تفاعل #41672

معادلة التفاعل

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

المذيبات

chloroform

water

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction liquid
2. 2
   استخلاصextracted with chloroform
3. 3
   تجفيفdried with anhydrous sodium sulfate
4. 4
   أخرىThe 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
   أخرىthe reaction liquid
7. 7
   workup.STIRRINGwas stirred at 40° C. for 2 hours
8. 8
   أخرىThe reaction liquid
9. 9
   درجة الحرارةwas cooled to room temperature
10. 10
    استخلاصextracted with ethyl acetate
11. 11
    تجفيفdried with anhydrous sodium sulfate
12. 12
    أخرىThe 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
    أخرىthe reaction liquid
15. 15
    workup.STIRRINGwas stirred at 40° C. for 15 minutes
16. 16
    أخرىThe reaction liquid
17. 17
    درجة الحرارةwas cooled to room temperature
18. 18
    استخلاصextracted with chloroform
19. 19
    تجفيفdried with anhydrous sodium sulfate
20. 20
    أخرىThe 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
    أخرىthe reaction liquid
23. 23
    workup.STIRRINGwas stirred at room temperature for 30 minutes
24. 24
    استخلاصextracted with chloroform
25. 25
    تجفيفdried with anhydrous sodium sulfate
26. 26
    أخرىThe solvent was evaporated away under reduced pressure
27. 27
    أخرىthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
28. 28
    أخرىto obtain the entitled compound as a colorless oily substance

الإجراء التجريبي

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.

المصدر