Cyclopropylamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-7-cyclopropylamino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369227Notes

Reaction equation

HRID 369227 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[NH2:5][C:6]1[C:7]([F:30])=[CH:8][C:9]([F:29])=[C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:24])=[C:19](F)[C:20]=3[Cl:22])[C:15](=[O:25])[C:14]([C:26]([OH:28])=[O:27])=[CH:13]2)[CH:11]=1>CN(C)C=O>[NH2:5][C:6]1[C:7]([F:30])=[CH:8][C:9]([F:29])=[C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:24])=[C:19]([NH:4][CH:1]4[CH2:3][CH2:2]4)[C:20]=3[Cl:22])[C:15](=[O:25])[C:14]([C:26]([OH:28])=[O:27])=[CH:13]2)[CH:11]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 232847731-(5-Amino-2,4-difluorophenyl)-8-chloro-7-cyclopropylamino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cyclopropylamine (50 mg) and 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg) were, added to N,N-dimethylformamide (2 ml), and the mixtures was stirred at 60° C. for 2 hours. After the reaction mixture was cooled back to room temperature, the solvent was, distilled off under reduced pressure. Ethanol was added to the residue, and solids deposited were collected by filtration to obtain the title compound (80 mg) as a pale yellow powder.

Workup

  1. temperatureAfter the reaction mixture was cooled back to room temperature
  2. distillationdistilled off under reduced pressure
  3. additionEthanol was added to the residue, and solids
  4. filtrationdeposited were collected by filtration

Sources & evidence

ORD record
ord-3eed61f86d2e4e31b0fbff88bf5772a5
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

Loading…