Acetonitrile → 1-(2', 4'-Difluorophenyl)-6-fluoro-1,4-dihydro-7-(piperidin-4-yl-amino)-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 11295Notes

Reaction equation

HRID 11295 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](F)[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([O:24]CC)=[O:23])=[CH:10]1.[C:27](#[N:29])[CH3:28]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16]([NH:29][CH:27]3[CH2:2][CH2:3][NH:9][CH2:10][CH2:28]3)[N:17]=2)[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 10406564Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-naphthyridine-3-carboxylate

Product 1

HCID 101127201-(2', 4'-Difluorophenyl)-6-fluoro-1,4-dihydro-7-(piperidin-4-yl-amino)-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 74%

Procedure

Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-naphthyridine-3-carboxylate (0.5 g, 1.3 mmole) and (3-N-ethoxycarbonyl)aminopyrrolidine (0.3 g, 1.74 mmole) in acetonitril (5 ml) was stirred at 80° C. for 3 hr and cooled. Solvent was concentrated to dryness and 5% aqueous NaOH (10 ml) was added to reaction mixture and stirred for 2 hr, acidified with conc. HCl solid separated was filtered, dried to furnish the required product. Yield 74%, m.p >320° C., C20H17F3N4O3, m/z 419. (M+1)

Workup

  1. temperaturecooled
  2. concentrationSolvent was concentrated to dryness and 5% aqueous NaOH (10 ml)
  3. additionwas added to reaction mixture
  4. customseparated
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-27aa6f8b4825442e9c6c524f48c6d1d4
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Reaction notes

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