Dichloromethane → 3-(4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride
Reaction equation
C(O)(C(F)(F)F)=O.CC1(C)[O:13][CH:12]([CH2:14][O:15][C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][C:23]=3[N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)[N:18](CC3C=CC(OC)=CC=3)[N:17]=2)[CH2:11][O:10]1.C(Cl)[Cl:49]>>[ClH:49].[ClH:49].[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][CH:12]([OH:13])[CH2:11][OH:10])[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-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.068 g, 0.123 mmol) in DCM (1 mL) and stirred at room temperature for 2 hours. The reaction was then concentrated to dryness and dried under vacuum for 1 hour. TFA (2 mL) was added, and the mixture was heated at 100° C. in a sealed tube for 20 hours. The reaction was concentrated to dryness. The resulting residue was dissolved in DCM (1 mL), and HCl in ether (1 mL, 2N) was added. The resulting solid was collected by filtration to give 3-(4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride (0.042 g, 70%). MS APCI (+) m/z 294.2 detected.
Workup
- concentrationThe reaction was then concentrated to dryness
- customdried under vacuum for 1 hour
- additionTFA (2 mL) was added
- temperaturethe mixture was heated at 100° C. in a sealed tube for 20 hours
- concentrationThe reaction was concentrated to dryness
- dissolutionThe resulting residue was dissolved in DCM (1 mL)
- additionHCl in ether (1 mL, 2N) was added
- filtrationThe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-ddf5ea1339844144b24ea9d7ccea6545
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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