HCID 58558018, compound → HCID 58557504, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)-1-(2-tosyl-2-azaspiro[3.3]heptan-6-yl)ethanone (0.631 g, 1.089 mmol, prepared using R with 2-tosyl-2-azaspiro[3.3]heptane-6-carboxylic acid [prepared as described in J. Org. Chem, 2010, 75, 5941] and trimethylsilyl diazomethane, S with Example #3 Step E, E with TFA) in MeCN (5 mL) was added PFPAA (2.15 mL, 10.9 mmol). The mixture was heated at about 60° C. for about 2 h. The reaction mixture was partitioned between DCM (30 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted further with DCM (2×30 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude material was purified using silica gel flash chromatography eluting with a gradient of 50-100% EtOAc in heptane to give 3-tosyl-8-(2-tosyl-2-azaspiro[3.3]heptan-6-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.467 g, 76%) as a white solid: LC/MS (Table 1, Method b) Rt=2.53 min; MS m/z 562 (M+H)+.

Provenance & Evidence