新产品编号:188767
2-丁基-N-(3,5-二氯吡啶-4-基)-7-甲氧基-1-苯并呋喃-4-甲酰胺Chemical Name: 2-Butyl-N-(3,5-dichloropyridin-4-yl)-7-methoxy-1-benzofuran-4-carboxamide
CAS No. 185400-42-4
项目整合开发状态: Preclinical
项目研究机构: Aventis Pharma (Originator)
合成路线:Cyclization of bromophenol (I) with 1-hexyne (II) in the presence of Pd (0) and CuI catalysts produced benzofuran (III).Then,oxidation of the aldehyde function of (III) with sodium chlorite provided carboxylic acid (IV).An alternative route to the intermediate (IV) consisted of a palladium/copper-catalyzed cyclization of bromophenol (V) with 1-hexyne (II),followed by basic hydrolysis of the resulting benzofuran methyl ester (VI).Treatment of carboxylic acid (IV) with oxalyl chloride yielded the corresponding acid chloride (VII),which was finally condensed with 4-amino-3,5-dichloropyridine (VIII) in the presence of NaEt2AlH2 to furnish the target amide.
📌 参考资料/链接:
参考文献标题:Benzofuran based PDE4 inhibitors
文献作者:McGarry,D.G.; Regan,J.R.; Volz,F.A.; Hulme,C.; Moriarty,K.J.; Djuric,S.W.; Souness,J.E.; Miller,B.E.; Travis,J.J.; Sweeney,D.M.
参考来源:Bioorg Med Chem 1999,7(6),1131