Reaktion #5537

Reaktionsgleichung

5-[2-(methylsulfonylamino)ethylthio] imidazo[1,2-a]pyridine

formalin

morpholin

→

desired product

Ausbeute 71.5%

5-[2-(methylsulfonylamino)ethylthio]3-morpholinomethylimidazo[1,2-a]pyridine

Ausbeute 71.5%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   workup.STIRRINGby stirring at 60° C. for 2 hours
4. 4
   workup.DISTILLATIONAfter the solvent was distilled off
5. 5
   workup.DISSOLUTIONthe residue was dissolved in chloroform (50 ml)
6. 6
   Waschenwashed with 1N NaOH (10 ml)
7. 7
   ExtraktionThen, the aqueous layer was extracted with chloroform (30 ml×3)
8. 8
   Trocknenthe combined chloroform layer was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off
10. 10
    SonstigeThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10→1:5)

Vorschrift

To a solution of 37% formalin (178 mg, 2.2 mmoles) in acetic acid (2 ml) was added morpholin (192 μl, 2.2 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. 5-[2-(methylsulfonylamino)ethylthio] imidazo[1,2-a]pyridine (543 mg, 2 mmoles) was added to the reaction mixture, followed by stirring at 60° C. for 2 hours. After the solvent was distilled off, the residue was dissolved in chloroform (50 ml) and washed with 1N NaOH (10 ml). Then, the aqueous layer was extracted with chloroform (30 ml×3) and the combined chloroform layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10→1:5) to obtain 530 mg of the desired product (71.5%, colorless solid).

Quelle