Hydrochloric Acid → 3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

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Reaction Steps

A mixture of methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (8.52 g, 18.3 mmol), LiOH (3.84 g, 91.5 mmol), water (30 mL) and methanol (60 mL) was stirred at room temperature overnight. The aqueous layer was acidified with 2 N HCl to pH around 1. Brine (30 mL) was added to the solution. White solid was precipitated out from the solution. The solid was filtered off and washed with water. The aqueous layer was extracted with ethyl acetate twice. The combined organic layers were concentrated under vacuum to give a solid. All solid was dissolved in DCM and combined into one batch. Solvent was concentrated to give crude residue. The crude residue was then triturated with ether to give 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid as a white solid (7.72 g, 86%). LC-MS m/z 452 (M+H)+.

Provenance & Evidence