[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]([CH3:35])([CH2:32][CH2:33][CH3:34])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:31])=[N:15][N:16]2[C:21]([O:22]CC3C=CC=CC=3)=[CH:20][C:19]([CH3:30])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2].C1CCCCC=1>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]([CH3:35])([CH2:32][CH2:33][CH3:34])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:31])=[N:15][N:16]2[C:21]([OH:22])=[CH:20][C:19]([CH3:30])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2]A solution of 207 mg (0.418 mmol) of rac-[1-{[7-benzyloxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl]amino}methyl}-1-methylbutyl)carbamic acid tert-butyl ester (Example 140A) in 6 ml of absolute ethanol was admixed with 47 mg of palladium on charcoal (loading 10% by weight, activated) and 1.3 ml of cyclohexene. The reaction mixture was heated to reflux under an argon atmosphere for 2.5 hours. The resulting mixture was cooled to room temperature, filtered through a layer of Celite and concentrated under reduced pressure, which gave 206 mg (99% yield, 81% pure) of the target compound.
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