New Practical Synthesis of the Key Intermediate of Candesartan

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• 作者：Má ; rta Porcs-Makkay ; Tibor Mezei ; Gyula Simig
• 刊名：Organic Process Research & Development
• 出版年：2007
• 出版时间：May 2007
• 年：2007
• 卷：11
• 期：3
• 页码：490 - 493
• 全文大小：75K
• 年卷期：v.11,no.3(May 2007)
• ISSN：1520-586X

文摘

The development of a new, practical synthesis of methyl3-amino-N-[(2'-cyanobiphenyl-4-yl)methyl]anthranilate, key intermediate of candesartan, is described, starting from methylanthranilate. The features of our approach are as follows: (i)introduction of the 3-nitro group by acid catalysed rearrangement of the corresponding methyl N-nitroanthranilate; (ii)introduction of a (2'-cyanobiphenyl-4-yl)methyl side chain byN-alkylation of the appropriate N-nitroanthranilic acid derivative. In the most efficient procedure methyl N,3-dinitroanthranilate was N-alkylated with 4'-bromomethyl-biphenyl-2-nitrile.Catalytic reduction of the aromatic nitro group was accompanied with the removal of the N-nitro function to affordthe required key intermediate in good yield.