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Dichloromethane → 4-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)pyrrolidin-2-one hydrochloride

HRID 387545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 387545
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]=1
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Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68765517tert-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

Produkt 1

HCID 687659134-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)pyrrolidin-2-one hydrochlorideAusbeute 98 %

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in TFA (4 mL)
  3. temperatureheated at 100° C. in a sealed tube overnight
  4. customThe TFA was removed
  5. dissolutionThe residue was dissolved in DCM (0.5 mL)
  6. additionHCl in ether (1 mL) was added
  7. customThe solid formed
  8. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1287ee1cd7494fa9b8c7873d55df1220
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08372842B2

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