SM-18163
4-[1-(1,3-苯并二噁唑-5-基羰基)哌啶-4-基]-6-(4-甲氧苄基)嘧啶-2-胺Chemical Name: 4-[1-(1,3-Benzodioxol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine; 1-[4-[2-Amino-6-(4-methoxybenzyl)pyrimidin-4-yl]piperidin-1-yl]-1-(1,3-benzodioxol-5-yl)methanone
CAS No. 198553-25-2
项目整合开发状态: Preclinical
项目研究机构: Sumitomo Pharmaceuticals (Originator)
合成路线:N-Benzoylisonipecotic acid (I) was chlorinated with SOCl2 to produce the corresponding acid chloride (II).Acylation of the lithium enolate of (4-methoxyphenyl)acetone (III) with acid chloride (II) provided a mixture of diketone regioisomers (IV) and (V); these were separated by column chromatography.The desired diketone (IV) was then cyclized with guanidine (VI) in hot pyridine to afford the pyrimidine (VII).Basic hydrolysis of the benzamide function of (VII) gave the piperidine derivative (VIII).The target amide was finally prepared by acylation of (VIII) with 3,4-methylenedioxybenzoic acid (IX) in the presence of EDC.
📌 参考资料/链接：
参考文献标题:Piperidinylpyramidine derivs.
文献作者:Fujiwara,N.; Ueda,Y.; Murata,S.; Hirota,F.; Kawakami,H.; Fujita,H.(Sumitomo Pharmaceuticals Co.,Ltd.)
参考来源:EP 0892795; JP 2001511764; US 5948786; WO 9738992
📄 详细内容
合成路线:N-Benzoylisonipecotic acid (I) was chlorinated with SOCl2 to produce the corresponding acid chloride (II).Acylation of the lithium enolate of (4-methoxyphenyl)acetone (III) with acid chloride (II) provided a mixture of diketone regioisomers (IV) and (V); these were separated by column chromatography.The desired diketone (IV) was then cyclized with guanidine (VI) in hot pyridine to afford the pyrimidine (VII).Basic hydrolysis of the benzamide function of (VII) gave the piperidine derivative (VIII).The target amide was finally prepared by acylation of (VIII) with 3,4-methylenedioxybenzoic acid (IX) in the presence of EDC.
参考文献标题:Synthesis and bioactivities of novel piperidylpyrimidine derivatives: Inhibitors of tumor necrosis factor-alpha production
文献作者:Fujiwara,N.; Fujita,H.; Iwai,K.; Kurimoto,A.; Murata,S.; Kawakami,H.
参考来源:Bioorg Med Chem Lett 2000,10(12),1317
产品链接: CAS No. 198553-25-2››