Pyridine → HCID 178474526, compound

HRID 1023866Notes

Reaction equation

HRID 1023866 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][NH2:13])=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.[C:20](Cl)(=[O:22])[CH3:21]>ClCCl>[NH:3]1[CH:4]=[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][NH:13][C:20](=[O:22])[CH3:21])[N:1]=[CH:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 21023616HCID 21023616, compound

Product 1

HCID 178474526HCID 178474526, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(1H-imidazol-5-yl)phenyl)methanamine (77 mg, 0.445 mmol) in dichloromethane (3 mL) was added pyridine (0.11 mL, 1.33 mmol) and acetyl chloride (76 μL, 1.07 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%-20% MeOH/DCM as eluent) to afford the desired product as a white solid (12 mg, 0.056 mmol, 13%). 1H NMR: 2.01 (s, 3H), 4.44 (d, 2H, J=6.3 Hz), 7.21 (d, 1H, J=1.2 Hz), 7.27-7.30 (m, 2H), 7.41-7.48 (m, 2H), 7.73 (d, 1H, J=0.9 Hz), 7.96 (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%-20% MeOH/DCM as eluent)

Sources & evidence

ORD record
ord-d95f60fce88d44c2ae7542b17112a37b
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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