Hydrochloric Acid → HCID 57635778, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1-phenyl-1H-pyrazol-5-amine (600 mg, 3.46 mmol) and 2-chloronicotinic acid (546 mg, 3.46 mmol) in DMF (6 mL), was added potassium carbonate (543 mg, 3.93 mmol) and copper (II) acetate (18 mg). The mixture was stirred at 150° C. for 18 h, and then cooled to rt, and diluted with ethyl acetate (2×) and water. The solution was adjusted to pH 2-3 using 1 N aqueous HCl. The mixture was extracted with EtOAc (3×5 mL), and then the combined organic extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by HPLC (20-90% acetonitrile in water) to afford the product (126 mg, 18%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 2.19 (s, 3H), 6.62 (s, 1H), 6.77 (m, 1H), 7.34 (m, 1H), 7.45 (m, 2H), 7.53 (m, 2H), 8.16 (d, 1H), 8.22 (d, 1H), 12.32 (s, 1H); ES-MS m/z 295.1 (MH+); HPLC RT (min) 2.17.

Provenance & Evidence