Sodium Cyanide → HCID 18187306, compound

HRID 1357649Notes

Reaction equation

HRID 1357649 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]=[C:7]3[C:12](=[C:13]2[C:16]([F:19])([F:18])[CH3:17])[CH:11]=[CH:10][CH:9]=[N:8]3)=[CH:4][CH:3]=1.[C-:20]#[N:21].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([C:20]#[N:21])([C:16]([F:19])([F:18])[CH3:17])[C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 18187293HCID 18187293, compound

Product 1

HCID 18187306HCID 18187306, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method NN: To a stirred solution of 7-chloro-9-(1,1-difluoroethyl)-4-azaacridine (47) (1.440 g, 5.167 mmol) in anhydrous DMF (25 mL) at room temperature was added NaCN (533 mg, 10.334 mmol). After 15 h at room temperature, the reaction was quenched with 1:1 saturated aqueous NaHCO3/H2O (50 mL), and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Flash chromatography (20%-40% EtOAc-hexane, gradient elution) furnished 49 (1.106 g, 70% yield) as a yellow solid.

Workup

  1. customthe reaction was quenched with 1:1 saturated aqueous NaHCO3/H2O (50 mL)
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash chromatography (20%-40% EtOAc-hexane, gradient elution)

Sources & evidence

ORD record
ord-0912c0d571524dab904db0735d2514f7
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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