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

HRID 369257Notes

Reaction equation

HRID 369257 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][NH:29][CH3:30]>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:29]([CH3:30])[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 674DimethylamineHCID 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 232848225-Amino-1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-7-dimethylamino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 81%

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 (100 mg) and an aqueous solution (about 50%; 170 mg) of dimethylamine were added to pyridine (500 mg), and the mixture was stirred at room temperature for 4 days. 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 (86 mg) as a 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-e2ed9ef0e03546638a9f60d060aa2472
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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