【结 构 式】 |
【分子编号】55915 【品名】6-(methylsulfanyl)-2H-3,1-benzoxazine-2,4(1H)-dione 【CA登记号】 |
【 分 子 式 】C9H7NO3S 【 分 子 量 】209.22552 【元素组成】C 51.67% H 3.37% N 6.69% O 22.94% S 15.33% |
合成路线1
该中间体在本合成路线中的序号:(V)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).
【1】 Tsuji, K.; et al.; Synthesis and antinephritic activities of quinoline-3-carboxamides and related compounds. Bioorg Med Chem Lett 2002, 12, 1, 85. |
【2】 Matsuo, M.; Tsuji, K.; Nakamura, K.; Spears, G.W. (Fujisawa Pharmaceutical Co., Ltd.); Quinoline derivs.. EP 0639182; JP 1994506925; WO 9218483 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 32996 | 5-chloro-2-nitrobenzoic acid | 2516-95-2 | C7H4ClNO4 | 详情 | 详情 |
(II) | 55912 | 2-nitro-5-sulfanylbenzoic acid | C7H5NO4S | 详情 | 详情 | |
(III) | 55913 | 5-(methylsulfanyl)-2-nitrobenzoic acid | C8H7NO4S | 详情 | 详情 | |
(IV) | 55914 | 2-amino-5-(methylsulfanyl)benzoic acid | C8H9NO2S | 详情 | 详情 | |
(V) | 55915 | 6-(methylsulfanyl)-2H-3,1-benzoxazine-2,4(1H)-dione | C9H7NO3S | 详情 | 详情 | |
(VI) | 55916 | 1-methyl-6-(methylsulfanyl)-2H-3,1-benzoxazine-2,4(1H)-dione | C10H9NO3S | 详情 | 详情 | |
(VII) | 55917 | ethyl 3-(methylanilino)-3-oxopropanoate | C12H15NO3 | 详情 | 详情 |