1-(2,4-Difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 1-(2',4'-Difluorophenyl)-6-fluoro-1,4-dihydro-7-(3',5'-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

HRID 11293

Reaction equation

HRID 11293 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)[CH:17]=2)[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1.[CH3:25][CH:26]1[CH2:31][CH:30]([CH3:32])[CH2:29][NH:28][CH2:27]1>>[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]([N:28]3[CH2:29][CH:30]([CH3:32])[CH2:31][CH:26]([CH3:25])[CH2:27]3)[CH:17]=2)[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1

Participants

3

Reactant 2

HCID 598041-(2,4-Difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 1182593,5-Dimethylpiperidine

Product 1

HCID 102029621-(2',4'-Difluorophenyl)-6-fluoro-1,4-dihydro-7-(3',5'-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acidYield 43%

Procedure

The condensation of with 1-(2′,4′-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid with 3,5-dimethylpiperidine in a similar manner as described in example 1 gave the titled product. Yield 43%, m.p 224–26° C., C23H21F3N2O3, m/z 431. (M+1)

Sources & evidence

ORD record
ord-ed84d5940c3742fc961e388b67925154
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Linked notes

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