|
【结 构 式】 
|
【分子编号】64385 【品名】ethyl 2-[2-(2,4-dichlorophenyl)hydrazono]-3-methyl-4-[4-(methyloxy)phenyl]-4-oxobutanoate 【CA登记号】 |
【 分 子 式 】C20H20Cl2N2O4 【 分 子 量 】423.29528 【元素组成】C 56.75% H 4.76% Cl 16.75% N 6.62% O 15.12% |
合成路线1
该中间体在本合成路线中的序号：(IV)Claisen condensation of the lithium enolate of 4-methoxypropiophenone (I) with diethyl oxalate leads to diketo ester (II). Treatment of (II) with 2,4-dichlorophenyl hydrazine (III), followed by cyclization of the resultant hydrazone (IV) in boiling AcOH furnishes the pyrazolecarboxylate (V). Alkaline hydrolysis of ester (V) yields carboxylic acid (VI), which is further activated as the acid chloride (VII) with SOCl2 in refluxing toluene. Finally, coupling of acid chloride (VII) with 1-aminopiperidine (VIII) produces the target hydrazide derivative.
| 【1】 Katoch-Rouse, R.; Pavlova, O.A.; Caulder, T.; Hoffman, A.F.; Mukhin, A.G.; Horti, A.G.; Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: Development of central cannabinoid receptor ligands with lower lipophilicity. J Med Chem 2003, 46, 4, 642. |
| 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) | 64383 | 1-[4-(methyloxy)phenyl]-1-propanone | C10H12O2 | 详情 | 详情 | |
| (II) | 64384 | ethyl 3-methyl-4-[4-(methyloxy)phenyl]-2,4-dioxobutanoate | C14H16O5 | 详情 | 详情 | |
| (III) | 35778 | 1-(2,4-dichlorophenyl)hydrazine | 5446-18-4 | C6H6Cl2N2 | 详情 | 详情 |
| (IV) | 64385 | ethyl 2-[2-(2,4-dichlorophenyl)hydrazono]-3-methyl-4-[4-(methyloxy)phenyl]-4-oxobutanoate | C20H20Cl2N2O4 | 详情 | 详情 | |
| (V) | 64386 | ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carboxylate | C20H18Cl2N2O3 | 详情 | 详情 | |
| (VI) | 64387 | 1-(2,4-dichlorophenyl)-4-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carboxylic acid | C18H14Cl2N2O3 | 详情 | 详情 | |
| (VII) | 64388 | 1-(2,4-dichlorophenyl)-4-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carbonyl chloride | C18H13Cl3N2O2 | 详情 | 详情 | |
| (VIII) | 35781 | 1-piperidinylamine; 1-piperidinamine | 2213-43-6 | C5H12N2 | 详情 | 详情 |