Potassium Hydroxide → HCID 18549727, compound

HRID 1861649Notes

Reaction equation

HRID 1861649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][NH:19][C:20]3[C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][N:23]=[C:22]4[N:31]([CH3:35])[N:32]=[C:33]([CH3:34])[C:21]=34)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][NH:19][C:20]3[C:25]([C:26]([OH:28])=[O:27])=[CH:24][N:23]=[C:22]4[N:31]([CH3:35])[N:32]=[C:33]([CH3:34])[C:21]=34)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 69959459HCID 69959459, compound

Product 1

HCID 18549727HCID 18549727, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.90 g (3.69 mmol) of the preceding ester and 4.05 ml (4.06 mmol) of 1 N KOH in 15 ml of tetrahydrofuran was stirred at room temperature for 2 days and then 0.75 ml of 1 N KOH was added and the mixture was refluxed overnight. The solvent was removed under vacuum and the toluene (25 ml) added to the residue and removed under vacuum. The residue was triturated with ethyl acetate and the solid filtered and dried under vacuum to give 1.6 g of 4-{[4-(4-chlorophenyloxy) benzenesulfonyl]methylamino}-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, potassium salt. Following the procedure of Example 52, 1.60 g of the preceding potassium salt was converted to the title compound to obtain 1.82 g of solid. This solid was purified on thick layer silica gel plates with 4% CH3OH in ethyl acetate as solvent to give 0.59 g of light yellow solid, m.p. 120° C. dec.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was removed under vacuum
  3. additionthe toluene (25 ml) added to the residue
  4. customremoved under vacuum
  5. customThe residue was triturated with ethyl acetate
  6. filtrationthe solid filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4e0af7650d8346c68f353dcb98894c54
Source dataset
uspto-grants-2003_03
Patent number
US06534491B2

Reaction notes

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