Reacción #1605834

Ecuación de reacción

aripiprazole

triethylamine

benzyl isocyanate

→

N-benzyl-7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxamide

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with water
2. 2
   Extracciónextracted with dichloromethane (3×20 mL)
3. 3
   Lavadowashed with brine (20 mL)
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by column chromatography on silica eluting with 0-10% tetrahydrofuran in ethyl acetate
7. 7
   OtroThe product was triturated in heptane
8. 8
   Otroto remove aliphatic impurities
9. 9
   Filtraciónfiltered
10. 10
    Otrodried
11. 11
    Otroto afford Compound-79 (0.575 g) as a colorless solid

Procedimiento

To a solution of aripiprazole (1.5 g, 3.35 mmol) in dichloromethane (33 mL) was added triethylamine (0.56 mL, 4.01 mmol) and benzyl isocyanate (0.82 mL, 6.69 mmol). The reaction was stirred at room temperature for 48 hours. The reaction was quenched with water and extracted with dichloromethane (3×20 mL). The organics were combined, washed with brine (20 mL), dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica eluting with 0-10% tetrahydrofuran in ethyl acetate. The product was triturated in heptane to remove aliphatic impurities and then filtered and dried to afford Compound-79 (0.575 g) as a colorless solid.

Fuente