Diisopropylethylamine → HCID 24968684, compound

Participants

Reaction Conditions

Reaction Steps

Phenyl 2-methylpicolinoylcarbamate (150 mg, 0.585 mmol, prepared according to the procedure in Example 15, Step 1 from 6-methyl-pyridine-2-carboxamide), 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. The residue was purified by silica gel chromatography (10-75% EtOAc in CH2Cl2) to provide the title compound (0.197 g). MS APCI M+ 497.2, 376.12, 335.12; 1H NMR (400 MHz, CD3OD) δ ppm 2.61 (s, 3H) 2.46-2.70 (m, 4H) 3.64 (m, 4H) 6.47 (s, 1H) 6.96-7.06 (m, 2H) 7.08-7.19 (m, 2H) 7.40 (td, J=7.69, 0.73 Hz, 1H) 7.50 (dd, J=7.80, 0.46 Hz, 1H) 7.88 (t, J=7.71 Hz, 1H) 7.98 (ddd, J=7.74, 0.99, 0.50 Hz, 1H) 8.08 (ddd, J=8.73, 2.48, 0.66 Hz, 1H) 8.42 (td, J=1.75, 0.87 Hz, 1H).

Provenance & Evidence