Diisopropylethylamine → HCID 24968343, compound

Participants

Reaction Conditions

Reaction Steps

Phenyl picolinoylcarbamate (145 mg, 0.599 mmol, from Step 1), 2-(3-piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (175 mg, 0.472 mmol) (from Example 1, Step 5), and diisopropylethyl amine (0.16 mL, 0.92 mmol) were combined in acetonitrile (5 mL) and warmed to 50° C. After 3 hours the mixture was cooled to room temperature and concentrated to form a residue. The residue was purified by silica gel chromatography (20-75% EtOAc in CH2Cl2) to provide the title compound (0.152 g). MS APCI M+ 483.1, 376.1, 335.1; M− 481.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.45-2.72 (m, 4H) 3.64 (m, 4H) 6.47 (s, 1H) 6.96-7.06 (m, 2H) 7.08-7.20 (m, 2H) 7.40 (td, J=7.65, 0.91 Hz, 1H) 7.63 (ddd, J=7.63, 4.76, 1.23 Hz, 1H) 8.02 (td, J=7.75, 1.69 Hz, 1H) 8.08 (ddd, J=8.71, 2.55, 0.61 Hz, 1H) 8.18 (dt, J=7.86, 1.08 Hz, 1H) 8.42 (td, J=1.72, 0.80 Hz, 1H) 8.67 (ddd, J=4.76, 1.69, 0.95 Hz, 1H).

Provenance & Evidence