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

HRID 1976684Notes

Reaction equation

HRID 1976684 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-ec0364474ffb4b6f85aa6299f994d3cd
Source dataset
uspto-grants-2001_05
Patent number
US06228869B1

Reaction notes

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