Ethyl Acetate → HCID 58392264, compound

HRID 561616Notes

Reaction equation

HRID 561616 reaction equation
[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:24]1[C:29]([F:30])=[CH:28][C:27]([Cl:31])=[CH:26][C:25]=1[F:32])[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.C(OCC)(=O)C>CS(C)=O>[Cl:31][C:27]1[CH:28]=[C:29]([F:30])[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]([F:32])[CH:26]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 58392538HCID 58392538, compound

Product 1

HCID 58392264HCID 58392264, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

0.30 g (4.57 mmol) of potassium cyanide was added to 1.05 g (2.28 mmol) of the compound from Example 111A in 21 ml of DMSO. The mixture was stirred at 80° C. for 3 h, ethyl acetate was added to the reaction solution, and the mixture was washed twice with water and once with saturated aqueous sodium chloride solution. The combined organic phases were freed of solvent, and the crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 0.74 g (83% of theory) of the target compound was obtained.

Workup

  1. washthe mixture was washed twice with water and once with saturated aqueous sodium chloride solution
  2. customthe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
  3. custom0.74 g (83% of theory) of the target compound was obtained

Sources & evidence

ORD record
ord-29152e874b4c4c57a3e0349484dbf1f9
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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