Gatifloxacin sesquihydrate

Base Information

• Chemical Name: Gatifloxacin sesquihydrate
• CAS No.: 160738-57-8
• Molecular Formula: C₂₂H₂₈FN₃O₇
• Molecular Weight: 465.47200
• Hs Code.: 2933990090
• European Community (EC) Number: 672-577-2
• UNII: L4618BD7KJ
• NCI Thesaurus Code: C29070
• RXCUI: 228476
• Mol file: 160738-57-8.mol

Synonyms:1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;AM 1155;AM-1155;BMS 206584;BMS-206584;BMS206584;CG 5501;gatifloxacin;gatifloxacine;Tequin;Zymar

Chemical Property of Gatifloxacin sesquihydrate

Chemical Property:

• Vapor Pressure: 1.73E-16mmHg at 25°C
• Melting Point: 162oC
• Boiling Point: 625.1oC at 760 mmHg
• Flash Point: 331.8oC
• PSA: 141.33000
• LogP: 1.82600
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 8
• Exact Mass: 804.35056276
• Heavy Atom Count: 57
• Complexity: 653

Purity/Quality:

99% ^*data from raw suppliers

Gatifloxacin hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F.CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F.O.O.O
• Description: Gatifloxacin is a novel orally-active fluoroquinolone antibiotic with a potent and broad spectrum of activity against gram-positive (S.pneumonia, S.aureus) and gram-negative bacteria. It shows good activity against strains resistant to established antituberculosis agents. Gatifloxacin was marketed for the treatment of respiratory tract and urinary infections, particularly the treatment of certain community-acquired infections (such as bronchitis, pneumonia and common sexually-transmitted diseases). Comparative studies with ciprofloxacin, ofloxacin and sparfloxacin against fluoroquinolone-resistant organisms indicated a better or equivalent effectiveness with less phototoxic adverse effects.

Technology Process of Gatifloxacin sesquihydrate

There total 30 articles about Gatifloxacin sesquihydrate 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:

1-cyclopropyl-6-fluoro-7-[4-[5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid

1-cyclopropyl-6-fluoro-7-[4-[5-(3-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid

1-cyclopropyl-6-fluoro-7-[4-[5-(2-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid

7-(4-benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Refernces

• 1、 -. "STREAMLINED SYNTHESES OF FLUOROQUINOLONES". Page/Page column 24. . Retrieved 2019/01/08.
• 2、 Villasante, F. Javier,Gude, Lourdes,Fernandez, Sara P.,Alonso, Olga,Garcia, Elena,Cosme, Antonio. "A high-throughput impurity-free process for gatifloxacin". . p. 900 - 903. Retrieved 2013/01/03.