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Note | Regular issue | Vol 65, No. 11, 2005, pp.2763-2770
Published online, 19th August, 2005
DOI: 10.3987/COM-05-10511
A Practical Synthesis of 1-Alkyl-3-amino-4-aryl-1,8-naphthyridin-2-(1H)-one, a Partial Structure of ACAT Inhibitor SMP-797

Hitoshi Ban,* Masami Muraoka, Kouji Morisita, and Naohito Ohashi

*Research Division, Sumitomo Pharmaceuticals Co., Ltd., 1-98, Kasugadenaka 3-chome, Konohana-ku, Osaka 554-0022, Japan

Abstract

3-Amino-4-[3-(3-benzyloxypropoxy)phenyl]-1-butyl-1,8- naphthyridin-2(1H)-one, which is a naphthyridine part of a potent ACAT (acyl-CoA: cholesterol acyltransferase) inhibitor SMP-797, was effectively synthesized from m-bromophenol in 5 steps without isolating intermediates. The synthesis involved the intramolecular aldol reaction as a key step.