Hydrogen Peroxide → HCID 67168088, compound

HRID 1517614Notes

Reaction equation

HRID 1517614 reaction equation
[F:1][C:2]1[S:6][C:5]2[C:7]3([O:28][CH2:29][CH2:30][C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([CH2:13][C:14]1[C:15]([CH3:27])=[N:16][N:17]([C:19]2[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:18]=1)[CH2:9][CH2:8]3.C(=O)([O-])[O-:32].[K+].[K+].OO.O>CS(C)=O>[F:1][C:2]1[S:6][C:5]2[C:7]3([O:28][CH2:29][CH2:30][C:4]=2[CH:3]=1)[CH2:12][CH2:11][N:10]([CH2:13][C:14]1[C:15]([CH3:27])=[N:16][N:17]([C:19]2[C:24]([C:25]([NH2:26])=[O:32])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:18]=1)[CH2:9][CH2:8]3

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 11430Potassium CarbonateHCID 67168341HCID 67168341, compound

Product 1

HCID 67168088HCID 67168088, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 2-[4-[(2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-1′-yl)methyl]-3-methyl-pyrazol-1-yl]pyridine-3-carbonitrile (0.71 mmol, 0.30 g) in dimethylsulfoxide (7.5 mL), potassium carbonate (0.049 g, 0.35 mmol) is added and the mixture is cooled to 0-5° C. before adding 33% hydrogen peroxide solution in water (0.39 mL, 3.78 mmol). The mixture is stirred at room temperature for 2 h. Then, water is added carefully and the reaction mixture is extracted with ethyl acetate. Organic layer is decanted, dried over magnesium sulfate and solvent is evaporated under reduced pressure. Crude is purified by normal phase Isco chromatography using as eluent dichloromethane/methanol mixtures to give 0.252 g that are further purified by reverse phase HPLC to yield 0.198 g of 2-[4-[(2-fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-1′-yl)methyl]-3-methyl-pyrazol-1-yl]pyridine-3-carboxamide. MS (m/z): 442 (M+1).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. customOrganic layer is decanted
  3. dry with materialdried over magnesium sulfate and solvent
  4. customis evaporated under reduced pressure
  5. customCrude is purified by normal phase Isco chromatography
  6. customto give 0.252 g that
  7. customare further purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e704aaa6eaea4c7fb81c6c063bd3b8ec
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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