6,8-Difluoro-1-(formylmethylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester synthesis
- Product Name:6,8-Difluoro-1-(formylmethylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
- CAS Number:158585-86-5
- Molecular formula:C19H22F2N4O4
- Molecular Weight:408.4
109-01-3
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100276-65-1
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158585-86-5
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Yield:158585-86-5 58%
Reaction Conditions:
at 100; for 1 h;
Steps:
21
Example 216, 8-Difluoro-l - (methylamino) - 7- (4-methylpiperazin-l -yl) - 4-Qxo-l , 4-quinoline-3-carboxylic acid (one-pot reaction) 6,7, 8-Trifluoro-1- (N-methylformamido ) -4-oxo-1, 4- quinoline-3-carboxylic acid ethyl ester (1.0 mmol, 324mg) was mixed with 2 equivalents of N-methylpiperazine (200mg) and stirred for one hour at 100°C. Reaction mixture liquefied in 10 minutes and solidified again within 30 minutes of reaction. After one hour of reaction the reaction mixture was cooled to room temperature and 10% aqueous H2S04 (5mL) was added and stirred again at 100°C for two hours. Yellow solution was cooled to 0°C so that product precipitated. It was isolated by filtration under reduced pressure. Pure 6 , 8-difluoro-1- (methylamino ) -7- ( 4- methylpiperazin-l-yl ) -4-oxo-1, 4-quinoline-3-carboxylic acid in the form of sulfate salt was obtained (as deter¬ mined by NMR) as slightly yellow powder (279mg, 58%).
References:
KRKA, TOVARNA ZDRAVIL, D.D., NOVO MESTO;ZUPET, Rok;ISKRA, Jernej;RUZIC, Milos;PECAVAR, Anica;KOLENC, Ivanka;PUCELJ, Jože;PLAPER, Igor WO2011/61292, 2011, A1 Location in patent:Page/Page column 43-44
109-01-3
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![2,3,4,5-Tetrafluoro-α-[(2-forMyl-2-Methylhydrazinyl)Methylene]-β-oxobenzenepropanoic Acid Ethyl Ester](/CAS/20180906/GIF/100276-64-0.gif)
100276-64-0
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158585-86-5
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