Potassium Carbonate → HCID 71294095, compound

HRID 1747532Notes

Reaction equation

HRID 1747532 reaction equation
C([O:4][CH:5]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=1)[C:6]([F:9])([F:8])[F:7])(=O)C.Br[CH2:18][C:19](=O)[CH3:20].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(O)CCC.O>[F:9][C:6]([F:7])([F:8])[CH:5]([C:10]1[CH:15]=[CH:14][N:13]2[CH:18]=[C:19]([CH3:20])[N:16]=[C:12]2[CH:11]=1)[OH:4]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 71294162HCID 71294162, compound

Product 1

HCID 71294095HCID 71294095, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

In n-butanol (2 mL) was dissolved 1-(2-aminopyridin-4-yl)-2,2,2-trifluoroethyl acetate (53.2 mg, 0.227 mmol) obtained in Step 2. Bromoacetone (0.042 mL, 0.45 mmol) was added and the mixture was stirred at 130° C. for 24 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure and the residue was dissolved in methanol (2.0 mL). Potassium carbonate (31.4 mg, 0.227 mmol) was added and the mixture was stirred at room temperature for 18 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=5/1) to give Compound A30 (20.7 mg, 40% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. dry with materialdrying over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent in the filtrate was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (2.0 mL)
  6. stirringthe mixture was stirred at room temperature for 18 hours
  7. extractionExtraction with ethyl acetate
  8. dry with materialdrying over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent in the filtrate was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (chloroform/methanol=5/1)
  12. customto give Compound A30 (20.7 mg, 40% yield)

Sources & evidence

ORD record
ord-adf425e4025845918ffea7648ef2c988
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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