Hydrochloric Acid → 2-(1H-pyrazolo(3,4-b)pyridin-1-yl)acetic acid

HRID 82196Notes

Reaction equation

HRID 82196 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[N:7]1)C.O[Li].O.Cl>C1COCC1.O>[N:6]1([CH2:5][C:4]([OH:15])=[O:3])[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57642798Ethyl (1H-pyrazolo[3,4-b]pyridin-1-yl)acetate

Product 1

HCID 586229612-(1H-pyrazolo(3,4-b)pyridin-1-yl)acetic acidYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of pyrazolo[3,4-b]pyridin-1-yl-acetic acid ethyl ester (210 mg, 1.02 mmol) (Preparation 133) in THF (4 mL) and water (1 mL) at 0° C. was added LiOH.H2O (129 mg, 3.06 mmol). The reaction mixture was stirred at room temperature for 2 hours. The pH was of the mixture was adjusted to pH 4 with 2 N aqueous hydrochoric acid and extracted with 20% isopropanol in dichloromethane (8×5 mL). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as an off-white solid in 40% yield, 70 mg.

Workup

  1. extractionextracted with 20% isopropanol in dichloromethane (8×5 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e66acda19e54af7a992eb97e2d0e342
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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