反应 #563380

反应方程式

2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Intermediate 1

2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

triethylamine

1-chloro-2-isothiocyanatoethane

water

→

title compound

8-Bromo-N-(2-chloroethyl)-1-(4-(2-cyanopropan-2-yl)phenyl)-2-oxo-1H-imidazo[4,5-c]quinoline-3(2H)-carbothioamide

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他was separated
2. 2
   萃取The aqueous layer was extracted with dichloromethane
3. 3
   洗涤The combined organic layer was washed with brine
4. 4
   干燥dried over sodium sulfate
5. 5
   其他evaporated to dryness
6. 6
   其他The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

实验过程

To a solution of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 50 mg, 0.12 mmol) and triethylamine (18.18 mg, 0.18 mmol) in dichloromethane (6 ml) was added 1-chloro-2-isothiocyanatoethane (21.87 mg, 0.18 mmol) at 0° C. The reaction was stirred at RT for 3 hours. The reaction mixture was poured into cold water and organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 10 mg (15%); 1H NMR (CDCl3, 300 MHz): δ 9.945 (s, 1H), 7.966-7.996 (d, 1H, J=9 Hz), 7.745-7.773 (d, 2H, J=8.4 Hz), 7.615-7.645 (dd, 1H, J=9, 2.1 Hz), 7.516-7.544 (d, 2H, J=8.4 Hz), 7.082-7.089 (d, 1H, J=2.1 Hz), 4.289-4.344 (t, 2H), 3.411-3.467 (t, 2H), 1.82 (s, 6H); MS: m/z 491 (M−HCl).

来源