GYKI-12743
3(2H)-吡啶嗪,2-[3-[[(2,3-二氢-1,4-苯并二恶英-2-基)甲基]丙基]-,盐酸盐(1:1)Chemical Name: (?-2-[3-[N-(2-Benzo[1,4]dioxanyl)methylamino]propyl]-3(2H)-pyridazinone hydrochloride
CAS No. 110714-10-8
项目整合开发状态: Phase I
项目研究机构: Gedeon Richter (Originator)
合成路线:Title compound can be prepared as shown in Scheme:1) 3,6-Dichloropyridazine (I) is converted to 3(2H)-pyridazinone (III) in two steps.2) 3-N-(2-Benzo[1,4]dioxanylmethyl)amino-1-propanol (V),obtained by the reaction of (2-benzo[1,4]dioxanylmethyl)-4-toluenesulfonate (IV) with 3-amino-1-propanol,is N-benzylated to form the N-protected amino alcohol (VI),which on treatment with thionyl chloride affords the chloroalkyl derivative (VII).3) Alkylation of 3(2H)-pyridazinone (III) with (VII) under phase-transfer catalysis conditions to the N-benzylated GYKI-12743 (VIII) and then removal of the N-benzyl group by hydrogenation gives GYKI-12743.
📌 参考资料/链接：
参考文献标题:3(2H)-Pyridazinone derivs.,a process and intermediates for preparing them and medicaments containing them and/or other 3(2H)-pyridazinone derivatives
文献作者:Kasztreiner,E.; Rabloczky,G.; Makk,N.; Jaszlits,L.; Matyus,P.; Cseh,G.; Pribusz,geb.Rapp,I.; Czak? K.; Diesler,E.; Elekes,I.; Kaufer,L.; Kuh醨,geb.K黵thy,M.; Kincsessy,J.; Kos醨y,J.; Nagy,Gy鰊gyi geb.C.(Richter Gedeon Vegyeszeti)
参考来源:AU 8664496; EP 0220735; JP 87161768
📄 详细内容
合成路线:Title compound can be prepared as shown in Scheme:1) 3,6-Dichloropyridazine (I) is converted to 3(2H)-pyridazinone (III) in two steps.2) 3-N-(2-Benzo[1,4]dioxanylmethyl)amino-1-propanol (V),obtained by the reaction of (2-benzo[1,4]dioxanylmethyl)-4-toluenesulfonate (IV) with 3-amino-1-propanol,is N-benzylated to form the N-protected amino alcohol (VI),which on treatment with thionyl chloride affords the chloroalkyl derivative (VII).3) Alkylation of 3(2H)-pyridazinone (III) with (VII) under phase-transfer catalysis conditions to the N-benzylated GYKI-12743 (VIII) and then removal of the N-benzyl group by hydrogenation gives GYKI-12743.
参考文献标题:GYKI-12743
文献作者:Kasztreiner,E.; M醫yus,P.; Rabloczky,G.; Jaszlits,L.
参考来源:Drugs Fut 1989,14(7),622
产品链接: CAS No. 110714-10-8››