L-775606
Chemical Name: 1-[2-(3-Fluorophenyl)ethyl]-4-[3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]piperazine
CAS No. 188400-51-3
项目整合开发状态: Preclinical
项目研究机构: Merck & Co. (Originator)
合成路线:Alkylation of N-Boc-piperazine (I) with bromoacetal (II) provided piperazine acetal (III).This was submitted to Fisher cyclization with 4-(1,2,4-triazol-4-yl)phenyl hydrazine (IV) in aqueous H2SO4 to afford the deprotected indole (V).Wittig reaction of 3-fluorobenzaldehyde (VII) with phosphorane prepared from (methoxymethyl)phosphonium salt (VI) and PhLi furnished the methoxyvinyl compound (VIII) as an E:Z mixture.Subsequent acid hydrolysis of the enol ether function of (VIII) yielded aldehyde (IX).The target compound was then obtained by reductive alkylation of piperazine (V) with aldehyde (IX) in the presence of NaBH3CN.
📌 参考资料/链接：
参考文献标题:3-(Piperazinylpropyl)indoles: Selective,orally bioavailable h5-HT1D receptor agonists as potential antimigraine agents
文献作者:Chambers,M.S.; Street,L.J.; Goodacre,S.; Hobbs,S.C.; Hunt,P.; Jelley,R.A.; Matassa,V.G.; Reeve,A.J.; Sternfeld,F.; Beer,M.S.; Stanton,J.A.; Rathbone,D.; Watt,A.P.; MacLeod,A.M.
参考来源:J Med Chem 1999,42(4),691