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

HRID 369233Notes

Reaction equation

HRID 369233 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1.[CH3:28][NH2:29]>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:29][CH3:28])[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:27])[C:5]([C:24]([OH:26])=[O:25])=[CH:6][N:7]2[C:15]1[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([NH2:23])[N:16]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 221211655-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 232847185-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-methylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (23 mg) and a 40% aqueous solution (60 mg) of methylamine were added to pyridine (240 mg), and the mixture was stirred at room temperature for 20 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 ethanol and diisopropyl ether to obtain the title compound (6 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 ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-e7d89a4db6e643bab79d65e5e98f4a1a
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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