Reacción #155331

Ecuación de reacción

Methyl iodide

Sodium hydride

DMF

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

→

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

Rendimiento 74.0%

Disolventes

ethyl acetate

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe thus-obtained mixture was stirred at room temperature for 15 hours
2. 2
   Otrofollowed by separation
3. 3
   LavadoThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified
6. 6
   ConcentraciónThe purified product was concentrated under reduced pressure
7. 7
   Otrothe residue was recrystallized from ethyl acetate

Procedimiento

Sodium hydride (60% oil base, 61 mg, 1.4 mmol) was added to a DMF solution (2 ml) of 2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamide (580 mg, 1.16 mmol), and the resulting mixture was stirred at room temperature for 5 minutes. Methyl iodide (230 mg, 1.62 mmol) was added thereto, and the thus-obtained mixture was stirred at room temperature for 15 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution 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-methyl-N-(2-morpholin-4-ylethyl)acetamide (440 mg, yield: 74%).

Fuente