Dichloromethane → 2-(4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol dihydrochloride

Reaction equation

C(O)(C(F)(F)F)=O.C([O:12][CH2:13][CH2:14][O:15][C:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][C:23]=2[N:25]2[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]2)[N:18](CC2C=CC(OC)=CC=2)[N:17]=1)(C)(C)C.C(Cl)[Cl:48]>>[ClH:48].[ClH:48].[N:25]1([C:23]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:18][N:17]=[C:16]([O:15][CH2:14][CH2:13][OH:12])[C:24]=23)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 68755474tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 687580382-(4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol dihydrochlorideYield 100%

Procedure

TFA (1 mL) was added to tert-butyl 4-(3-(2-tert-butoxyethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.080 g, 0.148 mmol) in DCM (1 mL) and stirred at room temperature for 4 hours. The reaction was then concentrated to dryness and dried under vacuum for 3 hours. TFA (2 mL) was then added, and the mixture was heated at 100° C. in a sealed tube for 18 hours. The reaction was then cooled to room temperature and concentrated to dryness. The resulting residue was dissolved in DCM (2 mL), and HCl in ether (1 mL, 2N) was added. The resulting solid was collected by filtration to give 2-(4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)ethanol dihydrochloride (0.050 g, 100%).