Sodium Hydroxide → 5-cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carboxylic acid

HRID 353446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353446
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][C:14]=2[Cl:23])[C:9]=1[CH:10]1[CH2:12][CH2:11]1)=[O:4].[OH-].[Na+]>O>[CH:10]1([C:9]2[N:8]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][C:14]=3[Cl:23])[N:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])[CH2:11][CH2:12]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 698588105-cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carboxylic acid methyl ester

Produkt 1

HCID 222679905-cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carboxylic acid methyl ester is hydrolyzed with a base such as sodium hydroxide in water to form 5-cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carboxylic acid, analogous to the formula IX′ acid. The carboxylic acid pyrazole is then activated with coupling agent such as thionyl chloride to form the activated compound, analogous to the formula X′ compound. The activated compound is then coupled with guanidine to form the NHE-1 inhibitor, N-{5-cyclopropyl-1-(2-chloro-4-methanesulfonylphenyl)-1H-pyrazole-4-carbonyl}-guanidine.

Quellen und Nachweise

ORD-Eintrag
ord-8f779cba557448a3b6eb3b3134ca7157
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753334B2

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