Methylamine → HCID 23284720, compound

HRID 369272Notes

Reaction equation

HRID 369272 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16](F)[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:26][NH2:27]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:21])=[C:16]([NH:27][CH3:26])[C:17]=3[Cl:19])[C:12](=[O:22])[C:11]([C:23]([OH:25])=[O:24])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23284736HCID 23284736, compound

Product 1

HCID 23284720HCID 23284720, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Amino-4-fluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg) and an aqueous solution (about 40%; 500 mg) of methylamine were added to pyridine (1,200 mg), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Ethanol (2 ml) was added to the resultant residue. Deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (210 mg) as a pale brown powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionEthanol (2 ml) was added to the resultant residue
  4. filtrationDeposits were collected by filtration
  5. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-2f3fb5bd09344980a7d42c4496aeb5bd
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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