Eticlopride hydrochloride, A-38503, FLB-131, -Drug Synthesis Database

【结构式】

【药物名称】Eticlopride hydrochloride, A-38503, FLB-131

【化学名称】(-)-(S)-3-Chloro-5-ethyl-N-(1-ethylpyrrolidin-2-ylmethyl)-6-hydroxy-2-methoxybenzamide hydrochloride
　　　　　　(-)-(S)-N-Ethyl-2-(3-chloro-5-ethyl-6-hydroxy-2-methoxybenzamidomethyl)pyrrolidine hydrochloride
　　　　　　(-)-(S)-5-Chloro-3-ethyl-N-(1-ethylpyrrolidin-2-ylmethyl)-6-methoxysalicylamide hydrochloride

【CA登记号】84226-12-0 (free base)

【分子式】C₁₇H₂₆Cl₂N₂O₃

【分子量】377.31437

【开发单位】AstraZeneca (Originator)

【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS, Dopamine D2 Antagonists

合成路线1

The reaction of 3-chloro-5-ethyl-2,6-dimethoxybenzoic acid (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with N-ethyl-2-(aminomethyl)pyrrolidine (III) in refluxing CHCl3 yielding N-ethyl-2-(3-chloro-5-ethyl-2,6-dimethoxybenzamidomethyl)pyrrolidine (IV). Finally, this compound is treated with BBr3 in methylene chloride.

参考文献中间体

【1】 Florvall, G.L.; Lundstroem, J.O.G.; Raemsby, S.I.; Oegren S.O. (AstraZeneca plc); Benzamido-derivatives. DD 201886; EP 0060235; JP 57159762; US 4789683 .
【2】 Serradell, M.N.; Castaner, J.; Eticlopride Hydrochloride. Drugs Fut 1985, 10, 4, 286.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29113	3-chloro-5-ethyl-2,6-dimethoxybenzoic acid	C₁₁H₁₃ClO₄	详情	详情
(II)	29114	3-chloro-5-ethyl-2,6-dimethoxybenzoyl chloride	C₁₁H₁₂Cl₂O₃	详情	详情
(III)	21345	(2S)-1-Ethyl-2-(aminomethyl)pyrrolidine; [(2S)-1-Ethylpyrrolidinyl]methanamine	C₇H₁₆N₂	详情	详情
(IV)	29115	3-chloro-5-ethyl-N-[[(2S)-1-ethylpyrrolidinyl]methyl]-2,6-dimethoxybenzamide	C₁₈H₂₇ClN₂O₃	详情	详情

Extended Information