Indisetron hydrochloride, N-3389, Indisetron HCl Nisshin, Sinseron-药物合成数据库

【药物名称】Indisetron hydrochloride, N-3389, Indisetron HCl Nisshin, Sinseron

化学结构式(Chemical Structure):

参考文献No.	20211
标题:	Azabicyclo derivs. and their use as antiemetics
作者:	Kikuchi, H.; Satoh, H.; Yahata, N.; Hagihara, K.; Hayakawa, T.; Mino, S.; Yanai, M. (Nisshin Flour Milling Co., Ltd.)
来源:	EP 0469449; JP 1993310749; US 5187166

合成路线图解说明: The condensation of bromoacetaldehyde dimethyl acetal (I) with methylamine (II) by means of KOH in refluxing ethylene glycol gives bis(2,2-dimethoxyethyl)methylamine (III), which is cyclized with acetonedicarboxylic acid (IV) and more methylamine (II), yielding 3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-one (V). The reaction of (V) with hydroxylamine affords the corresponding oxime (VI), which is reduced with H2 over RaNi in ethanol giving endo-3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-amine (VII). Finally, this compound is condensed with 1H-indazole-3-carbonyl chloride (VIII) by means of dimethylaminopyridine (DMAP) in pyridine.

参考文献No.	310410
标题:	N-3389
作者:	Casta馿r, J.; Rabasseda, X.; Mealy, N.
来源:	Drugs Fut 1995,20(8),780

合成路线图解说明: The condensation of bromoacetaldehyde dimethyl acetal (I) with methylamine (II) by means of KOH in refluxing ethylene glycol gives bis(2,2-dimethoxyethyl)methylamine (III), which is cyclized with acetonedicarboxylic acid (IV) and more methylamine (II), yielding 3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-one (V). The reaction of (V) with hydroxylamine affords the corresponding oxime (VI), which is reduced with H2 over RaNi in ethanol giving endo-3,9-dimethyl-3,9-diazabicyclo[3.3.1]nonan-7-amine (VII). Finally, this compound is condensed with 1H-indazole-3-carbonyl chloride (VIII) by means of dimethylaminopyridine (DMAP) in pyridine.