Reacción #85609

Ecuación de reacción

2-{3-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride

4-chloro-2-isocyanato-1-methylbenzene

water

→

N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide

Disolventes

dichloromethane

diisopropylethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added, at room temperature
2. 2
   OtroThe aqueous phase was removed
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   SecadoThe combined organic phases were dried over sodium sulphate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by chromatography

Procedimiento

To a suspension of 2-{3-[2-(piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde hydrochloride (1.43 g) in dichloromethane (30 ml) and diisopropylethylamine (0.73 ml) were added, at room temperature, 4-chloro-2-isocyanato-1-methylbenzene (700 mg) and one drop of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The mixture was stirred at room temperature overnight, and water was then added. The aqueous phase was removed and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave N-(5-chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide (1.23 g).

Fuente