Reacción #53453

Ecuación de reacción

isopropyl ether

3-Ethylaminoazetidine

1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

N-methyl-pyrrolidine

→

title compound

Rendimiento 77.6%

1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-7-(3-ethylaminoazetidin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Rendimiento 77.6%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturato cool down
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   Otroa clear layer at the top of the mixture was removed
5. 5
   Concentraciónthe residue was concentrated under reduced pressure
6. 6
   workup.ADDITIONEthanol (5 mL) was added
7. 7
   Temperaturathe mixture was heated
8. 8
   workup.STIRRINGunder stirring at 70° C. for 30 minutes
9. 9
   FiltraciónThe precipitated solid was collected by filtration

Procedimiento

3-Ethylaminoazetidine (700 mg), 1-(6-amino-3,5-difluoropyridin-2-yl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1.5 g), N-methyl-pyrrolidine (2.0 g)and dimethylsulfoxide (4.5 g) were combined, and the mixture was heated under stirring at 40° C. for 24 hours. After the mixture was allowed to cool down, isopropyl ether (10 mL) was added, the mixture was stirred, and a clear layer at the top of the mixture was removed. The same procedure was repeated once more, and the residue was concentrated under reduced pressure. Ethanol (5 mL) was added, and the mixture was heated under stirring at 70° C. for 30 minutes. The precipitated solid was collected by filtration. The title compound (1.38 g) was obtained.

Fuente