Trifluoroacetic acid methylene chloride → HCID 178500078, compound

HRID 387549Notes

Reaction equation

HRID 387549 reaction equation
[CH3:1][O:2][C:3](=[O:43])/[CH:4]=[CH:5]/[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:13]=2[N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[N:8](CC2C=CC(OC)=CC=2)[N:7]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:52]>>[ClH:52].[C:28]1([C:12]2[C:13]([N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[C:14]3[C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:43])=[N:7][NH:8][C:9]3=[N:10][CH:11]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68763880(E)-tert-butyl 4-(3-(3-methoxy-3-oxoprop-1-enyl)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 178500078HCID 178500078, compoundYield 106%

Conditions

Temperature
60 °C

Procedure

A solution of (E)-tert-butyl 4-(3-(3-methoxy-3-oxoprop-1-enyl)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (380 mg, 0.65 mmol) in 25% TFA/CH2Cl2 was stirred at room temperature. Next, the solvent was removed, and the residue was evaporated from toluene (2×30 mL). Neat TFA (10 mL) was added to the resulting residue and heated at 60° C. for 4 hours. TFA was removed in vacuo, and the residue was evaporated from toluene (2×10 mL). 2M HCl in ether (5 mL) was added to the residue, and the mixture was sonicated for a few minutes. The solid formed was filtered, washed with ether (3×10 mL) and dried under high vacuum for 6 hours to provide (E)-methyl 3-(5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)acrylate hydrochloride salt (300 mg, 106% yield) as a solid. LCMS (APCI+) m/z 364.1 (M+H)+, Retention time=2.61 minutes.

Workup

  1. customNext, the solvent was removed
  2. customthe residue was evaporated from toluene (2×30 mL)
  3. additionNeat TFA (10 mL) was added to the resulting residue
  4. customTFA was removed in vacuo
  5. customthe residue was evaporated from toluene (2×10 mL)
  6. addition2M HCl in ether (5 mL) was added to the residue
  7. customthe mixture was sonicated for a few minutes
  8. customThe solid formed
  9. filtrationwas filtered
  10. washwashed with ether (3×10 mL)
  11. customdried under high vacuum for 6 hours

Sources & evidence

ORD record
ord-1166884e13a34d60bfbc9605e069d754
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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