反応 #155330

反応方程式

[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

収率 77.0%

溶媒

Water

DMF

DMF

DMF

反応条件

後処理

1. 1
   温度cooling
2. 2
   抽出subjected to extraction
3. 3
   洗浄The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
4. 4
   乾燥dried over anhydrous sodium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   その他The residue was purified
7. 7
   濃縮The purified product was concentrated under reduced pressure
8. 8
   その他the residue was recrystallized from ethyl acetate

実験手順

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%).

出典