Hydrochloric Acid → 1-[(4-Fluorophenyl)methyl]pyrazolo[3,4-c]pyridine-5-carbohydroxamic acid

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Reaction Steps

To a stirring solution of methyl 1-(4-fluorobenzyl)-1H-pyrazolo[3,4-c]pyridine-5-carboxylate (96 mg, 0.33 mmol) in methanol (4 mL) was added a 50% v/v solution of hydroxylamine in water (2 mL) followed by 10% sodium hydroxide solution in water (1 mL). The mixture was stirred for 2 hours, then 10% hydrochloric acid solution in water (1 mL) was added until a neutral pH was obtained, and the mixture was concentrated under reduced pressure. Methanol was added and the mixture was purified by reverse phase preparative HPLC (Dionex, 0-40% acetonitrile:water v/v, 40 minutes) to provide a white solid (50 mg, 52% yield). 1H NMR (DMSO-d6): δ ppm 9.22 (s, 1H), 8.39 (s, 1H), 8.37 (s, 1H), 7.37 (m, 2H), 7.15 (m, 2H), 5.83 (s, 2H). Anal. HPLC: >95% (@ 254, 222 nM). HRMS calcd for C14H11FN4O2 (M+H) 287.0939, found 287.0936.

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