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【结 构 式】 
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【药物名称】Irampanel hydrochloride, BIIR-561-CL 【化学名称】N,N-Dimethyl-N-[2-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenoxy]ethyl]amine hydrochloride 【CA登记号】206260-34-6, 206260-33-5 (free base) 【 分 子 式 】C18H20ClN3O2 【 分 子 量 】345.832 |
【开发单位】Boehringer Ingelheim (Originator) 【药理作用】Antiepileptic Drugs, Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, AMPA Antagonists, Sodium Channel Blockers |
合成路线1
The condensation between benzamidoxime (I) and methyl salicylate (II) in the presence of NaOEt under microwave irradiation generated oxadiazole (III). Subsequent alkylation of the hydroxyl group of (III) with dimethylaminoethyl chloride and NaH in dioxan produced the target aminoethyl ether, which was finally isolated as the corresponding hydrochloride salt.
| 【1】 Brenner, M.; Maier, R.; Wienrich, M.; Weiser, T.; Palluk, R.; Bechtel, W.-D.; Sagrada, A.; Ensinger, H.; Pschorn, U.; Cesana, R. (Boehringer Ingelheim GmbH); Oxadiazoles, processes for their preparation and their use as medicaments. DE 19643037; EP 0934288; JP 2000505089; WO 9817652 . |
| 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) | 20438 | N'-hydroxybenzenecarboximidamide | 613-92-3 | C7H8N2O | 详情 | 详情 |
| (II) | 15754 | methyl salicylate | 119-36-8 | C8H8O3 | 详情 | 详情 |
| (III) | 32225 | 3,4,5-trimethoxybenzoic acid | 118-41-2 | C10H12O5 | 详情 | 详情 |
| (IV) | 11907 | Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine | 107-99-3 | C4H10ClN | 详情 | 详情 |