Triethylamine → HCID 24966553, compound

Participants

Reaction Steps

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(pyrrolidin-1-yl)pyridine (0.118 g, 0.352 mmol) in DMSO (2 mL) was added phenyl pyridazin-3-ylcarbamate (0.076 g, 0.352 mmol) followed by triethylamine (0.048 mL, 0.352 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the crude compound. The residue was purified by silica gel column chromatography (28% acetone/hexane) to give the title compound (0.125 g, 78% yield). 1H NMR (500 MHz, CDCl3): δ 8.78 (s, 1H), 8.39 (s, 1H), 7.59 (d, J=2.5 Hz, 1H), 7.45 (d, J=4.6 Hz, 1H), 7.27 (m, 2H), 6.95 (m, 1H), 6.92 (m, 2H), 6.84 (m, 2H), 6.38 (s, 1H), 3.69 (m, 2H), 3.58 (m, 2H), 3.27 (m, 4H), 2.59 (m, 2H), 2.45 (m, 2H), 2.03 (m, 4H); 13C NMR (125 MHz, CDCl3): δ 156.56, 153.78, 147.15, 141.50, 138.54, 137.14, 130.50, 129.31, 128.31, 125.21, 123.64, 122.70, 119.41, 117.31, 113.03, 47.85, 45.70, 44.70, 35.76, 29.12, 25.39; m/z (457.1, MH+); HPLC: 97.3%.

Provenance & Evidence