Dimethylacetamide → HCID 58235050, compound

HRID 1187251Notes

Reaction equation

HRID 1187251 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]2=[O:15].[F:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([F:28])[CH:27]=1)[NH2:24].[CH3:29][C:30](N(C)C)=O>O.C(OCC)(=O)C>[F:20][C:21]1[CH:22]=[C:23]([NH:24][CH:29]([C:2]2[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]3[C:11]=2[O:10][C:9]([S:12][CH2:13][CH3:14])=[CH:8][C:7]3=[O:15])[CH3:30])[CH:25]=[C:26]([F:28])[CH:27]=1

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 965953,5-DifluoroanilineHCID 58235026methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58235050HCID 58235050, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Methyl 8-bromo-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (850 mg, 2.29 mmol, prepared as described in Example 9) and 3,5-difluoroaniline (621 mg, 4.81 mmol) in DMA (10 mL) were stirred at 50° C. overnight. The reaction mixture was diluted with water/ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (550 mg, 57%) as a off-white solid. Mass Spectrum: M+H+ 420.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 25% ethyl acetate in dichloromethane
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-988896333ede4605b2f1e9b90907b179
Source dataset
uspto-grants-2014_03
Patent number
US08673906B2

Reaction notes

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