4-[6-(2-Cyclopropylmethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → Piperidine-4-carboxylic acid [6-(2-cyclopropylmethoxy-phenyl)-pyrimidin-4-yl]-amide
Reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:36])[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][CH2:32][CH:33]3[CH2:35][CH2:34]3)[N:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH:33]1([CH2:32][O:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:23]2[N:22]=[CH:21][N:20]=[C:19]([NH:18][C:17]([CH:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)=[O:36])[CH:24]=2)[CH2:34][CH2:35]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4-[6-(2-Cyclopropylmethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XV) (0.41 g, 0.84 mmol) was dissolved in methanol (20 ml) and 10% Pd/C (0.2 g) was added under an atmosphere of nitrogen. The reaction was stirred at room temperature under hydrogen balloon pressure for 18 hours. The catalyst was removed from the reaction mixture by filtration through a celite bed and the filtrate was evaporated to dryness. Then the crude product was triturated with dry diethyl ether (10 ml) and the solid was filtered off to obtain piperidine-4-carboxylic acid [6-(2-cyclopropylmethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #8A) (0.11 g, 37%) as a white solid.
Workup
- customThe catalyst was removed from the reaction mixture by filtration through a celite bed
- customthe filtrate was evaporated to dryness
- customThen the crude product was triturated with dry diethyl ether (10 ml)
- filtrationthe solid was filtered off
Sources & evidence
- ORD record
- ord-dd46623f3a6f4b3ba48107d1360c030b
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716296B2
Reaction notes
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