Tepoxalin, RWJ-20485, Orf-20485
替泊沙林Chemical Name: 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]-N-hydroxy-N-methylpropanamide; 5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-N-methylpyrazole-3-propionohydroxamic acid; 5-(4-Chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide
CAS No. 103475-41-8
项目整合开发状态: Phase II
项目研究机构: Ortho-McNeil (Originator)
合成路线:A new synthesis of tepoxalin has been described:The condensation of 4-chloroacetophenone (I) with succinic anhydride (II) by means of lithium bis(trimethylsilyl)amide in THF at -20 C gives 6-(4-chlorophenyl)-4,6-dioxohexanoic acid (III),which is cyclized with 4-methoxyphenylhydrazine (IV) by means of triethylamine in methanol at room temperature to afford 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic acid (V); finally this compound is condensed with methylhydroxylamine (VI) by means of oxalyl chloride and triethylamine at room temperature.
📌 参考资料/链接：
参考文献标题:The regioselective synthesis of tepoxalin,3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide and related 1,5-diarylpyrazole antiinflammatory agents
文献作者:Forerokelly,Y.; Murray,W.; Wachter,M.; Barton,D.
参考来源:Synthesis 1991,1(1),18
📄 详细内容
合成路线:A new method for the synthesis of tepoxalin has been reported:The cyclization of 6-(4-chlorophenyl)-4,6-dioxohexanoic acid (I) with refluxing acetic anhydride gives 5-[2-(4-chlorophenyl)-2-oxoethylidene]tetrahydrofuran-2-one (II),which is treated with methylhydroxylamine to afford the corresponding N-hydroxy-N-methylamide (III).Finally,this compound is cyclized with 4-methoxyphenylhydroazine (IV) by means of Na2CO3 in refluxing ethanol.
参考文献标题:A facile synthesis of tepoxalin,5-(4-chlorophenyl)-N-hydroxy-1-(4-methoxyphenyl)-N-methyl-1H-pyrazole-3-propanamide
文献作者:Murray,W.V.; Hadden,S.K.
参考来源:J Org Chem 1992,57(24),6662
产品链接: CAS No. 103475-41-8››