ZK-260255, AAL-993
Chemical Name: 2-(Pyridin-4-ylmethylamino)-N-[3-(trifluoromethyl)phenyl]benzamide
CAS No. 269390-77-4
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator), Schering AG (Originator)
合成路线:The intermediate anthranilamide (IV) is prepared by two alternative methods.Acylation of 3-(trifluoromethyl)aniline (I) with 2-nitrobenzoyl chloride (II) yields benzamide (III).The nitro group of (III) is then reduced to the corresponding amine (IV) by catalytic hydrogenation over Pd/C (1).Alternatively,3-(trifluoromethyl)aniline (I) is condensed with isatoic anhydride (V) to furnish directly anthranilamide (IV) (2).Finally,reductive alkylation of (IV) with pyridine-4-carbaldehyde (VI) employing NaBH3CN gives rise to the target pyridylmethyl amine.
📌 参考资料/链接：
参考文献标题:N-Aryl(thio)anthranilic acid amide derivs.,their preparation and their use as VEGF receptor tyrosine kinase inhibitors
文献作者:Seidelmann,D.; Huth,A.; Manley,P.W.; Thierauch,K.-H.; Kr黦er,M.; Bold,G.; Haberey,M.; Furet,P.; Altmann,K.-H.; Mestan,J.; Menrad,A.; Ferrari,S.; Wood,J.M.; Hofmann,F.(Novartis AG; Schering AG)
参考来源:EP 1129075; JP 2002529453; US 6448277; WO 0027820
📄 详细内容
合成路线:The intermediate anthranilamide (IV) is prepared by two alternative methods.Acylation of 3-(trifluoromethyl)aniline (I) with 2-nitrobenzoyl chloride (II) yields benzamide (III).The nitro group of (III) is then reduced to the corresponding amine (IV) by catalytic hydrogenation over Pd/C (1).Alternatively,3-(trifluoromethyl)aniline (I) is condensed with isatoic anhydride (V) to furnish directly anthranilamide (IV) (2).Finally,reductive alkylation of (IV) with pyridine-4-carbaldehyde (VI) employing NaBH3CN gives rise to the target pyridylmethyl amine.
参考文献标题:Anthranilic acid amides: A novel class of antiangiogenic VEGF receptor kinase inhibitors
文献作者:Manley,P.W.; Furet,P.; Bold,G.; Br黦gen,J.; Mestan,J.; Meyer,T.; Schnell,C.R.; Wood,J.; Haberey,M.; Huth,A.; Kruger,M.; Menrad,A.; Ottow,E.; Seidelmann,D.; Siemeister,G.; Thierauch,K.H.
参考来源:J Med Chem 2002,45(26),5687
产品链接: CAS No. 269390-77-4››