(S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one → HCID 178519138, compound

HRID 539051Notes

Reaction equation

HRID 539051 reaction equation
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5[N:32]=[CH:31][N:30](COCC[Si](C)(C)C)[N:29]=5)=[CH:24][CH:23]=4)=[C:15]3[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[NH:30]1[CH:31]=[N:32][C:28]([C:25]2[CH:24]=[CH:23][C:22]([C:21]3[CH:20]=[N:19][N:16]4[CH:17]=[CH:18][C:13]([N:8]5[C@@H:7]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=6)[CH2:11][O:10][C:9]5=[O:12])=[N:14][C:15]=34)=[CH:27][CH:26]=2)=[N:29]1

Participants

3

Reactant 1

HCID 67034450(S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

Product 1

HCID 178519138HCID 178519138, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To the solid (S)-4-phenyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.80 g, 1.4 mmol) was added TFA (20 mL) and the reaction stirred at room temperature for 3 hours. The reaction was concentrated and the residue slurried in methanol/acetonitrile (20 mL 1:1) and water (20 mL) added and the reaction stirred at ambient temperature for 1 hour. The organic solvents were removed in vacuo and the water layer basified to about pH 7 using a solution of saturated NaHCO3. The aqueous layer was then stirred for 5 minutes. The solids were filtered and dried in vacuo. The solids were then taken up in water and stirred for 2 hours. The solids were filtered and dried in vacuo. The solids were next slurried in methanol while nitrogen was bubbled through the solution for 2 hours. The slurry was concentrated to about 20 mL, and the solids filtered and dried in vacuo to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one (0.19 g, 0.45 mmol, 31% yield). LCMS (APCI+) m/z 424 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionwater (20 mL) added
  3. stirringthe reaction stirred at ambient temperature for 1 hour
  4. customThe organic solvents were removed in vacuo
  5. stirringThe aqueous layer was then stirred for 5 minutes
  6. filtrationThe solids were filtered
  7. customdried in vacuo
  8. stirringstirred for 2 hours
  9. filtrationThe solids were filtered
  10. customdried in vacuo
  11. customwas bubbled through the solution for 2 hours
  12. concentrationThe slurry was concentrated to about 20 mL
  13. filtrationthe solids filtered
  14. customdried in vacuo

Sources & evidence

ORD record
ord-be110689b3dd4f579c4be83e7f163333
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…