Dichloromethane → 5-(3-fluorophenyl)-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]([C:15]2[C:16]([N:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)=[C:17]3[CH:23]=[N:22][N:21](CC4C=CC(OC)=CC=4)[C:18]3=[N:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1.C(Cl)[Cl:47]>>[ClH:47].[ClH:47].[F:8][C:9]1[CH:10]=[C:11]([C:15]2[C:16]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[C:17]3[CH:23]=[N:22][NH:21][C:18]3=[N:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1Participants
4
Procedure
TFA (1 mL) was added to tert-butyl 4-(5-(3-fluorophenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.25 g, 0.483 mmol) in DCM (5 mL) and stirred at room temperature for 2 hours. The reaction was then concentrated to dryness and dried under vacuum for 3 hours. TFA (1.86 mL, 24.2 mmol) was then added, and the mixture was heated to 65° C. for 3 hours. The reaction was then concentrated to dryness. The resulting residue was dissolved in DCM (2 mL), and HCl in ether (2 mL, 2M) and ether (5 mL) were added. The resulting solid was collected by filtration to give 5-(3-fluorophenyl)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.17 g, 94%). MS ESI (+) m/z 298.1 detected.
Workup
- concentrationThe reaction was then concentrated to dryness
- customdried under vacuum for 3 hours
- temperaturethe mixture was heated to 65° C. for 3 hours
- concentrationThe reaction was then concentrated to dryness
- dissolutionThe resulting residue was dissolved in DCM (2 mL)
- additionHCl in ether (2 mL, 2M) and ether (5 mL) were added
- filtrationThe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-ba323c8770e245a1af6e7f57cdb98daa
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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