[C:1]([C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=2)[N:5]([CH3:20])[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=[O:22])#[CH:2]>CO.[Pd]>[CH2:1]([C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=2)[N:5]([CH3:20])[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:25][CH2:24]1)=[O:22])[CH3:2]A solution of 0.13 g (0.29 mmol) of [5-ethynyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 13) in 5 ml of MeOH was treated with 0.031 g (0.03 mmol) of Pd—C (10%) and the reaction mixture was then hydrogenated with H2 (1 bar) at RT for 2 hours. After removal the catalyst by filtration, the solvent was evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.12 g (92%) of the title compound as light yellow oil. MS: 451.1 (MH+).
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