Iodoethane → (3,5-Bis-trifluoromethyl-benzyl)-[2-(cyclobutyl-ethoxy-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine

Participants

Reaction Steps

To a solution of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclobutyl-methanol (23 mg; 0.041 mmol) in THF (1.5 mL) at 0° C. was added sodium hydride (15 mg; 0.375 mmol; 60% dispersion in mineral oil). After stirring at room temperature for 30 minutes ethyl iodide (0.05 mL; 0.625 mmol) was added. Reaction was stirred for 2 hours. More sodium hydride (15 mg; 0.375 mmol; 60% dispersion in mineral oil) and iodoethane (0.05 mL; 0.625 mmol) were added. Reaction stirred for 72 hours. Reaction was quenched with 2 drops of water. The reaction was filtered over a 1 g Bakerbond silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with ethyl acetate). The crude was purified by RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-30% ethyl acetate in heptane) to give 21 mg (87% yield) of a gum. MS (ES+): Calc: 595.5, Found: 596.4 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.65 (s, 2H), 7.53 (s, 2H), 7.33 (s, 1H), 4.83 (q, J=16.18 Hz, 2H), 4.73 (q, J=16.18, 14.11 Hz, 2H), 4.42 (d, J=6.64 Hz, 1H), 4.22 (s, 3H), 3.20 (m, J=7.05, 6.64 Hz, 2H), 2.49 (m, J=7.88, 7.05 Hz, 1H), 2.07-1.57 (m, 6H), 1.11 (t, J=7.05 Hz, 3H).

Provenance & Evidence