Benzyl {(2S)-3-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]butan-2-yl}carbamate → N-[(3S)-3-Aminobutan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide
Reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:30][CH2:31][C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])[C:5]2[N:6]([C:8]([C:12]([NH:14][CH:15]([CH3:29])[C@@H:16]([NH:18]C(=O)OCC3C=CC=CC=3)[CH3:17])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:7]=1>C(O)C.[Pd]>[NH2:18][C@@H:16]([CH3:17])[CH:15]([NH:14][C:12]([C:8]1[N:6]2[CH:7]=[CH:2][CH:3]=[C:4]([O:30][CH2:31][C:32]3[C:33]([F:39])=[CH:34][CH:35]=[CH:36][C:37]=3[F:38])[C:5]2=[N:10][C:9]=1[CH3:11])=[O:13])[CH3:29]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
155 mg of benzyl {(2S)-3-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]butan-2-yl}carbamate (Example 191A, 0.28 mmol, 1 equivalent) were dissolved in 50 ml of ethanol, and 40 mg of palladium on activated carbon (5%) were added. The mixture was hydrogenated at RT and standard pressure for 3 h. After the reaction had ended, the mixture was filtered through silica gel, the residue was washed with ethanol and the mother liquor was concentrated under reduced pressure. The crude product obtained was purified by preparative HPLC (Method 9).
Workup
- customwas hydrogenated at RT
- filtrationthe mixture was filtered through silica gel
- washthe residue was washed with ethanol
- concentrationthe mother liquor was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-956e0e359dd04db6a20b3d7bb8f89159
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126998B2
Reaction notes
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