Potassium Carbonate → HCID 71113151, compound
Reaction equation
[CH2:1]([C@@:3]1([CH3:18])[NH:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[N:11][C:12](F)=[C:13]([CH3:15])[CH:14]=2)[C:4]1=[O:17])[CH3:2].[CH3:19][C:20]1([CH3:30])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([OH:29])[CH:27]=2)[CH2:22][O:21]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:19][C:20]1([CH3:30])[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:29][C:12]3[N:11]=[CH:10][C:9]([N:5]4[C:4](=[O:17])[C@:3]([CH2:1][CH3:2])([CH3:18])[NH:7][C:6]4=[O:8])=[CH:14][C:13]=3[CH3:15])[CH:27]=2)[CH2:22][O:21]1Participants
Conditions
- Temperature
- 110 °C
Procedure
To a solution of (5R)-5-ethyl-3-(6-fluoro-5-methyl-3-pyridyl)-5-methyl-imidazolidine-2,4-dione (Intermediate 5, 48 mg, 0.19 mmol) in DMF (1 ml) 3,3-dimethyl-1H-isobenzofuran-5-ol (Intermediate 18, 45 mg, 0.27 mmol) and dipotassium carbonate (75.7 mg, 0.55 mmol) were added and the reaction mixture was stirred at 110° C. for 10 hours. The reaction was quenched with an aqueous saturated solution of ammonium chloride (5 ml) and extracted with ethyl acetate (10 ml). The organic layer was washed with brine (3×10 ml) dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage system) using a SNAP 10 g as column and cyclohexane/ethyl acetate from 85:15 to 20:80 as eluent to afford the title compound (20 mg) as white solid.
Workup
- customThe reaction was quenched with an aqueous saturated solution of ammonium chloride (5 ml)
- extractionextracted with ethyl acetate (10 ml)
- washThe organic layer was washed with brine (3×10 ml)
- dry with materialdried over sodium sulphate
- concentrationconcentrated under vacuum
- customThe residue was purified by flash chromatography on silica gel (Biotage system)
Sources & evidence
- ORD record
- ord-fa846b4e432243768b9fe0e24aea9ed5
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193704B2
Reaction notes
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