Triethylamine → HCID 73336018, compound

Participants

Reaction Steps

A mixture of 2-imidazo[4,5-b]pyridin-3-ylacetic acid (251.7 mg, excess), 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (42.7 mg, 0.23 mmol), triethyl amine (200 μL, 1.4 mmol), and HATU (87.9 mg, 0.23 mmol) in DMF (1 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with 10 mL of aqueous saturated sodium bicarbonate, and extracted with EtOAc (2×15 mL). The combined organic layers were then washed with water (2×20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 10% MeOH in EtOAc) to afford the desired product (26.1 mg, 0.07 mmol, 30%). 1H NMR (400 MHz, CDCl3) δ 8.38 (d, J=7.2 Hz 1H), 8.50 (s, 0.8H), 8.25 (s, 0.2H), 8.12 (d, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.28 (m, 1H), 7.15 (m, 2H), 5.46 (s, 0.2H), 5.33 (s, 0.8H), 3.95 (m, 2H), 2.88 (m, 2H), 2.15 (m, 2H); MS: (ES) m/z calculated for C20H17FN6O [M+H]+ 377.1, found 377.1.

Provenance & Evidence