Chloroacetyl chloride → N-[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide

HRID 1634559Notes

Reaction equation

HRID 1634559 reaction equation
[CH3:1][C:2]1[N:3]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[CH:7]=[C:6]([CH3:12])[N:5]=2.C(N(CC)C(C)C)(C)C.[Cl:31][CH2:32][C:33](Cl)=[O:34].C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[CH3:1][C:2]1[N:3]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][C:33](=[O:34])[CH2:32][Cl:31])[CH:7]=[C:6]([CH3:12])[N:5]=2

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 220341112,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridine-7-ylamine

Product 1

HCID 22034101N-[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-2-chloroacetamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Treat a solution of 2,5dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridine-7-ylamine (0.8 g, 2.85 mmol), and N,N-diisopropylethylamine (0.54 mL, 3.13 mmol) in 1,2-dichloroethane (10 mL) with chloroacetyl chloride (0.25 mL, 3.13 mmol). Heat the solution to reflux for 5 h, cool to ambient temperature, and pour into an aqueous potassium carbonate solution. Extract the resulting mixture wit CH2Cl2 and wash with saturated aq NaCl. Separate the organic layer, dry over Na2SO4, filter and concentrate. Purify by preparative TLC (5% MeOH in CH2Cl2) to obtain the title compound as a brown solid.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 5 h
  3. extractionExtract the resulting mixture wit CH2Cl2
  4. washwash with saturated aq NaCl
  5. customSeparate the organic layer
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by preparative TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4db6892ac3374b269d2730bb2b6f0eb2
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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