Potassium Cyanide → HCID 58392514, compound

HRID 561553Notes

Reaction equation

HRID 561553 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH2:11][CH:12]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:13]1[C:21]2[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)(=O)=O>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:12]([C:13]2[C:21]3[C:16](=[C:17]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:11][CH2:10][CH2:9][C:1]#[N:2])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 59293939HCID 59293939, compound

Product 1

HCID 58392514HCID 58392514, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

91.9 mg (1.41 mmol) of potassium cyanide were added to 309 mg (0.71 mmol) of the compound from Example 65A in 5 ml of DMF. The mixture was stirred at 80° C. for 2 h and then concentrated, and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). DMF was removed by taking the crude product up in dichloromethane, washing twice with water and saturated aqueous sodium chloride solution, drying over magnesium sulfate, filtering and concentrating. 134 mg (52% of theory) of the target compound were obtained.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)
  3. customDMF was removed
  4. washwashing twice with water and saturated aqueous sodium chloride solution
  5. dry with materialdrying over magnesium sulfate
  6. filtrationfiltering
  7. concentrationconcentrating
  8. custom134 mg (52% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-da4455eec4784ac1aa0ac7e9d982b189
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…