Trifluoroacetic acid → 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

HRID 1062782Notes

Reaction equation

HRID 1062782 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12](C(OC(C)(C)C)=O)=[C:11]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:10]([CH3:34])[N:9]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl.[Cl-].[NH4+]>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=2)(=[O:22])=[O:23])[N:10]([CH3:34])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22282018tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 222819172-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazol-3-yl)oxy}ethyl acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To tert-butyl 3-[2-(acetyloxy)ethoxy]-5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-1H-pyrazole-4-carboxylate (Preparation 9) (1.48 g) in dichloromethane (20 ml) was added trifluoroacetic acid (10 ml), at room temperature. The reaction mixture was stirred at room temperature for 2.5 hours and then refluxed for 3 hours. The reaction mixture was then diluted with a saturated solution of aqueous ammonium chloride (20 ml), and the aqueous was then extracted with ethyl acetate (2×20 ml). The organics were dried with magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by chromatography on a suction column packed with silica eluted with ethyl acetate:hexane (3:5) to yield the desired product as an off white solid (200 mg).

Workup

  1. customat room temperature
  2. temperaturerefluxed for 3 hours
  3. extractionthe aqueous was then extracted with ethyl acetate (2×20 ml)
  4. dry with materialThe organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by chromatography on a suction column
  8. washeluted with ethyl acetate:hexane (3:5)

Sources & evidence

ORD record
ord-d89db2f68b8241ae83a305faff8da471
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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