Potassium Cyanide → HCID 58392524, compound

HRID 561550Notes

Reaction equation

HRID 561550 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH3:31])[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>CN(C=O)C>[F: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)[CH2:10][CH2:9][C:1]#[N:2])=[C:25]([CH3:31])[CH:26]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 58392499HCID 58392499, compound

Product 1

HCID 58392524HCID 58392524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

90.8 mg (1.40 mmol) of potassium cyanide were added to 294 mg (0.70 mmol) of the compound from Example 62A in 15 ml of DMF. 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 crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 188 mg (77% 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-12bcfc2fdfc54cffa59212894b8d7d8a
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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