[ClH:1].C(O)C.C([N:12]1[CH2:19][C:16]2([CH2:18][CH2:17]2)[N:15]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:14][CH2:13]1)C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)C>[ClH:1].[F:24][C:21]([F:22])([F:23])[C:20]([N:15]1[CH2:14][CH2:13][NH:12][CH2:19][C:16]21[CH2:18][CH2:17]2)=[O:25]1 N Hydrochloric acid-ethanol (105 ml, 105 mmol) and 5% palladium carbon (3 g) were added to an ethanol (250 ml) solution of the compound (15.5 g, 51 mmol) obtained in Step 4 above and contact reduction was performed for 15 hours in a hydrogen atmosphere. The catalyst was filtrated through celite, then the filtrate was concentrated under reduced pressure, an ethanol-diethyl ether mixed solvent was added to the resulting residue, and the precipitated solid was collected by filtration to give the title compound (10.3 g, 83%) as a colorless solid.
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