Dichloromethane → (S)-3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride

HRID 387597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387597
C(O)(C(F)(F)F)=O.CC1(C)[O:13][C@H:12]([CH2:14][O:15][C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[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:55]>>[ClH:55].[ClH:55].[C:38]1([C:22]2[C:23]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)=[C:24]3[C:16]([O:15][CH2:14][C@@H:12]([OH:13])[CH2:11][OH:10])=[N:17][NH:18][C:19]3=[N:20][CH:21]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68757956HCID 68757956, Verbindung

Produkt 1

HCID 68756592(S)-3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochlorideAusbeute 96 %

Versuchsvorschrift

TFA (1 mL) was added to a solution of (R)-tert-butyl 4-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.14 g, 0.22 mmol) in DCM (1 mL), and the resulting solution was stirred at room temperature for 4 hours. The reaction was then concentrated to dryness and dried under vacuum for 1 hour. TFA (2 mL) was next added, and the mixture was stirred at 100° C. in a sealed tube for 18 hours. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (0.5 mL). HCl in ether (2 mL, 2N) and ether (3 mL) were then added, and the resulting solid was collected by filtration to give (S)-3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yloxy)propane-1,2-diol dihydrochloride (0.105, 96%) as a solid. MS APCI (+) m/z 370.2 detected.

Aufarbeitung

  1. concentrationThe reaction was then concentrated to dryness
  2. customdried under vacuum for 1 hour
  3. stirringthe mixture was stirred at 100° C. in a sealed tube for 18 hours
  4. concentrationThe reaction was then concentrated to dryness
  5. dissolutionthe resulting residue was dissolved in DCM (0.5 mL)
  6. additionHCl in ether (2 mL, 2N) and ether (3 mL) were then added
  7. filtrationthe resulting solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-7b3a40667ad743c98dbc88d642d370b9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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