Reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[NH2:23]>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:23][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[N:29]=[CH:30][CH:31]=[CH:32][N:33]=1Participants
Procedure
According to Scheme 3 Step 3: Picolinoyl chloride hydrochloride (1.33 mmol, 256 mg) and Et3N (2.67 mmol, 0.37 mL) were added sequentially to a solution of 3-methoxy-4-(pyrimidin-2-yloxy)aniline (0.89 mmol, 193 mg) in DCM (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over C18 column using water/ACN (70:30) as eluent to afford N-(3-methoxy-4-(pyrimidin-2-yloxy)phenyl)picolinamide (0.17 mmol, 55 mg, 19%) as a white solid.
Workup
- washThe organic phase was washed with a saturated solution of NaHCO3
- extractionThe aqueous phase was extracted with AcOEt
- washThe organic phase was washed with brine
- dry with materialwas dried over MgSO4
- filtrationwas filtered
- concentrationwas concentrated under reduced pressure
- customThe crude product was purified by flash chromatography over C18 column
Sources & evidence
- ORD record
- ord-a7f5fcf130d348a486c01d6789d738a7
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524726B2
Linked notes
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