Y-34959
Chemical Name: N-[5-[4-(4-Amino-5-chloro-2-methoxybenzamidomethyl)piperidin-1-yl]pentyl]-1-methyl-1H-indole-3-carboxamide hydrochloride
CAS No. 173339-89-4 (free base)
项目整合开发状态: Preclinical
项目研究机构: Mitsubishi Pharma (Originator)
合成路线:1-Benzyl-4-(aminomethyl)piperidine (I) was protected at the primary amino group as the Boc derivative (II) and the N-benzyl group was subsequently removed by transfer hydrogenolysis with hydrazine and Pd/C to give piperidine (III).Alkylation of (III) with N-(5-bromopentyl)phthalimide (IV) afforded (V),which was subjected to hydrazinolysis of the phthalimido group,yielding primary amine (VI).Coupling of (VI) with 1-methylindole-3-carboxylic acid (VII) by means of EDC and HOBt gave rise to amide (VIII).The Boc protecting group of (VIII) was then cleaved by acidic treatment to furnish amine (IX).Finally,coupling of (IX) with 4-amino-5-chloro-2-methoxybenzoic acid (X) provided the title benzamide.
📌 参考资料/链接：
参考文献标题:Benzoic acid cpd.and use thereof as medicine
文献作者:Kawakita,T.; Hakira,H.; Haga,K.; Murozono,T.; Kuroita,T.(Welfide Corporation)
参考来源:EP 0774460; WO 9526953
📄 详细内容
合成路线:1-Benzyl-4-(aminomethyl)piperidine (I) was protected at the primary amino group as the Boc derivative (II) and the N-benzyl group was subsequently removed by transfer hydrogenolysis with hydrazine and Pd/C to give piperidine (III).Alkylation of (III) with N-(5-bromopentyl)phthalimide (IV) afforded (V),which was subjected to hydrazinolysis of the phthalimido group,yielding primary amine (VI).Coupling of (VI) with 1-methylindole-3-carboxylic acid (VII) by means of EDC and HOBt gave rise to amide (VIII).The Boc protecting group of (VIII) was then cleaved by acidic treatment to furnish amine (IX).Finally,coupling of (IX) with 4-amino-5-chloro-2-methoxybenzoic acid (X) provided the title benzamide.
参考文献标题:Synthesis and pharmacological properties of novel benzamide derivatives acting as ligands to the 5-hydroxytryptamine 4 (5-HT4) receptor
文献作者:Haga,K.; Tomozane,H.; Sato,N.; Kawakita,T.; Itoh,K.; Sonda,S.; Asano,K.; Fujimura,M.; Hakira,H.
参考来源:Eur J Med Chem 1999,34(12),1101