Reacción #810593

Ecuación de reacción

(7R,8R,9R)-10-acetyl-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine

NCS

→

title compound

(7R,8R,9R)-10-Acetyl-3-chloro-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfterwards the reaction is quenched
2. 2
   workup.ADDITIONby adding of saturated aqueous sodium hydrogen carbonate solution
3. 3
   Extracciónis extracted twice with dichloromethane
4. 4
   LavadoThe combined organic layers are washed with brine
5. 5
   Secadodried over sodium sulphate
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe crude product is purified by column chromatography (ethyl acetate/cylohexane: 1/1)

Procedimiento

To a of 0° C. cooled solution of 1.00 g (2.10 mmol) (7R,8R,9R)-10-acetyl-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in ethanol (20 ml) is added 0.28 g (2.10 mmol) NCS and the mixture is stirred for 2 h. Afterwards the reaction is quenched by adding of saturated aqueous sodium hydrogen carbonate solution and is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (ethyl acetate/cylohexane: 1/1) to provide 0.89 g (1.73 mmol/82%) of the title compound as a colourless solid with a melting point of 167–170° C. (cyclohexane).

Fuente