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【结 构 式】 
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【分子编号】14217 【品名】4-(Chloromethyl)-5-methyl-1H-imidazole 【CA登记号】 |
【 分 子 式 】C5H7ClN2 【 分 子 量 】130.57676 【元素组成】C 45.99% H 5.4% Cl 27.15% N 21.45% |
合成路线1
该中间体在本合成路线中的序号：(II)The synthesis of CP-93,318 is summarized: Treatment of 4-methyl-5-imidazolemethanol (I) with thionyl chloride affords chloromethylimidazole (II). Exposure of (II) to potassium cyanide provides nitrile (III), and subsequent reaction of (III) with diethyldithiophosphate in the presence of hydrochloric acid gives thioamide (IV), as its hydrochloride salt. Condensation of this hygroscopic salt with 2-bromo-2'-methoxyacetophenone (V) provides thiazole CP-93,318. Analogues of CP-93,318, modified at the methoxyphenyl moiety, were prepared similarly by condensation of convergent intermediate (IV) and the appropriate alpha-haloketone.
| 【1】 Rizzi, J.P.; Guarino, K.; Vincent, L.A.; Ganong, A.H.; Siok, C.J.; Ives, J.L.; Nowakowski, J.T.; Seeger, T.F.; Rosen, T.; Heym, J.; Nagel, A.A.; Daffeh, J.B.; McLean, S.; Schmidt, A.W.; Thiazole as a carbonyl bioisostere. A novel class of highly potent and selective 5-HT3 receptor antagonists. J Med Chem 1990, 33, 2715-20. |
| 【2】 Rosen, T.; Nagel, A.A.; CP-93,318. Drugs Fut 1991, 16, 11, 992. |
| 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) | 14216 | (5-Methyl-1H-imidazol-4-yl)methanol | 29636-87-1 | C5H8N2O | 详情 | 详情 |
| (II) | 14217 | 4-(Chloromethyl)-5-methyl-1H-imidazole | C5H7ClN2 | 详情 | 详情 | |
| (III) | 14218 | 2-(5-Methyl-1H-imidazol-4-yl)acetonitrile | C6H7N3 | 详情 | 详情 | |
| (IV) | 14219 | 2-(5-Methyl-1H-imidazol-4-yl)ethanethioamide hydrochloride | C6H9N3S | 详情 | 详情 | |
| (V) | 14220 | 2-Bromo-1-(2-methoxyphenyl)-1-ethanone | 31949-21-0 | C9H9BrO2 | 详情 | 详情 |