FR-167356
2,6-二氯-N-[3-(1-羟基-1-甲基乙基)-2-甲基-1-苯并呋喃-7-基]苯酰胺Chemical Name: 2,6-Dichloro-N-[3-(1-hydroxy-1-methylethyl)-2-methyl-1-benzofuran-7-yl]benzamide
CAS No. 174185-16-1
项目整合开发状态: Preclinical
项目研究机构: Fujisawa (Originator)
合成路线:The condensation of 2-fluoronitrobenzene (I) with acetone oxime (II) by means of NaH in DMF gives acetone O-(2-nitrophenyl)oxime (III),which is cyclized to 2-methyl-7-nitrobenzofuran (IV) by means of H2SO4.The Friedel Crafts acylation of (IV) with acetyl chloride and AlCl3 in dichloromethane affords 3-acetyl-2-methyl-7-nitrobenzofuran (V),which is reduced to the corresponding amino derivative (VI) with Fe and HCl in ethanol.The condensation of (VI) with 2,6-dichlorobenzoyl chloride (VII) by means of triethylamine in dichloroethane yields N-(3-acetyl-2-methylbenzofuran-7-yl)-2,6-dichlorobenzamide (VIII),which is finally submitted to a Grignard reaction with methylmagnesium bromide in THF.
📌 参考资料/链接：
参考文献标题:Benzofuran derivs.useful as inhibitors of bone resorption
文献作者:Kawai,Y.; Yamazaki,H.; Kayakiri,N.; Yoshihara,K.; Yatabe,T.; Oku,T.(Fujisawa Pharmaceutical Co.,Ltd.)
参考来源:EP 0757682; JP 1997512795; US 5858995; WO 9529907
📄 详细内容
合成路线:The condensation of 2-fluoronitrobenzene (I) with acetone oxime (II) by means of NaH in DMF gives acetone O-(2-nitrophenyl)oxime (III),which is cyclized to 2-methyl-7-nitrobenzofuran (IV) by means of H2SO4.The Friedel Crafts acylation of (IV) with acetyl chloride and AlCl3 in dichloromethane affords 3-acetyl-2-methyl-7-nitrobenzofuran (V),which is reduced to the corresponding amino derivative (VI) with Fe and HCl in ethanol.The condensation of (VI) with 2,6-dichlorobenzoyl chloride (VII) by means of triethylamine in dichloroethane yields N-(3-acetyl-2-methylbenzofuran-7-yl)-2,6-dichlorobenzamide (VIII),which is finally submitted to a Grignard reaction with methylmagnesium bromide in THF.
参考文献标题:Synthesis and pharmacological activities of novel benzofuran derivatives as vacuolar type H+-ATPase inhibitors
文献作者:Yamazaki,H.; et al.
参考来源:Symp Med Chem 1998,Abst 2-P-32
产品链接: CAS No. 174185-16-1››