Acetic Acid → HCID 57475691, compound

HRID 218006Notes

Reaction equation

HRID 218006 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].Cl[C:9]1[N:10]=[CH:11][C:12]([C:15]([O:17][CH3:18])=[O:16])=[N:13][CH:14]=1.[C:19]([OH:22])(=O)C.[CH3:23]N(C=O)C>O>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:9]1[N:10]=[CH:11][C:12]([C:15]([O:17][CH2:18][CH2:23][O:22][CH3:19])=[O:16])=[N:13][CH:14]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228Dimethylformamide2×HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 57475691HCID 57475691, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% sodium hydride (27.8 mg) was added to a solution of 2-methoxyethanol (50.2 μl) in DMF (1 ml) under ice-cooling, followed by stirring for 10 minutes. A solution of methyl 5-chloropyrazine-2-carboxylate (100 mg) in DMF (1 ml) was added to the reaction solution at the same temperature, followed by stirring for one hour and 50 minutes. Acetic acid (50.0 μl) and water were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (19.7 mg).

Workup

  1. temperaturecooling
  2. stirringby stirring for one hour and 50 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-971ff2a381c04cd8b519a0c63d671d4c
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

Loading…