PNU-183792

Chemical Name: N-(4-Chlorobenzyl)-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
CAS No. 282536-25-8
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:The 4-hydroxyquinoline (III) was synthesized via Gould-Jacobs reaction from 4-iodoaniline (I) and diethyl ethoxymethylenemalonate (II).Displacement of the ethyl ester group with 4-chlorobenzylamine (IV) at 180 C furnished the chlorobenzyl amide (V).Subsequent palladium-catalyzed carbonylation of iodide (V) provided the methyl carboxylate (VI),which was further reduced to alcohol (VII) using LiAlH4.Methylation of the hydroxyquinoline (VII) with iodomethane gave rise to the N-methyl quinolone (VIII).After conversion of the alcohol function of (VIII) to the corresponding mesylate (IX),displacement with morpholine (X) yielded the target morpholinomethyl quinolone.