7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Base Information

Chemical Name:7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
CAS No.:138668-56-1
Molecular Formula:C₂₂H₁₉F₃N₄O₃
Molecular Weight:444.413
Hs Code.:

Synonyms:7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

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Chemical Property of 7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

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Technology Process of 7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

There total 9 articles about 7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-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:

: 82671-06-5
2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid

: 138668-56-1
7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) MeLi / 1.) ether, THF, -30 deg C, 2 h, 2.) ether, THF, from -60 to 0 deg C, 2 h

2: PCl₅ / 0.13 h / 100 °C

3: 2.) p-TsOH*H₂O / 1.) ether, RT, 2 h, 2.) H₂O, reflux, 2.5 h

4: 94 percent / Ac₂O / 15 h / 130 °C

5: ethanol / 1 h / Ambient temperature

6: 91 percent / NaH / dioxane / 1 h / Ambient temperature

7: DBU / acetonitrile / 1 h / 70 °C

8: 2 N aq. NaOH / 1 h / Heating

With sodium hydroxide; phosphorus pentachloride; methyllithium; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; ethanol; acetonitrile;
DOI:10.1021/jm00081a013

Reference yield:

: 367-25-9,76563-56-9
2,4-difluorophenylamine

: 138668-56-1
7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: ethanol / 1 h / Ambient temperature

2: 91 percent / NaH / dioxane / 1 h / Ambient temperature

3: DBU / acetonitrile / 1 h / 70 °C

4: 2 N aq. NaOH / 1 h / Heating

With sodium hydroxide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; ethanol; acetonitrile;
DOI:10.1021/jm00081a013

Reference yield:

: 132195-42-7
2,6-dichloro-5-fluoro-4-methylnicotinic Acid

: 138668-56-1
7-(2,5-Diaza-bicyclo[2.2.2]oct-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: PCl₅ / 0.13 h / 100 °C

2: 2.) p-TsOH*H₂O / 1.) ether, RT, 2 h, 2.) H₂O, reflux, 2.5 h

3: 94 percent / Ac₂O / 15 h / 130 °C

4: ethanol / 1 h / Ambient temperature

5: 91 percent / NaH / dioxane / 1 h / Ambient temperature

6: DBU / acetonitrile / 1 h / 70 °C

7: 2 N aq. NaOH / 1 h / Heating

With sodium hydroxide; phosphorus pentachloride; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; ethanol; acetonitrile;
DOI:10.1021/jm00081a013