HCID 67034134, compound → HCID 178519150, compound

HRID 539101Notes

Reaction equation

HRID 539101 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][C:38]([F:41])=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:42])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][C:38]([F:41])=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:42])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1

Participants

3

Reactant 1

HCID 67034134HCID 67034134, compound

Product 1

HCID 178519150HCID 178519150, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To the solid (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (5.8 g, 9.8 mmol) was added TFA (40 mL) and the reaction stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the residue was dissolved in acetonitrile/methanol (1:1, 70 mL). Water (30 mL) was added and the mixture was stirred at ambient temperature for 3 hours. The aqueous layer was made basic with NaHCO3 (saturated solution) and the organic layer was removed in vacuo. The solid that formed was filtered and dried in vacuo. The solid was taken up in acetone (100 mL) and water added (500 mL) slowly. After complete addition, the slurry was stirred for 1 hour at ambient temperature. The slurry was filtered and the solid dried in vacuo for 36 hours to yield (S)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (3.4 g, 7.4 mmol, 75% yield). LCMS (APCI+) m/z 461 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in acetonitrile/methanol (1:1, 70 mL)
  3. additionWater (30 mL) was added
  4. stirringthe mixture was stirred at ambient temperature for 3 hours
  5. customthe organic layer was removed in vacuo
  6. customThe solid that formed
  7. filtrationwas filtered
  8. customdried in vacuo
  9. additionwater added (500 mL) slowly
  10. additionAfter complete addition
  11. stirringthe slurry was stirred for 1 hour at ambient temperature
  12. filtrationThe slurry was filtered
  13. customthe solid dried in vacuo for 36 hours

Sources & evidence

ORD record
ord-c9522d7796024b438f3477481828a300
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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