1,1'-Carbonyldiimidazole → HCID 59457575, compound

HRID 1710719Notes

Reaction equation

HRID 1710719 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:21])[C:11]([NH2:20])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[NH:21][C:22](=[O:23])[NH:20][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 16070570HCID 16070570, compound

Product 1

HCID 59457575HCID 59457575, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3-fluorophenyl)-6-pyridin-4-ylpyrazine-2,3-diamine (Example 72, 200 mg, 0.71 mmol), 1,1′-carbonylbis-1H-imidazole (138 mg, 0.85 mmol) in THF (3 mL) was stirred and heated at reflux overnight. Solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The separated organic phase was dried (MgSO4) and evaporated to dryness. The residue was recrystallized from ethanol to give the title compound as a white solid (96 mg, 44%).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customSolvent was removed under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. dry with materialThe separated organic phase was dried (MgSO4)
  6. customevaporated to dryness
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9d2ae16daff94a45b65b0221ab2a59c9
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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