Trifluoroacetic acid methylene chloride → HCID 68759696, compound

HRID 387607Notes

Reaction equation

HRID 387607 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([CH3:30])[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:41]>>[ClH:41].[ClH:41].[CH3:30][C:15]1[C:16]([N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[C:11]2[CH:10]=[N:9][NH:8][C:12]2=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68762104HCID 68762104, compound

Product 1

HCID 68759696HCID 68759696, compoundYield 56.7%

Procedure

tert-Butyl 4-(1-(4-methoxybenzyl)-5-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (465 mg, 1.06 mmol) in 25% TFA/CH2Cl2 (25 mL) was stirred at room temperature for 2 hours. The solvent was removed, and the gum obtained was evaporated from toluene (3×20 mL; water bath 60° C.). Neat TFA was added to the residue and stirred at reflux for 3 hours. Next, TFA was removed under reduced pressure, and the resulting residue was evaporated form CH2Cl2 (2×10 mL). The residue was resuspended in CH2Cl2 (2 mL), and 2M HCl in diethyl ether (5 mL) was added. The resulting suspension was concentrated in vacuo, and the residue was crystallized from boiling EtOH to provide 5-methyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (175 mg, 0.603 mmol, 56.7% yield) as a powder after drying under high vacuum for 4 hours. LCMS (APCI+) m/z 218.1 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe gum obtained
  3. customwas evaporated from toluene (3×20 mL; water bath 60° C.)
  4. additionNeat TFA was added to the residue
  5. temperatureat reflux for 3 hours
  6. customNext, TFA was removed under reduced pressure
  7. customthe resulting residue was evaporated form CH2Cl2 (2×10 mL)
  8. addition2M HCl in diethyl ether (5 mL) was added
  9. concentrationThe resulting suspension was concentrated in vacuo
  10. customthe residue was crystallized

Sources & evidence

ORD record
ord-68adc1c469ef4c089946627b5c91a468
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

Loading…