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

Participants

Reaction Steps

tert-Butyl 6-methyl-8-(4-(6-methylpyridin-3-yl)-2-oxopyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (50 mg, 0.10 mmol) was treated with 1.25 M HCl in MeOH (6.0 mL), and the resulting solution was stirred at ambient temperature for 36 h. The solution was partially concentrated under reduced pressure and diluted with Et2O. The resulting solids were collected by filtration and washed with 99:1 CH2Cl2/MeOH to provide the title compound (37 mg, 85%) as a tan solid: mp 245-250° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.10 (br s, 2H), 9.04 (s, 1H), 8.44 (s, 1H), 7.82 (d, J=7.0 Hz, 1H), 7.70-7.68 (m, 2H), 7.58 (s, 1H), 7.09 (d, J=8.0 Hz, 1H), 6.96 (s, 1H), 6.79 (d, J=7.0 Hz, 1H), 4.45. (s, 2H), 3.74 (s, 3H), 3.45-3.44 (m, 2H), 3.11-3.09 (m, 2H), 2.66 (s, 3H), 2.08-2.07 (m, 2H); ESI MS m/z 385 [M+H]+; HPLC (Method A) 97.9% (AUC), tR=8.9 min.

Provenance & Evidence