【药物名称】GFKI-258, CHIR-258LC, CHIR-258
化学结构式(Chemical Structure):
参考文献No.54642
标题:Quinolinone derivs.
作者:Harris, A.; Renhowe, P.; Machajewski, T.; Shafer, C.; Wernette-Hammond, M.-E.; Pecchi, S.; Taylor, C.; McCrea, B.; McBride, C.; Jazan, E. (Chiron Corp.)
来源:WO 0222598
合成路线图解说明:

The cyclization of the phenylenediamine (I) with 3-ethoxy-3-iminopropionic acid ethyl ester (II) in refluxing ethanol gives the 2-(benzimidazol-2-yl)acetate (III), which is submitted to a new cyclization with 2-aminobenzonitrile (IV) by means of LiHMDS in THF to afford the target quinolinone.

合成路线图解说明:

Reaction of 2,4-difluoronitrobenzene (I) with liquid ammonia gives rise to 5-fluoro-2-nitroaniline (II). Subsequent displacement of the remaining fluoride group of (II) with N-methylpiperazine (III) provides the piperazinyl aniline (IV). Catalytic hydrogenation of nitroaniline (IV) over Pd/C yields the phenylenediamine (V). This is then condensed with ethyl 3-ethoxy-3-iminopropanoate (VI) to produce benzimidazole (VII). Finally, reaction of the lithium enolate of benzimidazoleacetate (VII) with 2-amino-6-fluorobenzonitrile (VIII) furnishes the title quinolinone compound. (1,2)

参考文献No.63346
标题:Quinolinone derivs.
作者:Renhowe, P.A.; Pecchi, S.; Taylor, C.; McBride, C.; Jazan, E.; Shafer, C.M.; Machajewski, T.D.; McCrea, W.R. Jr. (Chiron Corp.)
来源:US 2003028018; WO 0387095
合成路线图解说明:

Reaction of 2,4-difluoronitrobenzene (I) with liquid ammonia gives rise to 5-fluoro-2-nitroaniline (II). Subsequent displacement of the remaining fluoride group of (II) with N-methylpiperazine (III) provides the piperazinyl aniline (IV). Catalytic hydrogenation of nitroaniline (IV) over Pd/C yields the phenylenediamine (V). This is then condensed with ethyl 3-ethoxy-3-iminopropanoate (VI) to produce benzimidazole (VII). Finally, reaction of the lithium enolate of benzimidazoleacetate (VII) with 2-amino-6-fluorobenzonitrile (VIII) furnishes the title quinolinone compound. (1,2)

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