Ethylene carbonate → HCID 22672577, compound
Reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[Li+].C1(=O)O[CH2:27][CH2:26][O:25]1>CN(C)C=O.[I-].C[N+](C)(C)C>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:2]=3[O:1][CH2:27][CH2:26][OH:25])=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 8-(2-hydroxy-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.14 g, 0.5 mmol) in N,N-dimethylformamide (3 ml) was added lithium hydride (0.004 g, 0.51 mmol) and the mixture was stirred for 10 min at 100° C. Ethylene carbonate (0.055 g, 0.63 mmol) was added and the mixture was stirred for 10 min at 130° C. Tetramethylammonium iodide (0.054 g, 0.63 mmol) was added and the mixture was stirred for 12 h. at 140-145° C. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride, washed twice with saturated sodium bicarbonate. The organic layer was separated, dried and evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:6) as eluent to give 0.067 g (41%) of the title compound.
Workup
- stirringthe mixture was stirred for 10 min at 130° C
- stirringthe mixture was stirred for 12 h. at 140-145° C
- customThe solvent was evaporated under reduced pressure
- washwashed twice with saturated sodium bicarbonate
- customThe organic layer was separated
- customdried
- customevaporated under reduced pressure
- customthe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-17d3dc67aadc452fb0e5bf52ada6f72e
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579884B1
Reaction notes
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