Acemetacin, TVX-1322, Bay-f-4975, Emflex, Rantudil
阿西美辛Chemical Name: 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid carboxymethyl ester; 1-(4-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetoxyacetic acid
CAS No. 53164-05-9
项目整合开发状态: Launched-1980
项目研究机构: Bayer (Not Determined), Merck & Co. (Not Determined)
合成路线:1) By condensation of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (II) with benzyl bromoacetate (A) by means of K2CO3 in DMF.2) By cyclocondensation of a mixture of N-(p-methoxyphenyl)-N-(p-chlorobenzoyl)hydrazine (III) and benzyl levulinate (IV) at 80 C in acetic acid.
合成路线:3) The reaction of p-methoxyphenylhydrazine (V) with benzyl levulinate (IV) in acetic acid gives the corresponding hydrazone (VI),which,without isolation,is cyclized to benzyl 5-methoxy-2-methylindole-3-acetoxyacetate (VII) at 80 C in acetic acid.Then this compound is benzoylated with p-chlorobenzoyl chloride (B) by means of NaH in DMF.4) The hydrazone (VI) can also be benzoylated first giving the corresponding hydrazone (VIII),which is then cyclized at 80 C in acetic acid.
📌 参考资料/链接：
参考文献标题:Acemetacin
文献作者:Leeson,P.A.; Castar,J.
参考来源:Drugs Fut 1977,2(7),423
📄 详细内容
合成路线:1) By condensation of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (II) with benzyl bromoacetate (A) by means of K2CO3 in DMF.2) By cyclocondensation of a mixture of N-(p-methoxyphenyl)-N-(p-chlorobenzoyl)hydrazine (III) and benzyl levulinate (IV) at 80 C in acetic acid.
合成路线:3) The reaction of p-methoxyphenylhydrazine (V) with benzyl levulinate (IV) in acetic acid gives the corresponding hydrazone (VI),which,without isolation,is cyclized to benzyl 5-methoxy-2-methylindole-3-acetoxyacetate (VII) at 80 C in acetic acid.Then this compound is benzoylated with p-chlorobenzoyl chloride (B) by means of NaH in DMF.4) The hydrazone (VI) can also be benzoylated first giving the corresponding hydrazone (VIII),which is then cyclized at 80 C in acetic acid.
参考文献标题:Novel substituted indole compound,process for the preparation and therapeutic compositions containing it.
文献作者:Boltze,K.; Brendler,O.; Dell,H.-D.; Jacobi,H.
参考来源:DE 2234651; ES 416877; FR 2192828; JP 49043970; US 3910952
产品链接: CAS No. 53164-05-9››