3-(Trifluoromethyl)aniline → HCID 11515898, compound

Participants

Reaction Steps

2-(2-(4-amino-1,2,5-oxadiazol-3-yl)-4,5-dihydroimidazol-1-yl)acetic acid (170 mg, 0.8 mmol) was dissolved in DMF and to this solution 3-trifluoromethyl aniline (1.2 g, 7.4 mmol) was added followed by benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP reagent) (0.44 g, 1.0 mmol) and DIEA (0.4 mL, 2.3 mmol). The reaction mixture was stirred at room temperature overnight and then diluted with saturated sodium bicarbonate and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to an oil which was purified by column chromatography (20–60% ethyl acetate/hexanes) to afford the title compound as a white solid, 35 mg, (0.1 mmol, 12%. 1H NMR (500 MHz, CDCl3) δ 7.83 (s, 1H), 7.74 (d, J=8.1 Hz, 1H), 7.43 (t, J=8.0 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 4.47 (s, 2H), 4.06 (t, J=10.0 Hz, 2H), 3.65 (t, J=10.0 Hz, 2H).

Provenance & Evidence