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]1Participants
4
Reactant 3
Product 1
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%).
Workup
- concentrationThe reaction was then concentrated to dryness
- customdried under vacuum for 3 hours
- additionTFA (2 mL) was then added
- temperaturethe mixture was heated at 100° C. in a sealed tube for 18 hours
- temperatureThe reaction was then cooled to room temperature
- concentrationconcentrated to dryness
- dissolutionThe resulting residue was dissolved in DCM (2 mL)
- additionHCl in ether (1 mL, 2N) was added
- filtrationThe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-697d8a6209a24d86847202aa51e39412
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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