Methyl iodide → HCID 58968702, compound

Participants

Reaction Steps

To a solution of 1-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-1-cyclopentyl-ethanol (24.8 mg, 0.041 mmol) in THF (0.2 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 8 mg, 0.2 mmol). The mixture was stirred at room temperature for 30 minutes, cooled to 0° C. and methyl iodide (30 μL, 0.5 mmol) was added. The mixture was stirred at room temperature overnight. The reaction mixture was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexanes) to afford the title compound (17 mg, 67%). 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (t, J=8.09 Hz, 2H) 1.31-1.65 (m, 6H) 1.55 (s, 3H) 2.26-2.38 (m, 1H) 3.03 (s, 3H) 4.18 (s, 3H) 4.68-4.75 (m, J=16.18 Hz, 1H) 4.84 (d, J=16.18 Hz, 1H) 5.08 (d, J=17.84 Hz, 1H) 5.22 (d, J=17.43 Hz, 1H) 7.31 (d, J=8.71 Hz, 1H) 7.42-7.47 (m, 2H) 7.71 (s, 2H) 7.76 (s, 1H). MS (ES+) Calc: 609.2, Found: 610.5 (M+1).

Provenance & Evidence