Reacción #78463

Ecuación de reacción

ethyl acetate

ammonia hydroxide

title compound

6-[Amino-(6-chloro-pyridin-3-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1H-quinolin-2-one

p-anisaldehyde

→

title compound

Rendimiento 78.0%

4-(3-Chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-[(4-methoxy-benzylidene)-amino]-(3-methyl-3H-imidazol-4-yl)-methyl]-1H-quinolin-2-one

Rendimiento 78.0%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas cooled to 0° C
2. 2
   OtroAfter separation
3. 3
   Lavadothe organic layer was washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated under vacuum
6. 6
   Otroto yield the crude product
7. 7
   OtroIt was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents

Procedimiento

To a solution of the title compound of example 42 (11.89 g, 25.03 mmol) in acetic acid (75 ml) was added p-anisaldehyde (6.09 ml, 50.06 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 4 hours after which time it was cooled to 0° C. 10 ml of ammonia hydroxide was added followed by addition of ethyl acetate. After separation, the organic layer was washed with brine, dried over MgSO4 and concentrated under vacuum to yield the crude product. It was chromatographed on silica gel with MeOH—CHCl3—NH4OH (1:99:0.1 to 5:95:0.1) as eluents to afford the title compound of Example 43A as a white solid (11.58 g, 78% yield).

Fuente