Hydrochloric Acid → HCID 178426438, compound

Participants

Reaction Steps

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (107 mg, 0.334 mmol), HOBT hydrate (77 mg, 0.501 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (96 mg, 0.501 mmol) in DMF (2 mL), and added triethylamine (0.188 mL, 1.336 mmol), stirred at ambient temperature for 5 minutes and dimethylamine hydrochloride (54.5 mg, 0.668 mmol) was added. The reaction was stirred at 50° C. for 3 hours, then cooled to ambient temperature and diluted with MeOH (5 mL), water (5 mL), and acidified to pH 5 using 1N aqueous hydrochloric acid, to give a solid which was filtered, washed with water, and dried under vacuum to give the title compound (76.2 mg, 0.219 mmol, 66%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3 H) 3.01 (br. s., 6 H) 7.65 (dd, J=8.08, 1.52 Hz, 1 H) 7.70-7.82 (m, 2 H) 8.02-8.20 (m, 2 H) 8.37 (br. s., 1 H) 8.56 (dd, J=2.27, 0.76 Hz, 1 H) 13.11 (br. s., 1 H). ESI-MS m/z [M+H]+ 348.3.

Provenance & Evidence