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

HRID 1634556Notes

Reaction equation

HRID 1634556 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])[CH:9]=[N:10][C:5]2=[C:4]([NH2:20])[CH:3]=1.C(N(CC)C(C)C)(C)C.[Cl:30][CH2:31][C:32](Cl)=[O:33].C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[C:12]([CH3:19])=[CH:13][C:14]([CH3:18])=[CH:15][C:16]=3[CH3:17])[CH:9]=[N:10][C:5]2=[C:4]([NH:20][C:32](=[O:33])[CH2:31][Cl:30])[CH:3]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 220341085-Methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-ylamine

Product 1

HCID 22034148N-[5-methyl-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 5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-ylamine (0.05 g, 1.9 mmol), and N,N-diisopropylethylamine, (0.04 mL, 0.21 mmol) in 1,2-dichloroethane (5 mL) with chloroacetyl chloride (0.017 mL, 0.21 mmol). Heat the solution to reflux for 3 h, cool to ambient temperature, and pour into an aqueous potassium carbonate solution. Extract the resulting mixture with 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 yellow solid.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 3 h
  3. extractionExtract the resulting mixture with 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-f451973e9d8f46139b1447b54db6e394
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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