N-[cis-1-Benzyl-6-(2-hydroxyethyl)piperidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide → N-[cis-6-(2-Hydroxyethyl)piperidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide
Reaction equation
C([N:8]1[C@H:13]([CH2:14][CH2:15][OH:16])[CH2:12][CH2:11][C@H:10]([NH:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH:29]([CH3:31])[CH3:30])[N:21]=2)=[O:19])[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[OH:16][CH2:15][CH2:14][C@H:13]1[NH:8][CH2:9][C@@H:10]([NH:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH:29]([CH3:31])[CH3:30])[N:21]=2)=[O:19])[CH2:11][CH2:12]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The mixture of N-[cis-1-benzyl-6-(2-hydroxyethyl)piperidin-3-yl]-1-isopropyl-1H-indazole-3-carboxamide (276 mg, 0.66 mmol, step 9 of Example 1) and 10 wt. % palladium on carbon (30 mg) in methanol (5 mL) was stirred under hydrogen (1 atom) at room temperature for 4 h. The mixture was filtered through a pad of Celite washing with methanol and the filtrate was concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% ammonium hydroxide (10:1:0.2) to give 146 mg (67%) of the title compound as a white crystal.
Workup
- filtrationThe mixture was filtered through a pad of Celite
- washwashing with methanol
- concentrationthe filtrate was concentrated under reduced pressure
- customThe resulting residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol/25% ammonium hydroxide (10:1:0.2)
Sources & evidence
- ORD record
- ord-96b19f61f49944228eb99c26a503e9f7
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906532B2
Reaction notes
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