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

HRID 387597Notes

Reaction equation

HRID 387597 reaction equation
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

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68757956HCID 68757956, compound

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7b3a40667ad743c98dbc88d642d370b9
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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