Sodium Iodide → 2-Methyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide
Reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([CH:11]=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH2:15]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Cl)[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)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[CH2:15][CH3:16])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[CH:5][N:4]2[CH:11]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
8-Amino-2-methylimidazo[1,2-a]pyridine-6-carboxamide (3.8 g, 20 mmol), 2-ethyl-6-methylbenzylchloride (2.8 g, 17 mmol), potassium carbonate (5.5 g, 40 mmol) and sodium iodide (0.1 g, 0.6 mmol) were added to dimethylformamide (75 ml) and the mixture was stirred at 50° C. for 4 h. and at room temperature for 48 h. The reaction mixture was filtred through silica gel and the gel was washed with methylene chloride. The solvents were evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from a mixture of methylene chloride and hexane gave 0.13 g (2%) of the title compound.
Workup
- washthe gel was washed with methylene chloride
- customThe solvents were evaporated under reduced pressure
- customthe residue was purified by column chromatography on silica gel
- customCrystallization
- additionfrom a mixture of methylene chloride and hexane
Sources & evidence
- ORD record
- ord-6e113a46d2d6435da55d950a7f14f2a5
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313137B1
Reaction notes
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