Reacción #5554

Ecuación de reacción

5-[4-(amino)butylthio]imidazo[1,2-a]pyridine

triethylamine

1-naphthalenesulfonyl chloride

→

desired product

Rendimiento 53.3%

5-[4-(1-naphthalenesulfonylamino)butylthio]imidazo[1,2-a]pyridine

Rendimiento 53.3%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hour
3. 3
   LavadoThe reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter the solvent was distilled off
6. 6
   Otrothe residue was purified by column chromatography (eluent: ethyl acetate)

Procedimiento

To a solution of 5-[4-(amino)butylthio]imidazo[1,2-a]pyridine (300 mg, 1.36 mmoles) and triethylamine (0.29 ml, 2.08 mmoles) in methylene chloride (15 ml) was added 1-naphthalenesulfonyl chloride (307 mg, 1.35 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 1 hour. The reaction mixture was washed in turn with an aqueous sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 296 mg of the desired product (53.0%, colorless solid).

Fuente