Réaction #7586

Équation de réaction

hydrogen chloride

isopropanol

4-chloro-6-methoxy-7-[( 1-methylimidazol-2-yl)methoxy]cinnoline

2-fluoro-5-hydroxy-4-methylaniline

→

4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline hydrochloride

Rendement 79.5%

Solvants

2-pentanol

DMF

Conditions de réaction

Traitement

1. 1
   Autre(prepared
2. 2
   Températureat reflux for 3 hours
3. 3
   Filtrationthe resulting solid filtered off
4. 4
   Lavagewashed with ether

Mode opératoire

A suspension of 4-chloro-6-methoxy-7-[( 1-methylimidazol-2-yl)methoxy]cinnoline (109 mg, 0.35 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (70 mg, 0.5 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml), DMF (0.5 ml) and a 5M solution of hydrogen chloride in isopropanol (74 μl, 0.35 mmol) was heated at reflux for 3 hours. The solution was then cooled to 0° C. and the resulting solid filtered off and washed with ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline hydrochloride as a yellow solid (124 mg, 73%).

Source