Triethylamine → HCID 22340275, compound

HRID 585316Notes

Reaction equation

HRID 585316 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=2)[N:4]=1.[CH2:17]([N:19](CC)[CH2:20]C)C.CS(Cl)(=O)=O.Cl.CNC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][N:19]([CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=2)[N:4]=1)[CH3:20]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium Carbonate2×HCID 31297Methanesulfonyl chlorideHCID 22340299HCID 22340299, compound

Product 1

HCID 22340275HCID 22340275, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The N-[2-(hydroxymethyl)-6-quinolinyl]acetamide (92.3 mg, 0.427 mmol) obtained in Reference Example 5 and triethylamine (0.0712 ml, 0.512 mmol) were dissolved in N,N-dimethylformamide (2 ml), methanesulfonyl chloride (0.0396 ml, 0.512 mmol) was added under ice-cooling, and the mixture was stirred for 30 minutes. To the reaction solution were added dimethylamine hydrochloride (69.6 mg, 0.854 mmol) and potassium carbonate (177 mg, 1.28 mmol), and the mixture was stirred at 60° C. for 16 hours. To the reaction solution was added an aqueous potassium carbonate solution, followed by extraction with ethyl acetate. The extract was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate) to obtain N-[2-[(N,N-dimethylamino)methyl]-6-quinolinyl]acetamide (71.9 mg) as an oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 60° C. for 16 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by alumina column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-f705975e73be4db093aea5b7e1f7ae3e
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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