Cesium carbonate → 5-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:19]1([CH2:22]Br)[CH2:21][CH2:20]1>CN1C(=O)CCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[C:9](=[O:11])[N:10]([CH2:22][CH:19]3[CH2:21][CH2:20]3)[C:5]2=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3) (2.97 g, 16.2 mmol) and cesium carbonate (15.8 g, 48.6 mmol) were added to a round bottom flask and suspended in NMP (25 mL) under nitrogen. Cyclopropylmethyl Bromide (4.4, 32.4 mmol) was added to the suspension and then refluxed at 90° C. overnight. The reaction was then cooled to room temperature and suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine (×5), dried over sodium sulfate, filtered, and concentrated. The mixture was purified using normal phase chromatography (0-60% Ethyl Acetate/Hexanes), and the desired fractions were collected to produce the tan solid 5-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4). MS (M+H)+: observed=237.7, calculated=238.1.
Workup
- temperatureThe reaction was then cooled to room temperature
- washThe suspension was washed with sodium bicarbonate, brine (×5)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe mixture was purified
- customthe desired fractions were collected
Sources & evidence
- ORD record
- ord-b625b05f958f4cecad4c68aaf5b700d4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765784B2
Reaction notes
Loading…