Potassium Hydroxide → 4-[(4-Methoxybenzenesulfonyl) pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 1861641Notes

Reaction equation

HRID 1861641 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[C:13]2[C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][N:16]=[C:15]3[N:24]([CH3:28])[N:25]=[C:26]([CH3:27])[C:14]=23)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[K+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[C:13]2[C:18]([C:19]([OH:21])=[O:20])=[CH:17][N:16]=[C:15]3[N:24]([CH3:28])[N:25]=[C:26]([CH3:27])[C:14]=23)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 12044790Ethyl 4-[(4-methoxybenzenesulfonyl)pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 120447914-[(4-Methoxybenzenesulfonyl) pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acidYield 77.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1.34 g (2.7 mmol) of ethyl 4-[(4-methoxybenzenesulfonyl) pyridin-3-ylmethylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylate, 2.97 ml of 1N potassium hydroxide in 7.8 ml of ethanol and 4.83 ml of water was refluxed for 20 hr. Another 0.54 ml of 1N potassium hydroxide was added and the mixture refluxed 4 hrs. The solvent was removed under vacuum and toluene added and removed under vacuum. The residue was dissolved in water (20 ml) and extracted with ethyl acetate. The aqueous layer was acidified with 2 N citric acid and the precipitated solid filtered off and washed with water. The solid was dried under vacuum to give 0.98 g of solid, mp 256-258° C.

Workup

  1. temperaturewas refluxed for 20 hr
  2. temperaturethe mixture refluxed 4 hrs
  3. customThe solvent was removed under vacuum and toluene
  4. additionadded
  5. customremoved under vacuum
  6. dissolutionThe residue was dissolved in water (20 ml)
  7. extractionextracted with ethyl acetate
  8. filtrationthe precipitated solid filtered off
  9. washwashed with water
  10. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-63ea3ae848014a258b3b68fc3d3ee0d6
Source dataset
uspto-grants-2003_03
Patent number
US06534491B2

Reaction notes

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