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【结 构 式】

【分子编号】27136

【品名】2,3-dichloro-5-methyl-7-(trifluoromethyl)quinoxaline

【CA登记号】

【 分 子 式 】C10H5Cl2F3N2

【 分 子 量 】281.0637896

【元素组成】C 42.73% H 1.79% Cl 25.23% F 20.28% N 9.97%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The reaction of 2-methyl-4-(trifluoromethyl)aniline (I) with ethoxalyl chloride (II) by means of triethylamine in ethyl acetate gives the oxamic ester (III), which is nitrated at the aromatic ring with KNO3 and H2SO4 yielding the intermediate (IV). The reductocyclization of (IV) by means of TiCl3 in acetone affords the quinoxalinedione (V), which is treated with PCl5 in refluxing POCl3 affording the dichloroquinoxaline (VI). The reaction of (VI) with sodium methoxide in refluxing methanol gives the dimethoxyquinoxaline (VII), which is brominated with NBS and AIBN in refluxing benzene yielding the bromomethyl quinoxaline (VIII). The condensation of (VIII) with dimethyl 1(S)-aminoethylphosphonate (IX) by means of NaHCO3 in DMF affords the phosphonate derivative (X), which is finally submitted to acid hydrolysis to provide the target compound.

1 Auberson, Y.P.; et al.; N-Phosphonoalkyl-5-aminomethylquinoxaline-2,3-diones: In vivo active AMPA and NMDA(glycine) antagonists. Bioorg Med Chem Lett 1999, 9, 2, 249.
2 Acklin, P.; Allgeier, H.; Auberson, Y.; Ofner, S.; Veenstra, S.J. (Novartis AG); Substd. aminoalkane phosphonic acids. EP 0934326; US 6117873; WO 9817672 .
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) 27132 2-methyl-4-(trifluoromethyl)aniline C8H8F3N 详情 详情
(II) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(III) 27133 ethyl 2-[2-methyl-4-(trifluoromethyl)anilino]-2-oxoacetate C12H12F3NO3 详情 详情
(IV) 27134 ethyl 2-[2-methyl-6-nitro-4-(trifluoromethyl)anilino]-2-oxoacetate C12H11F3N2O5 详情 详情
(V) 27135 5-methyl-7-(trifluoromethyl)-1,4-dihydro-2,3-quinoxalinedione C10H7F3N2O2 详情 详情
(VI) 27136 2,3-dichloro-5-methyl-7-(trifluoromethyl)quinoxaline C10H5Cl2F3N2 详情 详情
(VII) 27137 2,3-dimethoxy-5-methyl-7-(trifluoromethyl)quinoxaline C12H11F3N2O2 详情 详情
(VIII) 27138 5-(bromomethyl)-2,3-dimethoxy-7-(trifluoromethyl)quinoxaline C12H10BrF3N2O2 详情 详情
(IX) 27139 dimethyl (1S)-1-aminoethylphosphonate C4H12NO3P 详情 详情
(X) 27140 dimethyl (1S)-1-([[2,3-dimethoxy-7-(trifluoromethyl)-5-quinoxalinyl]methyl]amino)ethylphosphonate C16H21F3N3O5P 详情 详情
Extended Information