Hydrochloric Acid → HCID 86700069, compound

HRID 1428116Notes

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+].Cl[CH2:27][C:28]([CH3:31])([OH:30])[CH3:29].Cl>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][N:12]([CH2:27][C:28]([OH:30])([CH3:31])[CH3:29])[CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (400 mg) was suspended in DMF (5.0 ml). Cesium carbonate (1200 mg), 1-chloro-2-methyl-2-propanol (345 μl) and tetra-n-butylammonium iodide (56 mg) were added sequentially, and the mixture was stirred at 70° C. for 10 hours. A 1 N aqueous hydrochloric acid solution was added at room temperature. The insoluble matter was removed by filtration through celite, followed by 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 57 mg of the title compound as a solid.

Workup

customThe insoluble matter was removed by filtration through celite
extractionfollowed by 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-9f2be6c5a403401aabad39c52e907e57
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933103B2

Reaction notes

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