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:13](=O)([O-])[O-].[Cs+].[Cs+].C(I)[C:20]([CH3:23])(C)[CH3:21]>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]([CH2:13][CH:21]3[CH2:23][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. Neopentyl iodide (6.4 g, 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 5-chloro-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4) as a tan solid. HRMS (M+H)+: observed=253.7341, calculated=253.7340.
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-d139a1eb6ae54df1bb60b64fe2bb27c5
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315518B2
Reaction notes
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