Ammonia → 7-(Cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 469201Notes

Reaction equation

C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:38])[C:25]([C:35]([OH:37])=O)=[CH:26][N:27]3[CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:22][C:21]=2[F:39])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.N>CN(C=O)C>[CH:13]1([NH:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24](=[O:38])[C:25]([C:35]([NH2:3])=[O:37])=[CH:26][N:27]3[CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:22][C:21]=2[F:39])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

2.6 g of 1,1′-carbonyldiimidazole was added to a 30 ml DMF suspension of 4.0 g 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, followed by stirring at 100° C. for 13.5 hours. 10 ml of 28% aqueous ammonia was added thereto under ice-cooling, followed by stirring under ice-cooling for 75 minutes and at room temperature for 5 hours. After evaporation of the solvent under a reduced pressure, ethanol was added, and heating under reflux was carried out. After cooling to room temperature, the insoluble materials were collected by filtration and dried to obtain 3.7 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide.

Workup

temperatureunder ice-cooling
stirringby stirring under ice-
temperaturecooling for 75 minutes and at room temperature for 5 hours
customAfter evaporation of the solvent under a reduced pressure, ethanol
additionwas added
temperatureheating
temperatureunder reflux
temperatureAfter cooling to room temperature
filtrationthe insoluble materials were collected by filtration
customdried

Sources & evidence

ORD record: ord-28da3a5eeb4d4e54a9f1dc0e2f17777f
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629126B2

Reaction notes

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