4-hydroxy-5,6-bis(4-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone -Drug Synthesis Database

【结构式】

【分子编号】52115

【品名】4-hydroxy-5,6-bis(4-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

【CA登记号】

【分子式】C₁₈H₁₈N₂O₄

【分子量】326.352

【元素组成】C 66.25% H 5.56% N 8.58% O 19.61%

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：(V)

Glyoxylic acid (II), generated in situ by oxidative cleavage of tartaric acid (I) with sodium periodate, was condensed with deoxyanisoin (III) to provide the aldol adduct (IV). Cyclization of hydroxyacid (IV) with hydrazine gave rise to the hydroxy dihydropyridazinone (V), which was further dehydrated to (VI) upon treatment with p-toluenesulfonic acid in refluxing benzene. Finally, alkylation of pyridazinone (VI) with 4-chlorocinnamyl chloride (VII) in the presence of potassium carbonate furnished the title compound.

参考文献中间体

合成目标

【1】 Matsuda, T.; et al.; Synthesis and bioactivities of novel 5,6-bis(4-methoxyphenyl)-2H-pyridazin-3-one derivatives: Inhibitors of interleukin-1 beta (IL-1beta) production. Bioorg Med Chem Lett 2001, 11, 17, 2373.
【2】 Yoshizaki, H.; Habata, Y.; Kumai, N.; Kotaki, K.; Ohkuchi, M.; Ohgiya, T.; Yamazaki, Y.; Matsuda, T.; Kitamura, T.; Koshi, T.; Kyotani, Y.; Shigyo, H. (Kowa Co., Ltd.); Novel pyridazine derivs. and drugs containing the same as the active ingredient. EP 1043317; JP 1999152274; JP 2000198776; US 6348468; WO 9925697 .

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)	52118	Uvic Acid; Tartaric acid; Dihydroxysuccinic acid; 2,3-Dihydroxybutanedioic acid	133-37-9	C₄H₆O₆	详情	详情
(II)	15618	2-Oxoacetic acid; Glyoxylic Acid	298-12-4	C₂H₂O₃	详情	详情
(III)	22991	1,2-bis(4-methoxyphenyl)-1-ethanone	120-44-5	C₁₆H₁₆O₃	详情	详情
(IV)	52114	2-hydroxy-3,4-bis(4-methoxyphenyl)-4-oxobutyric acid		C₁₈H₁₈O₆	详情	详情
(V)	52115	4-hydroxy-5,6-bis(4-methoxyphenyl)-4,5-dihydro-3(2H)-pyridazinone		C₁₈H₁₈N₂O₄	详情	详情
(VI)	52116	5,6-bis(4-methoxyphenyl)-3(2H)-pyridazinone		C₁₈H₁₆N₂O₃	详情	详情
(VII)	52117	1-chloro-4-[(E)-3-chloro-1-propenyl]benzene		C₉H₈Cl₂	详情	详情

Extended Information