Reaktion #42064

Reaktionsgleichung

water

N,N-diisopropyl-N-ethylamine

4-methyl-3-[4-(3-pyridyl)pyridin-2-ylamino]aniline

4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride

→

objective compound

Ausbeute 22.4%

4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-{4-methyl-3-[4-(3-pyridyl)pyridin-2-ylamino]phenyl}benzamide

Ausbeute 22.4%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder ice-cooling
2. 2
   workup.STIRRINGby stirring at room temperature for 2 hours
3. 3
   Extraktionthe mixture was subjected to extraction with ethyl acetate three times
4. 4
   WaschenThe organic layers were washed with saturated saline
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

200 mg of 4-methyl-3-[4-(3-pyridyl)pyridin-2-ylamino]aniline (Reference Example 23) was suspended in 4 ml of acetonitrile, and 78.8 mg of 4-(dimethylamino)pyridine and 484 μl of N,N-diisopropyl-N-ethylamine were added in turn. Under ice-cooling with stirring, 383 mg of 4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylbenzoyl chloride dihydrochloride (Reference Example 5) was added, followed by stirring at room temperature for 2 hours. To the reaction solution was added water and the mixture was subjected to extraction with ethyl acetate three times. The organic layers were washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 93 mg of the objective compound as pale yellow crystals.

Quelle