl]-2-chloroacetamide as a yellow solid. (0.410 g, yield 70%)

Provenance & Evidence