D-19274
Chemical Name: 3-[2-Amino-6-(4-fluorobenzylamino)pyridin-3-yl]oxazolidin-2-one hydrochloride
CAS No. 157840-43-2
项目整合开发状态: Preclinical
项目研究机构: Asta Medica (Originator)
合成路线:D-19274 can be obtained in a 6-step synthesis starting from 2,6-dichloropyridine (I).Compound (I) is nitrated with HNO3/H2SO4 yielding 2,6-dichloro-3-nitropyridine (II).Subsequent reaction with ammonia and 4-fluorobenzylamine leads to 2-amino-3-nitro-6-(4-fluorobenzylamino)pyridine (IV),which is hydrogenated using Raney Nickel as catalyst to the corresponding 3-amino derivative (V),which reacts with 2-bromoethyl chloroformate to 2-bromoethyl [N-(2-amino-6-(4-fluorobenzylamino)pyridin-3-yl)]carbamate hydrochloride (VI).(VI) is then treated with excess NaOH at 35 C,followed by treatment with isopropanol HCl to give the desired D-19274.
📌 参考资料/链接：
参考文献标题:3-(N-heterocyclyl)-2,6-diaminopyridines and N-oxides,their preparation and their use as medicines
文献作者:Engel,J.; Emig,P.; Nickel,B.; Szelenyi,I.(Asta Medica AG)
参考来源:DE 3915184; EP 0343429; JP 1990017186; US 4923858
📄 详细内容
合成路线:D-19274 can be obtained in a 6-step synthesis starting from 2,6-dichloropyridine (I).Compound (I) is nitrated with HNO3/H2SO4 yielding 2,6-dichloro-3-nitropyridine (II).Subsequent reaction with ammonia and 4-fluorobenzylamine leads to 2-amino-3-nitro-6-(4-fluorobenzylamino)pyridine (IV),which is hydrogenated using Raney Nickel as catalyst to the corresponding 3-amino derivative (V),which reacts with 2-bromoethyl chloroformate to 2-bromoethyl [N-(2-amino-6-(4-fluorobenzylamino)pyridin-3-yl)]carbamate hydrochloride (VI).(VI) is then treated with excess NaOH at 35 C,followed by treatment with isopropanol HCl to give the desired D-19274.
参考文献标题:D-19274
文献作者:Emig,P.; Engel,J.; Nickel,B.; Szelenyi,I.; Werner,U.
参考来源:Drugs Fut 1990,15(3),223