Ethylenediamine → HCID 86700317, compound

HRID 879500Notes

Reaction equation

HRID 879500 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=O)[C:12]([O-:14])=O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[CH2:16]([NH2:19])[CH2:17][NH2:18].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:12](=[O:14])[NH:18][CH2:17][CH2:16][N:19]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 24436Sodium SulfateHCID 86700318HCID 86700318, compound

Product 1

HCID 86700317HCID 86700317, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2-(1-methyl-1H-indazol-5-yl)-2-oxoacetate (520 mg, 2.2 mmol), ethylenediamine (0.15 mL, 2.2 mmol), and sodium sulfate in toluene (9 mL) was heated at reflux for 12 hours. The reaction was cooled, and diluted with ethyl acetate. The mixture was filtered through a pad of celite and was washed with ethyl acetate. Concentration and purification with flash column chromatography (EtOAc) gave 3-(1-methyl-1H-indazol-5-yl)-5,6-dihydropyrazin-2(1H)-one. LCMS-ESI+: calc'd for C12H13N4O: 229.3 (M+H+); Found: 229.2 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. temperatureThe reaction was cooled
  4. filtrationThe mixture was filtered through a pad of celite
  5. washwas washed with ethyl acetate
  6. concentrationConcentration and purification with flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-d8f19b7d137b4f9a97add1031fde3189
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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