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

Participants

Reaction Steps

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]+.

Provenance & Evidence