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【结 构 式】 
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【药物名称】DDE-934 【化学名称】N-[2-(5-Bromothien-2-yl)ethyl]-N'-(5-chloropyridin-2-yl)thiourea 【CA登记号】 【 分 子 式 】C12H11BrClN3S2 【 分 子 量 】376.72657 |
【开发单位】Parker Hughes Institute (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Reverse Transcriptase Inhibitors |
合成路线1
2-(2-Thienyl)ethylamine (I) was protected as the N-Boc derivative (II) with Boc2O in CHCl3. Regioselective halogenation of the thiophene ring of (II) with concomitant Boc group cleavage by means of bromine in cold HOAc yielded the 5-bromothiophene (III). The thioimidazolide (VI) was prepared by reaction of 2-amino-5-chloropyridine (IV) with thiocarbonyl diimidazole (V). Finally, condensation of (VI) with amine (III) in hot DMF furnished the target thiourea.
| 【1】 Uckun, F.M.; Sudbeck, E.A.; Venkatachalam, T.K.; Regiospecific synthesis, X-ray crystal structure and biological activities of 5-bromothiophenethyl thioureas. Tetrahedron Lett 2001, 42, 38, 6629. |
| 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) | 35253 | 2-(2-thienyl)ethylamine; 2-(2-thienyl)-1-ethanamine; 2-Thiophene ethylamine | 30433-91-1 | C6H9NS | 详情 | 详情 |
| (II) | 52887 | tert-butyl 2-(2-thienyl)ethylcarbamate | C11H17NO2S | 详情 | 详情 | |
| (III) | 52888 | 2-(5-bromo-2-thienyl)-1-ethanamine; 2-(5-bromo-2-thienyl)ethylamine | C6H8BrNS | 详情 | 详情 | |
| (IV) | 18559 | 5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine | 1072-98-6 | C5H5ClN2 | 详情 | 详情 |
| (V) | 11990 | Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole | 6160-65-2 | C7H6N4S | 详情 | 详情 |
| (VI) | 36903 | C9H7ClN4S | 详情 | 详情 |
Extended Information