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【结 构 式】

【分子编号】41405

【品名】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

【CA登记号】

【 分 子 式 】C13H13N7O

【 分 子 量 】283.2928

【元素组成】C 55.12% H 4.63% N 34.61% O 5.65%

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:(IX)

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
Extended Information