Dimethyl Sulfoxide → HCID 86633060, compound

HRID 1094195Notes

Reaction equation

HRID 1094195 reaction equation
CS(C)=O.[CH:5]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17](F)[CH:18]=3)[C:13](=[O:22])[C:12]([N+:23]([O-:25])=[O:24])=[CH:11]2)[CH2:9][CH2:8][CH2:7][CH2:6]1.[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>O>[CH:26]1([NH:32][C:17]2[CH:18]=[C:19]3[C:14]([C:13](=[O:22])[C:12]([N+:23]([O-:25])=[O:24])=[CH:11][N:10]3[CH:5]3[CH2:9][CH2:8][CH2:7][CH2:6]3)=[CH:15][C:16]=2[F:21])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7965CyclohexylamineHCID 86633061HCID 86633061, compound

Product 1

HCID 86633060HCID 86633060, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 40 ml DMSO solution of 2.0 g of 1-cyclopentyl-6,7-difluoro-3-nitroquinolin-4(1H)-one was added 2.3 ml of cyclohexylamine, followed by overnight stirring at 90° C. The reaction mixture was cooled to room temperature and poured into ice-cooled water, and then the insoluble materials were collected by filtration. By recrystallizing the resulting solid from ethanol, 2.5 g of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-nitroquinolin-4(1H)-one was obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured into ice-
  3. filtrationthe insoluble materials were collected by filtration
  4. customBy recrystallizing the resulting solid from ethanol

Sources & evidence

ORD record
ord-b29f187868a94994b5c9ef7fd568ed1b
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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