CI-930
6-[4-(1H-咪唑-1-基)苯基]-5-甲基-4,5-二氢-3(2H)-哒嗪酮Chemical Name: 4,5-Dihydro-6-[4-(1-imidazolyl)phenyl]-5-methyl-3(2H)-pyridazinone
CAS No. 86798-59-6, 90791-23-4 (diHCl)
项目整合开发状态: Phase I
项目研究机构: Pfizer (Originator)
合成路线:The reaction of 4-(1H-imidazol-1-yl)benzaldehyde (I) with morpholine (A) and KCN in dioxane water by means of p-toluenesulfonic acid gives [4-(1H-imidazol-1-yl)phenyl](4morpholinyl)acetonitrile (II),which is condensed with crotononitrile (III) by means of KOH in methanol yielding 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutyronitrile (IV).The hydrolysis of (IV) with hot aqueous HCl affords 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutanoic acid (V),which is finally cyclized with hydrazine in refluxing ethanol.
📌 参考资料/链接：
参考文献标题:Substituted 4,5-dihydro-6-(substituted)phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones
文献作者:Sircar,I.; Bristol,J.A.(Pfizer Inc.)
参考来源:CA 1190548; DD 208615; EP 0075436
📄 详细内容
合成路线:The reaction of 4-(1H-imidazol-1-yl)benzaldehyde (I) with morpholine (A) and KCN in dioxane water by means of p-toluenesulfonic acid gives [4-(1H-imidazol-1-yl)phenyl](4morpholinyl)acetonitrile (II),which is condensed with crotononitrile (III) by means of KOH in methanol yielding 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutyronitrile (IV).The hydrolysis of (IV) with hot aqueous HCl affords 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutanoic acid (V),which is finally cyclized with hydrazine in refluxing ethanol.
参考文献标题:CI-930
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1985,10(6),449
合成路线:The reaction of 4-(1H-imidazol-1-yl)benzaldehyde (I) with morpholine (A) and KCN in dioxane water by means of p-toluenesulfonic acid gives [4-(1H-imidazol-1-yl)phenyl](4morpholinyl)acetonitrile (II),which is condensed with crotononitrile (III) by means of KOH in methanol yielding 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutyronitrile (IV).The hydrolysis of (IV) with hot aqueous HCl affords 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutanoic acid (V),which is finally cyclized with hydrazine in refluxing ethanol.
参考文献标题:Cardiotonic agents.1.4,5-Dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)pyridazinones: Novel positive inotropic agents for the treatment of congestive heart failure
文献作者:Bristol,J.A.; Sircar,I.; Moos,W.H.; Evans,D.B.; Weishaar,R.E.
参考来源:J Med Chem 1984,27(9),1099
产品链接: CAS No. 86798-59-6›› 产品链接: CAS No.90791-23-4››