Acetonitrile → 8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

HRID 427505Notes

Reaction equation

HRID 427505 reaction equation
[NH2:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].Br[CH:13]([CH3:17])[C:14](=O)[CH3:15].C(#N)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[NH2:1][C:2]1[C:3]2[N:4]([C:13]([CH3:17])=[C:14]([CH3:15])[N:11]=2)[CH:5]=[C:6]([C:7]([NH2:9])=[O:8])[CH:10]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 131422-Butanone, 3-bromo-2×HCID 99421905,6-Diaminonicotinamide

Product 1

HCID 98557898-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamideYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5,6-Diaminonicotinamide (12.5 g, 82 mmol), 3-bromo-2-butanon (13.6, 90 mmol) and acetonitrile (150 ml) were refluxed for 20 h. Additional 3-bromo-2-butanon (4.0 g, 26.5 mmol) was added and the reaction mixture was refluxed for 5 h. Upon cooling the solids were removed by filtration. The solids were added to methylene chloride (150 ml), methanol (150 ml) and potassium carbonate (22 g, 160 mmol) and were stirred for 30 min. The solids were removed by filtration and evaporation of the solvents under reduced pressure gave an oily residue. Purification by column chromatography on silica gel eluting with methylene chloride:methanol (5:1) gave 3.3 g (20%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperatureUpon cooling the solids
  3. customwere removed by filtration
  4. customThe solids were removed by filtration and evaporation of the solvents under reduced pressure
  5. customgave an oily residue
  6. customPurification by column chromatography on silica gel eluting with methylene chloride:methanol (5:1)

Sources & evidence

ORD record
ord-ab813d9e3d75457b9a529a70e0d7a235
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

Loading…