7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• CAS No.: 100361-18-0
• Molecular Formula: C12H8FClN2O3
• Molecular Weight: 282.659
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10453583
• Nikkaji Number: J3.282.834E
• Wikidata: Q72518133
• Mol file: 100361-18-0.mol

Synonyms:100361-18-0;7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID;1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic Acid;MFCD08458865;1-Cyclopropyl-6-fluoro-7-chloride-4-oxo-1,4-dihydro-1,8-napthyridine-3- carboxylic acid;1-Cyclopropyl-6-fluoro-7-chloride-4-oxo-1,4-dihydro-1,8-napthyridine-3-carboxylic acid;SCHEMBL500472;DTXSID10453583;BCP08987;AC-298;AKOS015849947;AM10715;CS-W003524;DS-0399;1,8-Naphthyridine-3-carboxylic acid, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-;SY021142;C2650;FT-0653832;EN300-18527577;J-000118;Z1741974417;1,4-Dihydro-1-cyclopropyl-4-oxo-6-fluoro-7-chloro-1,8-naphthyridine-3-carboxylic acid;1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-napthyridine-3-carboxylic acid;1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carb oxylic acid;1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid;1-cyclopropyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid;7-chloro 1-cyclopropyl-6-fluoro-1,4 dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-cyclo-propyl-6-fluoro-1,4-dihydro-4-oxo-[1,8]naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro -1, 4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1,8-Naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4 dihydro-4-oxo 1,8-naphthyridine 3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro -4-oxo-[1,8]naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-[1,8]naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8 -naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyri dine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine- 3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylicacid;7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid;7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8 -naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid;7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid;7-chloro-l-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Chemical Property of 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 209-212 °C
• Refractive Index: 1.692
• Boiling Point: 485.919 °C at 760 mmHg
• PKA: 5.96±0.70(Predicted)
• Flash Point: 247.675 °C
• PSA: 72.19000
• Density: 1.727 g/cm³
• LogP: 2.22210
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 282.0207480
• Heavy Atom Count: 19
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1N2C=C(C(=O)C3=CC(=C(N=C32)Cl)F)C(=O)O
• Uses: Gemifloxacin intermediate as antibacterial agent. Gemifloxacin intermediate as antibacterial agent

Technology Process of 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

There total 10 articles about 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 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: 78.0%

ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (96568-07-9) → 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (100361-18-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; for 2h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.02.019

Reference yield:

ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (100361-18-0)

Guidance literature:

With hydrogenchloride; acetic anhydride; triethylamine; Yield given. Multistep reaction;

DOI:10.1021/jm00059a012

Reference yield:

ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6) → 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (100361-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Ac₂O / 1 h / 140 °C

1.2: 90 percent / ethanol / 20 °C

2.1: K₂CO₃ / dioxane

3.1: 20percent aq. HCl / Heating

With acetic anhydride; potassium carbonate; In 1,4-dioxane;

DOI:10.1021/jm010057b

upstream raw materials:

ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

orthoformic acid triethyl ester

Cyclopropylamine

ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Downstream raw materials:

1-cyclopropyl-6-fluoro-1,4-dihydro-7-<3-<(methylamino)methyl>-1-pyrrolidinyl>-4-oxo-1,8-naphthyridine-3-carboxylic acid

3R,1S-7-[3-(1-aminoethyl)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid-O³,O⁴-diacetic acid boric acid

gemifloxacin

Refernces

• 1、 Markad, Shankar D.,Kaur, Parvinder,Kishore Reddy,Chinnapattu, Murugan,Raichurkar, Anandkumar,Nandishaiah, Radha,Panda, Manoranjan,Iyer, Pravin S.. "Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: Exploring hybridization of pyrazinamide with multiple fragments". . p. 2986 - 2992. Retrieved 2015/03/14.
• 2、 -. "PROCESS FOR PREPARING 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID". Page/Page column 10-12. . Retrieved 2008/06/13.