Potassium Cyanide → HCID 58392197, compound

HRID 561612Notes

Reaction equation

HRID 561612 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[CH3:32])[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]([CH3:32])[CH:27]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392552HCID 58392552, compound

Product 1

HCID 58392197HCID 58392197, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

174 mg (2.67 mmol) of potassium cyanide and 8.1 mg (0.07 mmol) of 4-N,N-dimethylaminopyridine were added to 608 mg (1.33 mmol) of the compound from Example 107A in 30 ml of DMSO. The mixture was stirred at 120° 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 154 mg (30% 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-b01808dc75ff4bf4adbef0b4a19fbc94
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…