新产品编号:891175
Chemical Name: N-(1-Azabicyclo[2.2.2]oct-3-yl)-2-[4-(2-ethoxyphenyl)piperazin-1-ylmethyl]-1H-benzimidazole-4-carboxamide
CAS No. 363610-31-5
项目整合开发状态: Preclinical
项目研究机构: Universidad Complutense de Madrid (Originator)
合成路线:2,3-Diaminobenzoic acid (I) is condensed with glycolic acid (II) under acidic conditions to produce 2-(hydroxymethyl)benzimidazole-4-carboxylic acid (III).Chlorination of (III) with SOCl2,followed by acidic hydrolysis of the acid chloride group leads to the chloromethyl benzimidazole (IV).Condensation of chloride (IV) with 1-(2-ethoxyphenyl)piperazine (V) furnishes the disubstituted piperazine (VI).Acid (VI) is finally coupled to 3-aminoquinuclidine (VII) via activation with CDI to produce the title amide.(1-3)
📌 参考资料/链接：
参考文献标题:New mixed derivs.of benzimidazole-arylpiperazine with affinity for the serotoninergic receptors 5-HT1A and 5-HT3
文献作者:Morcillo Ortega,M.J.; Benhamu Salama,B.; L髉ez Rodr韌uez,M.L.; Ramos Atance,J.A.; Tejada Cazorla,I.D.(Universidad Complutense de Madrid)
参考来源:ES 2154605
📄 详细内容
合成路线:2-(Trichloromethyl)quinazolin-4-one (I) is chlorinated with oxalyl chloride in the presence of DMF producing 4-chloro-2-(trichloromethyl)quinazoline (II).Subsequent coupling of chloroquinazoline (II) with 4-(4'-aminophenylazo)phenylarsonic acid (III) in refluxing isopropanol furnishes the title compound.(1,2)
合成路线:The title compound is prepared by condensation between 4-chloro-2-(methylthio)pyrimidine (I) and p-arsanilic acid (II) in refluxing alcohol.
合成路线:2,3-Diaminobenzoic acid (I) is condensed with glycolic acid (II) under acidic conditions to produce 2-(hydroxymethyl)benzimidazole-4-carboxylic acid (III).Chlorination of (III) with SOCl2,followed by acidic hydrolysis of the acid chloride group leads to the chloromethyl benzimidazole (IV).Condensation of chloride (IV) with 1-(2-ethoxyphenyl)piperazine (V) furnishes the disubstituted piperazine (VI).Acid (VI) is finally coupled to 3-aminoquinuclidine (VII) via activation with CDI to produce the title amide.(1-3)
参考文献标题:Organic phenyl arsonic acid compounds with potent antileukemic activity
文献作者:Liu,X.-P.; Narla,R.K.; Uckun,F.M.
参考来源:Bioorg Med Chem Lett 2003,13(3),581
合成路线:2,3-Diaminobenzoic acid (I) is condensed with glycolic acid (II) under acidic conditions to produce 2-(hydroxymethyl)benzimidazole-4-carboxylic acid (III).Chlorination of (III) with SOCl2,followed by acidic hydrolysis of the acid chloride group leads to the chloromethyl benzimidazole (IV).Condensation of chloride (IV) with 1-(2-ethoxyphenyl)piperazine (V) furnishes the disubstituted piperazine (VI).Acid (VI) is finally coupled to 3-aminoquinuclidine (VII) via activation with CDI to produce the title amide.(1-3)
参考文献标题:Design and synthesis of new benzimidazole-arylpiperazine derivatives acting as mixed 5-HT1A/5-HT3 ligands
文献作者:L髉ez-Rodr韌uez,M.L.; Benham? B.; Morcillo,M.J.; Tejada,I.; Avila,D.; Marco,I.; Schiapparelli,L.; Frechilla,D.; del Rio,J.
参考来源:Bioorg Med Chem Lett 2003,13(19),3177