新产品编号:593759
Chemical Name: N-(3-tert-Butyl-1-methyl-1H-pyrazol-5-yl)-N'-[4-(pyridin-4-ylmethyl)phenyl]urea
CAS No. 229002-15-7
项目整合开发状态: Preclinical
项目研究机构: Bayer (Originator)
合成路线:In a related procedure,amino isoxazole (IV) was converted to the corresponding isocyanate (VI) by treatment with phosgene and pyridine.Isocyanate (VI) was then condensed with amine (III),producing the target urea.
合成路线:4-(4-Pyridinylmethyl)aniline (II) was prepared by catalytic hydrogenation of the corresponding nitro derivative (I) over Pd/C.Condensation of aniline (II) with N,N?carbonyldiimidazole produced the imidazolide (III).This was then condensed with 5-amino-3-tert-butyl-1-methylpyrazole (IV) to furnish the target urea.
📌 参考资料/链接：
参考文献标题:Inhibition of p38 kinase activity using substd.heterocyclic ureas
文献作者:Riedl,B.; Lee,W.; Lowinger,T.B.; Redman,A.; Smith,R.A.; Khire,U.; Dumas,J.; Scott,W.J.; Wood,J.E.; Johnson,J.; Paulsen,H.; Hatoum-Mokdad,H.(Bayer Corp.)
参考来源:WO 9932111
📄 详细内容
合成路线:Condensation of 4-aminophenol (I) with 4-chloropyridine (II) in the presence of potassium tert-butoxide afforded the intermediate diaryl ether (III).
合成路线:Treatment of 3-amino-5-tert-butylisoxazole (IV) with carbonyldiimidazole produced the imidazolide (V),which was then condensed with amine (III) to furnish the title urea.
合成路线:4-(4-Pyridinylmethyl)aniline (II) was prepared by catalytic hydrogenation of the corresponding nitro derivative (I) over Pd/C.Condensation of aniline (II) with N,N?carbonyldiimidazole produced the imidazolide (III).This was then condensed with 5-amino-3-tert-butyl-1-methylpyrazole (IV) to furnish the target urea.
参考文献标题:Inhibition of raf kinase using substd.heterocyclic ureas
文献作者:Redman,A.; Paulsen,H.; Lowinger,T.B.; Dumas,J.; Johnson,J.; Wood,J.E.; Scott,W.J.; Khire,U.; Hatoum-Mokdad,H.; Lee,W.; Smith,R.A.; Riedl,B.(Bayer Corp.)
参考来源:EP 1047418; WO 9932106
合成路线:The cyclization of 2-pivaloylacetonitrile (I) with methylhydrazine (II) in refluxing ethanol gives 5-amino-3-tert-butyl-1-methylpyrazole (III),which is finally condensed with 4-(4-pyridylmethyl)aniline (IV) and carbonyldimidazole (CDI) in dichloromethane to afford the target urea.The aniline (IV) has been obtained by reduction of the corresponding nitro derivative (V) with H2 over Pd/C in ethanol.
参考文献标题:Synthesis and pharmacological characterization of a potent,orally active p38 kinase inhibitor
文献作者:Dumas,J.; Hatoum-Mokdad,H.; Sibley,R.N.; Smith,R.A.; Scott,W.J.; Khire,U.; Lee,W.; Wood,J.; Wolanin,D.; Cooley,J.; Bankston,D.; Redman,A.M.; Schoenleber,R.; Caringal,Y.; Gunn,D.; Romero,R.; Osterhout,M.; Paulsen,H.; Housley,T.J.; et al.
参考来源:Bioorg Med Chem Lett 2002,12(12),1559