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【结 构 式】

【分子编号】29652

【品名】4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutyric acid

【CA登记号】

【 分 子 式 】C14H14N2O3

【 分 子 量 】258.27684

【元素组成】C 65.11% H 5.46% N 10.85% O 18.58%

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:(VI)

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.

1 Guengerich, F.P.; 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. J Med Chem 1984, 27, 9, 1099.
2 Sircar, I.; Bristol, J.A. (Pfizer Inc.); Substituted 4,5-dihydro-6-(substituted)phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones. CA 1190548; DD 208615; EP 0075436 .
3 Castaner, J.; Serradell, M.N.; CI-930. Drugs Fut 1985, 10, 6, 449.
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) 29649 4-(1H-imidazol-1-yl)benzaldehyde 10040-98-9 C10H8N2O 详情 详情
(II) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(III) 29650 2-[4-(1H-imidazol-1-yl)phenyl]-2-(4-morpholinyl)acetonitrile C15H16N4O 详情 详情
(IV) 24144 (E)-2-butenenitrile 4786-20-3 C4H5N 详情 详情
(V) 29651 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutanenitrile C14H13N3O 详情 详情
(VI) 29652 4-[4-(1H-imidazol-1-yl)phenyl]-3-methyl-4-oxobutyric acid C14H14N2O3 详情 详情
Extended Information