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

HRID 2300247Notes

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 10N 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 aqueous 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 aqueous 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-661e5553ef8b48ae8a1c2579df8271b6
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498167B2

Reaction notes

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