1,2-Dichloroethane → HCID 178426404, compound

Participants

Reaction Steps

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (500 mg, 1.561 mmol), EDC (449 mg, 2.342 mmol) and HOBT (316 mg, 2.342 mmol) in DMF (3122 μl) and treated with DIPEA (818 μl, 4.68 mmol). Octahydropyrrolo[1,2-a]pyrazine (296 mg, 2.342 mmol) was then added. The reaction was allowed to stir for 8 hours and filtered and the filtrate was purified by preparative HPLC (15-40% ACN/water under basic conditions) to give a solid which was recrystallized from MeOH, filtered, and dried in vacuum to give the title compound (286 mg, 0.603 mmol, 38.6%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34 (br. s., 1 H) 1.72 (br. s., 3 H) 2.12 (br. s., 1 H) 2.23 (d, J=7.07 Hz, 2 H) 2.42 (s, 3 H) 2.51-2.53 (m, 1 H) 3.06 (t, J=8.08 Hz, 3 H) 3.72 (br. s., 1 H) 4.44-4.56 (m, 1 H) 7.63 (dd, J=8.08, 1.77 Hz, 1 H) 7.69 (d, J=1.26 Hz, 1 H) 7.84 (d, J=8.08 Hz, 1 H) 8.04 (dd, J=8.59, 2.27 Hz, 1 H) 8.09 (s, 1 H) 8.40 (d, J=7.58 Hz, 1 H) 8.52 (d, J=2.27 Hz, 1 H); ESI-MS m/z (M+H)+ calc'd for C24H24N6O2, 429.20; found 429.3.

Provenance & Evidence