Pyridine → HCID 23284759, compound

HRID 369303Notes

Reaction equation

HRID 369303 reaction equation
CN.[NH2:3][C:4]1[C:5]([F:28])=[CH:6][C:7]([F:27])=[C:8]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17](F)[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]2)[CH:9]=1.[N:29]1C=CC=[CH:31][CH:30]=1>>[NH2:3][C:4]1[C:5]([F:28])=[CH:6][C:7]([F:27])=[C:8]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:22])=[C:17]([NH:29][CH2:30][CH3:31])[C:18]=3[Cl:20])[C:13](=[O:23])[C:12]([C:24]([OH:26])=[O:25])=[CH:11]2)[CH:9]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 23284759HCID 23284759, compoundYield 81.7%

Conditions

Temperature
70 °C

Procedure

Pyridine (200 mg) and a 40% aqueous solution (250 mg) of methylamine were added to 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg), and the mixture was heated and stirred overnight at 70° C. The solvent was distilled off under reduced pressure, ethanol (2 ml) was added to the residue, and solids were collected by filtration to obtain the title compound (87 mg) as an orange powder.

Workup

  1. temperaturethe mixture was heated
  2. distillationThe solvent was distilled off under reduced pressure, ethanol (2 ml)
  3. additionwas added to the residue, and solids
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4bfcdc7c539844e887deaa7e58e896f6
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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