Potassium Cyanide → HCID 57940678, compound

HRID 1437298Notes

Reaction equation

HRID 1437298 reaction equation
CS([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[N:15]([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[N:14]=[C:13]([C:24]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:25])[CH:12]=2)[CH:6]=1)(=O)=O.[C-:32]#[N:33].[K+]>CN(C)C=O>[C:32]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[N:15]([C:16]3[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[N:14]=[C:13]([C:24]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:25])[CH:12]=2)[CH:6]=1)#[N:33]

Participants

4

Reactant 2

HCID 9032Potassium Cyanide2×HCID 57940687HCID 57940687, compound

Product 1

HCID 57940678HCID 57940678, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-[5-(4-methanesulfonyl-2-pyridyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperidine (0.60 g) obtained in Example 97 in N,N-dimethylformamide (12 mL), potassium cyanide (97.3 mg) was added at room temperature. The mixture was stirred at 120° C. for 37 hours, and then potassium cyanide (97.3 mg) was further added thereto. The mixture was further stirred at 120° C. for 4 hours, and then cooled in air. The reaction mixture was partitioned between saturated brine and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform-ethyl acetate), to thereby give the title compound as a solid (0.441 g, 84%).

Workup

  1. stirringThe mixture was further stirred at 120° C. for 4 hours
  2. temperaturecooled in air
  3. customThe reaction mixture was partitioned between saturated brine and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified through silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record
ord-06a307c0fe844b07be2638360e6d9055
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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