Dimethylformamide → HCID 58968627, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (51 mg; 0.086 mmol) in 2-methyltetrahydrofuran (1.0 mL) was added sodium carbonate (38 mg; 0.358 mmol), N,N-dimethylformamide (0.4 mL) and (2-bromoethoxy)-tert-butyldimethylsilane (100 mg; 0.418 mmol). Reaction was stirred for 16 hours at 60° C. The reaction was diluted with ethyl acetate, washed twice with water and then brine. The organic was dried over sodium sulfate and concentrated in vacuo. The residue was purified by 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-35% ethyl acetate in heptane) to give 45 mg (70% yield) of a colorless gum. 1H NMR (400 MHz CDCl3) δ ppm 7.77 (s, 1H), 7.73 (s, 2H), 7.47 (d, J=9.96 Hz, 2H), 7.41 (d, J=8.30 Hz, 1H), 5.11 (s, 2H), 4.80 (s, 2H), 4.55 (t, J=5.39 Hz 2H), 4.08 (t, J=5.39 Hz, 2H), 2.94 (s, 3H), 2.12 (m, 2H), 1.98 (m, 2H), 1.8-1.45 (m, 8H), 0.82 (s, 9H), −0.07 (s, 6H).

Provenance & Evidence