N-Desmethyl ofloxacin

Base Information

• Chemical Name: N-Desmethyl ofloxacin
• CAS No.: 82419-52-1
• Molecular Formula: C17H18 F N3 O4
• Molecular Weight: 347.34
• Hs Code.: 2934990002
• European Community (EC) Number: 809-501-6
• UNII: 5S4363I4ED
• ChEMBL ID: CHEMBL966
• DSSTox Substance ID: DTXSID301017803
• Nikkaji Number: J1.000.064E
• Wikidata: Q27262803
• Mol file: 82419-52-1.mol

Synonyms:N-Desmethyl ofloxacin;82419-52-1;9-Fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid;N-Desmethyl ofloxacin, (+/-)-;DESMETHYL-OFLOXACIN;DESMETHYL-OFLOXACIN (5%);5S4363I4ED;Ofloxacin Impurity E;7-fluoro-2-methyl-10-oxo-6-piperazin-1-yl-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid;(3RS)-9-Fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-2,3-dihydro-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid;7H-Pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-7-oxo-10-(1-piperazinyl)-;(RS)-9-Fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid;UNII-5S4363I4ED;Ofloxacin Imp. E (EP);Ofloxacin USP Related Compound A;Ofloxacin USP RC A;(RS)-9-Fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid;Ofloxacin Related Compound A;Ofloxacin specified impurity E [EP];97791-27-0;CHEMBL966;SCHEMBL6246239;DTXSID301017803;BDBM50229966;AKOS027295018;N-Desmethyl ofloxacin, analytical standard;OFLOXACIN IMPURITY E [EP IMPURITY];FT-0666182;FT-0701405;NS00040617;A899988;Q27262803;Ofloxacin impurity E, European Pharmacopoeia (EP) Reference Standard;9-Fluoro-2,3-dihydro-3-methyl-7-oxo-10-(1-piperazinyl)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid;9-Fluoro-3-methyl-7-oxo-10-(piperazin-1-yl)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylicacid;Ofloxacin related compound a(25 mg)((rs)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-10-(pipera-zin-1-yl)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid)

Chemical Property of N-Desmethyl ofloxacin

Chemical Property:

• Melting Point: >2500C (dec.)
• Boiling Point: 600.7±55.0 °C(Predicted)
• PKA: 5.19±0.40(Predicted)
• PSA: 83.80000
• Density: 1.51±0.1 g/cm3(Predicted)
• LogP: 1.59560
• Storage Temp.: -20?C Freezer
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly,
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 347.12813423
• Heavy Atom Count: 25
• Complexity: 607

Purity/Quality:

98%Min ^*data from raw suppliers

DesmethylOfloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCNCC4)F)C(=O)O
• Uses: Desmethyl Ofloxacin (Ofloxacin EP Impurity E) is a metabolite of Ofoxacin (O245750), a fluorinated quinolone antibacterial.

Technology Process of N-Desmethyl ofloxacin

There total 8 articles about N-Desmethyl ofloxacin 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: 94.0%

piperazine (110-85-0) + 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid (82419-35-0) → N-Demethylofloxacin (82419-52-1)

Guidance literature:

With nano iron oxide on ZrO₂ coated sulfonic acid; In water; for 0.45h; Reflux;

DOI:10.2174/1570178615666171226162735

Reference yield:

ofloxacin (82419-36-1,83380-47-6) → C13H12N2O4 + C14H18FN3O4 + C15H20FN3O4 + C16H18FN3O4 + N-Demethylofloxacin (82419-52-1) + 10-amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (86794-33-4) + ofloxacin (123155-82-8,178964-53-9) + 9-fluoro-2,3-dihydro-3-methyl-10-(N-methyl-N',N-diformyl-2-aminoethylamino)-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (151377-74-1)

Guidance literature:

With water; Reagent/catalyst; Catalytic behavior; Kinetics; Irradiation;

DOI:10.1039/c7dt04360k

Reference yield:

2,3,4-trifluoronitrobenzene (771-69-7) → N-Demethylofloxacin (82419-52-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 29 percent / 10percent KOH / H₂O; dimethylsulfoxide / 2 h / 18 - 20 °C

2: 65 percent / K₂CO₃, KI / acetone / 4 h / Heating

3: 90 percent / H₂, Raney Ni / ethanol

4: 1 h / 140 - 145 °C

5: PPE / 1 h / 140 - 145 °C

6: 94 percent / conc. HCl / acetic acid / 3 h / Heating

7: 53 percent / dimethylsulfoxide / 3 h / 100 - 140 °C

With hydrogenchloride; potassium hydroxide; hydrogen; nickel; potassium carbonate; potassium iodide; In ethanol; water; acetic acid; dimethyl sulfoxide; acetone;

DOI:10.1248/cpb.32.4907

upstream raw materials:

piperazine

9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid

2,3,4-trifluoronitrobenzene

3,4-difluoro-2-(2-oxopropyloxy)nitrobenzene

Downstream raw materials:

8-fluoro-9-[4-(4-fluorophenylsulfonyl)piperazin-1-yl]-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid

8-fluoro-9-[4-(4-fluorobenzoyl)piperazin-1-yl]-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid

9-[4-benzoylpiperazin-1-yl]-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid

8-fluoro-3-methyl-9-[4-(4-methoxybenzoyl)piperazin-1-yl]-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid

Refernces

• 1、 Wang, Yingfei,Wang, Fengliang,Feng, Yiping,Xie, Zhijie,Zhang, Qianxin,Jin, Xiaoyu,Liu, Haijin,Liu, Yang,Lv, Wenying,Liu, Guoguang. "Facile synthesis of carbon quantum dots loaded with mesoporous g-C3N4 for synergistic absorption and visible light photodegradation of fluoroquinolone antibiotics". supporting information. p. 1284 - 1293. Retrieved 2018/02/07.
• 2、 Noel, Sabrina,Gasser, Veronique,Pesset, Benedicte,Hoegy, Franoise,Rognan, Didier,Schalk, Isabelle J.,Mislin, Gaetan L. A.. "Synthesis and biological properties of conjugates between fluoroquinolones and a N3′′-functionalized pyochelin". experimental part. p. 8288 - 8300. Retrieved 2012/04/10.