HCID 24693813, compound → HCID 57656518, compound

HRID 2041496Notes

Reaction equation

HRID 2041496 reaction equation
[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.FC(F)(F)C(O)=O.[Pd]>[NH2:13][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:9][CH:10]=1

Participants

6

Reactant 2

HCID 24693813HCID 24693813, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57656518HCID 57656518, compoundYield 63.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Charge a solution of 6-cyclohexylamino-nicotinonitrile (1.4 g, 7.1 mmol) in methanol (70 mL) and trifluoroacetic acid (5 mL) to a pressure vessel containing 10% Pd/C (Degussa type E101, 600 mg). Pressurize the vessel to 40 psi with hydrogen and stir for 2 h. Filter the mixture through Celite®, wash with warm ethanol, and dichloromethane. Concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with dichloromethane/2M ammonia in methanol (99:1 to 90:10 gradient) to obtain the title compound (920 mg, 54%). MS (ES+) m/z: 206.1 (M+H)+.

Workup

  1. filtrationFilter the mixture through Celite®
  2. washwash with warm ethanol, and dichloromethane
  3. concentrationConcentrate the filtrate in vacuo
  4. customPurify the crude mixture by chromatography on silica gel eluting with dichloromethane/2M ammonia in methanol (99:1 to 90:10 gradient)

Sources & evidence

ORD record
ord-e932c7f8ace0423585ee3cb1979938b9
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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