Tetrahydrofuran → 6-{[6-(1-oxa-5-azaspiro[2.4]hept-5-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a flamed dry 3N round bottom flask fitted with a thermometer and condenser was added 95% NaH (69 mg, 2.69 mmol) and anhydrous DMSO (5.0 ml). After stirring for 2 min at R.T. and 70° C. for 45 mins, the reaction mixture was cooled to 3° C. and a solution of trimethylsulfonium iodide (504.1 mg, 2.47 mmol) in DMSO (3.6 ml) was added. After stirring for 30 mins at 3° C., to the reaction mixture, a suspension of 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-one (200 mg, 0.58 mmol) in 1:1 THF: DMSO (16 ml) was added dropwise. After stirring at 0° C. for 3 h, the reaction mixture was poured into an ice cold water (15 ml) and extracted with CH2Cl2 (4×60 ml). The organic layer was washed with brine and dried with MgSO4 and concentrated under reduced pressure. The resulting residue was purified via flash column chromatography eluted with 10% MeOH:CH2Cl2 to give the desired product (130 mg 63%).

Herkunft & Nachweise