Trifluoroacetic acid → HCID 66748381, compound

HRID 1622788Notes

Reaction equation

HRID 1622788 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9]1[C:14]([C:15]2(O)[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1>[Pd].CO>[C:21]1([CH:18]2[CH2:17][CH2:16][CH:15]([C:14]3[C:9]([NH2:8])=[N:10][CH:11]=[CH:12][CH:13]=3)[CH2:20][CH2:19]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 64087922HCID 64087922, compound

Product 1

HCID 66748381HCID 66748381, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

TFA (3 ml) was added to 1-(2-aminopyridin-3-yl)-4-phenylcyclohexanol (246 mg) and the mixture was stirred at 40° C. under nitrogen for 6 hr. TFA was removed in vacuo and this product was subjected to the next reaction without further purification. MeOH (1 ml) and Pd/C (10 mg) were added and the mixture was stirred at room temperature under hydrogen for 2 days. The insoluble solid was removed by filtration through Celite-pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (38.6 mg) as colorless oil.

Workup

  1. customTFA was removed in vacuo
  2. customthis product was subjected to the next reaction without further purification
  3. stirringthe mixture was stirred at room temperature under hydrogen for 2 days
  4. customThe insoluble solid was removed by filtration through Celite-pad (eluted with EtOAc)
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-884909e5b6574345909cffb2ff61d925
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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