Trifluoroacetic acid → HCID 178497391, compound

HRID 1488150Notes

Reaction equation

HRID 1488150 reaction equation
[C:1](O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:13]([CH3:14])=[C:12]([C:15]2[C:16]([CH3:25])=[CH:17][C:18]([CH3:24])=[C:19]([CH:23]=2)[C:20]([O-:22])=[O:21])[N:11](COCC[Si](C)(C)C)[N:10]=1>C(Cl)Cl>[Cl:8][C:9]1[C:13]([CH3:14])=[C:12]([C:15]2[C:16]([CH3:25])=[CH:17][C:18]([CH3:24])=[C:19]([CH:23]=2)[C:20]([O:22][CH3:1])=[O:21])[NH:11][N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736852HCID 131736852, compound2×

Product 1

HCID 178497391HCID 178497391, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 mL) was carefully added to a solution of 5-(3-chloro-4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-2,4-dimethylbenzoate (compound 250.4, 2.0 g, 4.90 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 2 hours, then the solvents were removed under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with sat. NaHCO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc, 4:1) to yield the title compound as white foam (1.13 g, 83%) m/z (ES+) 279 (M+H)+.

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washwashed with sat. NaHCO3 (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-004e9777716f4111b93a34410249f055
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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