RTI-7527-33
Chemical Name: exo-5-(7-Azabicyclo[2.2.1]hept-2-yl)-2-chloropyridin-3-amine hydrochloride
CAS No. 426460-45-9 (free base)
项目整合开发状态: Preclinical
项目研究机构: Research Triangle Institute (Originator)
合成路线:Iodination of 2-amino-3-nitropyridine (I) using a combination of iodine and periodic acid yields 2-amino-5-iodo-3-nitropyridine (II).Sandmeyer reaction of aminopyridine (II) with sodium nitrite in concentrated HCl containing CuCl affords the chloro pyridine (III).The nitro group of (III) is then reduced to amine (IV) employing iron in ethanolic HCl.Palladium acetate-catalyzed addition of iodopyridine (IV) to N-Boc-7-azabicyclo[2.2.1]hept-2-ene (V) gives rise to the exo-adduct (VI).Finally,acidic cleavage of the Boc group of (VI) furnishes the title compound.
📌 参考资料/链接：
参考文献标题:Cpds.and methods for promoting smoking cessation
文献作者:Carroll,F.I.(Research Triangle Institute)
参考来源:US 6538010; WO 0237927
📄 详细内容
合成路线:Iodination of 2-amino-3-nitropyridine (I) using a combination of iodine and periodic acid yields 2-amino-5-iodo-3-nitropyridine (II).Sandmeyer reaction of aminopyridine (II) with sodium nitrite in concentrated HCl containing CuCl affords the chloro pyridine (III).The nitro group of (III) is then reduced to amine (IV) employing iron in ethanolic HCl.Palladium acetate-catalyzed addition of iodopyridine (IV) to N-Boc-7-azabicyclo[2.2.1]hept-2-ene (V) gives rise to the exo-adduct (VI).Finally,acidic cleavage of the Boc group of (VI) furnishes the title compound.
参考文献标题:Synthesis,nicotinic acetylcholine receptor binding,and antinociceptive properties of 2-exo-2-(2',3'-disubstituted 5'-pyridinyl)-7-azabicyclo[2.2.1]heptanes: Epibatidine analogues
文献作者:Carroll,F.I.; Lee,J.R.; Navarro,H.A.; Ma,W.; Brieaddy,L.E.; Abraham,P.; Damaj,M.I.; Martin,B.R.
参考来源:J Med Chem 2002,45(21),4755