BRL-20627
Chemical Name: (2alpha,6beta,9aalpha)-(?-4-Amino-5-chloro-2-methoxy-N-(octahydro-6-methyl-2H-quinolizin-2-yl)benzamide hydrochloride; (2alpha,6beta,9aalpha)-(?-4-Amino-5-chloro-2-methoxy-N-(6-methyl-2-quinolizidinyl)benzamide hydrochloride
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The reaction of quinolizidinone (I) with hydroxylamine and pyridine in refluxing ethanol gives the corresponding oxime (II),which is reduced with LiAlH4 in ether to yield 6-methyl-2-aminoquinolizidine (III).The acylation of (III) with 4-acetamido-5-chloro-2-methoxybenzoyl chloride (IV) [prepared from the corresponding acid (V) and SOCl2] by means of triethylamine in benzene affords the protected benzamide (VI),which is finally deprotected with KOH in refluxing ethanol.
📌 参考资料/链接：
参考文献标题:Treating gastro-intestinal disorders and emesis with n-(heterocyclic substituted)benzamides
文献作者:Hadley,M.S.; Watts,E.A.(SmithKline Beecham plc)
参考来源:BE 0860049; DE 2748260; FR 2370051; GB 1593146; JP 53059692; NL 7712203; US 4213983
📄 详细内容
合成路线:The reaction of quinolizidinone (I) with hydroxylamine and pyridine in refluxing ethanol gives the corresponding oxime (II),which is reduced with LiAlH4 in ether to yield 6-methyl-2-aminoquinolizidine (III).The acylation of (III) with 4-acetamido-5-chloro-2-methoxybenzoyl chloride (IV) [prepared from the corresponding acid (V) and SOCl2] by means of triethylamine in benzene affords the protected benzamide (VI),which is finally deprotected with KOH in refluxing ethanol.
合成路线:The condensation of 2-(2-aminothiazol-4-yl)-2(Z)-(trityoloxyimino)thioacetic acid 2-benzothiazolyl ester (I) with 7-amino-3-vinyl-3-cephem-4-carboxylic acid (II) by means of tributylamine in DMA gives the corresponding amide (III),which is deprotected by means of HCl and formic acid to provide cefdinir.
参考文献标题:Process for the preparation of cefdinir
文献作者:Singh,S.K.; Kumar,Y.; Prasad,M.; Prasad,A.; Kumar,N.P.(Ranbaxy Laboratories Ltd.)
参考来源:WO 0391261