Реакция #2301006

Уравнение реакции

4-chloro-7-methoxy-8-(2-morpholin-4-yl ethoxy)benzo[g]quinoline-3-carbonitrile

3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine

pyridine hydrochloride

→

4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile

Выход 59.1%

Растворители

ether

2-ethoxyethanol

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   ФильтрацияThe resulting solid is collected by filtration
3. 3
   Промывкаwashed with water, ether and ethyl acetate successively
4. 4
   ДругоеAfter drying in vacuo
5. 5
   Другоеthe solid is purified by silica gel chromatography
6. 6
   Другоеto provide a yellow solid
7. 7
   Фильтрацияfiltered
8. 8
   Промывкаfurther washed with ether
9. 9
   ДругоеAfter drying in vacuo

Методика

A mixture of 1.98 g (4.98 mmol) of 4-chloro-7-methoxy-8-(2-morpholin-4-yl ethoxy)benzo[g]quinoline-3-carbonitrile, 1.31 g (5.47 mmol) of 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine and 0.6 g (5.2 mmol) of pyridine hydrochloride in 2-ethoxyethanol is heated at 120° C. for 1.25 hours, then cooled. The crude mixture is poured into a solution of saturated sodium bicarbonate/ice and stirred for 45 minutes. The resulting solid is collected by filtration, then washed with water, ether and ethyl acetate successively. After drying in vacuo, the solid is purified by silica gel chromatography, using a 94:6 to 9:1 gradient of methylene chloride/methanol to provide a yellow solid. This solid is suspended in ether, filtered, and further washed with ether. After drying in vacuo, 1.77 g of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-7-methoxy-8-(2-morpholin-4-yl-ethoxy)benzo[g]quinoline-3-carbonitrile is obtained as a yellow solid, mp. >300° C.

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