Trifluoroacetic acid → HCID 178519144, compound

HRID 539131Notes

Reaction equation

HRID 539131 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][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>CC#N.CO.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][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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68089128(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-(pyridin-2-yl)oxazolidin-2-one

Product 1

HCID 178519144HCID 178519144, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 21864137Acetonitrile methanol waterSolvent

Procedure

To (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-(pyridin-2-yl)oxazolidin-2-one (0.090 g, 0.16 mmol) was added TFA (10 mL) and the reaction was stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the resulting material dissolved in MeOH/CH3CN/water (1:1:1, 30 mL total) and stirred for 20 minutes at ambient temperature. The mixture was basified by adding NaHCO3 (saturated aqueous solution) and the solid that formed was isolated by filtration. The solids were slurried in CH3CN/MeOH/water (1:1:5, 40 mL total) and the material filtered and dried in vacuo to yield (S)-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 (0.054 g, 77.1%). LCMS (APCI+) m/z 443 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe resulting material dissolved in MeOH/CH3CN/water (1:1:1, 30 mL total)
  3. stirringstirred for 20 minutes at ambient temperature
  4. additionby adding NaHCO3 (saturated aqueous solution)
  5. customthe solid that formed
  6. customwas isolated by filtration
  7. filtrationthe material filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-af080da5b2864b0b9cdb644c05df3d96
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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