Potassium Cyanide → HCID 58392461, compound

HRID 561542Notes

Reaction equation

HRID 561542 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH:10]([CH3:32])[CH:11]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[F:31])[C:12]1[C:20]2[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O>CS(C)=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:10]([CH3:32])[CH2:9][C:1]#[N:2])=[C:25]([F:31])[CH:26]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392312HCID 58392312, compound

Product 1

HCID 58392461HCID 58392461, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

16.2 mg (0.25 mmol) of potassium cyanide were added to 70 mg (0.12 mmol) of the compound from Example 55A in 3 ml of DMSO. The mixture was stirred at 80° C. for 4 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 residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid). 33.4 mg (69% of theory) of the title compound were obtained as a mixture of diastereomers.

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 residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-ff659ebfae51488f89d320b6dd41850e
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…