Grepafloxacin

Base Information

• Chemical Name: Grepafloxacin
• CAS No.: 119914-60-2
• Deprecated CAS: 126292-40-8,146863-02-7
• Molecular Formula: C₁₉H₂₂FN₃O₃
• Molecular Weight: 359.4
• European Community (EC) Number: 631-454-3
• UNII: L1M1U2HC31
• DSSTox Substance ID: DTXSID2048321
• Nikkaji Number: J384.494C
• Wikipedia: Grepafloxacin
• NCI Thesaurus Code: C65817
• Metabolomics Workbench ID: 42736
• ChEMBL ID: CHEMBL583
• Mol file: 119914-60-2.mol

Synonyms:(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;(+--)-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid monohydrochloride;3-quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-;3-quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-, monohydrochloride, (+--)-;grepafloxacin;grepafloxacin HCl;grepafloxacin hydrochloride;OPC 17116;OPC-17116;Raxar

Chemical Property of Grepafloxacin

Chemical Property:

• Melting Point: 189-192 ºC
• Boiling Point: 610 °C at 760mmHg
• PKA: 6.44±0.50(Predicted)
• Flash Point: 322.7 °C
• PSA: 74.57000
• Density: 1.366 g/cm³
• LogP: 2.67400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 359.16451973
• Heavy Atom Count: 26
• Complexity: 636

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCN1)C2=C(C(=C3C(=C2)N(C=C(C3=O)C(=O)O)C4CC4)C)F
• Uses: dl-Grepafloxacin is an antibacterial compound used to treat various respirator infections.

Technology Process of Grepafloxacin

There total 3 articles about Grepafloxacin 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: 90.0%

(RS)-2-methylpiperazine (109-07-9) + 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid (119915-47-8) → grepafloxacin (119914-60-2,146863-02-7)

Guidance literature:

In acetonitrile; for 5h; Heating;

DOI:10.1021/jm00107a040

Reference yield:

(RS)-2-methylpiperazine (109-07-9) + 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (119916-34-6) → grepafloxacin (119914-60-2,146863-02-7)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; ethanol;

Reference yield:

1N-NaOH + ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-4-oxoquinoline-3-carboxylate (119915-46-7) + (RS)-2-methylpiperazine (109-07-9) → grepafloxacin (119914-60-2,146863-02-7)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; lithium chloride; In water; acetonitrile;

upstream raw materials:

(RS)-2-methylpiperazine

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

ethyl 1-cyclopropyl-6,7-difluoro-5-methyl-4-oxoquinoline-3-carboxylate

Refernces

• 1、 Hagen, Susan E.,Domagala, Johan M.,Heifetz, Carl L.,Johnson, Judith. "Synthesis and Biological Activity of 5-Alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic Acids". . p. 1155 - 1161. Retrieved 2007/10/02.
• 2、 -. "Benzoheterocyclic compounds". . . Retrieved 2008/06/13.