Dichloromethane → 5-cyclobutyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine hydrochloride

Reaction equation

C(O)(C(F)(F)F)=O.[CH:8]1([C:12]2[C:13]([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[C:14]3[CH:20]=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1.C(Cl)[Cl:35]>>[ClH:35].[CH:8]1([C:12]2[C:13]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[C:14]3[CH:20]=[N:19][NH:18][C:15]3=[N:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 68767958tert-butyl 4-(5-cyclobutyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 687577895-cyclobutyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine hydrochlorideYield 97%

Procedure

TFA (0.60 mL, 7.83 mmol) was added to a solution of tert-butyl 4-(5-cyclobutyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.14 g, 0.39 mmol) in DCM (10 mL) and stirred at room temperature for 1 hour. The solvent was removed. The resulting residue was dissolved in DCM (0.5 mL), and 2N HCl in ether (2 mL) was added. The solid formed was collected by filtration to give 5-cyclobutyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine hydrochloride (0.125 g, 97%).