HCID 59508970, compound → HCID 25227433, compound

HRID 1020054Notes

Reaction equation

HRID 1020054 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH: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]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:33])[CH:24]=1

Participants

4

Reactant 1

HCID 59508970HCID 59508970, compound

Product 1

HCID 25227433HCID 25227433, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (3 g) in 20 mL of methanol was added 10% palladium hydroxide (300 mg) under an atmosphere of nitrogen and the mixture was stirred at room temperature under an atmosphere of hydrogen for 4 hours. The reaction mixture was filtered through celite and the solvent was evaporated. Diethyl ether was added to the product, the mixture was stirred, filtered and the obtained solid was rewashed with diethyl ether and dried under vacuum to yield piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #16A) as a white solid (1.8 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated
  3. additionDiethyl ether was added to the product
  4. stirringthe mixture was stirred
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c64d3f68636d42dcb41392a426bbb520
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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