Water → HCID 58392231, compound

HRID 561548Notes

Reaction equation

HRID 561548 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]([CH2:21][S:22][CH2:23][CH3:24])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O.O.C(OCC)(=O)C>CN(C=O)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:21][S:22][CH2:23][CH3:24])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[C:26]([CH3:32])[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 58392274HCID 58392274, compound

Product 1

HCID 58392231HCID 58392231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

86.4 mg (1.33 mmol) of potassium cyanide were added to 300 mg (0.66 mmol) of the compound from Example 60A in 4 ml of DMF. Stirring at 80° C. for 2 h was followed by addition of water, extraction with ethyl acetate, washing of the combined organic phases with saturated aqueous sodium bicarbonate solution, drying over magnesium sulfate, filtration and concentration. 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 207 mg (81% of theory) of the title compound.

Workup

  1. washwashing of the combined organic phases with saturated aqueous sodium bicarbonate solution
  2. dry with materialdrying over magnesium sulfate, filtration and concentration
  3. 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-ac11ca6a7036439ba150bfadb752bb5b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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