Potassium Cyanide → HCID 58392446, compound

HRID 561538Notes

Reaction equation

HRID 561538 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:22]1[C:30]2[C:25](=[C:26]([CH2:31][S:32][CH3:33])[CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=O)=O>CN(C=O)C>[CH3:33][S:32][CH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[NH:24][CH:23]=[C:22]2[CH:11]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=1)[CH2:10][CH2:9][C:1]#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392396HCID 58392396, compound

Product 1

HCID 58392446HCID 58392446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

28.5 g (0.44 mmol) of potassium cyanide were added to 100 mg (0.22 mmol) of the compound from Example 51A in 5 ml of DMF. 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. Purification by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient with addition of 0.1% formic acid) resulted in 77 mg (91% 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. customPurification
  7. additionby preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-a30365af8e0c4efab73b405f02f4393d
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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