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【结 构 式】

【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