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【结 构 式】 
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【分子编号】30605 【品名】N-[(4-[[(2-aminoethyl)sulfanyl]methyl]-1,3-thiazol-2-yl)methyl]-N,N-dimethylamine; 2-[([2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methyl)sulfanyl]-1-ethanamine 【CA登记号】 |
【 分 子 式 】C9H17N3S2 【 分 子 量 】231.3862 【元素组成】C 46.72% H 7.41% N 18.16% S 27.72% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of dimethylaminothioacetamide (I) with ethyl bromopyruvate (II) in refluxing ethanol gives ethyl 2-(dimethylaminomethyl)-4-thiazolecarboxylate (III), which is reduced with lithium triethyl borohydride in THF yielding 2-(dimethylaminomethyl)-4-thiazolemethanol (IV). The condensation of (IV) with 2-aminoethanethiol (V) by means of 48% HBr affords 2-(dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole (VI), which is finally condensed with 1-(methylthio)-2-nitro-N-methylethyleneamine (VII) in water.
| 【1】 Pioch, R.P. (Eli Lilly and Company); N-Methyl-N'-2-[[(2-dimethylaminomethyl)-4-thiazolyl]methylthio]ethyl-2-nitro-1,1-ethenediamine. EP 0049618; GB 2084581; JP 57091980; US 4375547 . |
| 【2】 Serradell, M.N.; Castaner, J.; Nizatidine. Drugs Fut 1984, 9, 9, 655. |
| 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) | 30602 | 2-(dimethylamino)ethanethioamide | C4H10N2S | 详情 | 详情 | |
| (II) | 25183 | ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate | 70-23-5 | C5H7BrO3 | 详情 | 详情 |
| (III) | 30603 | ethyl 2-[(dimethylamino)methyl]-1,3-thiazole-4-carboxylate | C9H14N2O2S | 详情 | 详情 | |
| (IV) | 30604 | [2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methanol | C7H12N2OS | 详情 | 详情 | |
| (V) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (VI) | 30605 | N-[(4-[[(2-aminoethyl)sulfanyl]methyl]-1,3-thiazol-2-yl)methyl]-N,N-dimethylamine; 2-[([2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methyl)sulfanyl]-1-ethanamine | C9H17N3S2 | 详情 | 详情 | |
| (VII) | 13852 | N-Methyl-N-[(E)-1-(methylsulfanyl)-2-nitroethenyl]amine; (E)-N-Methyl-1-(methylsulfanyl)-2-nitro-1-ethenamine; (E)-1-Methylthio-1-methylamino-2-nitroethylene | 61832-41-5 | C4H8N2O2S | 详情 | 详情 |