Dimethylformamide → HCID 117868449, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 mL sealed tube was added (2,4-dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)[6-(trifluoromethyl)pyridin-3-yl]methanol (200 mg, 0.38 mmol, 1 equivalent, Example 109), azetidine (108 mg, 1.89 mmol, 5 equivalents) and dimethylformamide (2 mL). The reaction vessel was sealed and heated in a 100° C. oil bath. After two days, the vessel was cooled and contents transferred to a reparatory funnel with ethyl acetate dilution. The organic phase was extracted with saturated, aqueous ammonium chloride solution and deionized water. The organic phase was separated, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The crude material was purified via reverse phase chromatography using acetonitrile with ammonium hydroxide in water as eluent to provide racemic (2-azetidin-1-yl-4-chloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl) [6-(trifluoromethyl)pyridin-3-yl]methanol. MS (ESI): mass calcd. for C29H23ClF3N5O, 549.15. m/z found, 550.3 [M+H]+. 1H NMR (600 MHz, MeOD) δ 8.76 (d, J=2.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.83 (d, J=8.2 Hz, 1H), 7.78-7.70 (m, 2H), 7.58 (dd, J=8.9, 2.2 Hz, 1H), 7.51-7.41 (m, 3H), 7.33 (d, J=7.8 Hz, 2H), 6.33 (s, 1H), 3.72-3.61 (m, 4H), 3.48 (s, 3H), 2.10-2.02 (m, 2H).

Provenance & Evidence