Hydrochloric Acid → HCID 86700044, compound

HRID 1428094Notes

Reaction equation

HRID 1428094 reaction equation
[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][NH:5][CH:4]=[C:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:31][C:32]([F:35])([F:34])[F:33])(=O)=O.Cl>CN(C=O)C>[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH:4]=[C:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 12624209HCID 12624209, compound

Product 1

HCID 86700044HCID 86700044, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylate (100 mg) was suspended in DMF (1.5 ml). Cesium carbonate (268 mg) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (83 μl) were sequentially added and the mixture was stirred at room temperature for three hours. A 1 N aqueous hydrochloric acid solution was added under ice cooling, 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->40:1 (v/v)] to give 159 mg of the title compound as an oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->40:1 (v/v)]

Sources & evidence

ORD record
ord-b1d3705f898141398bcb8bdba997eb28
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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