Dimethylformamide → HCID 58392550, compound

HRID 561552Notes

Reaction equation

HRID 561552 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)NC=1)[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)(=O)=O.C[N:35]([CH:37]=O)C>>[CH3:33][S:32][CH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[NH:2][CH:1]=[C:22]2[CH:11]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:10][CH2:9][C:37]#[N:35]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 58392519HCID 58392519, compound

Product 1

HCID 58392550HCID 58392550, compound

Conditions

Temperature
80 °C

Procedure

97.5 mg (1.50 mmol) of potassium cyanide were added to 329 mg (0.75 mmol) of the compound from Example 64A 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 181 mg (65% 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-a687d921ae7c40d0a00f5c13994bd178
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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