(R)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → (R)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020062Notes

Reaction equation

HRID 1020062 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]=1

Participants

4

Reactant 1

HCID 86645894(R)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 67185972(R)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amideYield 72%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXX) (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, the residue was washed with diethyl ether and dried under vacuum to yield (R)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #18A) as a white solid (3.5 g, 72%), melting point 210-213° C.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated
  3. stirringstirred
  4. filtrationfiltered
  5. washthe residue was washed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-068a51790d314f52a4e8df285ae1490a
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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