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【结 构 式】 
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【分子编号】67991 【品名】6-bromo-N2-(pentan-3-yl)pyrazine-2,3-diamine 【CA登记号】 |
【 分 子 式 】C9H15BrN4 【 分 子 量 】259.149 【元素组成】C 41.71% H 5.83% Br 30.83% N 21.62% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)Condensation of 2-amino-3,5-dibromopyrazine (I) with neat 3-amino-pentane (II) under microwave irradiation at 150 °C yields the diaminopyrazine (III), which is then subjected to cyclization with CDI in refluxing THF to give 6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol (IV). Sonogashira cross-coupling of aryl bromide (IV) with (trimethylsilyl)acetylene (V) in the presence of PdCl2(PPh3)2, CuI and Et3N in DMF at 80 °C affords adduct (VI), which is finally desilylated by treatment with KF in MeOH/THF/H2O .
| 【1】 Muci, A., Finer, J.T., Lu, P.-P., Russell, A.J., Morgan, B.P., Morgans, D.J. Jr. (Cytokinetics, Inc.). Certain chemical entities, compositions and methods. EP 2069352, JP 2009545596, US 2008146561, US 7598248, US 8227603, US 8299248, WO 200801669. |
| 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) | 26178 | 3,5-dibromo-2-pyrazinamine | 24241-18-7 | C4H3Br2N3 | 详情 | 详情 |
| (II) | 25924 | 1-ethylpropylamine; 3-pentanamine | 616-24-0 | C5H13N | 详情 | 详情 |
| (III) | 67991 | 6-bromo-N2-(pentan-3-yl)pyrazine-2,3-diamine | C9H15BrN4 | 详情 | 详情 | |
| (IV) | 67992 | 6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol | C10H13BrN4O | 详情 | 详情 | |
| (V) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (VI) | 67993 | 1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol | C15H22N4OSi | 详情 | 详情 |
Extended Information