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2015•Chinese Journal of PharmaceuticalsRequires access

Synthesis of 2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol

AN Chenhon

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Abstract

2-Methyl-3-amino-4-acethylanisole(2) was prepared from 2-methyl-3-nitrophenol via methylation,Friedel-Crafts reaction and reduction.2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol,the key intermediate of anti-HCV drug simeprevir,was synthesized from 3-methyl-2-butanone by bromination,cyclization,Sandmeyer reaction,cyano-substitution,and hydrolysis to give 4-isopropylthiazole-2-formic acid(3),which was subjected to chlorination,N-acylation with 2,and cyclization in the presence of t-BuOK.The overall yield was about 9%(based on3-methyl-2-butanone).

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What this paper is about

2-Methyl-3-amino-4-acethylanisole(2) was prepared from 2-methyl-3-nitrophenol via methylation,Friedel-Crafts reaction and reduction.2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol,the key intermediate of anti-HCV drug simeprevir,was synthesized from 3-methyl-2-butanone by bromination,cyclization,Sandmeyer reaction,cyano-substitution,and hydrolysis to give 4-isopropylthiazole-2-formic acid(3),which was subjected to chlorination,N-acylation with 2,and cyclization in the presence of t-BuOK.The overall yield was about 9%(based on3-methyl-2-butanone).

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Available abstract

2-Methyl-3-amino-4-acethylanisole(2) was prepared from 2-methyl-3-nitrophenol via methylation,Friedel-Crafts reaction and reduction.2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol,the key intermediate of anti-HCV drug simeprevir,was synthesized from 3-methyl-2-butanone by bromination,cyclization,Sandmeyer reaction,cyano-substitution,and hydrolysis to give 4-isopropylthiazole-2-formic acid(3),which was subjected to chlorination,N-acylation with 2,and cyclization in the presence of t-BuOK.The overall yield was about 9%(based on3-methyl-2-butanone).

Key concepts: Chemistry, Yield (engineering), Halogenation, Formic acid, Hydrolysis, Medicinal chemistry, Acylation, Organic chemistry

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Synthesis of 2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol — Research Paper | ScholarLens