Dimethylformamide → HCID 74221331, compound

Participants

Reaction Conditions

Reaction Steps

To a 75 mL sealed tube was added (2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol (2.50 g, 4.09 mmol, intermediate 60), azetidine (0.83 mL, 12.3 mmol) and dimethylformamide (30 mL). The reaction vessel was sealed and heated in a 100° C. oil bath. After overnight heating, the vessel was cooled and contents transferred to a separatory funnel with ethyl acetate dilution. The organic phase was extracted with a 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. Chromatography on silica gel (dichloromethane increasing to 10% ((2M ammonia in methanol) in dichloromethane)) provided the title compound. MS (ESI): mass calcd. for C31H24ClF6N5O, 631.16; m/z found, 632.5 [M+H]+. 1H NMR (600 MHz, Chloroform-d) δ 8.81 (d, J=2.2 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.87 (dd, J=8.3, 2.2 Hz, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.3 Hz, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.46 (dd, J=8.8, 2.2 Hz, 1H), 7.21 (d, J=8.0 Hz, 2H), 7.09 (d, J=1.1 Hz, 1H), 6.19 (d, J=1.1 Hz, 1H), 4.32 (s, 2H), 4.13 (t, J=7.7 Hz, 4H), 3.31 (s, 3H), 2.29-2.20 (m, 2H).

Provenance & Evidence