Acetic Acid → HCID 136359783, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of ((2S,5R)-2,5-Dimethyl-piperazin-1-yl)-[6-(2-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (200 mg, precursor of example 543) and pyridine-2-carboxaldehyde (46 mg) in dichloroethane (5 mL) containing acetic acid (7.4 μL) was added sodium triacetoxy borohydride (136 mg) at r.t., then the mixture was stirred at 40° C. overnight. Water was added carefully and the mixture was extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated to dryness giving ((2S,5R)-2,5-Dimethyl-4-pyridin-2-ylmethyl-piperazin-1-yl)-[6-(2-fluoro-4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone. This was dissolved in THF (7 mL) containing conc. hydrochloric acid (1.5 mL) and stirred r.t. overnight. The precipitate formed was filtered off and dried in air. ((2S,5R)-2,5-Dimethyl-4-pyridin-2-ylmethyl-piperazin-1-yl)-[6-(2-fluoro-4-hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone was obtained as a hydrochloride salt (263 mg, 100%).

Provenance & Evidence