Trifluoroacetic acid → HCID 66690453, compound

HRID 592290Notes

Reaction equation

HRID 592290 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.FC(F)(F)C(O)=O>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:21]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66690109HCID 66690109, compound

Product 1

HCID 66690453HCID 66690453, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(benzylamino)-6-(4-methylphenyl)isonicotinate (0.37 g, 0.98 mmol) in ethanol (4.67 mL) were added palladium dihydroxide (3.42 mg, 0.024 mmol) and trifluoroacetic acid (0.08 mL, 1.08 mmol). The mixture was purged with hydrogen and stirred under hydrogen (1 atm) at 60° C. After 30 min, the mixture was cooled to ambient temperature and filtered with Celite. The filtered cake was washed with methanol and the filtrate was concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (145 mg): LC-MS [M+1]=285.2.

Workup

  1. customThe mixture was purged with hydrogen
  2. temperaturethe mixture was cooled to ambient temperature
  3. filtrationfiltered with Celite
  4. washThe filtered cake was washed with methanol
  5. concentrationthe filtrate was concentrated
  6. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-176486b0a4ea42b388b8dfe8716ffeb3
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

Loading…