1,1'-Carbonyldiimidazole → HCID 136400729, compound

Participants

Reaction Steps

CDI (52 mg, 0.32 mmol) was added to a solution of 1-benzyl-4-benzylamino-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (80 mg, 0.21 mmol) and Hunnigs base (83 μl, 0.64 mmol) in dry DMF in a ReactiVial. The vial was sealed and the mixture was stirred at room temperature for 15 minutes. N-Hydroxyacetamidine (24 mg, 0.32 mmol) was added and mixture heated to 60° C. in an aluminium block. The mixture was left to stir at this temperature for 3 hrs then allowed to cool and concentrated in vacuo. The residue was partitioned between EtOAc (15 ml) and water (5 ml). The layers were separated and the organic phase was washed with brine (5 ml). At this point, some solid precipitated and was left inside the separating funnel. This was washed into the organic phase with MeOH then the organics were dried (MgSO4) and evaporated to yield the final product as a white solid (120 mg, 130%). Material probably contains inorganic material, but taken on with a view to purification after next step.

Provenance & Evidence