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

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Reaction Steps

1.25 M HCl in MeOH (4.0 mL) was added to tert-butyl 6-methyl-8-(6-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-1(6H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (43 mg, 0.075 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated under reduced pressure, and the resulting residue was diluted with MeOH (1.0 mL) and Et2O (10 mL). The resulting solids were collected by filtration to provide the title compound (23 mg, 61%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 8.91 (d, J=1.5 Hz, 1H), 8.87 (s, 2H), 8.22 (dd, J=8.5, 1.5 Hz, 1H), 8.02-8.00 (m, 2H), 7.64 (d, J=8.5 Hz, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.13 (dd, J=8.5, 2.0 Hz, 1H), 6.56 (d, J=3.0 Hz, 1H), 5.41 (s, 2H), 4.44 (s, 2H), 3.72 (s, 3H), 3.47-3.43 (m, 2H), 3.10 (t, J=5.5 Hz, 2H), 2.08-2.04 (m, 2H); ESI MS m/z 470 [M+H]+; HPLC (Method A)>99% (AUC), tR=14.1 min.

Provenance & Evidence