5-Amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 5-Amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 111542-93-9
• Molecular Formula: C₁₉H₂₂F₂N₄O₃
• Molecular Weight: 392.405
• DSSTox Substance ID: DTXSID9058652
• Nikkaji Number: J380.581F
• Wikidata: Q72508617
• ChEMBL ID: CHEMBL15273
• Mol file: 111542-93-9.mol

Synonyms:5-amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-;5-Amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,;MFCD00869619;NCGC00159333-02;5-amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;MLS001213240;CHEMBL15273;SCHEMBL1387460;DTXSID9058652;HMS3655C20;AKOS004119971;SMR000542848;LS-172156;FT-0631055;FT-0674635;5-Amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3,5-dimethyl-1-piperazinyl)quinoline-3-carboxylic acid;5-Amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;5-AMINO-1-CYCLOPROPYL-7-(3,5-DIMETHYLPIPERAZINO)-6,8-DIFLUORO-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID

Chemical Property of 5-Amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

• Appearance/Colour: off-white to yellow crystals
• Melting Point: 260-265 °C
• Boiling Point: 640.368 °C at 760 mmHg
• PKA: 6.42±0.50(Predicted)
• Flash Point: 341.082 °C
• PSA: 100.59000
• Density: 1.436 g/cm³
• LogP: 3.05660
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 392.16599690
• Heavy Atom Count: 28
• Complexity: 691

Purity/Quality:

99% ^*data from raw suppliers

Sparfloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CC(N1)C)C2=C(C(=C3C(=C2F)N(C=C(C3=O)C(=O)O)C4CC4)N)F
• Uses: Antibacterial.

Technology Process of 5-Amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 10 articles about 5-Amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-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: 70.0%

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (103772-14-1) + 3,5-dimethylpiperazine (108-49-6) → 5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (111542-93-9)

Guidance literature:

With triethylamine; In pyridine; Heating;

DOI:10.1021/jm00107a039

Reference yield:

2,3,4,5-tetrafluorobenzoic acid (1201-31-6) → 5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (111542-93-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 35 percent / fuming HNO₃, H₂SO₄ / 5.5 h / 70 °C

2: oxalyl chloride, DMF / CH₂Cl₂ / 16 h

3: 1.) n-BuLi, dipyridyl / 1.) THF, -30 deg C, 2.) THF, from -78 deg C to -35 deg C, 1 h

4: 95 percent / Ac₂O / 3 h / Heating

5: 2-methyl-propan-2-ol / 3.5 h / 45 °C

6: t-BuOK / 6 h / 60 °C

7: 100 percent / H₂ / RaNi / tetrahydrofuran; ethanol / 12 h / 1034.3 Torr

8: 100 percent / 6 M HCl / 2 h / Heating

9: 70 percent / Et₃N / pyridine / Heating

With hydrogenchloride; n-butyllithium; dipyridyl; oxalyl dichloride; sulfuric acid; potassium tert-butylate; hydrogen; nitric acid; acetic anhydride; triethylamine; N,N-dimethyl-formamide; RaNi; In tetrahydrofuran; pyridine; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jm00107a039

Reference yield:

2,3,4,5-tetrafluoro-6-nitrobenzoic acid (16583-08-7) → 5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (111542-93-9)

Guidance literature:

Multi-step reaction with 8 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 16 h

2: 1.) n-BuLi, dipyridyl / 1.) THF, -30 deg C, 2.) THF, from -78 deg C to -35 deg C, 1 h

3: 95 percent / Ac₂O / 3 h / Heating

4: 2-methyl-propan-2-ol / 3.5 h / 45 °C

5: t-BuOK / 6 h / 60 °C

6: 100 percent / H₂ / RaNi / tetrahydrofuran; ethanol / 12 h / 1034.3 Torr

7: 100 percent / 6 M HCl / 2 h / Heating

8: 70 percent / Et₃N / pyridine / Heating

With hydrogenchloride; n-butyllithium; dipyridyl; oxalyl dichloride; potassium tert-butylate; hydrogen; acetic anhydride; triethylamine; N,N-dimethyl-formamide; RaNi; In tetrahydrofuran; pyridine; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jm00107a039

upstream raw materials:

5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

3,5-dimethylpiperazine

2,3,4,5-tetrafluorobenzoic acid

2,3,4,5-tetrafluoro-6-nitrobenzoic acid

Refernces

• 1、 -. "Process for making antimicrobial quinolonyl lactams". . . Retrieved 2008/06/13.