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

HRID 387554Notes

Reaction equation

HRID 387554 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

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 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%).

Workup

  1. customThe solvent was removed
  2. dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
  3. addition2N HCl in ether (2 mL) was added
  4. customThe solid formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-dd554c57eac34cadbc051b329efb08c1
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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