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

HRID 369234Notes

Reaction equation

HRID 369234 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)[C:5]([F:25])=[CH:4][CH:3]=1.[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)[C:5]([F:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 221212881-(6-Amino-3-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 232848111-(6-Amino-3-fluoropyridin-2-yl)-8-chloro-6-fluoro-7-methylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(6-Amino-3-fluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (45 mg) and a 40% aqueous solution (50 mg) of methylamine were added to pyridine (200 mg), and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure, and ethanol (0.5 ml) was added to the residue. Deposits were collected by filtration and washed successively with methanol and diisopropyl ether to obtain the title compound (182 mg) as a yellow powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and ethanol (0.5 ml)
  2. additionwas added to the residue
  3. filtrationDeposits were collected by filtration
  4. washwashed successively with methanol and diisopropyl ether

Sources & evidence

ORD record
ord-5de797eda6f3448e9154c56272bab25f
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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