4-[6-(2-Ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → Piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020030Notes

Reaction equation

HRID 1020030 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([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][CH2:32][CH3:33])[N:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH2:32]([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:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[O:34])[CH:24]=1)[CH3:33]

Participants

4

Reactant 1

HCID 595090544-[6-(2-Ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 59508999Piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amideYield 58.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[6-(2-Ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (IX) (1.47 g, 3.19 mmol) was dissolved in methanol (20 ml) and 10% Pd/C (0.81 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 filtered from the reaction mixture through a celite bed and the filtrate was evaporated to dryness to obtain piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #1A) (0.61 g, 58%).

Workup

  1. filtrationThe catalyst was filtered from the reaction mixture through a celite bed
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-bce3c3f61a524e75971ded529828a9ab
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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