C([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])C1C=CC=CC=1.[H][H]>C1COCC1.CCO.[Pd]>[CH3:16][C:15]1[O:14][C:13]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[N:12][C:11]=1[CH2:10][CH2:9][OH:8]A solution of {4-[4-(2-benzyloxy-ethyl)-5-methyl-oxazol-2-yl]-phenyl}-methyl-phenyl-amine (195 mg, 0.490 mmol) in THF (2 mL) and EtOH (10 mL) was treated a slurry of Pd/C (200 mg) in EtOH (2 mL). The resulting mixture was treated with hydrogen under balloon pressure for 14 h and filtered through a pad of Celite. The filtrate was concentrated, and crude product was purified by silica gel chromatography column (50% EtOAc/hexanes) to yield the title compound (91 mg, 60%).
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