Triethylamine → 4-(3-(4-(trifluoromethyl)phenoxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

4-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride (200 mg, 0.541 mmol, from Example 53, Step 5), ethyl pyridazin-3-ylcarbamate (99 mg, 0.595 mmol) and triethylamine (0.15 mL, 1.08 mmol) were combined in acetonitrile (4.5 mL) and heated in a microwave at 180° C. for 40 min. The reaction mixture was cooled to RT and concentrated. The residue was purified by silica gel chromatography (50-100% EtOAc in CH2Cl2) to provide the title compound (156 mg). MS APCI M+ 455.2, 375.2, 334.2 M− 454.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.46 (td, J=5.81, 0.84 Hz, 2H) 2.56 (td, J=5.81, 0.84 Hz, 2H) 3.55-3.61 (m, 2H) 3.65-3.70 (m, 2H) 6.44 (s, 1H) 6.91-6.99 (m, 2H) 7.06-7.14 (m, J=8.32 Hz, 3H) 7.35-7.43 (m, 1H) 7.59 (dd, J=9.13, 4.68 Hz, 1H) 7.61-7.66 (m, J=9.08 Hz, 2H) 8.12 (d, J=9.30 Hz, 1H) 8.78 (d, J=4.68 Hz, 1H).

Provenance & Evidence