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【结 构 式】

【分子编号】29005

【品名】2-acetyl-N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide

【CA登记号】

【 分 子 式 】C17H17ClN2O3S

【 分 子 量 】364.85236

【元素组成】C 55.96% H 4.7% Cl 9.72% N 7.68% O 13.16% S 8.79%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

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.

1 Ali Fadia E. (SmithKline Beecham Corp.); N,N'-Bis[substituted-1,2,3,4-tetrahydroisoquinolino]disulfonylimides and antiallergic compositions and method of use. DD 158240; EP 0038177; US 4135935 .
2 Serradell, M.N.; Chu, S.S.; Castaner, J.; SKF-88046. Drugs Fut 1985, 10, 1, 42.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 14124 1,2,3,4-Tetrahydroisoquinoline 91-21-4 C9H11N 详情 详情
(II) 29003 1-[3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone C11H13NO 详情 详情
(III) 29004 2-acetyl-1,2,3,4-tetrahydro-7-isoquinolinesulfonyl chloride C11H12ClNO3S 详情 详情
(IV) 25239 3-chloroaniline; 3-chlorophenylamine 108-42-9 C6H6ClN 详情 详情
(V) 29005 2-acetyl-N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide C17H17ClN2O3S 详情 详情
(VI) 29006 N-(3-chlorophenyl)-1,2,3,4-tetrahydro-7-isoquinolinesulfonamide C15H15ClN2O2S 详情 详情
(VII) 29007 Bis(chlorosulfonyl)imide HCl2NO4S2 详情 详情
(VIII) 29008 Chlorosulfonic acid 7790-94-5 HClO3S 详情 详情
(IX) 14101 Chlorosulfonyl isocyanate 1189-71-5 CClNO3S 详情 详情
Extended Information