1,1'-Carbonyldiimidazole → HCID 49771647, compound

Participants

Reaction Conditions

Reaction Steps

CDI (821 mg, 5.06 mmol) was added to a solution of N*2*,N*4*-Dibenzyl-6-oxazol-2-yl-pyridine-2,3,4-triamine (940 mg, 2.53 mmol) in THF (15 ml). The solution was heated at 60° C. for 18 hrs under nitrogen. The reaction mixture was allowed to cool then concentrated in vacuo. The crude mixture was then dissolved in concentrated H2SO4 (15 ml) and left for 30 minutes at room temperature. The dark brown solution was added drop-wise onto crushed ice. The pH was adjusted to ˜9 by addition of a saturated aqueous solution of K2CO3 then the mixture was filtered. The solid was washed with EtOAc (200 ml) then the organic and aqueous filtrates were transferred to a separating funnel. The layers were separated and the aqueous was re-extracted with EtOAc (200 ml). The organics were combined, dried (MgSO4) and evaporated to an orange gummy solid. The crude material was triturated with EtOAc and toluene. The solid obtained was filtered and washed with EtOAc to give an off-white solid. This material was purified by HPLC on a Phenomenex Gemini 5 μm column (150×21.2 mmid), eluted with 0.05% formic acid (aq) and 0.05% formic acid in MeCN at a flow rate of 15 ml/min. The gradient was isocratic at 5% organic for 0.6 minutes, then increased linearly from 5% to 80% organic over 12 minutes.

Provenance & Evidence