Dimethylformamide → HCID 118071686, compound

HRID 2207747Notes

Reaction equation

HRID 2207747 reaction equation
[F:1][CH:2]([F:22])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH:20][CH3:21])=[O:19])=[O:4].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH2:34](I)[CH3:35]>O>[F:22][CH:2]([F:1])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:34][CH3:35])[CH:15]=2)[NH:10][C:9]=1[C:18]([NH:20][CH3:21])=[O:19])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118071484HCID 118071484, compound

Product 1

HCID 118071686HCID 118071686, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-{2-[(difluoroacetyl)amino]ethyl}-5-hydroxy-N-methyl-1H-indole-2-carboxamide (102 mg) and N,N-dimethyl formamide (3.00 mL) were added potassium carbonate (55.2 mg) and ethyl iodide (0.0318 mL), followed by stirring at room temperature for 2 hours, then warming to 60° C., and stirring overnight. To this mixture was added water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and subsequently dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel chromatography (chloroform:methanol=100:0 to 94:6) to obtain a colorless solid. The obtained solid was washed with hexane:ethyl acetate=2:1 to obtain 3-{2-[(difluoroacetyl)amino]ethyl}-5-ethoxy-N-methyl-1H-indole-2-carboxamide (9.00 mg) as a colorless solid.

Workup

  1. temperaturewarming to 60° C.
  2. stirringstirring overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialsubsequently dried over anhydrous sodium sulfate
  6. customThe insoluble materials were separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=100:0 to 94:6)
  9. customto obtain a colorless solid
  10. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-f3818f2e3d404478bb19d1df39530994
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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