Triethylamine → HCID 24967276, compound

Participants

Reaction Steps

4-Methyl-2-(3-piperidin-4-ylidenemethyl-phenoxy)-pyridine hydrochloride (530 mg, 1.5 mmol, from Example 72, Step 5), pyridazin-3-yl-carbamic acid phenyl ester (404 mg, 1.88 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-aminopyridazine) and triethylamine (0.79 mL, 5.66 mmol) were combined in acetonitrile (10 mL) and stirred at room temperature. After 16 hours, the reaction was concentrated forming a residue and the residue was partitioned between EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (60-100% EtOAc/DCM) to afford the desired product (289 mg) as a white foam. MS (APCI 10V) AP+ 402.0, 281.1 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.34 (s, 3H) 2.45 (td, J=5.72, 1.18 Hz, 2H) 2.57 (td, J=5.68, 1.17 Hz, 2H) 3.53-3.61 (m, 2H) 3.62-3.74 (m, 2H) 6.44 (s, 1H) 6.76 (dt, J=1.40, 0.76 Hz, 1H) 6.87-6.95 (m, 2H) 6.96 (ddd, J=5.28, 1.40, 0.63 Hz, 1H) 7.07 (d, J=7.55 Hz, 1H) 7.36 (dd, J=8.78, 7.71 Hz, 1H) 7.58 (dd, J=9.05, 4.67 Hz, 1H) 7.97 (d, J=5.51 Hz, 1H) 8.11 (d, J=8.77 Hz, 1H) 8.78 (d, J=4.73 Hz, 1H)

Provenance & Evidence