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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A solution of methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (460 mg, 1 mmol) in THF (30 mL) was treated with a solution of lithium hydroxide (237 mg, 10 mmol) in water (10 mL) and stirred at ambient temperature for 16 h. The residue was dissolve in minimum amount of water and the pH was adjusted to 4 by the addition of aqueous hydrochloric acid (2M). The resulting solution was concentrated to dryness to afford 446 mg of the title compound. LC-MS m/z 452 (M+H)+, 0.77 min (ret time).

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