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【结 构 式】 
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【分子编号】15712 【品名】4-(1H-imidazol-1-yl)-1,2-benzenediamine; 2-amino-4-(1H-imidazol-1-yl)phenylamine 【CA登记号】 |
【 分 子 式 】C9H10N4 【 分 子 量 】174.20536 【元素组成】C 62.05% H 5.79% N 32.16% |
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：(IV)The condensation of 5-chloro-2-nitroaniline (I) with imidazole (II) by means of KOH in DMSO gives 5-(1-imidazolyl)-2-nitroaniline (III). Hydrogenation of (III) over Pd/C in 1N HCl gives the diamine (IV), which is condensed with oxalic acid (V) in 4N HCl yielding 6-(1-imidazolyl)quinoxaline-2,3(1H,4H)-dione hydrochloride (VI). Finally, this compound is nitrated with HNO3/H2SO4.
| 【1】 Ngo, J.; Rabasseda, X.; Castaner, J.; YM-900. Drugs Fut 1997, 22, 3, 256. |
| 【2】 Sakamoto, S.; Ohmori, J.; Shimizu-Sasamata, M.; et al.; Imidazolylquinoxaline-2,3-diones: Novel and potent antagonists of alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate (AMPA) excitatory amino acid receptor. 12th Int Symp Med Chem (Sept 13-17, Basel) 1992, Abst P-022.A.. |
| 【3】 Ohmori, J.; Sakamoto, S.; Kubota, H.; Shimizu-Sasamata, M.; Okada, M.; Kawasaki, S.; Hidaka, K.; Togami, J.; Furuya, T.; Murase, K.; 6-(1H-Imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione hydrochloride (YM90K) and related compounds: Structure-activity relationships for the AMPA-type non-NMDA receptor. J Med Chem 1994, 37, 4, 467-75. |
| 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) | 15709 | 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline | 1635-61-6 | C6H5ClN2O2 | 详情 | 详情 |
| (II) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
| (III) | 15711 | 5-(1H-imidazol-1-yl)-2-nitroaniline; 5-(1H-imidazol-1-yl)-2-nitrophenylamine | C9H8N4O2 | 详情 | 详情 | |
| (IV) | 15712 | 4-(1H-imidazol-1-yl)-1,2-benzenediamine; 2-amino-4-(1H-imidazol-1-yl)phenylamine | C9H10N4 | 详情 | 详情 | |
| (V) | 15713 | Oxalic acid | 144-62-7 | C2H2O4 | 详情 | 详情 |
| (VI) | 15714 | 6-(1H-imidazol-1-yl)-1,4-dihydro-2,3-quinoxalinedione hydrochloride | C11H9ClN4O2 | 详情 | 详情 |
Extended Information