8-nitro-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one -Drug Synthesis Database

【结构式】

【分子编号】39727

【品名】8-nitro-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

【CA登记号】

【分子式】C₁₃H₈N₄O₃

【分子量】268.23168

【元素组成】C 58.21% H 3.01% N 20.89% O 17.89%

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 condensation of 2-bromo-1-indanone (I) with 1-methylimidazole-2-carboxamide (II) in hot DMF produced the tetracyclic ammonium salt (III), which was further demethylated to (IV) by means of imidazole at 160 C. Regioselective nitration of (IV) employing KNO3 in H2SO4 produced nitro derivative (V), which was reduced to amine (VI) by catalytic hydrogenation over Pd/C. Amine (VI) was converted to urea (VII) by treatment with methyl isocyanate. Subsequent base-catalyzed condensation of (VII) with glyoxylic acid monohydrate (VIII) produced hydroxyacid (IX). This was dehydrated with ZnCl2 and acetic anhydride to give unsaturated acid (X), which was finally hydrogenated over Pd/C to furnish the title compound.

参考文献中间体

合成目标

【1】 Genevois-Borella, A.; Aloup, J.-C.; Audiau, F.; Barreau, M.; Mignani, S.; Ribeill, Y.; Damour, D.; Jimonet, P. (Aventis Pharma SA); Imidazo (1,2-a)-indeno (1,2-e) pyrazin-4-one derivs. and pharmaceutical compsns. containing same. US 5807859; WO 9526350 .

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)	39723	2-bromo-1-indanone	1775-27-5	C₉H₇BrO	详情	详情
(II)	39724	1-methyl-1H-imidazole-2-carboxamide		C₅H₇N₃O	详情	详情
(III)	39725	3-methyl-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-3-ium bromide		C₁₄H₁₂BrN₃O	详情	详情
(IV)	39726	5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one		C₁₃H₉N₃O	详情	详情
(V)	39727	8-nitro-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one		C₁₃H₈N₄O₃	详情	详情
(VI)	39728	8-amino-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one		C₁₃H₁₀N₄O	详情	详情
(VII)	39729	N-methyl-N'-(4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-8-yl)urea		C₁₅H₁₃N₅O₂	详情	详情
(VIII)	39730	2,2-dihydroxyacetic acid		C₂H₄O₄	详情	详情
(IX)	39731	2-hydroxy-2-(8-[[(methylamino)carbonyl]amino]-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetic acid		C₁₇H₁₅N₅O₅	详情	详情
(X)	39732	2-(8-[[(methylamino)carbonyl]amino]-4-oxo-4,5-dihydro-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-ylidene)acetic acid		C₁₇H₁₃N₅O₄	详情	详情

Extended Information