6,8-Difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 6,8-Difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 100276-37-7
• Molecular Formula: C16H20F2N4O7S
• Molecular Weight: 450.4144064
• European Community (EC) Number: 807-867-1
• DSSTox Substance ID: DTXSID801113767
• Nikkaji Number: J3.643.409K
• Mol file: 100276-37-7.mol

Synonyms:100276-37-7;Marbofloxacin Impurity C;6,8-difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;6,8-difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;6,8-Difluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid;SCHEMBL2018897;DTXSID801113767

Chemical Property of 6,8-Difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

• Boiling Point: 522.2±60.0 °C(Predicted)
• PKA: 6.14±0.50(Predicted)
• PSA: 77.81000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 0.97890
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 352.13469677
• Heavy Atom Count: 25
• Complexity: 580

Purity/Quality:

99.9% ^*data from raw suppliers

6,8-Difluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylicAcidSulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNN1C=C(C(=O)C2=CC(=C(C(=C21)F)N3CCN(CC3)C)F)C(=O)O
• Uses: 6,8-Difluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate is an intermediate in the synthesis of Marbofloxacin (M197000), a fluorinated quinolone antibacterial agent.

Technology Process of 6,8-Difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 6 articles about 6,8-Difluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

ethyl 6,8-difluoro-1,4-dihydro-1-(N-methylformamido)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate (158585-86-5) → 6,8-Difluor-1-(methylamino)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeure (100276-37-7)

Guidance literature:

With sulfuric acid; at 100 ℃; for 2h; Product distribution / selectivity;

Reference yield: 80.0%

1-methyl-piperazine (109-01-3) + 6,7,8-Trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid (100276-67-3) → 6,8-Difluor-1-(methylamino)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeure (100276-37-7)

Guidance literature:

With triethylamine; In ethanol; at 100 ℃; for 19h; Product distribution / selectivity;

Reference yield:

6,7,8-Trifluor-1-(formylmethylamino)-1,4-dihydro-4-oxo-3-chinolincarbonsaeure-ethylester (100276-65-1) → 6,8-Difluor-1-(methylamino)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeure (100276-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / KOH / H₂O / 1 h / Heating

2: 76 percent / pyridine / 6 h / Heating

With potassium hydroxide; In pyridine; water;

upstream raw materials:

1-methyl-piperazine

6,7,8-Trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid

ethyl 2-(ethoxymethylene)-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate

2-(2,3,4,5-Tetrafluorbenzoyl)-3-(2-formyl-2-methylhydrazino)acrylsaeure-ethylester