5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole → N-(2-(1-methoxycyclohexyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine

Participants

Reaction Steps

To a solution of N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (26 mg; 0.079 mmol) in tetrahydrofuran (0.3 mL) was added potassium t-butoxide (80 uL; 0.08 mmol; 1.0M in tetrahydrofuran). A solution of 2-(bromomethyl)-1-(1-methoxycyclohexyl)-4-(trifluoromethyl)benzene (25 mg; 0.071 mmol) in tetrahydrofuran (0.2 mL) was added. The reaction was stirred at room temperature for 3 hours. The reaction was quenched with 2 drops of water. The mixture was diluted with ethyl acetate and filtered through a column containing silica and sodium sulfate and concentrated. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-45% ethyl acetate in heptane) to give 25 mg (59%) of a colorless gum. MS (ES+): Calc: 595.5, Found: 596 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.77 (s, 1H), 7.73 (s, 2H), 7.48 (d, J=7.47 Hz, 2H), 7.42 (d, J=8.30 Hz, 1H), 5.14 (s, 2H), 4.79 (s, 2H), 4.20 (s, 3H), 2.92 (s, 3H), 2.12 (d, J=11.62 Hz, 2H), 1.77-1.52(m, 8H).

Provenance & Evidence