3-Methoxypropylamine → HCID 68864093, compound

Participants

Reaction Steps

A solution of Example 149B (93.0 mg, 0.241 mmol) in dichloromethane (3.0 mL) was treated with 1-hydroxybenzotriazole hydrate (34 mg, 0.253 mmol) and 4-methylmorpholine (32 μL, 0.297 mmol), stirred at room temperature for 10 minutes, treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (51 mg, 0.266 mmol), 4-dimethylaminopyridine (3 mg, 0.025 mmol), and 1-methoxy-3-aminopropane (37 μL, 0.363 mmol), stirred for 1 hour, heated to 40° C., stirred overnight, treated with 4-dimethylaminopyridine (3 mg, 0.025 mmol) and 4-methylmorpholine (53 μL, 0.482 mmol), heated to 40° C. for 3 days, cooled to room temperature, and treated with distilled water. The aqueous layer was extracted with dichloromethane (2×) and the combined organic phases were washed with brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(+)) m/e 457 (M+H)+, 479, (M+Na)+; (ESI(−)) m/e 455 (M−H)−.

Provenance & Evidence