FR-137316
Chemical Name: 4-Hydroxy-N,1-dimethyl-6-(methylsulfanyl)-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
CAS No. 147079-63-8
项目整合开发状态: Preclinical
项目研究机构: Fujisawa (Originator)
合成路线:Nucleophilic displacement of 5-chloro-2-nitrobenzoic acid (I) with sodium sulfide produced thiol (II),which was further alkylated with dimethyl sulfate to furnish the methyl thioether (III).Nitro group reduction in (III) to yield 5-(methylthio)anthranilic acid (IV) was accomplished by treatment with hydrazine in the presence of FeCl3.The isatoic anhydride (V) was then prepared by treatment of anthranilic acid (IV) with either phosgene or ethyl chloroformate.Alkylation of benzoxazinedione (V) with iodomethane and NaH gave the N-methyl derivative (VI).The title compound was finally obtained by condensation of (VI) with the sodium enolate of malonic mono-amide (VII).
📌 参考资料/链接：
参考文献标题:Quinoline derivs.
文献作者:Matsuo,M.; Tsuji,K.; Nakamura,K.; Spears,G.W.(Fujisawa Pharmaceutical Co.,Ltd.)
参考来源:EP 0639182; JP 1994506925; WO 9218483
📄 详细内容
合成路线:Nucleophilic displacement of 5-chloro-2-nitrobenzoic acid (I) with sodium sulfide produced thiol (II),which was further alkylated with dimethyl sulfate to furnish the methyl thioether (III).Nitro group reduction in (III) to yield 5-(methylthio)anthranilic acid (IV) was accomplished by treatment with hydrazine in the presence of FeCl3.The isatoic anhydride (V) was then prepared by treatment of anthranilic acid (IV) with either phosgene or ethyl chloroformate.Alkylation of benzoxazinedione (V) with iodomethane and NaH gave the N-methyl derivative (VI).The title compound was finally obtained by condensation of (VI) with the sodium enolate of malonic mono-amide (VII).
参考文献标题:Synthesis and antinephritic activities of quinoline-3-carboxamides and related compounds
文献作者:Tsuji,K.; Spears,G.W.; Nakamura,K.; Tojo,T.; Seki,N.; Sugiyama,A.; Matsuo,M.
参考来源:Bioorg Med Chem Lett 2002,12(1),85
产品链接: CAS No. 147079-63-8››