Water → HCID 59853676, compound

HRID 2374282Notes

Reaction equation

HRID 2374282 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[K].[C:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:10])=[CH2:9].O>CS(C)=O.C1COCC1>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:8]2([CH3:2])[CH2:10][CH2:9]2)=[C:12]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=3)[CH2:27][CH2:28]2)=[O:22])[CH:13]=1)(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)2×HCID 5462222Potassium2×HCID 59853753HCID 59853753, compound

Product 1

HCID 59853676HCID 59853676, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Trimethylsulfoxonium iodide (21.9 mg, 0.1 mmol) in dry DMSO (300 uL) was added Potassium tert-butoxyde (11.3 mg, 0.101 mmol) portionwise. A solution of (2-Isopropenyl-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone; Example 44 (20 mg, 0.0442 mmol) in dry THF (200 uL) was prepared separately and then added to the above suspension dropwise at room temperature. The reaction mixture was stirred at room temperature for 1 hour and then at 60° C. for 20 hours.The it was cooled down to rt and a solution of Trimethylsulfoxonium iodide (21.9 mg, 0.1 mmol) and Potassium tert-butoxyde (11.3 mg, 0.101 mmol) in dry DMSO (300 uL) was slowly added. Water was added and the solution was extracted 2 times with Ethylacetate. The combined organic phases were washed with water (3 times), dried over Na2SO4 ,filtered and the solvent was removed in vacuo. The residue was chromatographed on SiO2 Eluent: Heptane/EtOAc to provide the title compound (4.2 mg, 20%, white solid; Solid; M+H=467.2)

Workup

  1. additionadded to the above suspension dropwise at room temperature
  2. waitat 60° C. for 20 hours
  3. temperatureThe it was cooled down to rt
  4. extractionthe solution was extracted 2 times with Ethylacetate
  5. washThe combined organic phases were washed with water (3 times)
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was chromatographed on SiO2 Eluent

Sources & evidence

ORD record
ord-dc21022a995545bc829e283f0182fa62
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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