Methylamine → HCID 23284707, compound

HRID 369287Notes

Reaction equation

HRID 369287 reaction equation
[CH3:1][NH2:2].[NH2:3][C:4]1[C:5]([F:30])=[CH:6][C:7]([F:29])=[C:8]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([CH3:24])=[C:17](F)[C:18]=3[N+:20]([O-:22])=[O:21])[C:13](=[O:25])[C:12]([C:26]([OH:28])=[O:27])=[CH:11]2)[CH:9]=1>CS(C)=O.N1C=CC=CC=1>[NH2:3][C:4]1[C:5]([F:30])=[CH:6][C:7]([F:29])=[C:8]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([CH3:24])=[C:17]([NH:2][CH3:1])[C:18]=3[N+:20]([O-:22])=[O:21])[C:13](=[O:25])[C:12]([C:26]([OH:28])=[O:27])=[CH:11]2)[CH:9]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 23284676HCID 23284676, compound

Product 1

HCID 23284707HCID 23284707, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

Pyridine (500 mg) and a 40% aqueous solution (300 mg) of methylamine were added to 1-(5-amino-2,4-difluorophenyl)-7-fluoro-6-methyl-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (70 mg), and the mixture was heated and stirred overnight at 40° C. Dimethyl sulfoxide (10 drops) was added to the reaction mixture, followed by stirring at 40° C. for 5 hours. The solvent and the like were distilled off under reduced pressure, and ethanol (0.5 ml) was added to the residue. Solids deposited were collected by filtration aid washed with ethanol and diethyl ether to obtain the title compound (53 mg) as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. stirringby stirring at 40° C. for 5 hours
  3. distillationThe solvent and the like were distilled off under reduced pressure, and ethanol (0.5 ml)
  4. additionwas added to the residue
  5. filtrationSolids deposited were collected by filtration aid
  6. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-e42d647693b3429d84eae841fff9dd80
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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