(S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → (S)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide
Reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](=[O:33])[NH:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[N:22]=[CH:21][N:20]=2)[CH2:12]1)=O)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:22]=[CH:21][N:20]=[C:19]([NH:18][C:17]([C@H:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:33])[CH:24]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXXIV) (7.0 g) in 50 ml of methanol was added 10% palladium hydroxide (1.5 g) under an atmosphere of nitrogen and the mixture was stirred at room temperature under an atmosphere of hydrogen for 8 hours. The reaction mixture was filtered through celite and the solvent was evaporated. The obtained product was taken in diethyl ether, stirred, filtered, washed with diethyl ether and dried under vacuum to obtain (S)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #17A) as a white solid (3.0 g, 62%), melting point 163-165° C.
Workup
- filtrationThe reaction mixture was filtered through celite
- customthe solvent was evaporated
- stirringstirred
- filtrationfiltered
- washwashed with diethyl ether
- customdried under vacuum
Sources & evidence
- ORD record
- ord-e84d6f71bdcc428bb1d9108d3eb8d0aa
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716296B2
Reaction notes
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