[CH3:1][NH:2][NH2:3].Cl[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH2:23][CH:22]([C:24]4[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=4[F:31])[O:21][N:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7]>O1CCCC1>[F:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=1[CH:22]1[O:21][N:20]=[C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][N:2]([CH3:1])[NH2:3])[CH2:13][CH2:12]3)[S:15][CH:16]=2)[CH2:23]1To a mixture of methyl hydrazine (532 μL, 10.0 mmol) in tetrahydrofuran (1 mL) at 0° C. was added dropwise a solution of 2-chloro-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]ethanone (i.e. the product of Example 2, Step A) (425 mg, 1.0 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature overnight, and then concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane, washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as an oil (0.59 g weight including residual tetrahydrofuran), which was used without further purification.
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