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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1425302Erstellt: 26. Oktober 2026

Hydrochloric Acid → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

https://huagongshe.com/reaction/1425302

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktHydrochloric AcidHCID 313—
EduktWaterHCID 962—
EduktLithium HydroxideHCID 3939—
EduktEthyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylateHCID 86648767—
LösungsmittelMethanolHCID 887—
LösungsmittelTetrahydrofuranHCID 8028—
Produktcis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acidHCID 8664876873,1%

Reaktionsbedingungen

Temperatur70 °C

Reaktionsschritte

A 2 N aqueous lithium hydroxide solution (1.18 mL, 2.37 mmol) was added to a mixed solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (196c) (105 mg, 0.237 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) at room temperature, and the mixture was stirred at 70° C. for two hours. The reaction solution was concentrated under reduced pressure. A 1 N aqueous hydrochloric acid solution (2.37 mL, 2.37 mmol) and water were added to the resulting residue, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over anhydrous sodium sulfate, and then the insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure to obtain 72 mg of the title compound (73%) as a colorless solid.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08927588B2
Quelldatensatzuspto-grants-2015_01
ORD IDord-ddc5bd76f1e84cf5a54a4d4f1ca44748
Quellennotizuspto-grants-2015_01