Dimethylformamide → HCID 24853310, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2H-tetrazol-5-amine (145 mg; 0.243 mmol) in 2-methyltetrahydrofuran (2.5 mL) was added sodium carbonate (110 mg; 1.03 mmol), N,N-dimethylformamide (1.0 mL) and dimethyl sulfate (70 uL; 0.739 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 sodium sulfate and concentrated under reduced pressure. The residue was purified by 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-30% ethyl acetate in heptane) to give 120 mg (80.9% yield) of a colorless gum which crystallized into a white solid upon sitting. Melting point: 103-104° C. MS (ES+): Calc: 609.5, Found: 610.5 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.77 (s, 1H), 7.72 (s, 2H), 7.47 (d, J=7.47 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=8.30 Hz, 1H), 5.10 (s, 2H), 4.79 (s, 2H), 4.20 (s, 3H), 2.94 (s, 3H), 2.12 (m, 2H), 1.97 (m, 2H), 1.8-1.46 (m, 8H).

Provenance & Evidence