新产品编号:1248707
Chemical Name:
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合成路线:The optical resolution of 4-amino-5-chloro-2-methyl-2,3-dihydrobenzofuran-7-carboxylic acid (I) by means of brucine in methanol gives the (+)-isomer (II),which is then condensed with the ethylamino derivative (III) by means of carbonyldiimidazole in THF to afford the amide (IV).Finally,this compound is salified with fumaric acid (V) in ethanol.
📌 参考资料/链接：
参考文献标题:Benzo[b]furancarboxamide derivs.,process for their preparation and their use as gastrointestinal mobility-enhancing agents
文献作者:Baba,Y.; Usui,T.; Iwata,N.(Sanwa Kagaku Kenkyusho Co.,Ltd.)
参考来源:EP 0640602; JP 1995112985; US 5442077
📄 详细内容
合成路线:The hydrolysis of 4-acetamido-2-methyl-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester (I) with NaOH gives the corresponding free acid (II),which is esterified with benzyl alcohol and carbonyldiimidazole (CDI) to the benzyl ester (III).Optical resolution of (III) by chiral HPLC yielded the 2(S)-isomer (IV),which is chlorinated with N-chlorosuccinomide (NCl) affords the 5-chloro derivative (V).The treatment of (V) with NaOH provides 4-amino-5-chloro-2(S)-methyl-2,3-dihydrobenzofuran-7-carboxylic acid (VI),which is condensed with the ethylamino derivative (VII) by means of CDI to give the amide (VIII).Finally,this compound is salified with fumaric acid (IX).
参考文献标题:Serotonin 5-HT4 receptor agonistic activity of the optical isomers of (?-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide
文献作者:Kakigami,T.; Usui,T..; Ikami,T.; Tsukamoto,K.; Miwa,Y.; Taga,T.; Kataoka,T.
参考来源:Chem Pharm Bull 1998,46(6),1039