Dichloromethane → 4-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)pyrrolidin-2-one hydrochloride
Reaction equation
C(O)(C(F)(F)F)=O.COC1C=CC(C[N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:23]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[C:18]3[C:17]([NH:43][CH:44]3[CH2:48][C:47](=[O:49])[N:46](CC4C=CC(OC)=CC=4)[CH2:45]3)=[N:16]2)=CC=1.C(Cl)[Cl:62]>>[ClH:62].[C:37]1([C:22]2[C:23]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[C:18]3[C:17]([NH:43][CH:44]4[CH2:45][NH:46][C:47](=[O:49])[CH2:48]4)=[N:16][NH:15][C:19]3=[N:20][CH:21]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1Participants
4
Reactant 3
Product 1
Procedure
TFA (0.52 mL, 6.79 mmol) was added to a solution of tert-butyl 4-(1-(4-methoxybenzyl)-3-(1-(4-methoxybenzyl)-5-oxopyrrolidin-3-ylamino)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.195 g, 0.27 mmol) in DCM (1 mL) and stirred at room temperature for 1 hour. The solvent was removed. The residue was dissolved in TFA (4 mL) and heated at 100° C. in a sealed tube overnight. The TFA was removed. The residue was dissolved in DCM (0.5 mL), and HCl in ether (1 mL) was added. The solid formed was collected by filtration to give 4-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)pyrrolidin-2-one hydrochloride (0.20 g, 98% yield) as a solid.
Workup
- customThe solvent was removed
- dissolutionThe residue was dissolved in TFA (4 mL)
- temperatureheated at 100° C. in a sealed tube overnight
- customThe TFA was removed
- dissolutionThe residue was dissolved in DCM (0.5 mL)
- additionHCl in ether (1 mL) was added
- customThe solid formed
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-1287ee1cd7494fa9b8c7873d55df1220
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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