PD-188669
Chemical Name: 4-Benzyl-1-[4-(4-imidazolyl)-3-butynyl]piperidine
项目整合开发状态: Preclinical
项目研究机构: CoCensys (Originator), Pfizer (Originator)
合成路线:Coupling of 3-butyn-1-ol (I) with 4-iodo-1-phenylsulfonylimidazole (II) in the presence of CuI and Pd(PPh3)4 afforded the imidazolylbutynol (III),which was activated as the tosylate (IV) with p-toluenesulfonyl chloride in pyridine.Subsequent displacement of the tosylate group of (IV) by 4-benzylpiperidine (V) using NaHCO3 in hot DMF produced the corresponding N-(imidazolylbutynyl)piperidine with simultaneous cleavage of the benzenesulfonyl protecting group.
📌 参考资料/链接：
参考文献标题:Novel series of 4-benzyl-N-(4-imidazole-1-alkynyl)piperidines as potent subtype selective NMDA receptor antagonists
文献作者:Boxer,P.A.; Woodward,R.M.; Meltzer,L.T.; D'Wise,L.; Gregory,T.F.
参考来源:218th ACS Natl Meet (Aug 22 1999,New Orleans) 1999,Abst MEDI 94
📄 详细内容
合成路线:Coupling of 3-butyn-1-ol (I) with 4-iodo-1-phenylsulfonylimidazole (II) in the presence of CuI and Pd(PPh3)4 afforded the imidazolylbutynol (III),which was activated as the tosylate (IV) with p-toluenesulfonyl chloride in pyridine.Subsequent displacement of the tosylate group of (IV) by 4-benzylpiperidine (V) using NaHCO3 in hot DMF produced the corresponding N-(imidazolylbutynyl)piperidine with simultaneous cleavage of the benzenesulfonyl protecting group.
参考文献标题:Discovery of subtype-selective NMDA receptor ligands: 4-benzyl-1-piperidinylalkynylpyrroles,pyrazoles and imidazoles as NR1A/2B antagonists
文献作者:Wright,J.L.; Gregory,T.F.; Boxer,P.A.; Meltzer,L.T.; Serpa,K.A.; Wise,L.D.
参考来源:Bioorg Med Chem Lett 1999,9(19),2815