Triethylamine → HCID 86690866, compound

Participants

Reaction Steps

To a solution of 4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (12-6, 180 mg, 0.5 mmol) in CH2Cl2 (2.0 mL) was added triethylamine (0.20 mL, 1.5 mmol) followed by 2-fluoroisonicotinic acid (82.3 mg, 0.70 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (186.3 mg, 1.0 mmol), and hydroxybenzotriazole (131.4 mg, 1.0 mmol). The reaction mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure and added with hot water. The resultant precipitate was filtered, and dried under vacuum to give fluoro-N-(4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (20, 186.3 mg) as yellow solids in 35% yield: 1H NMR (500 MHz, DMSO-d6) δ 13.10 (s, 1 H), 8.47 (s, 1 H), 7.94-7.95 (m 1H), 7.80 (s, 1 H), 7.19 (s, 1 H), 6.97-7.02 (m, 4 H), 6.69 (s, 2 H), 4.02-4.09 (m, 2 H), 3.65-3.67 (m, 2 H), 3.29 (s, 3 H), 2.05 (m, 6 H). ESI-MS: m/z 494.1 (M+H)+.

Provenance & Evidence