methyl 2-(8-amino-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetate -Drug Synthesis Database

【结构式】

【分子编号】39736

【品名】methyl 2-(8-amino-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetate

【CA登记号】

【分子式】C₁₆H₁₄N₄O₃

【分子量】310.31232

【元素组成】C 61.93% H 4.55% N 18.06% O 15.47%

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：(XIV)

In a related procedure, tetracyclic compound (IV) was first condensed with glyoxylic acid (VIII) giving hydroxyacid (XI), which was dehydrated to (XII) with ZnCl2 and Ac2O. Subsequent nitration of (XII) with KNO3 and H2SO4 afforded nitro derivative (XIII). Reduction of (XIII) with simultaneous esterification using iron and HCl in MeOH gave rise to amino ester (XIV). Urea (XV) was then obtained by condensation of (XIV) with methyl isocyanate. Finally, saponification of the ester group provided the title carboxylic acid.

参考文献中间体

合成目标

【1】 Boireau, A.; Bohme, G.A.; Mignani, S.; et al.; 8-Methylureido-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazines: Highly potent in vivo AMPA antagonists. Bioorg Med Chem Lett 2000, 10, 6, 591.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	39726	5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one	C₁₃H₉N₃O	详情	详情
(VIII)	39730	2,2-dihydroxyacetic acid	C₂H₄O₄	详情	详情
(XI)	39733	2-hydroxy-2-(4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetic acid	C₁₅H₁₁N₃O₄	详情	详情
(XII)	39734	2-(4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-ylidene)acetic acid	C₁₅H₉N₃O₃	详情	详情
(XIII)	39735	2-(8-nitro-4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-ylidene)acetic acid	C₁₅H₈N₄O₅	详情	详情
(XIV)	39736	methyl 2-(8-amino-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetate	C₁₆H₁₄N₄O₃	详情	详情
(XV)	39737	methyl 2-(8-[[(methylamino)carbonyl]amino]-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetate	C₁₈H₁₇N₅O₄	详情	详情

Extended Information