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

Reaction equation

C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[O:12][C:13]1[C:14]([N:31]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)=[C:15]2[CH:21]=[N:20][N:19](CC3C=CC(OC)=CC=3)[C:16]2=[N:17][CH:18]=1.C(Cl)[Cl:48]>>[ClH:48].[ClH:48].[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[O:12][C:13]1[C:14]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[C:15]2[CH:21]=[N:20][NH:19][C:16]2=[N:17][CH:18]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 68765011tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 687580405-(3-fluorophenoxy)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochlorideYield 99%

Procedure

TFA (0.5 mL) was added to tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.020 g, 0.0375 mmol) in DCM (2 mL) and stirred at room temperature for 1 hour. The reaction was concentrated to dryness. The resulting residue was dissolved in TFA (1 mL) and heated at 65° C. for 2 hours. The reaction was concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), and HCl in ether (1 mL, 2N) was added. The reaction was concentrated to dryness to give 5-(3-fluorophenoxy)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.014 g, 99%) as a solid. MS APCI (+) m/z 314.1 detected.