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【结 构 式】

【分子编号】34183

【品名】N-[4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenethyl]acetamide

【CA登记号】

【 分 子 式 】C19H28N4O3S

【 分 子 量 】392.52248

【元素组成】C 58.14% H 7.19% N 14.27% O 12.23% S 8.17%

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:(III)

The condensation of 4-[2-(acetylamino)ethyl]benzenesulfonyl chloride (I) with 1-cyclohexyl-2-iminoimidazolidine (III) by means of NaOH in refluxing acetone gives 1-[[4-(2-acetamidoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (III), which is hydrolyzed with refluxing 2N HCl yielding 1-[[4-(2-aminoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (IV). Finally, this compound is acylated with crotonic anhydride (V) in dioxane. The starting products (I) and (II) are obtained as follows: 1) The acetylation of 2-phenylethylamine (VI) with acetic anhydride gives N-(2-phenylethyl)acetamide (VII), which is sulfonated with chlorosulfonic acid yielding compound (I). 2) The reductocondensation of cyclohexanone (IX) with ethylenediamine (VIII) gives N-cyclohexylethylenediamine (X), which is then cyclized with cyanogen chloride to compound (II).

1 Lehmann, C.; Dietrich, H.; Schweizer, E.H.; Marki, F.; Sulfonyliminoimidazolidines. A new clas of oral hypoglycemic agents. I. 1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidies. J Med Chem 1983, 26, 7, 964-970.
2 Serradell, M.N.; Castaner, J.; Thorpe, P.J.; CGP-11112. Drugs Fut 1984, 9, 5, 315.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIIII) 14754 ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine;1,2-Ethanediamine 107-15-3 C2H8N2 详情 详情
(I) 34181 4-[2-(acetamido)ethyl]benzenesulfonyl chloride C10H12ClNO3S 详情 详情
(II) 34182 1-cyclohexyl-2-imidazolidinimine C9H17N3 详情 详情
(III) 34183 N-[4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenethyl]acetamide C19H28N4O3S 详情 详情
(IV) 34184 2-[4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenyl]-1-ethanamine; 4-[(3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenethylamine C17H26N4O2S 详情 详情
(V) 34185 (E)-2-butenoic anhydride C8H10O3 详情 详情
(VI) 18333 Phenethylamine; 2-Phenyl-1-ethanamine 64-04-0 C8H11N 详情 详情
(VII) 34186 N-phenethylacetamide 877-95-2 C10H13NO 详情 详情
(IX) 11059 Cyclohexanone 108-94-1 C6H10O 详情 详情
(X) 34187 N(1)-cyclohexyl-1,2-ethanediamine; N-(2-aminoethyl)-N-cyclohexylamine C8H18N2 详情 详情
Extended Information