Pyridine → HCID 178474110, compound

HRID 1023868Notes

Reaction equation

HRID 1023868 reaction equation
[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

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14698017HCID 14698017, compound

Product 1

HCID 178474110HCID 178474110, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-96b99bbba78a415eba4f069feab7eb3d
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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