Etazolate, SQ-20009(hydrochloride)
乙酰腙吡唑啶 盐酸依他唑酯 Chemical Name: 1-Ethyl-4-(isopropylidenehydrazino)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
CAS No. 51022-77-6, 35838-58-5 (HCl)
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The condensation of 1-ethyl-5-aminopyrazole (I) with diethyl ethoxymethylenemalonate (II) by heating at 120 C gives diethyl [((1-ethyl-5-pyrazolyl)amino)methylene]malonate (III),which by heating at 235-5 C in diphenyl ether is converted into ethyl 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (IV).The reaction of (IV) with ethyl iodide (A) and K2CO3 in DMF affords ethyl 1-ethyl-4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (V),which is condensed with hydrazine in refluxing ethanol with ZnCl2 yielding ethyl 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (VI).Finally,(VI) is condensed with refluxing acetone (B).
📌 参考资料/链接：
参考文献标题:Hydrazines and hydrazones of pyrazolopyridine carboxylic acids and esters
文献作者:Hoehn,H.; Chasin,M.(Bristol-Myers Squibb Co.)
参考来源:DE 2028869; GB 1317797; NL 165461C; NL 7008768
📄 详细内容
合成路线:The condensation of 1-ethyl-5-aminopyrazole (I) with diethyl ethoxymethylenemalonate (II) by heating at 120 C gives diethyl [((1-ethyl-5-pyrazolyl)amino)methylene]malonate (III),which by heating at 235-5 C in diphenyl ether is converted into ethyl 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (IV).The reaction of (IV) with ethyl iodide (A) and K2CO3 in DMF affords ethyl 1-ethyl-4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (V),which is condensed with hydrazine in refluxing ethanol with ZnCl2 yielding ethyl 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (VI).Finally,(VI) is condensed with refluxing acetone (B).
参考文献标题:Etazolate
文献作者:Chatterjee,S.S.
参考来源:Drugs Fut 1977,2(4),243
产品链接: CAS No. 51022-77-6›› 产品链接: CAS No.35838-58-5››