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【结 构 式】 
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【分子编号】10063 【品名】ethyl 6,8-difluoro-7-(4-methylpiperazino)-1-[2-[(methylsulfonyl)oxy]ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C20H25F2N3O6S 【 分 子 量 】473.4979264 【元素组成】C 50.73% H 5.32% F 8.02% N 8.87% O 20.27% S 6.77% |
合成路线1
该中间体在本合成路线中的序号：(VI)A new synthesis of fleroxacin, labeled with fluorine-18, has been described: The reaction of 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (I) with 2-bromoethanol (II) gives 6,7,8-trifluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (III), which is condensed with N-methylpiperazine (IV), yielding 6,8-difluoro-1-(2-hydroxyethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (V). The reaction of (V) with methanesulfonyl chloride affords the corresponding mesylate (VI), which is treated with [18F]-KF in dichloromethane at 80 C to give 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (VII). Finally, this compound is hydrolyzed with NaOH.
| 【1】 Liu, Y.Y.; Cleeland, R.; Livni, E.; Rubin, R.H.; Thom, E.; Strauss, H.W.; Fischman, A.J.; Fleroxacin, a quinolone antibacterial agent. Labeling with fluorine-18 for pharmacokinetic studies. J Label Compd Radiopharm 1993, 32, 576. |
| 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) | 10058 | ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate | 79660-46-1 | C12H8F3NO3 | 详情 | 详情 |
| (II) | 10059 | Ethylene bromohydrin; 2-Bromo-1-ethanol | 540-51-2 | C2H5BrO | 详情 | 详情 |
| (III) | 10060 | ethyl 6,7,8-trifluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C14H12F3NO4 | 详情 | 详情 | |
| (IV) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (V) | 10062 | ethyl 6,8-difluoro-1-(2-hydroxyethyl)-7-(4-methylpiperazino)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C19H23F2N3O4 | 详情 | 详情 | |
| (VI) | 10063 | ethyl 6,8-difluoro-7-(4-methylpiperazino)-1-[2-[(methylsulfonyl)oxy]ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C20H25F2N3O6S | 详情 | 详情 | |
| (VII) | 10064 | ethyl 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazino)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C19H22F3N3O3 | 详情 | 详情 | |
| (VII) | 44571 | ethyl 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C19H22F3N3O3 | 详情 | 详情 |