ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate

Base Information

• Chemical Name: ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate
• CAS No.: 145122-69-6
• Molecular Formula: C₂₃H₂₁F₃N₄O₃
• Molecular Weight: 458.44
• Mol file: 145122-69-6.mol

Synonyms:

Chemical Property of ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate

There total 5 articles about ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<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: 53.0%

ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (100491-29-0) + 4,7-diazaspiro<2,5>octane dihydrochloride (145122-56-1) → ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate (145122-69-6)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 100 ℃;

DOI:10.1139/v92-171

Reference yield:

1-(2-Benzyloxycarbonylamino-acetylamino)-cyclopropanecarboxylic acid ethyl ester (140195-93-3) → ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate (145122-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10percent Pd/C / ethanol / 18 h / 3040 Torr

2: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h

3: 53 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, 1-methyl-2-pyrrolidinone / 100 °C

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; borane-THF; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In ethanol;

DOI:10.1139/v92-171

Reference yield:

[(1-benzyloxycarbonylaminocyclopropanecarbonyl)amino]acetic acid ethyl ester (145122-59-4) → ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate (145122-69-6)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 18 h / 3040 Torr

2: DBU / toluene / 22 h / 115 °C

3: 1.) borane*THF complex 2.) HCl / 1.) THF, 60 deg C, 20 h 2.) methanol, reflux, 2 h

4: 53 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene, 1-methyl-2-pyrrolidinone / 100 °C

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; borane-THF; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In ethyl acetate; toluene;

DOI:10.1139/v92-171

upstream raw materials:

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

4,7-diazaspiro<2,5>octane dihydrochloride

1-(2-Benzyloxycarbonylamino-acetylamino)-cyclopropanecarboxylic acid ethyl ester

4,7-diazaspiro[2.5]octane-5,8-dione

Downstream raw materials:

1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylic acid trifluoroacetic acid salt