6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide → HCID 178434418, compound

Participants

Reaction Conditions

Reaction Steps

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1-benzyl-4-phenyl-piperidin-4-yl)-amide (275 mg) was dissolved in methanol (10 mL) and purged with argon, then hydrogen. Palladium (10% on charcoal, 82 mg) was added and the mixture was stirred at 40° C. for 2 h, then at r.t. over night. The catalyst was filtered off, the solvent was evaporated and the residue was dissolved in methanol (4 mL) and water (1 ml). Concentrated aqueous hydrochloric acid (1 mL) was added and the solution was stirred for 3 d. The solution was kept at −20° C. in a freezer until a precipitate appeared, which was filtered off and washed with methanol giving 6-(2-Fluoro-4-hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (4-phenyl-piperidin-4-yl)-amide (144 mg). A second fraction of title compound was obtained by storing the filtrate at −20° C. for a day and filtering off the precipitated product (31 mg, 95% overall yield).

Provenance & Evidence