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

HRID 496585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496585
[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

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 22322112Ethyl 4-[benzyl-(4-methoxybenzenesulfonyl)amino]-1,3-dimethyl-1H-pyrazolo[3,4-b] pyridine-5-carboxylate

Produkt 1

HCID 223221134-[Benzyl-(4-methoxybenzenesulfonyl)amino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7360Tetrahydrofurfuryl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 0.48 g (0.97 mmol) of ethyl 4-[benzyl-(4-methoxybenzene-sulfonyl)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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f35e427f665543f9b04b15707f2af633
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06946473B2

Notizen zur Reaktion

Wird geladen…