Trifluoroacetic acid → (3-Acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid

HRID 1527272Notes

Reaction equation

HRID 1527272 reaction equation
C([O:5][C:6](=[O:21])[CH2:7][N:8]1[C:12]2=[CH:13][N:14]=[C:15]([CH3:17])[CH:16]=[C:11]2[C:10]([C:18](=[O:20])[CH3:19])=[N:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:18]([C:10]1[C:11]2[C:12](=[CH:13][N:14]=[C:15]([CH3:17])[CH:16]=2)[N:8]([CH2:7][C:6]([OH:21])=[O:5])[N:9]=1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283035(3-Acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 68283539(3-Acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-acetyl-5-methyl-pyrazolo[3,4-c]pyridin-1-yl)-acetic acid tert-butyl ester (126 mg, 0.37 mmol) and TFA (0.171 mL, 2.22 mmol) in CH2Cl2 (5 mL) was stirred at RT for 24 h. Solvents were removed under reduced pressure, Et2O was added and the precipitate was filtered, washed with Et2O and dried under high vacuum. The material thus obtained was used without further purification in the next step. MS (UPLC/MS): 234 [M+H]+, 232 [M−H]−, 465 [2M−H]−; tR (HPLC conditions f): 0.53 min.

Workup

  1. customSolvents were removed under reduced pressure, Et2O
  2. additionwas added
  3. filtrationthe precipitate was filtered
  4. washwashed with Et2O
  5. customdried under high vacuum
  6. customThe material thus obtained
  7. customwas used without further purification in the next step
  8. custom0.53 min.

Sources & evidence

ORD record
ord-51abe66e203b461bbaac33338cfa7462
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…