تفاعل #41633

معادلة التفاعل

pyridine-2-carboxylic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride

t-butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate

sodium bicarbonate

→

compound

pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-3-fluoro-phenyl)-amide

المذيبات

pyridine

chloroform

chloroform

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction liquid
2. 2
   أخرىThe reaction liquid
3. 3
   غسيلwashed with water and saturated saline
4. 4
   تجفيفdried with anhydrous magnesium sulfate
5. 5
   أخرىThe solvent was evaporated away under reduced pressure, and 2 ml of 4 N hydrochloric acid-dioxane solution
6. 6
   workup.ADDITIONwas added to 300 mg of the resulting residue
7. 7
   أخرىthe reaction liquid
8. 8
   workup.STIRRINGwas stirred at room temperature for 1 hour
9. 9
   أخرىThe reaction liquid
10. 10
    workup.ADDITIONadded
11. 11
    غسيلthe organic layer was washed with saturated saline
12. 12
    تجفيفdried with anhydrous magnesium sulfate
13. 13
    أخرىThe solvent was evaporated away under reduced pressure, and 0.020 ml of acetic anhydride
14. 14
    workup.ADDITIONwas added to a pyridine (1 ml) solution of the resulting residue
15. 15
    أخرىthe reaction liquid
16. 16
    workup.STIRRINGwas stirred at room temperature for 20 minutes
17. 17
    أخرىThe reaction liquid
18. 18
    غسيلwashed with water and saturated saline in order
19. 19
    تجفيفdried with anhydrous magnesium sulfate
20. 20
    أخرىThe solvent was evaporated away under reduced pressure
21. 21
    أخرىthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)

الإجراء التجريبي

90 mg of pyridine-2-carboxylic acid and 190 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added in order to a pyridine (2 ml) solution of 181 mg of t-butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate, and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was diluted with chloroform, washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and 2 ml of 4 N hydrochloric acid-dioxane solution was added to 300 mg of the resulting residue, and the reaction liquid was stirred at room temperature for 1 hour. The reaction liquid was diluted with chloroform, and made basic with aqueous saturated sodium bicarbonate solution added thereto, and the organic layer was washed with saturated saline and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and 0.020 ml of acetic anhydride was added to a pyridine (1 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 20 minutes. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a yellow solid.

المصدر