8-Desmethoxy-8-fluoro Moxifloxacin

Base Information

• Chemical Name: 8-Desmethoxy-8-fluoro Moxifloxacin
• CAS No.: 151213-15-9
• Molecular Formula: C₂₀H₂₁F₂N₃O₃
• Molecular Weight: 389.402
• Hs Code.: 29339900
• European Community (EC) Number: 604-776-7
• UNII: 3QPU25JTSN
• DSSTox Substance ID: DTXSID80164735
• Wikidata: Q27257911
• ChEMBL ID: CHEMBL109031
• Mol file: 151213-15-9.mol

Synonyms:151213-15-9;8-Desmethoxy-8-fluoro Moxifloxacin;1-Cyclopropyl-6,8-difluoro-7-((4aS,7aS)-hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;UNII-3QPU25JTSN;3QPU25JTSN;8-Desmethoxy-8-fluoro moxifloxacin, (-)-;7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid;EC 604-776-7;1-Cyclopropyl-6,8-difluoro-7-((4aS,7aS)-hexahydro-1H-pyrrolo-[3,4-b]pyridin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;1-Cyclopropyl-6,8-difluoro-7-((4aS,7aS)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-((4aS,7aS)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-;Moxifloxacin hydrochloride specified impurity A [EP];1-cyclopropyl-6,8-difluoro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-;7-((4aS,7aS)-1,2,4a,5,7,7a-Hexahydropyrrolo(3,4-b)pyridin-6-yl)-1-cyclopropyl-6,8-difluoro-4-oxo-3H-quinoline-3-carboxylic acid;7-[(4aS,7aS)-1,2,4a,5,7,7a-hexahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-3H-quinoline-3-carboxylic acid;CHEMBL109031;SCHEMBL8982729;DTXSID80164735;BCP18299;AKOS016006333;CS-W007161;DS-4217;8-DESMETHOXY-8-FLUOROMOXIFLOXACIN;F19417;J-008788;Q27257911;MOXIFLOXACIN HYDROCHLORIDE IMPURITY A [EP IMPURITY];1-Cyclopropyl-6,8-difluoro-7-((4aS,7aS)-hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid;1-Cyclopropyl-6,8-difluoro-7-((4aS,7aS)hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-, (4aS-cis)-

Chemical Property of 8-Desmethoxy-8-fluoro Moxifloxacin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 247-249°C
• Refractive Index: 1.637
• Boiling Point: 596.909ºC at 760 mmHg
• PKA: 6.41±0.50(Predicted)
• Flash Point: 314.799ºC
• PSA: 74.57000
• Density: 1.468g/cm3
• LogP: 2.89480
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly, Heated. Sonicated), Methanol (Slightly, Heated, Sonicated)
• Water Solubility.: 2.5g/L at 20℃
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 389.15509786
• Heavy Atom Count: 28
• Complexity: 713

Purity/Quality:

99.9% ^*data from raw suppliers

8-Desmethoxy-8-fluoro moxifloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2CN(CC2NC1)C3=C(C=C4C(=C3F)N(C=C(C4=O)C(=O)O)C5CC5)F
• Isomeric SMILES: C1C[C@H]2CN(C[C@H]2NC1)C3=C(C=C4C(=C3F)N(C=C(C4=O)C(=O)O)C5CC5)F
• Uses: 8-Desmethoxy-8-fluoro Moxifloxacin (Moxifloaxacin EP Impurity A) is an impurity of Moxifloxacin (M745000). Moxifloxacin

Technology Process of 8-Desmethoxy-8-fluoro Moxifloxacin

There total 4 articles about 8-Desmethoxy-8-fluoro Moxifloxacin 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: 87.1%

1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid (94695-52-0) + (1S,6S)-2,8-diazabicyclo[4.3.0]nonane (151213-40-0,158060-81-2,169533-56-6) → 1-cyclopropyl-6,8-difluoro-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (151096-44-5,151213-15-9)

Guidance literature:

1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid; With isobutylamine; copper dichloride; In methanol; ethylene glycol; at 50 ℃; for 4h; Inert atmosphere;

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane; In methanol; ethylene glycol; for 5h; Reflux;

Reference yield:

2,8-diazabicyclo-[4.3.0]-nonane (5654-94-4,158060-81-2,169533-56-6) + 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid (94695-52-0) → 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (151096-44-5,151213-15-9)

Guidance literature:

Reference yield:

C7H12N2O → 1-cyclopropyl-6,8-difluoro-7-((4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (151096-44-5,151213-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide; hydrazine / dimethyl sulfoxide / 7 h / 20 - 50 °C

2.1: isobutylamine; copper dichloride / ethylene glycol; methanol / 4 h / 50 °C / Inert atmosphere

2.2: 5 h / Reflux

With isobutylamine; potassium hydroxide; copper dichloride; hydrazine; In methanol; ethylene glycol; dimethyl sulfoxide;

upstream raw materials:

1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid

(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

2,8-diazabicyclo-[4.3.0]-nonane

Refernces

• 1、 -. "Quinolonecarboxylic acids". . . Retrieved 2008/06/13.