1,1'-Carbonyldiimidazole → HCID 178446212, compound

HRID 2262675Notes

Reaction equation

HRID 2262675 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:5]([NH2:8])=[N:6][CH:7]=1.C1N=CN([C:20](N2C=NC=C2)=[O:21])C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[C:20]([OH:21])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 59594561HCID 59594561, compound

Product 1

HCID 178446212HCID 178446212, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of 5-chloro-N3-(pentan-3-yl)pyridine-2,3-diamine (1.5 g, 7.0 mmol, 1.0 equiv) in THF (10 mL) was added CDI portionwise until starting material was consumed as judged by TLC (50% EtOAC/Hexanes; UV). Approximately 10 equiv of carbonyldiimidazole were required. The resulting reaction mixture was cooled to room temperature, and the excess carbonyldiimidazole was quenched by the careful addition of water. The mixture was diluted with EtOAc, and the layers were separated. The organic layer was washed with satd. aq. NaHCO3 twice, and brine once. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC provided 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol as a white solid (1.2 g, 71%). m/z=240.1 [M+H]+

Workup

  1. customwas consumed
  2. customThe resulting reaction mixture
  3. customthe excess carbonyldiimidazole was quenched by the careful addition of water
  4. additionThe mixture was diluted with EtOAc
  5. customthe layers were separated
  6. washThe organic layer was washed with satd
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by silica gel MPLC

Sources & evidence

ORD record
ord-373d3db87d304edc97d935269ad0961e
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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