Ethanolamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(2-hydroxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethanolamine salt

HRID 369273Notes

Reaction equation

HRID 369273 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[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:7]=1.[CH2:27]([CH2:29][NH2:30])[OH:28]>N1C=CC=CC=1>[CH2:27]([CH2:29][NH2:30])[OH:28].[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:30][CH2:29][CH2:27][OH:28])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 699596811-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(2-hydroxyethylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethanolamine saltYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (600 mg) and ethanolamine (600 mg) were added to pyridine (2,500 mg), and the mixture was stirred at 50° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and ethanol (6 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 (603 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethanol (6 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-3ef117c1da7c4dad8fdef301fafffebc
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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