Acetone → N-(5-Chloropyridin-2-yl)-2-[4-(N,N-dimethylamino)-2-(1-isopropyl-piperidin-4-yloxy)benzoylamino]benzamide Hydrochloride

Participants

Reaction Steps

To a mixture of N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylamino)-2-(piperidin-4-yloxy)benzoylamino]benzamide (250 mg, 0.51 mmol), acetone (0.07 mL, 1.0 mmol) and 20% AcOH/MeOH (2 mL) was added a solution of 0.25 M NaCNBH3/MeOH (2 mL, 0.5 mmol). The reaction was stirred for 24 hours and then it was diluted with water and CH2Cl2. After partitioning, the organic layer was washed with 50% satd Na2 CO3, dried over Na2 SO4, and concentrated. The residue was HPLC chromatographed (Vydac, 5% CH3 CN in 0.1% TFA/H2O to 70% CH3 CN in 0.1% TFA/H2O, t=28.8 m) and then treated with HCl to give the desired product as a white solid (66 mg, 23%).

Provenance & Evidence