Reacción #9537

Ecuación de reacción

tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate

triethyl orthopropionate

→

tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

Rendimiento 77.1%

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter completion, the reaction mixture was concentrated under reduced pressure
2. 2
   Otrothe residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA)
3. 3
   Otrofollowed by recrystallization from ethyl acetate

Procedimiento

The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with triethyl orthopropionate (6.68 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA) followed by recrystallization from ethyl acetate to provide 12.6 g of tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white powder, mp 208–209° C.

Fuente