Potassium Cyanide → HCID 86691861, compound

HRID 1616249Notes

Reaction equation

HRID 1616249 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:25])=[C:7]([C:9]2[N:14]=[C:13]3[N:15]([CH3:24])[C:16](=[O:23])[N:17]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]3=[CH:11][CH:10]=2)[CH:8]=1.[C-:26]#[N:27].[K+]>CN1C(=O)CCC1>[CH3:22][C:19]([CH3:21])([CH3:20])[CH2:18][N:17]1[C:12]2[C:13](=[N:14][C:9]([C:7]3[CH:8]=[C:3]([CH2:2][C:26]#[N:27])[CH:4]=[CH:5][C:6]=3[CH3:25])=[CH:10][CH:11]=2)[N:15]([CH3:24])[C:16]1=[O:23]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 86691860HCID 86691860, compound

Product 1

HCID 86691861HCID 86691861, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 82-1 (180 mg, 0.45 mmol) in NMP was added potassium cyanide (32 mg, 0.49 mmol), the vessel was sealed and heated to 120 C. After 15 hours, the reaction was purified by reverse phase chromatography (Sunfire C18, 40-95% CH3CN/0.1% TFA/water). Fractions containing product were partially concentrated, quenched with aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give 82-2 as an oil. HRMS (M+H)+: observed=349.1, calculated=349.4.

Workup

  1. customthe vessel was sealed
  2. temperatureheated to 120 C
  3. customthe reaction was purified by reverse phase chromatography (Sunfire C18, 40-95% CH3CN/0.1% TFA/water)
  4. additionFractions containing product
  5. concentrationwere partially concentrated
  6. customquenched with aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe combined organics were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-41f5089ab11949f3a115d38eca2927c5
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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