Reacción #6259

Ecuación de reacción

4-(3-aminopropylthio)pyridine dihydrochloride

2-pyrazinecarboxylic acid

N-hydroxysuccinimide

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

desired compound

Rendimiento 34.0%

4-[3-(2-pyrazinecarbonylamino)propylthio]pyridine

Rendimiento 34.0%

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
   workup.STIRRINGthe mixture was stirred at room temperature for 3 hours
4. 4
   LavadoThe reaction mixture was washed with saturated aqueous sodium bicarbonate and water
5. 5
   Otrodried
6. 6
   workup.DISTILLATIONThe solvent was distilled off
7. 7
   Otrothe residue was purified by column chromatography (eluent: ethyl acetate)

Procedimiento

To a solution of 1.00 g (8.06 mmol) of 2-pyrazinecarboxylic acid and 1.21 g (10.5 mmol) of N-hydroxysuccinimide in 70 ml of methylene-chloride, 1.85 g (9.67 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 1 hour. Further, 1.94 g (8.06 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.751 g of the desired compound (34.0% yield, colorless powder).

Fuente