Potassium Iodide → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427487Notes

Reaction equation

HRID 427487 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH3:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(Cl)Cl.CC(C)=O>[CH3:14][C:12]1[N:13]=[C:3]2[C:2]([NH:1][CH2:19][C:18]3[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:17]=3[CH3:16])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[CH:5][N:4]2[C:11]=1[CH3:15]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 98557898-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 97972452,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamideYield 83.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide (0.6 g, 2.9 mmol), 2,6-dimethylbenzylchloride (0.45 g, 2.9 mmol), sodium carbonate (1.0 g, 9.4 mmol) and potassium iodide (0.2 g, 1.3 mmol) were added to acetone (25 ml) and refluxed for 19 h. Methylene chloride was added and inorganic salts were filtered off. The solution was washed with a bicarbonate solution, the organic layer was separated, dried and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:5) as eluent and the product was washed with diethyl ether to give 0.78 g (82%) of the title compound.

Workup

  1. temperaturerefluxed for 19 h
  2. filtrationinorganic salts were filtered off
  3. washThe solution was washed with a bicarbonate solution
  4. customthe organic layer was separated
  5. customdried
  6. customthe solvents were evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washthe product was washed with diethyl ether

Sources & evidence

ORD record
ord-902502254b77418a9937de17c4e2f2b3
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

Loading…