Y-26611

合成路线:The condensation of 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (I) with 2-(formylamino-methyl)- morpholine (II) by means of 1,8-diazabicyclo[5.4.0]-7-undecene (DABU) in refluxing acetonitrile gives the formamido derivative (III),which is then hydrolyzed with concentrated HCl in refluxing methanol.

参考文献标题:Y-26611
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1992,17(2),114


合成路线:A new synthesis for Y-26611 has been reported:The reaction of 4-benzyl-2-(chloromethyl)morpholine (I) with potassium phthalimide (II) in refluxing DMF gives 4-benzyl-2-(phthalimidomethyl)morpholine (III),which is treated with hydrazine hydrate in refluxing ethanol yielding 2-(aminomethyl)-4-benzylmorpholine (IV).The acetylation of (IV) with acetic anhydride in cool toluene affords 2-(acetamidomethyl)-4-benzylmorpholine (V),which is debenzylated by hydrogenation with hydrazine hydrate over Pd/C in isopropanol to give 2-(acetamidomethyl)morpholine (VI).The condensation of (VI) with 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (VII) by means of triethylamine in refluxing acetonitrile yields 7-[2-(acetamidomethyl)morpholin-4-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (VIII),which is finally deacetylated with refluxing aqueous HCl.
参考文献标题:Quinolone antimicrobial agents substituted with morpholines at the 7-position.Syntheses and structure-activity relationships
文献作者:Araki,K.; Kuroda,T.; Uemori,S.; Moriguchi,A.; Ikeda,Y.; Hirayama,F.; Yokoyama,Y.; Iwao,E.; Yakushiji,T.
参考来源:J Med Chem 1993,36(10),1356