Trifluoroacetic acid → HCID 89666840, compound

HRID 2171246Notes

Reaction equation

HRID 2171246 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([NH:20]C(=O)OC(C)(C)C)[CH:12]=[N:13][C:14]=1[N:15]1[N:19]=[CH:18][CH:17]=[N:16]1>>[F:8][C:9]1[CH:10]=[C:11]([NH2:20])[CH:12]=[N:13][C:14]=1[N:15]1[N:19]=[CH:18][CH:17]=[N:16]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89666804HCID 89666804, compound

Product 1

HCID 89666840HCID 89666840, compoundYield 98.7%

Procedure

TFA (1 ml) was added to tert-butyl (5-fluoro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)carbamate (30 mg) obtained in the 2nd step, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, a 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as to alkalify the mixture, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and a light brown solid of 5-fluoro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-amine (19 mg) was thus obtained.

Workup

  1. customobtained in the 2nd step
  2. distillationThe solvent was distilled away under reduced pressure
  3. additiona 5M sodium hydroxide aqueous solution was added to the obtained residue at 0° C. so as
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layers were washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b9a1d73eec284551b13300f3f0cf276f
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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