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-(pyridin-2-yl)oxazolidin-2-one → HCID 178519097, compound

HRID 539056Notes

Reaction equation

HRID 539056 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[CH:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:41])=[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[CH:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:41])=[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 670347823-(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-(pyridin-2-yl)oxazolidin-2-one

Product 1

HCID 178519097HCID 178519097, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To the solid 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-(pyridin-2-yl)oxazolidin-2-one (0.36 g, 0.63 mmol) was added TFA (20 mL) and the reaction stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the material slurried in 1:1 methanol/acetonitrile (20 mL) with 10 mL of water, then stirred for 2 hours at ambient temperature. The reaction was concentrated in vacuo and the water layer basified to about pH 7 by the addition of saturated NaHCO3. The solids were filtered and washed with water. The solids were then slurried in 1:1 methanol/acetonitrile (20 mL) with 10 mL of water, and the organic solvents were removed in vacuo (3×). The residue was slurried in 1:1 methanol/acetonitrile (5 mL) with 10 mL of water and the solid filtered and washed with water to yield 3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.30 g, 0.68 mmol, 108% yield). LCMS (APCI+) m/z 443 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. stirringstirred for 2 hours at ambient temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe water layer basified to about pH 7 by the addition of saturated NaHCO3
  5. filtrationThe solids were filtered
  6. washwashed with water
  7. customthe organic solvents were removed in vacuo (3×)
  8. filtrationthe solid filtered
  9. washwashed with water

Sources & evidence

ORD record
ord-387456fd9daf4746af586ed613d7915b
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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