3-chloro-N-(2,2-diethoxyethyl)-4-methylaniline -Drug Synthesis Database

【结构式】

【分子编号】26795

【品名】3-chloro-N-(2,2-diethoxyethyl)-4-methylaniline

【CA登记号】

【分子式】C₁₃H₂₀ClNO₂

【分子量】257.76004

【元素组成】C 60.58% H 7.82% Cl 13.75% N 5.43% O 12.41%

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：(III)

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.

参考文献中间体

合成目标

【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