BPDZ-176
Chemical Name: N-Cyclopentyl-7-fluoro-4H-1,2,4-benzothiadiazin-3-amine 1,1-dioxide
CAS No. 201224-27-3
项目整合开发状态: Biological Testing
项目研究机构: Novo Nordisk (Originator)
合成路线:The target thiadiazine dioxide has been obtained by reaction of 7-methoxy--3-(methylsulfanyl)-4H-1,2,4-benzothiadiazine-1,1-dioxide (I) or 3-(1-imidazolyl)-7-methoxy-4H-1,2,4-benzothiadiazine-1,1-dioxide (II) with isopropylamine (III) at 120-150 C in a pressure vessel.
合成路线:Reaction of 4-fluoroaniline (I) with chlorosulfonyl isocyanate (II) in the presence of aluminum trichloride gives rise to the benzothiadiazine dioxide (III).After conversion of the 3-oxo compound (III) into the corresponding thioxo derivative (IV) by means of phosphorus pentasulfide in pyridine,methylation with iodomethane and NaHCO3 affords the 3-methylsulfanyl benzothiadiazine (V) (1).Finally,the methylsulfanyl group in (V) is displaced by cyclopentylamine (VI) to furnish the target compound (1,2).
📌 参考资料/链接：
参考文献标题:1,2,4-Benzothiadiazine derivs.their preparation and use
文献作者:Pirotte,B.; Lebrun,P.; De Tullio,P.; Somers,F.; Delarge,J.; Hansen,J.B.; Nielsen,F.E.; Hansen,H.C.; Mogensen,J.P.; Tagmose,T.M.(Novo Nordisk A/S)
参考来源:EP 0906297; JP 2000512641; US 6242443; WO 9749692
📄 详细内容
合成路线:Reaction of 4-fluoroaniline (I) with chlorosulfonyl isocyanate (II) in the presence of aluminum trichloride gives rise to the benzothiadiazine dioxide (III).After conversion of the 3-oxo compound (III) into the corresponding thioxo derivative (IV) by means of phosphorus pentasulfide in pyridine,methylation with iodomethane and NaHCO3 affords the 3-methylsulfanyl benzothiadiazine (V) (1).Finally,the methylsulfanyl group in (V) is displaced by cyclopentylamine (VI) to furnish the target compound (1,2).
参考文献标题:Toward tissue-selective pancreatic B-cells KATP channel openers belonging to 3-alkylamino-7-halo-4H-1,2,4-benzothiadiazine 1,1-dioxides
文献作者:De Tullio,P.; Becker,B.; Boverie,S.; Dabrowski,M.; Wahl,P.; Antoine,M.-H.; Somers,F.; Sebille,S.; Ouedraogo,R.; Hansen,J.B.; Lebrun,P.; Pirotte,B.
参考来源:J Med Chem 2003,46(15),3342