Reacción #155330

Ecuación de reacción

[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetic acid

4-(2-aminoethyl)morpholine

triethylamine

diethylphosphorocyanidate

→

2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamide

Rendimiento 77.0%

Disolventes

Water

DMF

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Extracciónsubjected to extraction
3. 3
   LavadoThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified
7. 7
   ConcentraciónThe purified product was concentrated under reduced pressure
8. 8
   Otrothe residue was recrystallized from ethyl acetate

Procedimiento

To a DMF solution (2 ml) of [5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetic acid (800 mg, 2.07 mmol) were sequentially added a DMF solution (1 ml) of 4-(2-aminoethyl)morpholine (273 mg), triethylamine (506 mg, 5.0 mmol), diethylphosphorocyanidate (DEPC, 405 mg, 2.48 mmol) and DMF (1 ml) while ice-cooling, followed by stirring at room temperature for 23 hours. Water was added to the reaction mixture and then subjected to extraction using ethyl acetate. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=30:1→15:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate, giving a white powder of 2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamide (789 mg, yield: 77%).

Fuente