合成路线:Hydrogenation of 2-nitro-5-fluorobenzoic acid (I),followed by in situ condensation with acetic anhydride produced benzoxazinone (II).Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV).Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI).The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3).The two atropisomers were separated by means of preparative chiral HPLC.
参考文献标题:Atropisomers of 3-aryl-4(3H)-quinazolinones and their use as AMPA-receptor antagonists
文献作者:Welch,W.M.Jr.; DeVries,K.M.(Pfizer Inc.)
参考来源:EP 0968194; JP 2000509731; WO 9838173
合成路线:Hydrogenation of 2-nitro-5-fluorobenzoic acid (I),followed by in situ condensation with acetic anhydride produced benzoxazinone (II).Subsequent reaction of (III) with 2-chloroaniline (III) in refluxing AcOH furnished quinazolinone (IV).Treatment of (IV) with 2,6-pyridinedicarboxaldehyde (V) in the presence of ZnCl2 and Ac2O gave rise to the pyridinylvinyl derivative (VI).The title amine was finally obtained by reductive amination of aldehyde (VI) with diethylamine using NaBH(OAc)3).The two atropisomers were separated by means of preparative chiral HPLC.
参考文献标题:Atropisomeric quinazolin-4-one derivatives are potent noncompetitive alpha-amino-3-hydroxy-5-ethyl-4-isoxazolepropionic acid (AMPA) receptor antagonists
文献作者:Welch,W.M.; Ewing,F.E.; Huang,J.; Menniti,F.S.; Pagnozzi,M.J.; Kelly,K.; Seymour,P.A.; Guanowsky,V.; Guhan,S.; Guinn,M.R.; Critchett,D.; Lazzaro,J.; Ganong,A.H.; DeVries,K.M.; Staigers,T.L.; Chenard,B.L.
参考来源:Bioorg Med Chem Lett 2001,11(2),177
产品链接: CAS No. 199655-36-2››