Hydrochloric Acid → 1-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochloride

Participants

Reaction Steps

A solution of tert-butyl 6-methyl-8-(2-oxo-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (0.11 g, 0.20 mmol) in 1.25 M HCl in MeOH (25 mL) was stirred at ambient temperature for 18 h. The mixture was concentrated to dryness and diluted with MeOH (5.0 mL) and Et2O (25 mL). The resulting solids were collected by filtration and dried to provide the title compound (77 mg, 80%) as a yellow solid: mp 248-252° C. decomp; 1H NMR (500 MHz, DMSO-d6) δ 9.03 (s, 2H), 8.71 (d, J=9.0 Hz, 1H), 8.46 (d, J=8.5 Hz, 1H), 7.91 (d, J=7.0 Hz, 1H), 7.71 (d, J=8.5 Hz, 1H), 7.63 (d, J=2.0 Hz, 1H), 7.38 (d, J=2.0 Hz, 1H), 7.17 (dd, J=7.0, 2.0 Hz, 1H), 7.13 (dd, J=8.5, 1.5 Hz, 1H), 4.46-4.45 (m, 2H), 3.75 (s, 3H), 3.46-3.44 (m, 2H), 3.12 (t, J=5.5 Hz, 2H), 2.08-2.07 (m, 2H); ESI MS m/z 440 [M+H]+; HPLC (Method A) 99.2% (AUC), tR=13.2 min.

Provenance & Evidence