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ChemicalBook--->CAS DataBase List--->112984-60-8

112984-60-8

112984-60-8 Structure

112984-60-8 Structure
IdentificationMore
[Name]

6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid
[CAS]

112984-60-8
[Synonyms]

6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-FLUORO-1-METHYL-4-OXO-7-PIPERAZIN-1-YL-4H-2-THIA-8B-AZA-CYCLOBUTA[A] NAPHTHALENE-3-CARBOXYLIC ACID
PRULIFLOXACIN INTERMEDIATE 3
6-Fluoro-1-Methyl-4-Oxo-7-(1-Piperazinyl)-4H-(1,3)-Thiazeto(3,2-Alpha)Quinoline-3-Carboxylic Acid
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPRAZINYL)-4H-(1,3)-THIAZETO(3,2-A)QUINOLINE-3-CAR
1H,4H-[1,3]Thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPRAZINYL)-1H,4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)-thiazeto(3,2-a)quinoline-3-carboxylic acid cas:(intermediate of prulifloxacin)
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)-HIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-FLUORO-7-PIPERAZINE-1-METHYL-4-OXY-[1,3]THIOAZACYCLIC[3,2-A]-QUINOLINE-3-CARBOXYLIC ACID
NM 394
6-Fluoro-1-methyl-7-(1-piperazinyl)-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acid
ulifloxacin
Prulifloxacin Intermediate PL-11
6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)-thiazeto
[EINECS(EC#)]

601-220-5
[Molecular Formula]

C16H16FN3O3S
[MDL Number]

MFCD00882994
[Molecular Weight]

349.38
[MOL File]

112984-60-8.mol
Chemical PropertiesBack Directory
[Melting point ]

215-218 °C (decomp)
[Boiling point ]

577.0±50.0 °C(Predicted)
[density ]

1.58±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO (Sparingly), Methanol (Slightly)
[form ]

Solid
[pka]

5.85±0.40(Predicted)
[color ]

Pale Yellow to Yellow
[CAS DataBase Reference]

112984-60-8(CAS DataBase Reference)
Questions And AnswerBack Directory
[Synthesis]

Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piprazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

113028-17-4

6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

112984-60-8

The general procedure for the synthesis of 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazolo[3,2-a]quinoline-3-carboxylic acid from ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1,4-dihydro-[1,3]thiazolo[3,2-a]quinoline-3-carboxylate was as follows: 1. ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazolo[3,2-a]quinoline-3-carboxylate (100 g, 0.265 mol) was dissolved in water (600 ml) at 25-30 °C with stirring. 2. potassium hydroxide solution (50 g of potassium hydroxide flakes dissolved in 200 ml of water) was slowly added to this solution. 3. the reaction mixture is heated to 80-85°C and stirred at this temperature for 1 hour. 4. After completion of the reaction, the reaction mixture was cooled down to 25-30 °C. The reaction mixture was then cooled down to 25-30 °C. 5. The pH of the reaction mixture was adjusted to 6.5-7.0 using a 1:1 aqueous solution of acetic acid. 6. The reaction mixture was stirred at room temperature for 1 hour to allow the product to fully precipitate. 7. The precipitated solid was collected by filtration and washed with distilled water (2 x 100 mL). 8. The solid was slurried in methanol (300 ml) at 25-30 °C for 1 h. The reaction mixture was stirred for 1 h at room temperature. 9. After filtration, the solid was washed with methanol (2 x 50 ml). 10. The product was dried under vacuum at 70-75 °C to afford 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (90 g, 97% yield, 96% HPLC purity).

references:

[1] Patent: WO2012/1357, 2012, A1. Location in patent: Page/Page column 22

[2] Patent: CN103113392, 2016, B. Location in patent: Paragraph 0024; 0037; 0038; 0039

[3] Patent: CN107383069, 2017, A. Location in patent: Paragraph 0063; 0064

[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 25, p. 4727 - 4738

[5] Patent: WO2009/93268, 2009, A1. Location in patent: Page/Page column 15

Hazard InformationBack Directory
[Chemical Properties]

Yellow Solid
[Uses]

A labelled metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia.
[Uses]

A metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia.
[Definition]

ChEBI: Ulifloxacin is a member of quinolines.
[Biological Activity]

Ulifloxacin is an orally availablebroad-spectrum fluoroquinolone antibacterial agent. Ulifloxacin is an active metabolite of Prulifloxacin. It potently inhibits bacterial DNA gyrase and topoisomerase IV.
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