Pyridine → HCID 178474110, 화합물

HRID 1023868노트

반응식

HRID 1023868 반응식
[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

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14698017HCID 14698017, 화합물

생성물 1

HCID 178474110HCID 178474110, 화합물수율 44.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-96b99bbba78a415eba4f069feab7eb3d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722720B2

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