Trifluoroacetic acid → HCID 178519137, compound

HRID 539114Notes

Reaction equation

HRID 539114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:33]=[CH:32][N:31](COCC[Si](C)(C)C)[N:30]=4)=[C:25]([F:42])[CH:24]=3)=[C:16]2[N:15]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[N:33]=[CH:32][NH:31][N:30]=4)=[C:25]([F:42])[CH:24]=3)=[C:16]2[N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67034362(S)-4-(2-chlorophenyl)-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)oxazolidin-2-one

Product 1

HCID 178519137HCID 178519137, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-4-(2-chlorophenyl)-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)oxazolidin-2-one (20 mg, 0.033 mmol) in DCM (5 mL) was added TFA (1 mL) and the reaction was stirred at ambient temperature for 6 hours. The reaction was concentrated to dryness and the residue dissolved in MeOH/ammonia (7N). After stirring at ambient temperature for 30 minutes, the reaction was concentrated then purified by reverse phase chromatography (SP4, 12M, water/CH3CN 100:0 to 0:100, 20 column volumes) to yield (S)-4-(2-chlorophenyl)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (9 mg, 57% yield) as a pale yellow solid. LCMS (APCI+) m/z 476.2 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionthe residue dissolved in MeOH/ammonia (7N)
  3. stirringAfter stirring at ambient temperature for 30 minutes
  4. concentrationthe reaction was concentrated
  5. customthen purified by reverse phase chromatography (SP4, 12M, water/CH3CN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-0608fbe5d77c4481b4ba1aced9a111c8
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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