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【结 构 式】 
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【药物名称】SCH-442416 【化学名称】2-(2-Furyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine-5-amine 【CA登记号】316173-57-6, 316173-59-8 (labeled) 【 分 子 式 】C20H19N7O2 【 分 子 量 】389.42013 |
【开发单位】Schering-Plough (Originator) 【药理作用】DIAGNOSTIC AGENTS, Adenosine A2A Antagonists |
合成路线1
The condensation between 3-(4-methoxyphenyl)propyl hydrazine (I) and (ethoxymethylene)malononitrile (II) afforded the pyrazole (III), which was transformed to the corresponding imidate (IV) by refluxing in triethyl orthoformate. Reaction of imidate (IV) with 2-furoic acid hydrazide (V) provided the pyrazolopyrimidine intermediate (VI), which was thermally cyclized in diphenyl ether to the tricyclic derivative (VII). Hydrolysis of (VII) with HCl induced the pyrimidine ring opening to furnish (VIII). This was finally converted into the title compound by treatment with cyanamide in N-methylpyrrolidone.
| 【1】 Moresco, R.M.; Simonelli, P.; Todde, S.; et al.; Design, radiosynthesis, and biodistribution of a new potent and selective ligand for in vivo imaging of the adenosine A2A receptor system using positron emission tomography. J Med Chem 2000, 43, 23, 4359. |
| 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) | 47277 | 1-[3-(4-methoxyphenyl)propyl]hydrazine; 4-(3-hydrazinopropyl)phenyl methyl ether | C10H16N2O | 详情 | 详情 | |
| (II) | 13017 | Ethoxymethylenemalononitrile; 2-(Ethoxymethylene)malononitrile | 123-06-8 | C6H6N2O | 详情 | 详情 |
| (III) | 47278 | 5-amino-1-[3-(4-methoxyphenyl)propyl]-1H-pyrazole-4-carbonitrile | C14H16N4O | 详情 | 详情 | |
| (IV) | 47279 | ethyl 4-cyano-1-[3-(4-methoxyphenyl)propyl]-1H-pyrazol-5-yliminoformate | C17H20N4O2 | 详情 | 详情 | |
| (V) | 41402 | 2-furohydrazide | 3326-71-4 | C5H6N2O2 | 详情 | 详情 |
| (VI) | 47280 | N-[4-imino-1-[3-(4-methoxyphenyl)propyl]-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl]-2-furamide | C20H20N6O3 | 详情 | 详情 | |
| (VII) | 47281 | 2-(2-furyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine; 4-[3-[2-(2-furyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl]propyl]phenyl methyl ether | C20H18N6O2 | 详情 | 详情 | |
| (VIII) | 47282 | 4-[3-(2-furyl)-1H-1,2,4-triazol-5-yl]-1-[3-(4-methoxyphenyl)propyl]-1H-pyrazol-5-amine; 4-[3-(2-furyl)-1H-1,2,4-triazol-5-yl]-1-[3-(4-methoxyphenyl)propyl]-1H-pyrazol-5-ylamine | C19H20N6O2 | 详情 | 详情 |