SB-414240
Chemical Name: 2-Phenyl-3-[4-(1-piperidinyl)piperidin-1-ylmethyl]-N-[1(S),2,2-trimethylpropyl]quinoline-4-carboxamide
CAS No. 272104-60-6
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Esterification of the commercially available carboxylic acid (I) by treatment with oxalyl chloride in DCM followed by reaction with MeOH in CH2Cl2 provides methyl carboxylate (II),which is then brominated with NBS and catalytic dibenzoylperoxide in refluxing acetonitrile to afford 3-bromomethylquinoline derivative (III).Treatment of (III) with secondary amine (IV) and DIEA in THF furnishes compound (V),which is then converted into the desired product by acidic hydrolysis in refluxing HCl followed by coupling with primary amine (VI) by means of HBTU and Et3N in refluxing THF/CH2Cl2.
📌 参考资料/链接：
参考文献标题:Quinoline derivs.as NK-2 and NK-3 receptor ligands
文献作者:Giardina,G.; Grugni,M.; Raveglia,L.F.; Nadler,G.M.M.G.; Farina,C.(SmithKline Beecham SpA)
参考来源:EP 1131294; WO 0031038
📄 详细内容
合成路线:Esterification of the commercially available carboxylic acid (I) by treatment with oxalyl chloride in DCM followed by reaction with MeOH in CH2Cl2 provides methyl carboxylate (II),which is then brominated with NBS and catalytic dibenzoylperoxide in refluxing acetonitrile to afford 3-bromomethylquinoline derivative (III).Treatment of (III) with secondary amine (IV) and DIEA in THF furnishes compound (V),which is then converted into the desired product by acidic hydrolysis in refluxing HCl followed by coupling with primary amine (VI) by means of HBTU and Et3N in refluxing THF/CH2Cl2.
参考文献标题:Stepwise modulation of neurokinin-3 and neurokinin-2 receptor affinity and selectivity in quinoline tachykinin receptor antagonists
文献作者:Blaney,F.E.; Raveglia,L.F.; Artico,M.; Cavagnera,S.; Dartois,C.; Farina,C.; Grugni,M.; Gagliardi,S.; Luttmann,M.A.; Martinelli,M.J.; Nadler,G.M.; Parini,C.; Petrillo,P.; Sarau,H.M.; Scheideler,M.A.; Hay,D.W.P.; Giardina,G.A.
参考来源:J Med Chem 2001,44(11),1675
产品链接: CAS No. 272104-60-6››