1,2-Dichloroethane → HCID 178426411, compound

Participants

Reaction Conditions

Reaction Steps

Combined EDC (599 mg, 3.12 mmol), HOBT (211 mg, 1.561 mmol) and 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (500 mg, 1.561 mmol) in DMF (10 ml) and added 1-methylpiperazine (519 μl, 4.68 mmol) and DIPEA (818 μl, 4.68 mmol) and the solution was stirred at 20° C. overnight. The reaction mixture was then purified by preparative HPLC (15-40% ACN in water under basic conditions) to give the free base, which was suspended in acetonitrile (28 mL) and treated with 1N aqueous hydrochloric acid (2.341 mL, 2.341 mmol). The resulting cloudy mixture was heated until cleared and allowed to cool to ambient temperature. The mixture was filtered and the filtrate was cooled to 0° C. and filtered again. The filtrate was diluted with ethyl ether (10 mL) to give a solid and the mixture was heated until all solids dissolved, and then cooled to ambient temperature to give a solid. The mixture was cooled to 0° C. and filtered, and the solid was dried in vacuum at 80° C. for 1 hour to give the title compound as a hydrochloride salt (94 mg, 13.7%) as a light pink solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3 H) 2.79 (s, 3 H) 3.16 (br. s., 4 H) 3.64-4.57 (m, 4 H) 7.67 (d, J=7.83 Hz, 1 H) 7.74 (s, 1 H) 7.78 (br. s., 1 H) 8.12 (d, J=7.33 Hz, 1 H) 8.21 (br. s., 1 H) 8.51 (br. s., 1 H) 8.57-8.61 (m, 1 H); ESI-MS m/z (M+H)+ calc'd for C22H22N6O2, 403.18; found 403.2.

Provenance & Evidence