Isopropylamine → N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)propan-2-amine

Participants

Reaction Conditions

Reaction Steps

(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol (100 mg, 0.26 mmol) was dissolved in DCM (2 mL). N-ethyldiisopropylamine (0.090 mL, 0.52 mmol) was added and the mixture was cooled to 0° C. Methanesulfonyl chloride (22 μl, 0.29 mmol) was added and the resulting mixture was stirred at 0° C. for 10 minutes, and then at RT for 2 hours. The reaction mixture was then poured into a solution of isopropylamine (223 μl, 2.60 mmol) in ACN (2 mL) and stirred at RT for 15 hours. It was diluted with EtOAc, washed with water and brine and dried over MgSO4. After concentration under vacuum, the crude product was purified by flash chromatography (silica, cHex/EtOAc containing 1% of TEA) to give the title compound as a colorless oil. HPLC (Method A) Rt 4.25 min (Purity: 97.1%).

Provenance & Evidence