Diethyl Oxalate → HCID 54710325, compound

HRID 2109835Notes

Reaction equation

HRID 2109835 reaction equation
[H-].[Na+].[C:3]([N:6]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:8](=[O:20])[CH2:7]1)(=[O:5])[CH3:4].[C:21](OCC)(=[O:27])[C:22](OCC)=[O:23]>CS(C)=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[CH:10]=[CH:11][N:6]3[C:3](=[O:5])[CH:4]=[C:21]([OH:27])[C:22]([OH:23])=[C:7]3[C:8]2=[O:20])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 57634629HCID 57634629, compound

Product 1

HCID 54710325HCID 54710325, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of anhydrous DMSO and sodium hydride (0.24 g, 60% oil dispersion, washed 3× with hexane) under an atmosphere of nitrogen was heated with stirring at 50° C. for 3 h. After cooling to room temperature, a solution of 4-acetyl-1-(4-fluorobenzyl)-3,4-dihydropyrazin-2(1H)-one (0.5 g, 2.0 mmol; Example 2, Step 3) in anhydrous DMSO (5 mL) was added over a period of 10 min and the resultant mixture stirred at room temperature for 30 min. The mixture was then treated with diethyl oxalate (0.29 mL, 2.1 mmol) and stirred at room temperature overnight. The product mixture was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling to room temperature
  3. stirringstirred at room temperature overnight
  4. customThe product mixture was subjected to HPLC purification on C-18 stationary phase
  5. washeluted with water/acetonitrile/TFA mobile phase
  6. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-a946b03c27094b9aaf8c9606c1bc2df2
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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