Hydrochloric Acid → HCID 70818125, compound

Participants

Reaction Steps

To a solution of tert-butyl {1-[4-(8-methoxy-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-11 (0.055 g, 0.12 mmol) in a mixture of MeOH (0.7 mL) and DCM (1.1 mL) was added a concentrated aqueous HCl solution (approximately 12 N, 0.6 mL). The resulting mixture was stirred at room temperature for 60 h, then poured onto ice water (15 mL). The resulting mixture was made basic with a 2 N NaOH solution, then was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4 anh.) and concentrated under reduced pressure. The resulting oil (34 mg) was purified using preparative HPLC (Agilent Prep 1200 equipped with 2× Prep Pump, DLA, MWD, ELSD and Prep FC using an XBrigde C18 5 μm 100×30 mm column; gradient from 70% water with 0.2% NH3/30% CH3CN to 40% water with 0.2% NH3/60% CH3CN over 17.5 min, gradient from 40% water with 0.2% NH3/60% CH3CN to 100% CH3CN over 2.5 min) to give 1-[4-(8-methoxy-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutanamine (0.021 g, 48% yield): UPLC-MS (Method 3): RT=1.18 min; m/z (rel intensity) 371 (30, (M+H)+).

Provenance & Evidence