【结 构 式】 |
【分子编号】58528 【品名】ethyl 2-(5-fluoro-2-nitroanilino)acetate 【CA登记号】 |
【 分 子 式 】C10H11FN2O4 【 分 子 量 】242.2068232 【元素组成】C 49.59% H 4.58% F 7.84% N 11.57% O 26.42% |
合成路线1
该中间体在本合成路线中的序号:(III)The title compound has been obtained by two related ways: Condensation of glycine ethyl ester (II) with 2,4-difluoronirobenzene (I) provided the N-arylglycine (III), which was further reduced to the phenylenediamine derivative (IV) by catalytic hydrogenation. Acylation of diamine (IV) with ethyl chloroglyoxylate, followed by ring closure in refluxing ethanol, yielded the quinoxalinedione (V). Subsequent electrophyllic nitration of (V) furnished the 6-nitroquinoxaline (VI). The fluoride group of (III) was then displaced with imidazole (VII) in hot DMF yielding the imidazolyl quinoxaline (VIII). Finally, basic hydrolysis of the ethyl ester function of (VIII) gave the target carboxylic acid.
【1】 Shishikura, J.; Inami, H.; Sakamoto, S.; Tsukamoto, S.; Sasamata, M.; Okada, M.; Fujii, M. (Yamanouchi Pharmaceutical Co., Ltd.); 1,2,3,4-Tetrahydroquinoxalindione deriv.. EP 0784054; US 6096743; WO 9610023 . |
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) | 32036 | 2,4-difluoro-1-nitrobenzene | 446-35-5 | C6H3F2NO2 | 详情 | 详情 |
(II) | 10309 | ethyl 2-aminoacetate; Glycine ethyl ester | 459-73-4 | C4H9NO2 | 详情 | 详情 |
(III) | 58528 | ethyl 2-(5-fluoro-2-nitroanilino)acetate | C10H11FN2O4 | 详情 | 详情 | |
(IV) | 58529 | ethyl 2-(2-amino-5-fluoroanilino)acetate | C10H13FN2O2 | 详情 | 详情 | |
(V) | 58530 | ethyl 2-[7-fluoro-2,3-dioxo-3,4-dihydro-1(2H)-quinoxalinyl]acetate | C12H11FN2O4 | 详情 | 详情 | |
(VI) | 58531 | ethyl 2-[7-fluoro-6-nitro-2,3-dioxo-3,4-dihydro-1(2H)-quinoxalinyl]acetate | C12H10FN3O6 | 详情 | 详情 | |
(VII) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
(VIII) | 58532 | ethyl 2-[7-(1H-imidazol-1-yl)-6-nitro-2,3-dioxo-3,4-dihydro-1(2H)-quinoxalinyl]acetate | C15H13N5O6 | 详情 | 详情 |