1-(2,4-dichlorophenyl)-4-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carbonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】64388

【品名】1-(2,4-dichlorophenyl)-4-methyl-5-[4-(methyloxy)phenyl]-1H-pyrazole-3-carbonyl chloride

【CA登记号】

【分子式】C₁₈H₁₃Cl₃N₂O₂

【分子量】395.6716

【元素组成】C 54.64% H 3.31% Cl 26.88% N 7.08% O 8.09%

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：(VII)

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.

参考文献中间体

合成目标

【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

Extended Information