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【结 构 式】

【分子编号】39728

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

【CA登记号】

【 分 子 式 】C13H10N4O

【 分 子 量 】238.24876

【元素组成】C 65.54% H 4.23% N 23.52% O 6.72%

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:(VI)

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.

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