[CH:1]1([NH:4][C:5]([NH:7][C:8](=[O:20])[C:9]2[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=2F)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[NH4+].[Cl-]>O1CCCC1.CN(C)C=O>[CH:1]1([N:4]2[C:10]3[C:9](=[CH:14][C:13]([F:15])=[C:12]([F:16])[C:11]=3[O:17][CH3:18])[C:8](=[O:20])[NH:7][C:5]2=[O:6])[CH2:3][CH2:2]1A solution of 1-cyclopropyl-3-(3-methoxy-2,4,5-trifluorobenzoyl)urea (Example 27b, 0.94 g, 3.26 mmol) in tetrahydrofuran (20 mL) and N,N-dimethylformamide (5 mL) is treated with sodium hydride (0.275 g, 6.8 mmol, 60% in mineral oil dispersion) and heated at reflux for 16 hours. The mixture is cooled, treated with saturated NH4Cl and extracted with dichloromethane. The organic layer is then washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Flash column chromatography (1:3 ethyl acetate/hexanes) afforded the title compound. MS (EI, M+1) m/z 269.
Loading…
