|
【结 构 式】 
|
【分子编号】17772 【品名】4'-(Imidazol-1-yl)acetophenone; 1-[4-(1H-imidazol-1-yl)phenyl]-1-ethanone 【CA登记号】10041-06-2 |
【 分 子 式 】C11H10N2O 【 分 子 量 】186.21328 【元素组成】C 70.95% H 5.41% N 15.04% O 8.59% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 4-(1H-imidazol-1-yl)acetophenone (I) with dimethyl carbonate (III) by means of NaH in THF gives methyl 4-(1H-imidazol-1-yl)-beta-oxobenzenepropanoate (III), which by condensation with ethyl bromoacetate (IV) by means of NaH in THF is converted into ethyl 4-(1H-imidazol-1-yl-beta-(methoxycarbonyl)-gamma-oxobenzenebutanoate (V). Hydrolytic decarboxylation of (VI) in refluxing 6N HCl yields 4-(1H-imidazol-1-yl)-gamma-oxobenzenebutanoic acid (VI), which is finally cyclized with hydrazine in refluxing ethanol.
| 【1】 Sircar, I.; Bristol, J.A.; Substituted 4,5-dihydro-6-(substituted)-phenyl-3(2H)-pyridazinones and 6-(substituted)phenyl-3(2H)-pyridazinones. CA 1190548; DD 208615; EP 0075436 . |
| 【2】 Serradell, M.N.; Castaner, J.; CI-914. Drugs Fut 1984, 9, 4, 256. |
| 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) | 17772 | 4'-(Imidazol-1-yl)acetophenone; 1-[4-(1H-imidazol-1-yl)phenyl]-1-ethanone | 10041-06-2 | C11H10N2O | 详情 | 详情 |
| (II) | 34197 | dimethyl carbonate | 616-38-6 | C3H6O3 | 详情 | 详情 |
| (III) | 34198 | methyl 3-[4-(1H-imidazol-1-yl)phenyl]-3-oxopropanoate | C13H12N2O3 | 详情 | 详情 | |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 34199 | 4-ethyl 1-methyl 2-[4-(1H-imidazol-1-yl)benzoyl]succinate | C17H18N2O5 | 详情 | 详情 | |
| (VI) | 34200 | 4-[4-(1H-imidazol-1-yl)phenyl]-4-oxobutyric acid | C13H12N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)The compound is prepared by aldol condensation between 4-dimethylaminobenzaldehyde (I) and imidazolyl acetophenone (II) in the presence of NaOH in methanol.
| 【1】 Cohen, F.E.; McKerrow, J.H.; Kenyon, G.L.; Li, Z.; Chen, X.; Gong, B.; Li, R. (University of California, Oakland); Inhibitors of metazoan parasite proteases. WO 9630004 . |