Triethylamine → HCID 22340275、化合物

HRID 585316ノート

反応式

HRID 585316 の反応式
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]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium Carbonate2 回HCID 31297Methanesulfonyl chlorideHCID 22340299HCID 22340299、化合物

生成物 1

HCID 22340275HCID 22340275、化合物収率 69.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f705975e73be4db093aea5b7e1f7ae3e
出典データセット
uspto-grants-2005_08
特許番号
US06930185B2

反応ノート

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