Sodium Hydroxide → 4-[Benzyl-(4-methoxybenzenesulfonyl)amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid

HRID 1266319Notes

Reaction equation

[CH2:1]([N:8]([S:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[C:9]1[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][N:12]=[C:11]2[N:20]([CH3:24])[N:21]=[C:22]([CH3:23])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1CO>[CH2:1]([N:8]([S:25]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)(=[O:27])=[O:26])[C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]2[N:20]([CH3:24])[N:21]=[C:22]([CH3:23])[C:10]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 0.48 g (0.97 mmol) of ethyl 4-[benzyl-(4-methoxybenzenesulfonyl) amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate and 0.29 ml of ION NaOH in 4 ml of tetrahydrofuran-methanol (1:1) was heated in an oil bath at 70° C. for 2 hours and the solvent removed under vacuum. The residue was dissolved in 20 ml of H2O and the solution extracted with 10 ml of diethyl ether. To the aqucous layer was added 2N citric acid (pH 4-5) and the precipitated solid filtered and washed with H2O to give a white solid which was dried under vacuum overnight to give crystals, mp 165-167° C.

Workup

customthe solvent removed under vacuum
dissolutionThe residue was dissolved in 20 ml of H2O
extractionthe solution extracted with 10 ml of diethyl ether
additionTo the aqucous layer was added 2N citric acid (pH 4-5)
filtrationthe precipitated solid filtered
washwashed with H2O
customto give a white solid which
customwas dried under vacuum overnight
customto give crystals, mp 165-167° C.

Sources & evidence

ORD record: ord-62b22f4a47c745a4a02c6acdab6c54ac
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548524B2

Reaction notes

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