AD-8717
Chemical Name: N-(2,6-Dimethyl-4-pyridyl)-2-(2,4-dimethoxybenzylsulfinyl)pyridine-3-carboxamide
CAS No. 181821-99-8
项目整合开发状态: Preclinical
项目研究机构: Dainippon Pharmaceutical (Originator)
合成路线:AD-8717 was obtained as shown in Scheme 24060801a.The condensation of 2-mercaptonicotinic acid (I) with 2,4-dimethoxybenzyl alcohol (II) by means of HCl in acetone yields 2-[(2,4-dimethoxybenzyl)thio]nicotinic acid (III).The reaction of (III) with oxalyl chloride in dioxane yields the corresponding chloride,which is condensed with 4-amino-2,6-dimethylpyridine N-oxide (IV) by means of triethylamine in tetrahydrofuran affording 4-[2-[(2,4-dimethoxybenzyl)thio]nicotinoylamino]-2,6-dimethylpyridine N-oxide (V).The reduction of (V) with phosphorus trichloride in dichloromethane yields 2-[(2,4-dimethoxybenzyl)thio]-N-(2,6-dimethyl-4-pyridyl)nicotinamide (VI),which is finally oxidized with m-chloroperbenzoic acid in dichloromethane.
📌 参考资料/链接：
参考文献标题:2-Sulfinylnicotinamide derivs.,intermediate thereof,process for producing 2-sulfinylnicotinamide derivs.,and medicinal compsn.containing the same as active ingredient
文献作者:Nishikawa,Y.; Terauchi,H.; Tanitame,A.; Tada,K.; Komiya,M.; Nakamura,K.; Tominaga,Y.(Dainippon Pharmaceutical Co.,Ltd.)
参考来源:WO 9732854
📄 详细内容
合成路线:AD-8717 was obtained as shown in Scheme 24060801a.The condensation of 2-mercaptonicotinic acid (I) with 2,4-dimethoxybenzyl alcohol (II) by means of HCl in acetone yields 2-[(2,4-dimethoxybenzyl)thio]nicotinic acid (III).The reaction of (III) with oxalyl chloride in dioxane yields the corresponding chloride,which is condensed with 4-amino-2,6-dimethylpyridine N-oxide (IV) by means of triethylamine in tetrahydrofuran affording 4-[2-[(2,4-dimethoxybenzyl)thio]nicotinoylamino]-2,6-dimethylpyridine N-oxide (V).The reduction of (V) with phosphorus trichloride in dichloromethane yields 2-[(2,4-dimethoxybenzyl)thio]-N-(2,6-dimethyl-4-pyridyl)nicotinamide (VI),which is finally oxidized with m-chloroperbenzoic acid in dichloromethane.
参考文献标题:AD-8717
文献作者:Nakamura,K.; Terauchi,H.; Komiya,M.
参考来源:Drugs Fut 1997,22(12),1309