1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2'-Methoxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

関与物質

反応手順

DIPEA (140 mg, 0.19 mL, 1.08 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method as described above) (119 mg, 0.38 mmol) in DMF (5 mL). HOBT (45 mg, 0.33 mmol) and EDCI (118 mg, 0.61 mmol) were then added at room temperature. After 2 minutes, 2′-Methoxy-biphenyl-4-carboxylic acid (70 mg, 0.30 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by preparative HPLC to afford 71 mg (44.1% yield) 2′-Methoxy-biphenyl-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 98.92%. 1H NMR (CDCl3): δ 7.94-7.84 (t, 1H), 7.8-7.72 (d, 1H), 7.7-7.56 (m, 4H), 7.5-7.44 (t, 1H), 7.4-7.3 (m, 3H), 7.1-7.0 (dd, 2H), 4.4-4.2 (m, 2H), 4.1-3.86 (m, 2H), 3.84-3.8 (s, 3H), 3.76-3.5 (m, 4H), 3.44-3.38 (t, 1H), 3.3-3.2 (bs, 2H).

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