Trifluoroacetic acid → HCID 178448159, compound

HRID 539062Notes

Reaction equation

HRID 539062 reaction equation
[CH2:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:29]=[CH:28][N:27](COCC[Si](C)(C)C)[N:26]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)[CH2:2][CH3:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:27]1[CH:28]=[N:29][C:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]3[CH:17]=[N:16][N:13]4[CH:14]=[CH:15][C:10]([N:5]5[C@@H:4]([CH2:1][CH2:2][CH3:3])[CH2:8][O:7][C:6]5=[O:9])=[N:11][C:12]=34)=[CH:24][CH:23]=2)=[N:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67035120(S)-4-propyl-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 178448159HCID 178448159, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-4-propyl-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 (0.039 g, 0.075 mmol) in DCM (0.4 mL) was treated with trifluoroacetic acid (0.4 mL) at ambient temperature. The mixture was stirred for 18 hours. The solvent was concentrated and the residue was partitioned between EtOAc and aqueous saturated NaHCO3. The aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with brine, dried, concentrated and purified by column chromatography (1-5% 20% 7N ammonia in MeOH/dichloromethane) to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one (0.018 g, 62%) as a beige solid. LCMS (APCI+) m/z 390 [M+H]+.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between EtOAc and aqueous saturated NaHCO3
  3. extractionThe aqueous layer was further extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography (1-5% 20% 7N ammonia in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-0efd72eca3904908ab4726d1ede632d1
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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