Methanol → HCID 69103782, compound

HRID 2217247Notes

Reaction equation

HRID 2217247 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.S(Cl)(Cl)=O.[CH3:31]O>>[NH2:1][C:2]1[C:3]([C:24]([O:26][CH3:31])=[O:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69103454HCID 69103454, compound

Product 1

HCID 69103782HCID 69103782, compound

Procedure

To a suspension of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (350 mg) in MeOH (7.0 ml), was added thionyl chloride (0.146 m) dropwise under ice-bath cooling. After 1 hour stirring at the same temperature, the mixture was allowed to warm to room temperature. The mixture was stirred for 6 hours and then refluxed with stirring for 15 hours. After cooling, the solvent was removed under reduced pressure. Water was poured into the residue and the pH of the mixture was adjusted to 10 with 1N aq. NaOH. A precipitate was isolated by filtration, washed with water, and dried in vacuo to give methyl 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylate (244 mg).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 6 hours
  3. temperaturerefluxed
  4. stirringwith stirring for 15 hours
  5. temperatureAfter cooling
  6. customthe solvent was removed under reduced pressure
  7. additionWater was poured into the residue
  8. customA precipitate was isolated by filtration
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c3fe12f83ce94c91883259e9bf3c2724
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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