Reaktion #356936

Reaktionsgleichung

4-chloro-7-fluoro-6-methoxyquinoline-3-carbonitrile

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

pyridine hydrochloride

→

4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile

Lösungsmittel

2-ethoxyethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   FiltrationThe resulting solid is filtered
3. 3
   Waschenwashed with cold 2-ethoxyethanol
4. 4
   SonstigeAfter drying in vacuo
5. 5
   Filtrationcollected by filtration
6. 6
   WaschenThe reaction product is washed with water
7. 7
   Sonstigedried in vacuo

Vorschrift

A mixture of 1.0 g (4.23 mmol) of 4-chloro-7-fluoro-6-methoxyquinoline-3-carbonitrile (AM100856), 1.114 g (4.65 mmol) of 3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamine and 0.489 g (4.23 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol is heated at 120° C. for 1.5 hours, then cooled to room temperature. The resulting solid is filtered, washed with cold 2-ethoxyethanol, then ethyl acetate. After drying in vacuo, the solid is suspended in a saturated solution of sodium bicarbonate, stirred for 45 minutes and collected by filtration. The reaction product is washed with water and dried in vacuo, to provide 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile as a tan solid, mp 295-297° C.

Quelle