Reaktion #41672

Reaktionsgleichung

triethylamine

methanesulfonyl chloride

N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide

sodium bicarbonate

sodium bicarbonate

sodium bicarbonate

→

N-(4-(1-acetyl-3-methylpyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide

Lösungsmittel

chloroform

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction liquid
2. 2
   Extraktionextracted with chloroform
3. 3
   Trocknendried with anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated away under reduced pressure, and 23 mg of sodium azide
5. 5
   workup.ADDITIONwas added to a dimethylformamide (4 ml) solution of the resulting residue
6. 6
   Sonstigethe reaction liquid
7. 7
   workup.STIRRINGwas stirred at 40° C. for 2 hours
8. 8
   SonstigeThe reaction liquid
9. 9
   Temperaturwas cooled to room temperature
10. 10
    Extraktionextracted with ethyl acetate
11. 11
    Trocknendried with anhydrous sodium sulfate
12. 12
    SonstigeThe solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate
13. 13
    workup.ADDITIONwere added in order to a methanol (5 ml) solution of the resulting residue
14. 14
    Sonstigethe reaction liquid
15. 15
    workup.STIRRINGwas stirred at 40° C. for 15 minutes
16. 16
    SonstigeThe reaction liquid
17. 17
    Temperaturwas cooled to room temperature
18. 18
    Extraktionextracted with chloroform
19. 19
    Trocknendried with anhydrous sodium sulfate
20. 20
    SonstigeThe solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine
21. 21
    workup.ADDITIONwere added in order to a chloroform (4 ml) solution of the resulting residue
22. 22
    Sonstigethe reaction liquid
23. 23
    workup.STIRRINGwas stirred at room temperature for 30 minutes
24. 24
    Extraktionextracted with chloroform
25. 25
    Trocknendried with anhydrous sodium sulfate
26. 26
    SonstigeThe solvent was evaporated away under reduced pressure
27. 27
    Sonstigethe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
28. 28
    Sonstigeto obtain the entitled compound as a colorless oily substance

Vorschrift

0.18 ml of triethylamine and 0.07 ml of methanesulfonyl chloride were added in order to a chloroform (5 ml) solution of 100 mg of N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 23 mg of sodium azide was added to a dimethylformamide (4 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled to room temperature, water was added to it, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate were added in order to a methanol (5 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 15 minutes. The reaction liquid was cooled to room temperature, and then aqueous saturated sodium bicarbonate was added to it, extracted with chloroform and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine were added in order to a chloroform (4 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.

Quelle