NT-702, NM-702
帕格雷利Chemical Name: 4-Bromo-6-[3-(4-chlorophenyl)propoxy]-5-(pyridin-3-ylmethylamino)pyridazin-3(2H)-one hydrochloride
CAS No. 139145-27-0 (free base), 139145-89-4 (fumarate salt (2:1)), 139145-87-2 (maleate salt (1:1)), 139145-84-9 (monoHCl)
项目整合开发状态: Phase II
项目研究机构: Nissan Chemical (Originator), Catalyst Pharmaceutical (Licensee), Taisho (Codevelopment)
合成路线:The title compound was prepared by condensation of the dibromopyridiazinone (I) with 3-picolylamine (II),followed by conversion to the corresponding hydrochloride salt
📌 参考资料/链接：
参考文献标题:Pyridazinone deriv.
文献作者:Tanikawa,K.; Saito,A.; Matsumoto,T.; Sakoda,R.; Tsuruzoe,N.; Shikada,K.-I.(Nissan Chemical Industry,Ltd.)
参考来源:EP 0482208; JP 1992507543; US 5202323; US 5314883; US 5318968; WO 9116314
📄 详细内容
合成路线:An improved procedure,amenable to the industrial synthesis of the precursor (I) was further developed.Heck coupling of p-chloroiodobenzene (III) with allyl alcohol (IV) in the presence of tetramethylammonium chloride and a catalytic amount of palladium acetate provided 3-(p-chlorophenyl)propanal (V) along with minor amounts of its branched isomer (VI).Further reduction of this mixture with NaBH4 led to the respective alcohols (VII) and (VIII).Only the desired alcohol (VII) underwent bromination to the desired bromide (IX) in the presence of PBr3 in hot toluene,whereas the branched alcohol (VIII) was dehydrohalogenated to olefin (X).Subsequent alkylation of pyridazinedione (XI) with the above reaction mixture afforded the pure intermediate
参考文献标题:Processes for the preparation of (p-chlorophenyl)propanol derivs.
文献作者:Matsumoto,H.; Kamikawaji,M.; Horiuchi,T.(Nissan Chemical Industry,Ltd.)
参考来源:EP 1138660; WO 0035843
产品链接: CAS No. 139145-27-0››