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

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Reaction Steps

tert-Butyl 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 (54 mg, 0.10 mmol) was treated with 1.25 M HCl in MeOH (9.9 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was diluted with Et2O. The resulting solids were collected by filtration, washed with Et2O and dried to yield the title compound (33 mg, 70%) as a yellow powder: mp 310-315° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 11.54 (s, 1H), 8.90 (s, 2H), 8.70 (d, J=9.0 Hz, 1H), 8.46 (d, J=9.0 Hz, 1H), 7.89 (d, J=7.5 Hz, 1H), 7.69 (d, J=8.5 Hz, 1H), 7.43 (d, J=1.5 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.16 (dd, J=7.0, 2.0 Hz, 1H), 7.08 (dd, J=8.5, 2.0 Hz, 1H), 4.44 (s, 2H), 3.48-3.46 (m, 2H), 3.05 (t, J=5.5 Hz, 2H), 2.03-2.01 (m, 2H); ESI MS m/z 426 [M+H]+; HPLC (Method A) 97.3% (AUC), tR=12.3 min.

Provenance & Evidence