Dichloromethane → (S)-3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride

Participants

Reaction Steps

TFA (1 mL) was added to a solution of (R)-tert-butyl 4-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.14 g, 0.22 mmol) in DCM (1 mL), and the resulting solution was stirred at room temperature for 4 hours. The reaction was then concentrated to dryness and dried under vacuum for 1 hour. TFA (2 mL) was next added, and the mixture was stirred at 100° C. in a sealed tube for 18 hours. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (0.5 mL). HCl in ether (2 mL, 2N) and ether (3 mL) were then added, and the resulting solid was collected by filtration to give (S)-3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride (0.105, 96%) as a solid. MS APCI (+) m/z 370.2 detected.

Provenance & Evidence