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【结 构 式】

【分子编号】58530

【品名】ethyl 2-[7-fluoro-2,3-dioxo-3,4-dihydro-1(2H)-quinoxalinyl]acetate

【CA登记号】

【 分 子 式 】C12H11FN2O4

【 分 子 量 】266.2288232

【元素组成】C 54.14% H 4.16% F 7.14% N 10.52% O 24.04%

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:(V)

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
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