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

Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate (0.706 g, 1.518 mmol), lithium hydroxide (0.0545 g, 2.28 mmol), THF (60 mL), and water (20 mL) were combined and stirred under argon at room temperature overnight. Solvents were pumped off, and the residue taken up in water (20 mL). The mixture was acidified with HCl until it appeared that no more precipitate was forming. The pH at this time was about 6. The solid was filtered off and washed 2× with a small volume of water. The material was dried under vacuum for two days until weight loss was minimal to give the title compound as a white solid. LC-MS m/z 451.8 (M+H)+, 1.48 min (ret time); mp 207-209° C.; analytical HPLC shows 100% purity, (ret time 10.177 min).

Provenance & Evidence