ABT-866
Chemical Name: N-[3-(1H-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide
CAS No. 258526-74-8, 258526-75-9 (maleate salt (1:1))
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:Reaction of methanesulfonamide derivative (I) with 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (I) and EtMgBr in CH2Cl2 followed by heating with diluted HCl affords compound (III),which is debenzylated and reduced by hydrogenation over Pd/C in MeOH.
合成路线:Treatment of 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (I) with EtMgBr and 3-nitrobenzaldehyde (II) in CH2Cl2 yields derivative (III),whose nitro moiety is reduced by hydrogenation over Pd/C in EtOAc to afford aminophenyl derivative (IV).Treatment of (IV) with Et3SiH in TFA provides aminobenzyl derivative (V),which is finally converted into the desired compound by treatment with pyridine and ethanesulfonyl chloride (VI) followed by reflux in HCl.
📌 参考资料/链接：
参考文献标题:Imidazoles and related cpds.as alpha1A agonists
文献作者:Altenbach,R.J.; Holladay,M.W.; Carroll,W.A.; Meyer,M.D.; Kerwin,J.F.Jr.; Kolasa,T.; Rohde,J.; Khilevich,A.(Abbott Laboratories Inc.)
参考来源:WO 0007997
📄 详细内容
合成路线:The condensation of 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (I) with 3-nitrobenzaldehyde (II) by means of Et-MgBr in dichloromethane gives the carbinol (III),which is reduced with triethylsilane in refluxing TFA to yield 4-(3-nitrobenzyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (IV).The reduction of the nitro group of (IV) by means of H2 over Pd/C in ethyl acetate affords the amino derivative (V),which is acylated with ethanesulfonyl chloride (VI) and pyridine in dichloromethane to give the ethanesulfonamide (VII).Finally,this compound is treated with aqueous refluxing HCl to yield the target compound.
参考文献标题:N-[3-(1H-Imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866,1),(1) a novel alpha1-adrenoceptor ligand with an enhanced in vitro and in vivo profile relative to phenylpropanolamine and midodrine
文献作者:Altenbach,R.J.; Khilevich,A.; Meyer,M.D.; Buckner,S.A.; Milicic,I.; Daza,A.V.; Brune,M.E.; O'Neill,A.B.; Gauvin,D.M.; Cain,J.C.; Nakane,M.; Holladay,M.W.; Williams,M.; Brioni,J.D.; Sullivan,J.P.
参考来源:J Med Chem 2002,45(20),4395
产品链接: CAS No. 258526-74-8››