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【结 构 式】 
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【药物名称】BGC-20-1178, RS-1178 【化学名称】5-Methyl-8-(1-phenylethyl)-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 【CA登记号】62052-82-8 【 分 子 式 】C16H17N5 【 分 子 量 】279.34739 |
【开发单位】BTG (Proprietary), Sankyo (Originator) 【药理作用】Alzheimer's Dementia, Treatment of , Cognition Disorders, Treatment of, NEUROLOGIC DRUGS |
合成路线1
The cyclization of 1,2,4-triazol-5-amine (I) with 3-acetyltetrahydrofuran-2-one (II) by heating at 155 C gives the triazolopyrimidinone (III) (1), which is treated with refluxing POCl3 to yield 7-chloro-6-(2-chloroethyl)5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (IV). Finally this compound is cyclized with 1-phenylethylamine (V) by means of Na2CO3 in refluxing ethanol to afford the target pyrrolo-triazolo-pyrimidine derivative.
| 【1】 Sato, Y.; et al.; Studies on cardiovascular agents. 6. Synthesis and coronary vasodilating and antihypertensive activities of 1,2,4-triazolo[1,5-a]pyrimidines fused to heterocyclic systems. J Med Chem 1980, 23, 8, 927. |
| 【2】 Takagi, H.; Sato, Y.; Shimoji, Y.; Kumakura, S. (Sankyo Co., Ltd.); Pyrrolotriazolopyrimidine derivs. and process for the preparation thereof. US 4007189 . |
| 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) | 55760 | 1H-1,2,4-triazol-5-amine; 1H-1,2,4-triazol-5-ylamine | C2H4N4 | 详情 | 详情 | |
| (II) | 24709 | 3-acetyldihydro-2(3H)-furanone | 517-23-7 | C6H8O3 | 详情 | 详情 |
| (III) | 55761 | 6-(2-hydroxyethyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one | C8H10N4O2 | 详情 | 详情 | |
| (IV) | 55762 | 7-chloro-6-(2-chloroethyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine | C8H8Cl2N4 | 详情 | 详情 | |
| (V) | 15148 | 1-phenylethylamine; DL-a-methylbenzylamine; 1-phenyl-1-ethanamine | 618-36-0 | C8H11N | 详情 | 详情 |
Extended Information