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【结 构 式】 
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【分子编号】33268 【品名】6-(5-chloro-2-pyridinyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione 【CA登记号】 |
【 分 子 式 】C11H5ClN4O2 【 分 子 量 】260.63916 【元素组成】C 50.69% H 1.93% Cl 13.6% N 21.5% O 12.28% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of pyrazine-2,3-dicarboxylic acid anhydride (I) with 2-amino-5-chloropyridine (II) in refluxing acetonitrile gives 3-(5-chloro-2-pyridyl)carbamoyl pyrazine-2-carboxylic acid (III), which is cyclized by treatment with refluxing SOCl2 affording 6-(5-chloropyrid-2-yl)-5,7-dioxo-5,6-dihydropyrrolo[3,4-b]pyrazine (IV). The partial reduction of (IV) with KBH4 in dioxane-water yields 6-(5-chloro-2-pyridyl)-7-hydroxy-5,6-dihydropyrrolo[3,4-b]pyrazin-5-one (V), which is finally esterified with 4-methylpiperazine-1-carbonyl chloride (VI) by means of NaH in DMF.
| 【1】 Cotrel, C.; et al. (Aventis Pharma SA); Pyrrolo-[3,4,b]pyrazine derivatives. DE 2300491; GB 1358680; JP 52048687; US 3862149 . |
| 【2】 Castaner, J.; Serradell, M.N.; Zopiclone. Drugs Fut 1979, 4, 1, 59. |
| 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) | 33266 | furo[3,4-b]pyrazine-5,7-dione | C6H2N2O3 | 详情 | 详情 | |
| (II) | 18559 | 5-Chloro-2-pyridinylamine; 5-Chloro-2-pyridinamine; 2-Amino-5-chloropyridine | 1072-98-6 | C5H5ClN2 | 详情 | 详情 |
| (III) | 33267 | 3-[[(5-chloro-2-pyridinyl)amino]carbonyl]-2-pyrazinecarboxylic acid | C11H7ClN4O3 | 详情 | 详情 | |
| (IV) | 33268 | 6-(5-chloro-2-pyridinyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione | C11H5ClN4O2 | 详情 | 详情 | |
| (V) | 32796 | 6-(5-chloro-2-pyridinyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one | C11H7ClN4O2 | 详情 | 详情 | |
| (VI) | 30370 | 4-methyl-1-piperazinecarbonyl chloride | C6H11ClN2O | 详情 | 详情 |