Triethylamine → 2-(2-(2-((1H-Pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-ylethyl)phenyl)propanamide

HRID 592462Notes

Reaction equation

HRID 592462 reaction equation
CCN(CC)CC.[NH:8]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]([CH3:32])[C:29]([NH2:31])=[O:30])[C:17]([C:33]([F:36])([F:35])[F:34])=[CH:16][N:15]=2)[CH:10]=[N:9]1>CN(C=O)C.CCOC(C)=O.[Pd]>[NH:8]1[CH:12]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]([CH3:32])[C:29]([NH2:31])=[O:30])[C:17]([C:33]([F:35])([F:34])[F:36])=[CH:16][N:15]=2)[CH:10]=[N:9]1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 867123362-(2-((2-((1H-Pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide

Product 1

HCID 732951212-(2-(2-((1H-Pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-ylethyl)phenyl)propanamideYield 26%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Et3N (0.5 mL) was added to 2-(2-((2-((1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)propanamide A63 (0.211 g, 0.527 mmol) and 10% Pd/C (0.155 g) in DMF (4 mL) and EtOAc (16 mL) and the mixture was stirred under a hydrogen atmosphere for 16 hours. The mixture was filtered through Celite, concentrated under reduced pressure and purified using silica gel column chromatography (80-100% EtOAc in petroleum benzine 40-60° C. then 0-10% MeOH in EtOAc). The resulting product was further triturated with a mixture of Et2O and acetone and the precipitate was collected by vacuum filtration to give the title compound 54 (0.055 g, 26%). LCMS-D: rt 3.178 min; m/z 405.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. custompurified
  4. custom80-100% EtOAc in petroleum benzine 40-60° C.
  5. customThe resulting product was further triturated with a mixture of Et2O and acetone
  6. filtrationthe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-c76c8cf0808c44b58449de93ce669ff3
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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