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【结 构 式】 
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【分子编号】26800 【品名】N-(5-quinolinyl)-1H-imidazole-1-carboxamide 【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：(VIII)Alkylation of 3-chloro-4-methylaniline (I) with bromoacetaldehyde diethyl acetal (II) afforded secondary amine (III). Subsequent cyclization of (III) in boiling trifluoroacetic acid/trifluoroacetic anhydride provided a (3:2) mixture of indoles (IV) and (V), from which the desired 6-chloro isomer (IV) was isolated by column chromatography, and then reduced to indoline (VI) using NaBH3CN in AcOH. 5-Aminoquinoline (VII) was treated with carbonyl diimidazole to give intermediate (VIII). This was finally coupled with indoline (VI) in DMF at 100 C to yield the corresponding urea.
| 【1】 Ham, P.; Jones, G.E.; Forbes, I.T. (SmithKline Beecham plc); Indoline derivs. as 5HT2C antagonists. EP 0707581; JP 1996512299; US 5834494; WO 9501976 . |
| 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) | 26794 | 3-Chloro-4-methylaniline; 4-Amino-2-chlorotoluene | 95-74-9 | C7H8ClN | 详情 | 详情 |
| (II) | 12113 | 2-Bromo-1-ethoxyethyl ethyl ether; 2-Bromo-1,1-diethoxyethane; Bromoacetaldehyde diethylacetal | 2032-35-1 | C6H13BrO2 | 详情 | 详情 |
| (III) | 26795 | 3-chloro-N-(2,2-diethoxyethyl)-4-methylaniline | C13H20ClNO2 | 详情 | 详情 | |
| (IV) | 26796 | 6-chloro-5-methyl-1H-indole | C9H8ClN | 详情 | 详情 | |
| (V) | 26797 | 4-chloro-5-methyl-1H-indole | C9H8ClN | 详情 | 详情 | |
| (VI) | 26798 | 6-chloro-5-methylindoline | C9H10ClN | 详情 | 详情 | |
| (VII) | 26799 | 5-Aminoquinoline; 5-quinolinamine | 611-34-7 | C9H8N2 | 详情 | 详情 |
| (VIII) | 26800 | N-(5-quinolinyl)-1H-imidazole-1-carboxamide | C13H10N4O | 详情 | 详情 |
Extended Information