Dimethylformamide → N-(5-Acetyl-2-fluorophenyl)acetamide

HRID 2189916ノート

反応式

HRID 2189916 の反応式
ClC1C(NC2C=C(C3CC3)NN=2)=NC(N[C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=CN=2)C)=C(C=1)C#N.[C:29](Cl)(=[O:31])[CH3:30].[CH3:33]CN(C(C)C)C(C)C.[CH3:42][N:43]([CH:45]=[O:46])C>>[C:29]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:42]([NH:43][C:45](=[O:46])[CH3:33])[CH:11]=1)(=[O:31])[CH3:30]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 11711016(S)-5-Chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-(1-(5-fluoropyridin-2-yl)ethylamino)nicotinonitrile

生成物 1

HCID 53431926N-(5-Acetyl-2-fluorophenyl)acetamide

実験手順

To a round, bottom flask was added 3-amino-4-fluoroacetophenone (Method 64, 1 g, 6.54 mmol) in DMF (15 ml), followed by the addition of acetyl chloride (0.56 ml, 7.84 mmol) and DIEA (2.3 ml, 13.08 mmol). The solution was set to stir at room temperature. The reaction appeared complete by TLC after 30 min. The reaction was then quenched with water and partitioned with EtOAc. The layers were cut, followed by an additional wash of the aqueous with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude residue obtained (1.17 g), was used directly in the next step. 1H NMR (CDCl3) δ 8.94 (d, J=7.54 Hz, 1H) 7.71 (d, 1H) 7.43 (s, 1H) 7.15 (s, 1H) 2.56-2.60 (m, 3H) 2.21-2.28 (m, 3H).

後処理

  1. customThe reaction was then quenched with water
  2. custompartitioned with EtOAc
  3. washan additional wash of the aqueous with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b9ef40ac170e4df7921656b89c2d0993
出典データセット
uspto-grants-2012_12
特許番号
US08324252B2

反応ノート

読み込み中…