Water → HCID 86648829, Verbindung

Methyl cis(±)-5-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-methylthiophene-2-carboxylate obtained in Example (245d) (65 mg, 0.15 mmol) was dissolved in methanol (1.5 mL). A 2 N aqueous lithium hydroxide solution (0.74 mL, 1.47 mmol) was added, and the mixture was stirred at room temperature for 50 minutes. THF (1 mL) was added, and the mixture was stirred for 19 hours, and then further stirred at 40° C. for 6.5 hours and at 70° C. for two hours. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (2.5 mL) was added to the aqueous layer, followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting solid was suspended and washed in diethyl ether to obtain 23 mg of the title compound as a pale blue solid (37%).

1. stirringthe mixture was stirred for 19 hours
2. stirringfurther stirred at 40° C. for 6.5 hours and at 70° C. for two hours
3. washthe mixture was washed with ethyl acetate
4. additionA 1 N aqueous hydrochloric acid solution (2.5 mL) was added to the aqueous layer
5. extractionfollowed by extraction with ethyl acetate
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated under reduced pressure
9. washwashed in diethyl ether

ORD-Eintrag

ord-469f764698214fb18800265c13356147

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08927588B2