Potassium Carbonate → HCID 20430478, compound

HRID 2413122Notes

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]

Participants

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

temperaturethe mixture is heated at 70°-80° C.
stirringwith stirring
customthe insoluble substance is removed by filtration
concentrationThe filtrate is concentrated to dryness under reduced pressure
filtrationthe precipitate is collected by filtration
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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