SK&F-88046
Chemical Name: N7-(3-Chlorophenyl)-N2-[[7-[[(3-chlorophenyl)amino]sulfonyl]-3,4-dihydro-2(1H)-isoquinolinyl]sulfonyl]-3,4-dihydro-2,7(1H)-isoquinolinedisulfonamide; N,N'-Bis[7-(3-chlorophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinolyl]disulfonylimide
CAS No. 80565-83-9, 80566-05-8 (Na salt)
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The acetylation of 1,2,3,4-tetrahydroisoquinoline (I) with acetic anhydride gives 2-acetyl-1,2,3,4-tetrahydroisoquinoline (II),which is sulfonated with chloro sulfonic acid in methylene chloride yielding 2-acetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline (III).The reaction of (III) with 3-chloroaniline (IV) and triethylamine in refluxing acetone affords 2-acetyl-7-(3-chlorophenylamino sulfonyl)-1,2,3,4-tetrahydroisoquinoline (V),which is deacetylated by a treatment with HCl in refluxing butanol to 7-(3-chlorophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (VI).Finally,this compound is condensed with bis(chlorosulfonyl)imide (VII) [prepared with chlorosulfonic acid (VIII) and chlorosulfonyl isocyanate (IX)] in acetonitrile containing triethylamine.
📌 参考资料/链接：
参考文献标题:N,N'-Bis[substituted-1,2,3,4-tetrahydroisoquinolino]disulfonylimides and antiallergic compositions and method of use
文献作者:Ali Fadia,E.(SmithKline Beecham Corp.)
参考来源:DD 158240; EP 0038177; US 4135935
📄 详细内容
合成路线:The acetylation of 1,2,3,4-tetrahydroisoquinoline (I) with acetic anhydride gives 2-acetyl-1,2,3,4-tetrahydroisoquinoline (II),which is sulfonated with chloro sulfonic acid in methylene chloride yielding 2-acetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline (III).The reaction of (III) with 3-chloroaniline (IV) and triethylamine in refluxing acetone affords 2-acetyl-7-(3-chlorophenylamino sulfonyl)-1,2,3,4-tetrahydroisoquinoline (V),which is deacetylated by a treatment with HCl in refluxing butanol to 7-(3-chlorophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline (VI).Finally,this compound is condensed with bis(chlorosulfonyl)imide (VII) [prepared with chlorosulfonic acid (VIII) and chlorosulfonyl isocyanate (IX)] in acetonitrile containing triethylamine.
参考文献标题:SKF-88046
文献作者:Serradell,M.N.; Chu,S.S.; Castar,J.
参考来源:Drugs Fut 1985,10(1),42