Trifluoroacetic acid → HCID 68696215, compound

HRID 2236838Notes

Reaction equation

HRID 2236838 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:15]([O-])=O.FC(F)(F)C(O)=O.C(N(CC)CC)C>C(O)C>[F:1][C:2]1[C:3]([NH2:15])=[CH:4][CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 68695860HCID 68695860, compound

Product 1

HCID 68696215HCID 68696215, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-(6-fluoro-5-nitropyridin-2-yl)-4-methylpiperazine.trifluoroacetic acid salt (0.38 g, 1.1 mmol) in ethanol (30 mL) is added triethylamine dropwise with agitation until all of the solid had dissolved. The mixture is then degassed with dry ice and treated with an aqueous slurry of Raney nickel (approx 1.5 mL). After shaking under 50 psi of hydrogen, the reaction mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 2-fluoro-6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamine (contaminated with triethylammonium trifluoroacetate) as a red wine colored solid.

Workup

  1. dissolutionhad dissolved
  2. customThe mixture is then degassed with dry ice
  3. additiontreated with an aqueous slurry of Raney nickel (approx 1.5 mL)
  4. filtrationthe reaction mixture is filtered through a pad of diatomaceous earth
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-801fdd4893134ff19bf7ca6db3ca6132
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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