Tifluadom, KC-5103
替氟朵Chemical Name: N-[5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-2-ylmethyl]thiophene-3-carboxamide; 1-Methyl-2-(3-thienylcarboxamidomethyl)-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine
CAS No. 83386-35-0, 81656-30-6 ((?-isomer)
项目整合开发状态: Preclinical
项目研究机构: Kali-Chemie (Originator), Novartis (Originator)
合成路线:The cyclization of N1-(2-fluorobenzoyl)-N2-methyl-N2-phenyl-2-hydroxy-1,3-diaminopropane (I) with refluxing POCl3 gives 1-methyl-2-chloromethyl-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine (II),which by condensation with potassium phthalimide (III) in refluxing methanol yields the corresponding phthalimido derivative (IV).The cleavage of (IV) with hydrazine in refluxing ethanol affords 1-methyl-2-aminomethyl-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine (V),which is finally condensed with thiophene-3-carbonyl chloride (VI) by means of triethylamine in methylene chloride.
📌 参考资料/链接：
参考文献标题:2-Acylaminomethyl-1,4-benzodiazepine derivs.and their salts and pharmaceutical compsns.thereof
文献作者:Zeugner,H.; R鰉er,D.; Liepmann,H.; Milkowski,W.(Kali-Chemie AG)
参考来源:US 4325957
📄 详细内容
合成路线:The cyclization of N1-(2-fluorobenzoyl)-N2-methyl-N2-phenyl-2-hydroxy-1,3-diaminopropane (I) with refluxing POCl3 gives 1-methyl-2-chloromethyl-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine (II),which by condensation with potassium phthalimide (III) in refluxing methanol yields the corresponding phthalimido derivative (IV).The cleavage of (IV) with hydrazine in refluxing ethanol affords 1-methyl-2-aminomethyl-5-(2-fluorophenyl)-1H-2,3-dihydro-1,4-benzodiazepine (V),which is finally condensed with thiophene-3-carbonyl chloride (VI) by means of triethylamine in methylene chloride.
参考文献标题:Tifluadom
文献作者:Serradell,M.N.; Paton,D.M.; Blancafort,P.; Castar,J.
参考来源:Drugs Fut 1983,8(6),519
产品链接: CAS No. 83386-35-0›› 产品链接: CAS No.81656-30-6››