|
【结 构 式】 
|
【分子编号】47278 【品名】5-amino-1-[3-(4-methoxyphenyl)propyl]-1H-pyrazole-4-carbonitrile 【CA登记号】 |
【 分 子 式 】C14H16N4O 【 分 子 量 】256.3074 【元素组成】C 65.61% H 6.29% N 21.86% O 6.24% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |