Ethyl Acetate → HCID 58392410, compound

HRID 561554Notes

Reaction equation

HRID 561554 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][CH:26]=1)[C:12]1[C:20]2[C:15](=[C:16]([CH2:22][S:23][CH3:24])[C:17]([F:21])=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O.C(OCC)(=O)C>CN(C=O)C>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:22][S:23][CH3:24])[C:17]([F:21])=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 58392331HCID 58392331, compound

Product 1

HCID 58392410HCID 58392410, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.46 g (7.01 mmol) of potassium cyanide were added to 1.55 g (3.50 mmol) of the compound from Example 66A in 32 ml of DMF. 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 dried over sodium sulfate, the solid was filtered off, and the solvents were removed. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.00 g (77% 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. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationthe solid was filtered off
  4. customthe solvents were removed
  5. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
  6. custom1.00 g (77% of theory) of the target compound was obtained

Sources & evidence

ORD record
ord-87d10c55bf434df195b542f58724c61e
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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