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

HRID 2189916노트

반응식

HRID 2189916 반응식
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]

참가 물질

5

반응물 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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b9ef40ac170e4df7921656b89c2d0993
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324252B2

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