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| | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate Basic information |
| Product Name: | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | | Synonyms: | 6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOYLIC ACID ETHYL ESTER;6-FLUORO-1-METHYL-4-OXO-7-(1-PIPRAZINYL)-1H,4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID, ETHYL ESTER;6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]-thiazeto[3,2-a]-3-quinolinecarboxylic acid ethyl ester;Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-(1,3)-thiazeto(3,2-a);ETHYL 6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)-THIAZETO(3,2-A) QUINOLINE-3-CARBOXYLATE;Prulifloxacin Intermediate PL-10;Ethyl 6-fluoro-1-Methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate;6- fluoro -1-Methyl-4- oxo-7-(1-piperazinyl)-4H-(1,3) S,N-containing heterocyclic bi-(3,2-a) quinoline -3- carboxylic acid ethyl ester | | CAS: | 113028-17-4 | | MF: | C18H20FN3O3S | | MW: | 377.43 | | EINECS: | 601-222-6 | | Product Categories: | Other Products;API intermediates;PRULIFLOXACIN | | Mol File: | 113028-17-4.mol | ![Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate Structure](CAS/GIF/113028-17-4.gif) |
| | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate Chemical Properties |
| Melting point | 224 °C | | Boiling point | 579.1±50.0 °C(Predicted) | | density | 1.44±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 8.69±0.10(Predicted) | | CAS DataBase Reference | 113028-17-4(CAS DataBase Reference) |
| | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate Usage And Synthesis |
| Uses | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate is an off-white to slightly yellow powder used as an intermediate for prulifloxacin. | | Synthesis | The general procedure for the synthesis of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazepine[3,2-a]quinoline-3-carboxylate from ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazepine[3,2-a]quinoline-3-carboxylate and piperazine was carried out as follows: 50 g of ethyl 6,7-difluoro-1-methyl-4 -oxo-4H-[1,3]thiazino[3,2-a]quinoline-3-carboxylic acid ethyl ester was dissolved in 5 volumes of DMSO and heated to 60 °C. Subsequently, 40 g of piperazine was added and the reaction was kept stirred at 60°C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, 5 volumes of acetonitrile was added and stirring was continued at room temperature for 4 hours. The precipitate was collected by filtration and dried to give 52.8 g of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-[1,3]thiazolocyclo[3,2-a]quinoline-3-carboxylate in 87% yield. After further purification, the yield of ethyl 6-fluoro-7-piperazine-1-methyl-4-oxo-[1,3]thiazolocyclo[3,2-a]quinoline-3-carboxylate was up to 99%. | | References | [1] Patent: CN107383069, 2017, A. Location in patent: Paragraph 0061; 0062
[2] Patent: CN107501298, 2017, A. Location in patent: Paragraph 0055; 0056
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 25, p. 4727 - 4738
[4] Patent: US4843070, 1989, A
[5] Patent: WO2009/93268, 2009, A1. Location in patent: Page/Page column 15 |
| | Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate Preparation Products And Raw materials |
| Raw materials | Carbamodithioic acid, N-(3,4-difluorophenyl)-, compd. with N,N-diethylethanamine (1:1)-->6,7-Difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylicacidethylester-->113028-76-5-->3,4-Difluoroaniline-->113028-77-6-->3,4-Difluorophenyl isothiocyanate-->Ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate-->Piperazine |
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