HCID 59509049, compound → HCID 59508959, compound

HRID 1020067Notes

Reaction equation

HRID 1020067 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:34])[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]=[C:21]([CH3:33])[N:20]=2)[CH2:12]1)=O)C1C=CC=CC=1>CO.CCOCC.[OH-].[OH-].[Pd+2]>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:22]=[C:21]([CH3:33])[N:20]=[C:19]([NH:18][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:34])[CH:24]=1

Participants

5

Reactant 1

HCID 59509049HCID 59509049, compound

Product 1

HCID 59508959HCID 59508959, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

3-[6-(2-Methoxy-phenyl)-2-methyl-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXXVII) (0.270 g, 0.586 mmol) was taken in methanol (5 ml) to which 10% Pd(OH)2 (0.125 g) was added and the mixture was stirred overnight under an atmosphere of hydrogen. The reaction was monitored by TLC. After completion, the reaction mixture was filtered through a celite bed and concentrated to get a viscous oil which was stirred in ether to precipitate a white solid. Filtration provided 0.160 g of piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-2-methyl-pyrimidin-4-yl]-amide (compound #22A).

Workup

  1. additionwas added
  2. filtrationAfter completion, the reaction mixture was filtered through a celite bed
  3. concentrationconcentrated
  4. customto get a viscous oil which
  5. customto precipitate a white solid
  6. filtrationFiltration

Sources & evidence

ORD record
ord-c21930b5e03d46f689774ee2705d9d84
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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