1,1'-Carbonyldiimidazole → HCID 178461678, compound

HRID 1817033Notes

Reaction equation

HRID 1817033 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([NH2:17])=[N:4][CH:3]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:10])[C:18]([OH:19])=[N:17][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 57880841HCID 57880841, compound

Product 1

HCID 178461678HCID 178461678, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (1.0 equiv) in refluxing anhydrous THF (5 volume equivalents) was added carbonyldiimidazole (CDI). Successive portions of CDI were added until the starting material was consumed (approx. 3.6 equiv total) as judged by TLC (50% EtOAc/Hexanes). After complete reaction, the mixture was cooled to room temperature and quenched by the careful addition of water until gas evolution had ceased. The mixture was diluted with 25 volume equivalents of EtOAc and washed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound (66%) as a white solid. LCMS m/z (APCI)=319.0, 321.0 (M+H).

Workup

  1. customwas consumed (approx. 3.6 equiv total)
  2. customAfter complete reaction
  3. customquenched by the careful addition of water until gas evolution
  4. additionThe mixture was diluted with 25 volume equivalents of EtOAc
  5. washwashed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5495b79dd11143d7be9991bfc34d8421
Source dataset
uspto-grants-2009_10
Patent number
US07598248B2

Reaction notes

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