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【结 构 式】 
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【药物名称】LY-127210 【化学名称】7,8-Dimethoxy-1H-3-benzazepine-2-amine hydrochloride 【CA登记号】93270-40-7 【 分 子 式 】C12H15ClN2O2 【 分 子 量 】254.71855 |
【开发单位】Lilly (Originator) 【药理作用】Cardiovascular Diseases (Not Specified), CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Vasodilators |
合成路线1
The condensation of 3,4-dimethoxyphenyacetic acid (I) with 2-aminoacetaldehyde diethylacetal (II) by means of 1,1'-carbonyldiimidazole (CDI) in CHCl3 gives N-(2,2-diethoxyethyl)-3,4-dimelhoxyphenylacetamide (III), which is cyclized by means of 48% aqueous HBr yielding 1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one (IV). The reaction of (IV) with triethyloxonium tetrafluoroborate (V) in methylene chloride affords 2-ethoxy-7,8-dimethoxy-1H-3-benzazepine (VI), which is finally treated with ammonium chloride in refluxing methanol.
| 【1】 Paget, C.J. Jr.; Ruffolo, R.R. Jr. (Eli Lilly and Company); Benzazepine derivs.. EP 0116444; ES 8602681; ES 8801215; GB 2134519 . |
| 【2】 Prous, J.; Castaner, J.; LY-127210. Drugs Fut 1986, 11, 9, 748. |
| 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) | 24049 | 2-(3,4-dimethoxyphenyl)acetic acid | 93-40-3 | C10H12O4 | 详情 | 详情 |
| (II) | 10331 | 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal | 645-36-3 | C6H15NO2 | 详情 | 详情 |
| (III) | 24284 | N-(2,2-diethoxyethyl)-2-(3,4-dimethoxyphenyl)acetamide | C16H25NO5 | 详情 | 详情 | |
| (IV) | 24285 | 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one | C12H13NO3 | 详情 | 详情 | |
| (VI) | 24287 | 2-ethoxy-7,8-dimethoxy-1H-3-benzazepine | C14H17NO3 | 详情 | 详情 |