Pyridine → HCID 178474110、化合物

HRID 1023868ノート

反応式

HRID 1023868 の反応式
[NH:1]1[C:5]([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[NH:3]1[CH:4]=[C:5]([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH:8][C:19](=[O:21])[CH3:20])[N:1]=[CH:2]1

参加物

5

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14698017HCID 14698017、化合物

生成物 1

HCID 178474110HCID 178474110、化合物収率 44.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(1H-imidazol-5-yl)aniline (18 mg, 0.113 mmol) in dichloromethane (3 mL) was added pyridine (47 μL, 0.339 mmol) and acetyl chloride (19 μL, 0.271 mmol). The reaction was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The crude product was dissolved in methanol (4 mL) and refluxed for 2 h. The solution was concentrated and the residue was purified by flash column chromatography (silica gel, 5%-30% MeOH/DCM as eluent) to afford the desired product as a white solid (10 mg, 0.050 mmol, 44%). 1H NMR (MeOH-d4): 2.17 (s, 3H), 7.05-7.26 (m, 2H), 7.46 (s, 1H), 7.62 (d, 1H, J=7.8 Hz), 7.78 (s, 1H), 8.18 (s, 1H).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe crude product was dissolved in methanol (4 mL)
  3. temperaturerefluxed for 2 h
  4. concentrationThe solution was concentrated
  5. customthe residue was purified by flash column chromatography (silica gel, 5%-30% MeOH/DCM as eluent)

出典と根拠

ORDレコード
ord-96b99bbba78a415eba4f069feab7eb3d
出典データセット
uspto-grants-2014_05
特許番号
US08722720B2

反応ノート

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