7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-1,4-dihydro-7-[3-(methoxymethyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1.Cl[C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:26])[C:16]([C:23]([OH:25])=[O:24])=[CH:17][N:18]2[CH2:21][CH3:22])=[CH:13][C:12]=1[F:27]>N1C=CC=CC=1>[CH2:21]([N:18]1[C:19]2[C:14](=[CH:13][C:12]([F:27])=[C:11]([N:8]3[CH2:7][CH2:6][NH:5][CH:4]([CH2:3][O:2][CH3:1])[CH2:9]3)[CH:20]=2)[C:15](=[O:26])[C:16]([C:23]([OH:25])=[O:24])=[CH:17]1)[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.7 g portion of 2-(methoxymethyl)piperazine was dissolved in 8 ml of pyridine. A 0.88 g portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours. The solvents were removed and the resulting gum evaporated three times from toluene. The residue was purified by column chromatography, eluting with chloroform:methanol saturated with water (90:10). The appropriate fractions were combined and evaporated, giving 550 mg of the desired product, mp 169°-170° C.
Workup
- temperaturethe mixture was heated in a pressure bottle, under argon, at 120°-130° C. for 18 hours
- customThe solvents were removed
- customthe resulting gum evaporated three times from toluene
- customThe residue was purified by column chromatography
- washeluting with chloroform
- customevaporated
Sources & evidence
- ORD record
- ord-918049ea410843299dc6d2e567da89b0
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210193
Reaction notes
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