1,1'-Carbonyldiimidazole → HCID 68675744, compound

HRID 2233032Notes

Reaction equation

HRID 2233032 reaction equation
FC(F)(F)S(O)(=O)=O.[Br:9][C:10]1[C:11]([NH:22][NH2:23])=[N:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1.C1N=CN([C:29](N2C=NC=C2)=[O:30])C=1>C1COCC1.CCOC(C)=O>[Br:9][C:10]1[C:11]2[N:12]([C:29](=[O:30])[NH:23][N:22]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86615894HCID 86615894, compound

Product 1

HCID 68675744HCID 68675744, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 15.3 g of NaH (60% suspension in mineral oil) and 80.0 g of 3-bromo-5-phenyl-pyrazin-2-ol (J Het. Chem., 665 (1978)) was stirred together for 15 min. After gas evolution ceased, 90.0 g of trifluoromethanesulfonic anhydride was added dropwise over one h. The mixture was stirred an additional 30 min. and was filtered through a pad of silica gel and the solids were washed with methylene chloride. Concentration of the filtrate provided 3-bromo-5-phenyl-pyrazin-2-trifluoromethansulfonate that was dissolved in IPA (200 mL) and stirred as 4.48 g of hydrazine was added. The mixture was stirred at ambient temperature for 16 h. The resulting solid was collected, washed with methylene chloride, and dried under reduced pressure. The filtrate was re-subjected to the above reaction conditions a second and third time to provide (3-bromo-5-phenyl-pyrazin-2-yl)-hydrazine as the trifluoromethane sulfonate salt. A solution of 265 mg of (3-bromo-5-phenyl-pyrazin-2-yl)-hydrazine trifluoromethane sulfonate in THF (5.0 mL) was stirred as 243 mg of CDI was added in portions over 15 min. The resulting solution was stirred for 1.5 h and was diluted with EtOAc and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated to provide 8-bromo-6-phenyl-2H-[1,2,4]triazolo[4,3-a]pyrazin-3-one as a tan solid. MS (M+H−)=290.2.

Workup

  1. additionwas added in portions over 15 min
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11efa0fef985481abe0a9b7164735096
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

Loading…