Hydrochloric Acid → HCID 66603452, compound

Participants

Reaction Steps

According to the procedure of Example 2 (step b), except substituting 4-((5-chloropyridin-2-yl)methoxy)pyridin-2(1H)-one for 4-(benzyloxypyridin-2(1H)-one and substituting 10-Bromo-12-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow oil was obtained in 23% (46 mg). The yellow oil was dissolved in CH3OH (1 mL) and was treated with 2 N HCl in Et2O (1 mL). The resulting solid was isolated by filtration and dried under vacuum to give the title compound (47 mg, 95%) as a yellow-brown solid: mp 204-208° C.; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 7.97 (dd, J=8.5, 2.5 Hz, 1H), 7.65-7.63 (m, 3H), 7.48 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.0, 2.0 Hz, 1H), 6.39 (dd, J=7.5, 3.0 Hz, 1H), 6.16 (d, J=3.0 Hz, 1H), 5.30 (s, 2H), 4.91 (dd, J=12.0, 3.5 Hz, 1H), 4.13-4.09 (m, 1H), 3.74 (s, 3H), 3.66-3.60 (m, 3H), 3.22-3.19 (m, 2H), 2.34-2.31 (m, 1H), 2.11-2.01 (m, 3H), 1.91-1.85 (m, 2H); ESI MS m/z 475 [M+H]+; HPLC (Method A) 97.7% (AUC), tR=12.8 min.

Provenance & Evidence