1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate

Base Information

• Chemical Name: 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate
• CAS No.: 112811-59-3
• Molecular Formula: C₁₉H₂₂FN₃O₄
• Molecular Weight: 375.4
• Hs Code.: 29335990
• Mol file: 112811-59-3.mol

Synonyms:1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate;160738-57-8;C19H22FN3O4;AKOS005702286

Chemical Property of 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.26E-15mmHg at 25°C
• Melting Point: 162 °C
• Refractive Index: 1.616
• Boiling Point: 607.8 °C at 760 mmHg
• PKA: 6.43±0.50(Predicted)
• Flash Point: 321.4 °C
• PSA: 83.80000
• Density: 1.386 g/cm³
• LogP: 2.37420
• Storage Temp.: Store at 0-5°C
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 375.15943435
• Heavy Atom Count: 27
• Complexity: 647

Purity/Quality:

99%min ^*data from raw suppliers

Gatifloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CC[NH2+]1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)[O-])C4CC4)F
• Description: Gatifloxacin belongs to a class of drugs known as quinolone antibiotics and is used to treat acute sinus, lung, or urinary tract infections and sexually transmitted bacterial infection.This drug may be taken orally, in tablet form, or by injection.Common side effects associated with gatifloxacin include nausea, vaginitis(irritation or inflammation of the vagina)，diarrhea, headache, dizziness, and irregular heart beats. In general, gatifloxacin is used in people who are unresponsive to other AOM therapies.In one study, gatifloxacin was compared with amoxicillin/clavulanate in the treatment of recurrent otitis media (OM) and AOM in treatment failures in children.Three hundred fifty-four infants and children with recurrent OM or AOM failure received gatifloxacin or amoxicillin/clavulanate.Results showed that both drugs were well tolerated; the most common side effect was diarrhea.Researchers concluded that treatment with gatifloxacin once daily was as effective as amoxicillin/clavulanate twice daily.In other medical literature, gatifloxacin has been noted as a third-line treatment option in AOM.
• Uses: An antibacterial An antibacterial.

Technology Process of 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate

There total 30 articles about 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylate 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: 91.7%

1-cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate (835920-87-1) → gatifloxacin (160738-57-8,112811-59-3)

Guidance literature:

With water; In ethanol; at 70 - 80 ℃; for 2h;

Reference yield: 91.0%

(+/-)-2-methylpiperazine bis(hydrochloride) (13264-88-5,66918-24-9,75336-85-5,75336-89-9,93334-99-7,475640-80-3) + 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (112811-72-0) → gatifloxacin (160738-57-8,112811-59-3)

Guidance literature:

(+/-)-2-methylpiperazine bis(hydrochloride); 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid; With boron trifluoride-tetrahydrofuran complex; triethylamine; In acetonitrile; at 20 ℃; for 25h;

With methanol; for 5h; Reflux;

With sodium hydroxide; In methanol; water; at 20 ℃; for 16h; pH=7;

Reference yield: 81.8%

(RS)-2-methylpiperazine (109-07-9) + 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (112811-72-0) → gatifloxacin (160738-57-8,112811-59-3)

Guidance literature:

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid; With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 76 - 80 ℃; for 1h; Heating / reflux;

With boron trifluoride diethyl etherate; In acetonitrile; at 0 - 25 ℃; for 2h;

(RS)-2-methylpiperazine; With triethylamine; In acetonitrile; at 15 - 25 ℃; for 3h; pH=~ 9;

upstream raw materials:

(RS)-2-methylpiperazine

1-cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid difluoroborate ester

1-cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Downstream raw materials:

C₃₈H₃₄F₂N₈O₇S

C₃₉H₃₇FN₈O₇S

C₃₈H₃₅FN₈O₇S

C₃₈H₃₄ClFN₈O₇S

Refernces

• 1、 -. "Gatifloxacin and synthesis method thereof". Paragraph 0061; 0063-0064; 0065; 0067-0068; 0069; 0071-0072. . Retrieved 2020/03/23.
• 2、 -. "METHOD FOR PRODUCING QUINOLONE CARBOXYLIC ACID DERIVATIVE". Page/Page column 12. . Retrieved 2009/12/24.