HCID 58968656, compound → HCID 58968647, compound

Participants

Reaction Steps

To a solution of (2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl)(cyclobutyl)methanone (Preparation 29, 28 mg; 0.050 mmol) in tetrahydrofuran (0.5 mL) was added methylmagnesium bromide (50 uL; 0.15 mmol; 3.0M in diethyl ether). The reaction was stirred at room temperature for 2 hours. The reaction was quenched with 2 drops water and 1 drop aqueous 2N hydrochloric acid. The mixture was diluted with ethyl acetate and filtered over a column containing silica gel and sodium sulfate. The crude was purified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-50% ethyl acetate in heptane) to give 22 mg (76% yield) of the title compound as a colorless gum. MS (ES−): Calc: 581.4, Found: 580.6 (M−H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.74 (s, 2H), 7.42 (d, 1H), 7.41 (s, 1H), 7.33 (d, J=9.13 Hz, 1H), 5.27(d, J=16.60 Hz, 1H), 5.15 (d, J=16.18 Hz, 1H), 4.85 (s, 2H), 4.18 (s, 3H), 2.97 (m, 1H), 2.12-1.69 (m, 6H), 1.43 (s, 3H).

Provenance & Evidence