Water → HCID 59797320, compound

HRID 34007Notes

Reaction equation

HRID 34007 reaction equation
[CH2:1]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]([OH:19])=[O:18])[CH:16]=[C:11]2[C:10]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:26][O:18][C:17]([C:15]1[CH:16]=[C:11]2[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12]2=[N:13][CH:14]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 230701481-Benzyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid

Product 1

HCID 59797320HCID 59797320, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg of 1-benzyl-3-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid obtained by Example 32 was dissolved in 5 mL of N,N-dimethylformamide, added with 60 mg of potassium carbonate and 30 μl of methyl iodide, and stirred all day and night at room temperature. The residue was added with water, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. After distilling off the solvent, the reaction was crystallized from diisopropyl ether, to afford 100 mg of the title compound as a pale brown powder.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationAfter distilling off the solvent
  4. customthe reaction was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a0bb9f25ca034e989ade58fd625f1be3
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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