Dichloromethane → HCID 68756523, compound
Reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[C:11]3[CH:10]=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:46]>>[ClH:46].[ClH:46].[C:30]1([C:15]2[C:16]([N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[C:11]3[CH:10]=[N:9][NH:8][C:12]3=[N:13][CH:14]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1Participants
4
Procedure
A solution of tert-butyl 4-(1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.440 g, 0.881 mmol) in DCM (5 mL) was added to TFA (1 mL) and stirred at room temperature for 1 hour. The reaction was then concentrated to dryness and dried under vacuum for 1 hour. TFA (3.39 mL, 44.0 mmol) was then added, and the mixture was stirred at 65° C. for 4 hours. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (3 mL). HCl in ether (2 mL, 2N) and ether (10 mL) were then added, and the resulting solid was collected by filtration to give 5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.29 g, 75%). MS ESI (+) m/z 280.1 detected.
Workup
- concentrationThe reaction was then concentrated to dryness
- customdried under vacuum for 1 hour
- stirringthe mixture was stirred at 65° C. for 4 hours
- concentrationThe reaction was then concentrated to dryness
- dissolutionthe resulting residue was dissolved in DCM (3 mL)
- additionHCl in ether (2 mL, 2N) and ether (10 mL) were then added
- filtrationthe resulting solid was collected by filtration
Sources & evidence
- ORD record
- ord-89391c7063b742b6af71d771c25465b2
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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