【结 构 式】 |
【分子编号】41401 【品名】ethyl 4-cyano-2-propyl-1H-2lambda(5)-pyrazol-3-yliminoformate 【CA登记号】 |
【 分 子 式 】C10H16N4O 【 分 子 量 】208.2634 【元素组成】C 57.67% H 7.74% N 26.9% O 7.68% |
合成路线1
该中间体在本合成路线中的序号:(V)The alkylation of 5-amino-4-cyanopyrazole (I) with n-propyl iodide led to a 4:1 inseparable mixture of regioisomers (II) and (III). This mixture was transformed into the respective imidates (IV) and (V) through refluxing in triethyl orhoformate. Subsequent addition of 2-furoic hydrazide (VI) to the nitrile group of (IV)+(V), followed by thermal cyclization in diphenyl ether at 260 C furnished the corresponding pyrazolotriazolopyrimidines. The desired regioisomer (VII) was then isolated by flash chromatography. Hydrolysis of (VII) with aqueous HCl afforded the aminopyrazole (VIII), which was further converted to the tricyclic compound (IX) by reaction with cyanamide and p-toluenesulfonic acid. Finally, coupling of (IX) with p-methoxyphenyl isocyanate (X) provided the title urea.
【1】 Cacciari, B.; Klotz, K.-N.; Borea, P.A.; Leung, E.; Merighi, S.; Varani, K.; Gessi, S.; Spalluto, G.; Baraldi, P.G.; Ropmagnoli, R.; Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists. J Med Chem 1999, 42, 22, 4473. |
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) | 11987 | 3-Amino-4-pyrazolecarbonitrile; 3-Amino-1H-pyrazole-4-carbonitrile; 3-Amino-4-cyanopyrazole | 16617-46-2 | C4H4N4 | 详情 | 详情 |
(II) | 41398 | 3-amino-1-propyl-1H-pyrazole-4-carbonitrile | C7H10N4 | 详情 | 详情 | |
(III) | 41399 | 3-amino-2-propyl-1H-2lambda(5)-pyrazole-4-carbonitrile | C7H12N4 | 详情 | 详情 | |
(IV) | 41400 | ethyl 4-cyano-1-propyl-1H-pyrazol-3-yliminoformate | C10H14N4O | 详情 | 详情 | |
(V) | 41401 | ethyl 4-cyano-2-propyl-1H-2lambda(5)-pyrazol-3-yliminoformate | C10H16N4O | 详情 | 详情 | |
(VI) | 41402 | 2-furohydrazide | 3326-71-4 | C5H6N2O2 | 详情 | 详情 |
(VII) | 41403 | 2-(2-furyl)-8-propyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine | C13H12N6O | 详情 | 详情 | |
(VIII) | 41404 | 4-[3-(2-furyl)-1H-1,2,4-triazol-5-yl]-1-propyl-1H-pyrazol-3-amine; 4-[3-(2-furyl)-1H-1,2,4-triazol-5-yl]-1-propyl-1H-pyrazol-3-ylamine | C12H14N6O | 详情 | 详情 | |
(IX) | 41405 | 2-(2-furyl)-8-propyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine; 2-(2-furyl)-8-propyl-8H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine | C13H13N7O | 详情 | 详情 | |
(X) | 41406 | 4-methoxyphenyl isocyanate; 1-isocyanato-4-methoxybenzene | 5416-93-3 | C8H7NO2 | 详情 | 详情 |