Methylamine → 1-(6-Amino-5-fluoropyridin-2-yl)-8-chloro-6-fluoro-7-methylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369256Notes

Reaction equation

HRID 369256 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:5]=[CH:4][C:3]=1[F:25].[CH3:26][NH2:27]>N1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH3:26])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:5]=[CH:4][C:3]=1[F:25]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 221212661-(6-Amino-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 232847721-(6-Amino-5-fluoropyridin-2-yl)-8-chloro-6-fluoro-7-methylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 103.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(6-Amino-5-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (158 mg) and an aqueous solution (about 40%; 165 mg) of methylamine were added to pyridine (480 mg), and the mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, and ethanol (1 ml) was added to the residue. Deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (168 mg) as a pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethanol (1 ml)
  2. additionwas added to the residue
  3. filtrationDeposits were collected by filtration
  4. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-5e73a7593842475787cc5903e1fddf99
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

Loading…