Hydrochloric Acid → HCID 86700070, compound

HRID 1428117Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br.Br[CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32].Cl>CN(C=O)C>[CH2:29]([N:30]([CH2:33][CH3:34])[CH2:31][CH2:32][N:12]1[CH:13]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11]1)[CH3:28]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (270 mg) was suspended in DMF (3.0 ml). Cesium carbonate (1180 mg) and 2-bromo-N,N-diethylethylamine hydrobromide (405 mg) were added sequentially, and the mixture was stirred at 50° C. for six hours. A 1 N aqueous hydrochloric acid solution was added under ice cooling, and the insoluble matter was then removed by filtration through celite. After extraction with ethyl acetate, the organic layer was washed with water and brine and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)] to give 89 mg of the title compound as an oily substance.

Workup

customthe insoluble matter was then removed by filtration through celite
extractionAfter extraction with ethyl acetate
washthe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->60:1 (v/v)]

Sources & evidence

ORD record: ord-54f910477f6940d78bfaa3b34f6dec4f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933103B2

Reaction notes

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