Dichloromethane → HCID 49868677, compound

Participants

Reaction Steps

To a solution of tert-butyl 6-methyl-8-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyrimidin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-]indole-2(1H) carboxylate (55 mg, 0.13 mmol) in DCM (10 mL) was added TFA (0.50 mL). The reaction solution was stirred at room temperature for 2 h and then concentrated under reduced pressure. The resulting residue was purified by semi-preparative HPLC (Phenomenex Luna C18 (2), 250.0×21.20 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA). The resulting free base was converted to the HCl salt using HCl in methanol to afford the title compound (23.0 mg, 37%) as a brown-reddish solid: 1H NMR (500 MHz, CD3OD) δ 9.47 (d, J=1.5 Hz, 1H), 8.80 (dd, J=6.0, 2.0 Hz, 1H), 8.41 (d, J=6.5 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.71 (d, J=8.5 Hz, 1H), 6.64 (d, J=1.5 Hz, 1H), 7.37 (d, J=7.0 Hz, 1H), 7.23 (dd, J=8.5, 2.0 Hz, 1H), 4.58 (s, 2H), 3.72 (s, 3H), 3.61-3.58 (m, 2H), 3.24-3.21 (m, 2H), 2.27-2.20 (m, 2H); ESI MS m/z 440 [M+H]+.

Provenance & Evidence