Sodium Cyanide → HCID 69201361, compound

HRID 2252240Notes

Reaction equation

HRID 2252240 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:9]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:28][N:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)[CH:25]=4)[C:10]=3[N:11](COCC[Si](C)(C)C)[N:12]=2)=[CH:4][CH:3]=1.[C-:36]#[N:37].[Na+]>CN(C=O)C>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([CH2:28][C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][CH:23]=2)[C:10]2[NH:11][N:12]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([C:36]#[N:37])=[N:7][CH:6]=4)[C:9]=2[CH2:27]3)[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 69201902HCID 69201902, compound

Product 1

HCID 69201361HCID 69201361, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of Example 123D (70.6 mg, 0.142 mmol) and NaCN (9.7 mg, 0.199 mmol) in DMF (1.2 mL) in a capped vial was heated to 210° C. for 1200 seconds in a Smith Synthesizer (300W). The reaction was cooled using 40 psi pressurized air. The mixture was extracted with EtOAc and the organic layer was washed with 50% brine, NaHCO3, dried over MgSO4, filtered, concentrated. The crude product was treated with HCl (conc., 2 drops) and EtOH (3 mL) and the mixture was heated at 75° C. for 2.5 hours. The solvent was evaporated and the residue was purified using reversed-phase HPLC to give 7.5 mg of the desired product as TFA salt.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with 50% brine, NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe crude product was treated with HCl (conc., 2 drops) and EtOH (3 mL)
  8. customThe solvent was evaporated
  9. customthe residue was purified

Sources & evidence

ORD record
ord-a2dca0efacc04f1a85620bc4f5664913
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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