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【结 构 式】 
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【药物名称】Orconazole nitrate, R-15556 【化学名称】1-[2-(4-Chlorophenyl)-2-(2,6-dichlorobenzyloxy)ethyl]-1H-imidazole nitrate 【CA登记号】66778-38-9, 22833-02-9 (free base) 【 分 子 式 】C18H16Cl3N3O4 【 分 子 量 】444.70492 |
【开发单位】 【药理作用】 |
合成路线1
Reaction of p-chlorophenacyl bromide (I) with imidazole (II) affords 4'-chloro-2-(1-imidazolyl)acetophenone (III). Sodium borohydride reduction gives the corresponding alcohol (IV) which is then alkylated with 2,6-dichlorobenzyl chloride (V) to give orconazole (VI). Treatment of (VI) with nitric acid yield the title compound
| 【1】 Godefroi, E.F.; et al.; The preparation and properties of derivatives of 1-phenethyl imidazole. J Med Chem 1969, 12, 5, 784. |
| 【2】 Godefroi, E.F.; Heeres, J. (Janssen Pharmaceutica NV); BE 737575; DE 1940388; FR 2015913; GB 1244530; JP 76115; US 3717655; US 3839574; ZA 6905965 . |
| 【3】 Arya, V.P.; Orconazole nitrate. Drugs Fut 1979, 4, 6, 432. |
| 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) | 16720 | 2-bromo-1-(4-chlorophenyl)-1-ethanone; 2-Bromo-4'-chloroacetophenone | 536-38-9 | C8H6BrClO | 详情 | 详情 |
| (II) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
| (III) | 60948 | 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone | C11H9ClN2O | 详情 | 详情 | |
| (IV) | 60949 | 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol | C11H11ClN2O | 详情 | 详情 | |
| (V) | 60951 | 1,3-dichloro-2-(chloromethyl)benzene | C7H5Cl3 | 详情 | 详情 | |
| (VI) | 60950 | 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethyl 2,6-dichlorobenzyl ether; 1-{2-(4-chlorophenyl)-2-[(2,6-dichlorobenzyl)oxy]ethyl}-1H-imidazole | C18H15Cl3N2O | 详情 | 详情 |
Extended Information