Reacción #433589

ord-66fb621122b84a2b986c4ce07a4fd5a3

Ecuación de reacción

c1ccc2ncncc2c1
quinazoline
Nc1cc(Cl)c(Cl)cc1F
3,4-dichloro-6-fluoroaniline
O=[N+]([O-])c1cc2c(Cl)ncnc2cc1F
4-chloro-7-fluoro-6-nitroquinazoline
O=[N+]([O-])c1cc2c(Nc3cc(Cl)c(Cl)cc3F)ncnc2cc1F
4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

In another particular, which includes a quinazoline that is substituted by two different reactive groups at positions 6 and 7 thereof, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-7-fluoro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline. The 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline is then reacted with a sodium salt of 3-(4-morpholinyl-1-propanol), so as to produce 4-[(3,4-dichloro-6-fluoro-phenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 6-amino-4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline. The product is then reacted with a carbon-11 labeled acryloyl chloride so as to produce a carbon-11 labeled N-{4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline-6-yl}acrylamide (carbon-11 labeled morpholino-substituted Compound 3).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07172749B2uspto-grants-2007_02