Potassium Cyanide → HCID 58392204, compound

HRID 561543Notes

Reaction equation

HRID 561543 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[F:32])[C:12]1[C:20]2[C:15](=[C:16]([CH2:22][S:23][CH3:24])[CH:17]=[C:18]([F:21])[CH:19]=2)[NH:14][CH:13]=1)(=O)=O>CS(C)=O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:22][S:23][CH3:24])[CH:17]=[C:18]([F:21])[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[C:26]([F:32])[CH:27]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392247HCID 58392247, compound

Product 1

HCID 58392204HCID 58392204, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

190 mg (2.91 mmol) of potassium cyanide and 8.9 mg (0.07 mmol) of 4-N,N-dimethylaminopyridine were added to 670 mg (1.46 mmol) of the compound from Example 56A in 40 ml of DMSO. The mixture was stirred at 80° C. for 2 h and then concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 522 mg (92% of theory) of the title compound.

Workup

  1. concentrationconcentrated
  2. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-f1882aaf1cff418ca210e4e3db4a802f
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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