Trifluoroacetic acid → HCID 85472603, compound

Participants

Reaction Steps

A solution of Example 36F (0.315 g, 0.612 mmol) in dichloromethane (8 mL) was treated with trifluoroacetic acid (0.472 mL, 6.12 mmol). The mixture was stirred for 16 hours at room temperature then heated at 40° C. for 4 hours. The reaction was concentrated and the residue was dissolved in 2 mL of methanol and treated slowly with 1.5 mL of 2M HCl in ether. The suspension was stirred for 15 minutes then diluted with ether. The solids were filtered, washed with ether, and vacuum oven dried to give the title compound as the hydrochloride salt. 1H NMR (400 MHz, methanol-d4) δ ppm 1.41-1.60 (m, 4H), 2.33-2.50 (m, 1H), 2.80-2.95 (m, 2H), 3.40 (dd, J=11.4, 3.0 Hz, 1H), 3.51 (t, J=6.1 Hz, 2H), 3.87-4.01 (m, 4H), 4.74 (d, J=7.1 Hz, 2H), 6.55 (dt, J=3.5, 2.0 Hz, 1H), 6.91 (s, 1H), 7.53 (d, J=5.6 Hz, 1H), 7.88 (dd, J=8.7, 1.5 Hz, 1H), 8.11-8.28 (m, 2H), 8.40 (d, J=5.6 Hz, 1H). MS (ESI+) m/z 415.2 (M+H)+.

Provenance & Evidence