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Fezolamine fumarate, Win-41528-2

非唑拉明 Chemical Name: N,N-Dimethyl-3,4-diphenyl-1H-pyrazole-1-propanamine (E)-2-butenedioate (1:1); 1-[3-(Dimethylamino)propyl]-3,4-diphenylpyrazole fumarate (1:1)
CAS No. 80410-37-3, 80410-36-2 (free base)
项目整合开发状态: Phase II
项目研究机构: Sanofi-Aventis (Originator)
合成路线:1) The condensation of 3,4-diphenylpyrazole (I) with acrylonitrile (II) by means of benzyl-trimethyl-ammonium hydroxide (Triton B) in dioxane gives 1-(2-cyanoethyl)-3,4-diphenylpyrazole (III),which is then reductocondensed with dimethylamine by means of H2 over Pd/C in ethanol.

合成路线:2) The condensation of (I) with methyl acrylate (IV) by means of Triton B as before gives methyl 3-(3,4-diphenylpyrazol-1-yl)propionate (V),which is saponified with KOH in refluxing methanol yielding the corresponding free acid (VI).The reaction of (VI) with SOCl2 in refluxing CHCl3 affords the acyl chloride (VII),which is treated with dimethylamine in THF to give N,N-dimethyl-3-(3,4-diphenylpyrazol-1-yl)propionamide (VIII).Finally,this compound is reduced with LiAlH4 in refluxing THF.
📌 参考资料/链接:
参考文献标题:1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles
文献作者:Bailey,D.M.(Sanofi-Synthabo)
参考来源:US 4182895

📄 详细内容


合成路线:1) The condensation of 3,4-diphenylpyrazole (I) with acrylonitrile (II) by means of benzyl-trimethyl-ammonium hydroxide (Triton B) in dioxane gives 1-(2-cyanoethyl)-3,4-diphenylpyrazole (III),which is then reductocondensed with dimethylamine by means of H2 over Pd/C in ethanol.

合成路线:2) The condensation of (I) with methyl acrylate (IV) by means of Triton B as before gives methyl 3-(3,4-diphenylpyrazol-1-yl)propionate (V),which is saponified with KOH in refluxing methanol yielding the corresponding free acid (VI).The reaction of (VI) with SOCl2 in refluxing CHCl3 affords the acyl chloride (VII),which is treated with dimethylamine in THF to give N,N-dimethyl-3-(3,4-diphenylpyrazol-1-yl)propionamide (VIII).Finally,this compound is reduced with LiAlH4 in refluxing THF.

参考文献标题:Fezolamine fumarate
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1988,13(10),913


合成路线:1) The condensation of 3,4-diphenylpyrazole (I) with acrylonitrile (II) by means of benzyl-trimethyl-ammonium hydroxide (Triton B) in dioxane gives 1-(2-cyanoethyl)-3,4-diphenylpyrazole (III),which is then reductocondensed with dimethylamine by means of H2 over Pd/C in ethanol.
参考文献标题:3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants
文献作者:Bailey,D.M.; Hansen,P.E.; Hlavac,A.G.; Baizman,E.R.; Pearl,J.; DeFelice,A.F.; Feigenson,M.E.
参考来源:J Med Chem 1985,28256


产品链接: CAS No. 80410-37-3››

产品链接: CAS No.80410-36-2››