Dichloromethane → HCID 58382137, compound

Participants

Reaction Conditions

Reaction Steps

4-(Cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.713 g, 1.83 mmol) and TEA (0.638 mL, 4.58 mmol) were combined in 1,4-dioxane (14 mL) to give a suspension. The mixture was stirred until the suspension had dissolved. Diphenylphosphoryl azide (0.790 mL, 3.66 mmol) was added and the reaction heated at about 100° C. for about 5 h. DCM (50 mL) and saturated aqueous NaHCO3 (25 mL) were added and the layers separated. The aqueous layer was extracted with DCM (25 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (40 g Silicycle™ column) eluting with 20-80% EtOAc in DCM. The solvents were removed under reduced pressure. The material was triturated with heptane and the solid was collected by vacuum filtration and washed with heptane. The solid was dried under vacuum at about 50° C. to a constant weight to give 1-cyclohexyl-6-((2-(trimethylsilyl)ethoxy)methyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (0.501 g, 70%): LC/MS (Table 2, Method b) Rt=2.78 min.; MS m/z: 387 (M+H)+.

Provenance & Evidence