Chemical Name: N-[3-Chloro-5-(trifluoromethyl)phenyl]-4-(pyridin-4-ylmethyl)phthalazin-1-amine
项目整合开发状态: Biological Testing
项目研究机构: Novartis (Originator)
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3,4-bis(trifluoromethyl)aniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-4-methylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-chloro-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 4-chloro-3-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
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合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine affords the phthalazinone (V),which is finally condensed with 4-chloroaniline (VI) by means of P2O5 and TEA at 170 C to provide the target phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3,4-bis(trifluoromethyl)aniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-4-methylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-chloro-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 4-chloro-3-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
参考文献标题:New anilinophthalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis
文献作者:Bold,G.; Altmann,K.-H.; Frei,J.; Lang,M.; Manley,P.W.; Traxler,P.; Wietfeld,B.; Bruggen,J.; Buchdunger,E.; Cozens,R.; Ferrari,S.; Furet,P.; Hofmann,F.; Martiny-Baron,G.; Mestan,J.; Rosel,J.; Sills,M.; Stover,D.; Acemoglu,F.; et al.
参考来源:J Med Chem 2000,43(12),2310
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine affords the phthalazinone (V),which is finally condensed with 4-chloroaniline (VI) by means of P2O5 and TEA at 170 C to provide the target phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3,4-bis(trifluoromethyl)aniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-4-methylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-chloro-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 4-chloro-3-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
参考文献标题:A Study of the chemistry of pyrophthalone and related compounds
文献作者:Manly,D.G.; Tilford,C.H.; Richardson,A.; Stock,A.M.; Amstutz,E.D.
参考来源:J Org Chem 1958,23373-80
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine affords the phthalazinone (V),which is finally condensed with 4-chloroaniline (VI) by means of P2O5 and TEA at 170 C to provide the target phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3,4-bis(trifluoromethyl)aniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-4-methylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-chloro-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 4-chloro-3-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
参考文献标题:beta-Dic閠o 閚amines h閠閞ocycliques: 1.Indanediones-1,3-disubstitut閑s en 2 par un h閠閞ocycle azot?
文献作者:Letourneux,Y.; Floc'h,R.; Le Baut,G.; Ploquin,J.; Sparfel,L.
参考来源:J Heterocycl Chem 1980,17961-73
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine affords the phthalazinone (V),which is finally condensed with 4-chloroaniline (VI) by means of P2O5 and TEA at 170 C to provide the target phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3,4-bis(trifluoromethyl)aniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-4-methylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-bromo-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 3-chloro-5-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
合成路线:The reaction of phthalide (I) with pyridine-4-carbaldehyde (II) by means of NaOMe in methanol gives the nonisolated intermediate (III),which rearranges in the reaction medium to yield indenone (IV).The reaction of (IV) with hydrazine hydrate affords the phthalazinone (V),which was activated as the imidoyl chloride (VI) by means of POCl3 and then reacted with 4-chloro-3-trifluoromethylaniline (VII) in ethanol to afford the 1-anilino-phthalazine.
参考文献标题:CGP 79787D (PTK787/ZK222584),CGP 84738,NVP-AAC789,NVP-AAD777 and related 1-anilino-(4-pyridylmethyl)phthalazines as inhibitors of VEGF- and bFGF-induced angiogenesis
文献作者:Manley,P.W.; Martiny-Baron,G.; Br黦gen,J.; Mestan,J.; Meyer,T.; Wood,J.M.; Ferrari,S.; Hofmann,F.; Bold,G.; Frei,J.; Furet,P.; Cozens,R.M.
参考来源:Drugs Fut 2002,27(1),43