Cl[C:2]1[N:9]=[C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])[C:7]([F:17])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23].[F-].[K+]>CS(C)=O>[C:4]([C:3]1[C:2]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23])=[N:9][C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])=[C:7]([F:17])[CH:6]=1)#[N:5]A mixture of 2-chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrile (120 mg, 0.47 mmol), 3-amino-N-methoxy-4-methyl-benzamide (120 mg, 0.66 mmol) and potassium fluoride (30 mg, 0.51 mmol) in DMSO (1 mL) was heated to 150° C. overnight. The reaction mixture was allowed to cool down to room temp and then partitioned between water and ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The product (7.5 mg, 4%) was obtained after purification by silica gel chromatography with 30% EtOAc in hexane as eluent. C21H26FN5O2 MS m/e=400 (M+H).
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