Trifluoroacetic acid → HCID 178455828, compound

HRID 539066Notes

Reaction equation

HRID 539066 reaction equation
[CH2:1]([C@H:3]1[CH2:7][O:6][C:5](=[O:8])[N:4]1[C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[CH:16][C:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=4)=[CH:20][CH:19]=3)=[C:11]2[N:10]=1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:26]1[CH:27]=[N:28][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]3[CH:16]=[N:15][N:12]4[CH:13]=[CH:14][C:9]([N:4]5[C@@H:3]([CH2:1][CH3:2])[CH2:7][O:6][C:5]5=[O:8])=[N:10][C:11]=34)=[CH:23][CH:22]=2)=[N:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68088869(S)-4-ethyl-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 178455828HCID 178455828, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-4-ethyl-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 (0.024 g, 0.047 mmol) in DCM (1 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 partitioned between EtOAc and aqueous satd. NaHCO3. The aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (1-5% 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-ethyloxazolidin-2-one (0.008 g, 45%) as a beige solid. MS (APCI+) m/z 376 [M+H]+.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue partitioned between EtOAc and aqueous satd
  3. extractionThe aqueous layer was further extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. addition(phase separator silicone treated filter paper)
  7. concentrationconcentrated
  8. custompurified on silica gel (1-5% 7N ammonia in MeOH/dichloromethane)

Sources & evidence

ORD record
ord-7ec1a014f1414329869583b8259fbd9a
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…