[CH:1]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14]>CN(C=O)C>[CH:1]1([NH:9][C:15]2[CH:16]=[CH:17][CH:18]=[C:11]([F:10])[C:12]=2[C:13]#[N:14])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Cyclooctylamine (1.4 mL; 10 mmol) was added dropwise to a solution of 2,6-difluorobenzonitrile (1.39 g, 10 mmol) in DMF (6 ml) at 0° C. The reaction mixture was stiffed at room temperature for 4.5 hours. The reaction mixture was added to vigorously stirred ice water (40 ml) and extracted with ethyl acetate. Solvent was removed to yield 1.63 grams of 2-cyclooctylamino-6-fluorobenzonitrile.
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