Trifluoroacetic acid → HCID 68616622, compound

HRID 2406708Notes

Reaction equation

HRID 2406708 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[O:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:20]=1)(C)(C)C>C(Cl)(Cl)Cl>[CH3:26][C:23]1[O:22][C:21]([C:19]2[CH:20]=[C:15]([NH2:14])[CH:16]=[N:17][CH:18]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89546857HCID 89546857, compound

Product 1

HCID 68616622HCID 68616622, compoundYield 118.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

TFA (1 ml) was added to a chloroform solution (2 ml) containing tert-butyl(5-(5-methylfuran-2-yl)pyridin-3-yl)carbamate (61 mg) obtained in the 1st step, stirring at room temperature for 2 hours. The solvent was distilled away under reduced pressure, the obtained residue was dissolved in chloroform, and the resultant was washed with water and a saturated aqueous sodium hydrogen carbonate solution. Subsequently, the aqueous layers were combined, followed by extraction with chloroform (×2). The organic layers was combined and dried over anhydrous sodium sulfate. The solvent was distilled away from the obtained organic layers under reduced pressure, and a white solid of 5-(5-methylfuran-2-yl)pyridin-3-amine (46 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. distillationThe solvent was distilled away under reduced pressure
  3. dissolutionthe obtained residue was dissolved in chloroform
  4. washthe resultant was washed with water
  5. extractionfollowed by extraction with chloroform (×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away from the obtained organic layers under reduced pressure

Sources & evidence

ORD record
ord-369de32a9b484d26a754616941e3eec4
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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