Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate
• CAS No.: 104051-62-9
• Molecular Formula: C21H19F3N4O3
• Molecular Weight: 432.402
• DSSTox Substance ID: DTXSID10551199
• Wikidata: Q82430729
• Mol file: 104051-62-9.mol

Synonyms:104051-62-9;ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate;SCHEMBL5571971;DTXSID10551199;CSGZDBLFJFQRTH-UHFFFAOYSA-N;ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate

Chemical Property of Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 432.14092497
• Heavy Atom Count: 31
• Complexity: 718

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN(C2=NC(=C(C=C2C1=O)F)N3CCNCC3)C4=C(C=C(C=C4)F)F

Technology Process of Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

There total 7 articles about Ethyl 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate 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: 91.2%

piperazine (110-85-0) + ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(2,4,6-triisopropylbenzenesulfonyloxy)-1,8-naphthyridine-3-carboxylate → ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate (104051-62-9)

Guidance literature:

In diethyl ether; dichloromethane; water; ethyl acetate;

Reference yield: 81.4%

piperazine (110-85-0) + ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (100491-29-0) → ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate (104051-62-9)

Guidance literature:

With pyridine; for 3h; Ambient temperature;

Reference yield:

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate (104051-62-9)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / 2 h / 80 °C

2: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h

3: 1.) Ac₂O / 1.) 130 deg C, 1 h, 2.) CH₂Cl₂, RT, 0.5 h

4: 86.5 percent / NaH / tetrahydrofuran / 1 h / Heating

5: 81.4 percent / pyridine / 3 h / Ambient temperature

With pyridine; n-butyllithium; thionyl chloride; biquinoline; acetic anhydride; sodium hydride; In tetrahydrofuran;

upstream raw materials:

piperazine

ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

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

2,6-dichloro-5-fluoro-3-nicotinoyl chloride

Downstream raw materials:

1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid hydrochloride

A 57274