【结 构 式】 |
【分子编号】29038 【品名】7-chloro-6-fluoro-1-(methylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C11H8ClFN2O3 【 分 子 量 】270.6473032 【元素组成】C 48.82% H 2.98% Cl 13.1% F 7.02% N 10.35% O 17.73% |
合成路线1
该中间体在本合成路线中的序号:(VI)The reaction of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (I) with O-(2,4-dinitrophenyl)hydroxylamine (II) by means of K2CO3 in DMF gives ethyl 1-amino-6-fluoro-7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (III), which is formylated with HCOOH in acetic anhydride yielding the corresponding 1-(formylamino) compound (IV). The methylation of (IV) with MeI and K2CO3 in DMF affords the 1-(formylmethylamino) compound (V), which is hydrolyzed with NaOH in refluxing water to give 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-(methylamino)quinoline-3-carboxylic acid (VI). Finally, this compound is condensed with N-methylpiperazine (VII) in refluxing pyridine.
【1】 Powles, R.G.; Wentland, M.P.; Wagner, R.B.; Dobson, .A.; Bailey, D.M.; Cornett, J.B.; Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: Synthesis and stucture-activity relationships. J Med Chem 1984, 27, 9, 1103. |
【2】 Wentland, M.P.; Bailey, D.M. (Sterling Winthrop Inc.); New quinolone compounds and preparation thereof. EP 0090424; JP 8401468 . |
【3】 Castaner, J.; Serradell, M.N.; Burnie, J.; Matthews, R.; Amifloxacin. Drugs Fut 1985, 10, 3, 183. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 19904 | ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C12H9ClFNO3 | 详情 | 详情 | |
(II) | 29034 | 1-(aminooxy)-2,4-dinitrobenzene | C6H5N3O5 | 详情 | 详情 | |
(III) | 29035 | ethyl 1-amino-7-chloro-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C12H10ClFN2O3 | 详情 | 详情 | |
(IV) | 29036 | ethyl 7-chloro-6-fluoro-1-(formylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C13H10ClFN2O4 | 详情 | 详情 | |
(V) | 29037 | ethyl 7-chloro-6-fluoro-1-[formyl(methyl)amino]-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C14H12ClFN2O4 | 详情 | 详情 | |
(VI) | 29038 | 7-chloro-6-fluoro-1-(methylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid | C11H8ClFN2O3 | 详情 | 详情 | |
(VII) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |