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Potassium Carbonate → HCID 20430478, compound

HRID 2413122
Notes
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Reaction equation

HRID 2413122 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:25])[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][NH:17]3)=[CH:12][C:11]=2[F:26])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:43][CH2:44][F:45])(=O)=O)=CC=1>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:25])[C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][N:17]3[CH2:43][CH2:44][F:45])=[CH:12][C:11]=2[F:26])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 13268404Ethyl 7-(4-acetyl-1-piperazinyl)-6-F-4-hydroxy(1,8)naphthyridine-3-carboxylate

Product 1

HCID 20430478HCID 20430478, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

Ethyl 7-(4-acetyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (7.2 g) and anhydrous potassium carbonate (4.1 g) are added to dimethylformamide (60 ml). The mixture is heated at 50° C. for 30 minutes with stirring. 2-Fluoroethyl p-toluenesulfonate (6.5 g) is added to the mixture, and the mixture is heated at 70°-80° C. with stirring. After the reaction is completed, the insoluble substance is removed by filtration. The filtrate is concentrated to dryness under reduced pressure, and the precipitate is collected by filtration. The precipitate is recrystallized from acetone to give 6.3 g of ethyl 7-(4-acetyl-1-piperazinyl)-6-fluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (m.p. 183°-185° C.).

Workup

  1. temperaturethe mixture is heated at 70°-80° C.
  2. stirringwith stirring
  3. customthe insoluble substance is removed by filtration
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure
  5. filtrationthe precipitate is collected by filtration
  6. customThe precipitate is recrystallized from acetone

Sources & evidence

ORD record
ord-669fcbc9544a4b6cb297616487e6302d
Source dataset
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04496566

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes