Acetic Acid → HCID 57863424, compound

Participants

Reaction Steps

Dissolve 1-(5-tert-butyl-isoxazol-3-yl)-3-(2-fluoro-4-{7-[4-(piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea hydrochloride (0.290 g, 0.469 mmol) in methanol (5 mL) and acetone (0.041 mL, 0.563 mmol). Add acetic acid (0.032 mL, 0.563 mmol); stir the mixture for five minutes. Add sodium cyanoboro-hydride (0.053 g, 0.845 mmol). Stir the mixture at room temperature for 14 hours. Concentrate to dryness and quench with 1 N HCl (5 mL). Partition between ethyl acetate and 1 N NaOH, wash with aqueous saturated sodium chloride, dry the organics over magnesium sulfate, filter, and concentrate. Purify by column chromatography (hexanes→5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 M NH3 in methanol in dichloromethane) to afford product (0.019 g, 7%). MS(ES), m/z 624 (M+1).

Provenance & Evidence