p-Chloroperbenzoic acid → HCID 15952963, compound

HRID 1896414Notes

Reaction equation

HRID 1896414 reaction equation
ClC1C=CC(C(OO)=[O:9])=CC=1.[CH3:12][S:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH2:27][N:28]3[CH2:32][CH:31]([CH2:33][CH2:34][CH3:35])[CH2:30][C:29]3=[O:36])=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=2)[N:19]=1>C(Cl)(Cl)Cl>[CH3:12][S:13]([C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH2:27][N:28]3[CH2:32][CH:31]([CH2:33][CH2:34][CH3:35])[CH2:30][C:29]3=[O:36])=[C:21]([C:23]([F:25])([F:24])[F:26])[N:22]=2)[N:19]=1)=[O:9]

Participants

4

Reactant 2

HCID 70299p-Chloroperbenzoic acidHCID 15952855HCID 15952855, compound

Product 1

HCID 15952963HCID 15952963, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-chloroperbenzoic acid (36 mg, 0.134 mmol, 1 eq) is added to a solution of 1-{[6-(methylthio)-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-propyl pyrrolidin-2-one 33 (50 mg, 0.134 mmol) in chloroform (2 ml) at −30° C. After 30 minutes, the mixture is warmed to room temperature then stirred for additional 16 hours. After hydrolysis with a saturated aqueous NaHCO3 solution (2 ml) and extraction with CHCl3 (2 ml), the cumulated organic layers are dried over MgSO4 and condensed under reduced pressure. The resulting crude product is purified by reverse phase liquid chromatography (gradient acetonitrile/water/TFA) to yield 1-{[6-(methylsulfinyl)-2-(trifluoromethyl)imidazo[1,2-b]pyridazin-3-yl]methyl}-4-propylpyrrolidin-2-one 82.

Workup

  1. customAfter hydrolysis
  2. extractionwith a saturated aqueous NaHCO3 solution (2 ml) and extraction with CHCl3 (2 ml)
  3. dry with materialthe cumulated organic layers are dried over MgSO4 and condensed under reduced pressure
  4. customThe resulting crude product is purified by reverse phase liquid chromatography (gradient acetonitrile/water/TFA)

Sources & evidence

ORD record
ord-4c3e964d604249cbb22b40ee05280752
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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