[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:3][CH2:2]1.[H][H]>[C].[Pd].O1CCCC1>[NH2:18][C:9]1[CH:10]=[C:11]([C:14]([F:16])([F:17])[F:15])[CH:12]=[CH:13][C:8]=1[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1A 3-neck flask (200 mL) was charged with 1-(tetrahydropyran-4-yl)amino-2-nitro-4-trifluoromethylbenzene (see Synthesis Example 4-1) (1.00 g, 3.45 mmol) and tetrahydrofuran (17 mL), and this was shaken to give a homogeneous solution. To this was added palladium-carbon (Pd: 10%, 0.09 g), and this was again shaken. Hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and after vigorous shaking at room temperature under these conditions for 4 h, this was purged with nitrogen, distilled water (40 mL) was added and this was shaken for 10 minutes, then insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was further washed with ethyl acetate. The filtrate and wash solutions were combined and the solvent was distilled off under reduced pressure to yield the title compound (0.66 g, 73.6% yield) as a white powder.
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