Midaglizole hydrochloride, DG-5128
咪格列唑Chemical Name: 2-[2-Phenyl-2-(2-pyridyl)ethyl]imidazoline dihydrochloride sesquihydrate; 2-[2-(4,5-Dihydro-1H-imidazol-2-yl)-1-phenylethyl]pyridine dihydrochloride sesquihydrate
CAS No. 72157-07-4 (anhydrous, monoHCl), 66529-17-7 (free base, anhydrous)
项目整合开发状态: Phase II
项目研究机构: Daiichi Pharmaceutical (Originator)
合成路线:This compound can be obtained by two related ways:1) The Wittig condensation of 2-benzoylpyridine (I) with diethyl cyanomethylphosphonate (II) by means of sodium ethoxide in hot ethanol gives 3-phenyl-3-(2-pyridyl)acrylonitrite (III),which is reduced with NaBH4 in refluxing ethanol to yield 3-phenyl-3-(2-pyridyl)propionitrite (IV).Finally,this compound is cyclized with ethylenediamine (V) at reflux temperature.2) The cyctization of 3-phenyl-3-(2-pyridyl)acrylonitrite (III) with ethylenediamine (V) at reflux temperature gives 2-[2-phenyl-2-(2-pyridyl)viny]-2-imidazoline (VI),which is then reduced with H2 over Pd/C in ethanol.
📌 参考资料/链接：
参考文献标题:DG-5128
文献作者:Castar,J.; Hillier,K.; Blancafort,P.; Serradell,M.N.
参考来源:Drugs Fut 1982,7(8),550
📄 详细内容
合成路线:This compound can be obtained by two related ways:1) The Wittig condensation of 2-benzoylpyridine (I) with diethyl cyanomethylphosphonate (II) by means of sodium ethoxide in hot ethanol gives 3-phenyl-3-(2-pyridyl)acrylonitrite (III),which is reduced with NaBH4 in refluxing ethanol to yield 3-phenyl-3-(2-pyridyl)propionitrite (IV).Finally,this compound is cyclized with ethylenediamine (V) at reflux temperature.2) The cyctization of 3-phenyl-3-(2-pyridyl)acrylonitrite (III) with ethylenediamine (V) at reflux temperature gives 2-[2-phenyl-2-(2-pyridyl)viny]-2-imidazoline (VI),which is then reduced with H2 over Pd/C in ethanol.
参考文献标题:Cyclic guanidines.X.Synthesis of 2-(2,2-disubstituted ethenyl- and ethyl)-2-imidazolines as potent hypoglycemics
文献作者:Ishikawa,F.
参考来源:Chem Pharm Bull 1980,28(5),1394-1402
产品链接: CAS No.66529-17-7››