تفاعل #155330

معادلة التفاعل

[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

المردود 77.0%

المذيبات

Water

DMF

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   استخلاصsubjected to extraction
3. 3
   غسيلThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
4. 4
   تجفيفdried over anhydrous sodium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe residue was purified
7. 7
   تركيزThe purified product was concentrated under reduced pressure
8. 8
   أخرىthe residue was recrystallized from ethyl acetate

الإجراء التجريبي

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%).

المصدر