Hydrochloric Acid → HCID 178422218, compound

Participants

Reaction Steps

Combined 6-hydrazinylnicotinic acid (1.10 g, 7.18 mmol), methyl 2-(4-cyano-3-fluoro-2-methylphenyl)-3-(dimethylamino)acrylate (2.072 g, 7.90 mmol), 2-propanol (18 mL), and 0.5M aqueous hydrochloric acid (17.24 mL, 8.62 mmol). After 2 hours, N-ethyl-N-isopropylpropan-2-amine (6.26 mL, 35.9 mmol) was added. After another hour the reaction mixture was diluted with water and washed twice with IPAc. The aqueous phase was acidified to ˜pH=3.5 and stirred for 30 minutes to give a solid which was collected by filtration, washed with water, ethanol, and heptanes, and dried overnight under vacuum to give the title compound (1.60 g, 66%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (d, J=2.27 Hz, 3 H) 7.64 (d, J=8.08 Hz, 1 H) 7.69-7.80 (m, 1 H) 8.26 (br. s., 1 H) 8.48 (br. s., 2H) 8.98 (t, J=1.52 Hz, 1 H) 13.45 (br. s., 2 H). ESI-MS m/z [M+H]+ 339.2.

Provenance & Evidence