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【结 构 式】

【分子编号】47590

【品名】ethyl 7-chloro-4-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate

【CA登记号】

【 分 子 式 】C12H9ClN4O3

【 分 子 量 】292.68132

【元素组成】C 49.25% H 3.1% Cl 12.11% N 19.14% O 16.4%

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:(VIII)

Diazotization of substituted aniline (I) followed by reaction with ethyl 2-chloro-3-oxobutanoate (II) in MeOH yields hydrazono chloroacetate derivative (III), which is converted into oxamidrazonate (IV) by means of NH3 (gas). Treatment of derivative (IV) with ethyloxalyl chloride (V) affords ethoxalyl derivative (VI), which is then heated until cyclization occurs, providing derivative (VII). Reduction of triazole dicarboxylate (VII) with iron in HOAc gives tricyclic compound (VIII), which is nitrated by means of HNO3 to afford nitro derivative (IX). Reduction of the nitro group of (IX) by means of iron in HOAc provides the corresponding 8-amino derivative (X), which is treated with diformylhydrazine and trimethylsilyl chloride (TMSCl) in pyridine to furnish ethyl carboxylate (XI). Finally, saponification of (XI) with NaOH in EtOH gives the desired compound.

1 Catarzi, D.; et al.; 4,5-Dihydro-1,2,4-triazolo[1,5-a]quinoxalin-4-ones: Excitatory amino acid antagonists with combined glycine/NMDA and AMPA receptor affinity. J Med Chem 1999, 42, 13, 2478.
2 Colotta, V.; Carlà, V.; Costagli, C.; Filacchioni, G.; Varano, F.; Cecchi, L.; Galli, A.; Catarzi, D.; 7-Chloro-4,5-dihydro-8-(1,2,4-triazol-4-yl)-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates as novel highly selective AMPA receptor antagonists. J Med Chem 2000, 43, 21, 3824.
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) 47585 1-Amino-4-chloro-2-nitrobenzene; 2-Nitro-4-chloroaniline; p-chloro-o-nitroaniline; 4-chloro-2-nitroaniline; 4-chloro-2-nitrophenylamine 89-63-4 C6H5ClN2O2 详情 详情
(II) 21337 ethyl 2-chloro-3-oxobutanoate 609-15-4 C6H9ClO3 详情 详情
(III) 47586 N-(4-chloro-2-nitrophenyl)-2-ethoxy-2-oxoethanehydrazonoyl chloride C10H9Cl2N3O4 详情 详情
(IV) 47587 N'-(4-chloro-2-nitrophenyl)-2-ethoxy-2-oxoethanehydrazonamide C10H11ClN4O4 详情 详情
(V) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(VI) 47588 ethyl 2-([1-[(E)-2-(4-chloro-2-nitrophenyl)hydrazono]-2-ethoxy-2-oxoethyl]amino)-2-oxoacetate C14H15ClN4O7 详情 详情
(VII) 47589 diethyl 1-(4-chloro-2-nitrophenyl)-1H-1,2,4-triazole-3,5-dicarboxylate C14H13ClN4O6 详情 详情
(VIII) 47590 ethyl 7-chloro-4-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate C12H9ClN4O3 详情 详情
(IX) 47591 ethyl 7-chloro-8-nitro-4-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate C12H8ClN5O5 详情 详情
(X) 47592 ethyl 8-amino-7-chloro-4-oxo-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate C12H10ClN5O3 详情 详情
(XI) 47593 ethyl 7-chloro-4-oxo-8-(4H-1,2,4-triazol-4-yl)-4,5-dihydro[1,2,4]triazolo[1,5-a]quinoxaline-2-carboxylate C14H10ClN7O3 详情 详情
Extended Information