SNAP-5399
Chemical Name: 2-(2-Aminoethoxymethyl)-N3-[3-(4,4-diphenylpiperidin-1-yl)propyl]-6-ethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxamide
CAS No. 166807-77-8, 166810-98-6 ((-)-enantiomer), 166810-99-7 ((+)-enantiomer)
项目整合开发状态: Preclinical
项目研究机构: Synaptic (Originator)
合成路线:Hantzsch condensation of the (azidoethoxy)ketoester (I) with the benzylidene ketoester (II) formed the protected dihydropyridine (III).Selective deprotection of the cyanoethyl ester under basic conditions provided carboxylic acid (IV),which was further converted to amide (V).Then,acid cleavage of the tert-butyl ester gave acid (VI).Coupling with the (aminopropyl)piperidine (VII) furnished the corresponding amide (VIII).Finally,the azido group was reduced to the target amine by means of trimethyl phosphine.
📌 参考资料/链接：
参考文献标题:Design and synthesis of novel dihydropyridine alpha-1A antagonists
文献作者:Hong,X.; Marzbadi,M.R.; Nagarathnam,D.; Miao,S.W.; Chiu,G.; Wong,W.C.; Wetzel,J.M.; Fang,J.; Forray,C.; Chen,T.B.; O'Malley,S.S.; Chang,R.S.; Gluchowski,C.
参考来源:Bioorg Med Chem Lett 1999,9(19),2843
📄 详细内容
合成路线:Hantzsch condensation of the (azidoethoxy)ketoester (I) with the benzylidene ketoester (II) formed the protected dihydropyridine (III).Selective deprotection of the cyanoethyl ester under basic conditions provided carboxylic acid (IV),which was further converted to amide (V).Then,acid cleavage of the tert-butyl ester gave acid (VI).Coupling with the (aminopropyl)piperidine (VII) furnished the corresponding amide (VIII).Finally,the azido group was reduced to the target amine by means of trimethyl phosphine.
参考文献标题:
文献作者:Tyring,S.K.; Vander Straten,M.; Carrasco,D.
参考来源:Tetrahedron Lett 1998,39(30),5293-96