新产品编号:652293
Chemical Name: 2-[(1R,2S)-2-(3,5-Dibromo-2-ethoxybenzylamino)cyclopentylmethylamino]quinolin-4(1H)-one
CAS No. 248607-39-8
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The optically pure aminocyclopentanecarboxylate (I) is reduced with LiAlH4 to the corresponding amino alcohol (II).Subsequent coupling of alcohol (II) with N-(trichloroethoxycarbonyl)-2-amino-4-ethoxyquinoline (III) under Mitsunobu conditions leads to carbamate (IV).Removal of the trichloroethoxycarbonyl and benzyl groups of (IV) by transfer hydrogenation with ammonium formate and Pd/C furnishes diamine (V).Then,acidic hydrolysis of the ethoxy group of (V) leads to quinolone (VI).Finally,reductive alkylation of amine (VI) with 3,5-dibromo-2-ethoxybenzaldehyde (VII) provides the target benzylamine derivative.(1,2)
📌 参考资料/链接：
参考文献标题:Quinolones used as MRS inhibitors and bactericides
文献作者:Berge,J.M.; Forrest,A.K.; Elder,J.S.; Jarvest,R.L.; Brown,P.; McNair,D.J.; Hamprecht,D.W.; Sheppard,R.J.(GlaxoSmithKline plc)
参考来源:EP 1084110; JP 2002513005; US 6320051; WO 9955677
📄 详细内容
合成路线:The optically pure aminocyclopentanecarboxylate (I) is reduced with LiAlH4 to the corresponding amino alcohol (II).Subsequent coupling of alcohol (II) with N-(trichloroethoxycarbonyl)-2-amino-4-ethoxyquinoline (III) under Mitsunobu conditions leads to carbamate (IV).Removal of the trichloroethoxycarbonyl and benzyl groups of (IV) by transfer hydrogenation with ammonium formate and Pd/C furnishes diamine (V).Then,acidic hydrolysis of the ethoxy group of (V) leads to quinolone (VI).Finally,reductive alkylation of amine (VI) with 3,5-dibromo-2-ethoxybenzaldehyde (VII) provides the target benzylamine derivative.(1,2)
参考文献标题:Conformational restriction of methionyl tRNA synthetase inhibitors leading to analogues with potent inhibition and excellent Gram-Positive antibacterial activity
文献作者:Jarvest,R.L.; Berge,J.M.; Brown,P.; Houge-Frydrych,C.S.V.; O'Hanlon,P.J.; McNair,D.J.; Pope,A.J.; Rittenhouse,S.
参考来源:Bioorg Med Chem Lett 2003,13(7),1265