Methyl iodide → HCID 58968622, compound

Participants

Reaction Steps

To a solution of (2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-5-methyl-4-trifluoromethyl-phenyl)-cyclohexyl-methanol (8 mg, 0.01 mmol) in THF (0.15 mL) at 0° C. was added sodium hydride (4.2 mg, 0.11 mmol). The mixture was stirred at room temperature for 30 minutes. Methyl iodide (10 μL, 0.2 mmol) was added at 0° C. The mixture was stirred at room temperature overnight. The mixture was quenched with methanol and purified by chromatography over 12+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound (3.6 mg, 40%). 1H NMR (400 MHz, CDCl3) δ ppm 0.92-1.20 (m, 6H) 1.41-1.51 (m, 1H) 1.61 (d, J=8.71 Hz, 2H) 1.67-1.74 (m, 1H) 1.93 (d, J=11.62 Hz, 1H) 2.46 (s, 3H) 3.04 (s, 3H) 4.04 (d, J=7.05 Hz, 1H) 4.21 (s, 3H) 4.63-4.72 (m, 3H) 4.84 (d, J=16.18 Hz, 1H) 7.27 (s, 1H) 7.30 (s, 1H) 7.63 (s, 2H) 7.77 (s, 1H). MS (ES30) Calc: 623.2, Found: 624.6 (M+1) According to the procedure described in example 23 and using the corresponding aryl bromide and aldehyde reagent, example 24 was prepared.

Provenance & Evidence