Acetic Acid → HCID 178474664, compound

Participants

Reaction Steps

Acetic acid (24 μL, 0.43 mmol) was added to an ambient temperature solution of 1-[4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)phenyl]ethanamine (for synthesis see Example 8) (76 mg, 0.22 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (83 mg, 0.43 mmol), 1-hydroxybenzotriazole (59 mg, 0.43 mmol) and sodium bicarbonate (183 mg, 2.2 mmol) in methylene chloride (3 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with brine and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparative plate chromatography eluting with 5% methanol/ethyl acetate afforded the title compound. High pressure liquid chromatography (Chiralcel AD column) eluting with 10% ethanol/hexane afforded the two pure enantiomers. 1H NMR (500 MHz, CD3OD) δ 8.48 (s, 1H), 7.87-7.80 (m, 3H), 7.68-7.62 (m, 2H), 7.24 (d, J=10 Hz, 2H), 6.66 (s, 1H), 5.22 (t, J=10 Hz, 1H), 3.35 (s, 3H), 3.29 (m, 1H), 3.18 (m, 1H), 2.40 (s, 2H) 0.86 (s, 9H); (M+H) found: 395.

Provenance & Evidence