Reacción #10855

Ecuación de reacción

8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline

(E)-3-(6-acetamidopyridin-3-yl)acrylic acid

1-hydroxybenzotriazole

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

→

8-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2methylquinoline

Rendimiento 53.8%

Disolventes

N,N-dimethylformamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with chloroform
2. 2
   LavadoThe organic layer was washed with an aqueous solution of saturated sodium hydrogencarbonate, water and brine successively
3. 3
   Secadodried over magnesium sulfate
4. 4
   Otrothe solvent was removed under reduced pressure
5. 5
   OtroThe residue was purified by preparative thin-layer chromatography (methanol

Procedimiento

To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (100 mg), (E)-3-(6-acetamidopyridin-3-yl)acrylic acid (56.1 mg) and N,N-dimethylformamide (2 ml) were added 1-hydroxybenzotriazole (43.4 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (56.9 mg) in a nitrogen stream at 0° C., and the resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into water, and extracted with chloroform. The organic layer was washed with an aqueous solution of saturated sodium hydrogencarbonate, water and brine successively, and dried over magnesium sulfate, and thereafter the solvent was removed under reduced pressure. The residue was purified by preparative thin-layer chromatography (methanol:dichloromethane=1:10, v/v), and solidified with diethyl ether and ethyl acetate to give 8-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2methylquinoline (FR173657) (78.8 mg) as a grayish white solid.

Fuente