HCID 59508997, compound → HCID 59509002, compound

HRID 1020048Notes

Reaction equation

HRID 1020048 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[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=3[F:33])[N:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[F:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:25]=1[C:23]1[N:22]=[CH:21][N:20]=[C:19]([NH:18][C:17]([CH:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)=[O:34])[CH:24]=1

Participants

4

Reactant 1

HCID 59508997HCID 59508997, compound

Product 1

HCID 59509002HCID 59509002, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[6-(2-Fluoro-6-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXIII) (0.05 g, 0.1 mmol) was dissolved in methanol (5 ml) and 10% Pd/C (0.03 g) was added under an atmosphere of nitrogen. The mixture 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. The resulting crude product was triturated with dry diethyl ether (2 ml) and concentrated to yield piperidine-4-carboxylic acid [6-(2-fluoro-6-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #12A) (0.029 g, 81%) as a white solid.

Workup

  1. customThe catalyst was removed from the reaction mixture by filtration through a celite bed
  2. customthe filtrate was evaporated to dryness
  3. customThe resulting crude product was triturated with dry diethyl ether (2 ml)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e291aa1987ce4d76b55e6fa4076267ea
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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