N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-2-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetamide

Participants

Reaction Steps

To a solution (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)acetic acid (preparation described in Example 24 Step 1, 100 mg, 0.24 mmol) in DMF (2 mL) at 0° C., was added DIEA (126 4, 0.72 mmol) and HATU (92 mg, 0.24 mmol). After 10 min, a solution of 2-dimethylaminoethylamine (21 mg, 0.24 mmol) in DMF (2 mL) was added and the reaction mixture stirred at RT overnight. Et2O was added and the mixture was washed with water. The organic phase was then dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by preparative HPLC affording the title compound as a colorless oil. LC/MS (Method B): 485.0 (M+H)+. HPLC (Method A) Rt 4.59 min (Purity: 91.3%).

Provenance & Evidence