Hydrogen Peroxide → HCID 178513672, compound

HRID 459919Notes

Reaction equation

HRID 459919 reaction equation
C([O-])([O-])=[O:2].[K+].[K+].[CH2:7]([NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][N:23]=2)[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.OO>CS(C)=O>[CH2:7]([NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([O:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]([NH2:27])=[O:2])=[CH:24][N:23]=2)[CH2:19][CH2:20]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 18445309HCID 18445309, compound

Product 1

HCID 178513672HCID 178513672, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add K2CO3 (200 mg, 1.44 mmol) to a solution of 6-(4-benzylamino-cyclohexyloxy)-nicotinonitrile (890 mg, 2.89 mmol) in DMSO (25 mL). Cool the reaction to 0° C. and add hydrogen peroxide (0.87 mL). Stir the resulting reaction mixture at room temperature for 2 h. Then quench the reaction mixture with water (25 mL) and extract with EtOAc (30 mL). Dried over sodium sulfate, filter and concentrate. Further purify the residue by SCX chromatography to provide the title compound (700 mg, 74%). Mass spectrum (ion spray): m/z=326.0 (M+1); 1H NMR (CDCl3): 8.61 (s, 1H), 8.04 (m, 1H), 7.36 (m, 5H), 6.74 (d, J=8.8 Hz, 1H), 5.10 (m, 1H), 3.87 (s, 2H), 2.64 (m, 1H), 2.22–2.07 (m, 4H), 1.58–1.33 (m, 4H).

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. customthe resulting reaction mixture at room temperature for 2 h
  4. customThen quench the reaction mixture with water (25 mL)
  5. extractionextract with EtOAc (30 mL)
  6. dry with materialDried over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customFurther purify the residue by SCX chromatography

Sources & evidence

ORD record
ord-ae2f8147a420411580b61e932a26533f
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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