• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】44103

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

【CA登记号】

【 分 子 式 】C18H18N6O3

【 分 子 量 】366.37956

【元素组成】C 59.01% H 4.95% N 22.94% O 13.1%

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:(X)

The tetracyclic imidazoindenopyrazinone (IV) was obtained by condensation of 2-bromoindanone (I) with 1-methylimidazole-2-carboxamide (II), followed by demethylation of the resulting imidazolium salt (III) in molten imidazole at 160 C (1). Reaction of (IV) with isoamyl nitrite in the presence of NaH produced oxime (V), which was reduced with zinc powder in acetic acid to yield acetamide (VI). Regioselective methylation of (VI) using methyl iodide and NaH gave (VII). Subsequent nitration of (VII) by means of KNO3 and H2SO4 afforded the 8-nitro derivative (VIII), which was reduced to amine (IX) by hydrogenation over Pd/C. Condensation of amine (IX) with methyl isocyanate in DMF produced urea (X). Finally, the acetamido group of (X) was hydrolyzed in refluxing 6 M HCl.

1 Chevé, M.; Jimonet, P.; Bohme, G.A.; et al.; 8-Methylureido-10-amino-10-methyl-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-ones: Highly in vivo potent and selective AMPA receptor antagonists. Bioorg Med Chem 2000, 8, 8, 2211.
2 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) 42829 4H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4,10(5H)-dione 10-oxime C13H8N4O2 详情 详情
(VI) 42830 N-(4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetamide C15H12N4O2 详情 详情
(VII) 44100 N-(10-methyl-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetamide C16H14N4O2 详情 详情
(VIII) 44101 N-(10-methyl-8-nitro-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetamide C16H13N5O4 详情 详情
(IX) 44102 N-(8-amino-10-methyl-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetamide C16H15N5O2 详情 详情
(X) 44103 N-(10-methyl-8-[[(methylamino)carbonyl]amino]-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)acetamide C18H18N6O3 详情 详情
Extended Information