[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]#[N:18])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].C(Cl)(=O)C.[NH3:27]>C1(C)C=CC=CC=1.CO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17](=[NH:27])[NH2:18])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]To a solution of 3-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)propanenitrile (20.0 g, 61.4 mmol) in toluene (30 mL) and methanol (30 mL) was added dropwise acetyl chloride (18.8 g, 239 mmol) over 5 min at 0° C. under N2. The reaction mixture was stirred at 25° C. for 8 h, then concentrated. It was dissolved with toluene (5 mL), cooled to 0° C. in an ice-bath, slowly mixed with ammonia (30.0 mL, 210 mmol), stirred at 25° C. overnight, filtered, washed with toluene/methanol (1/1) and concentrated. Purification via recrystallization with diethyl ether (50 mL) then afforded the title compound as a white solid (5.4 g, 25.7%).
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