Hydrochloric Acid → HCID 11270980, compound

Participants

Reaction Steps

The title compound of example 6 (34 mg, 70 μmol) was dissolved in MeOH (3 mL) and treated with 4 M HCl in dioxane (0.5 mL). The reaction was then treated with 10% Pd/C (7 mg) and the atmosphere was exchanged for hydrogen by sparging the solution with a needle and a balloon. After 2 h under a hydrogen balloon, the atmosphere was exchanged back to nitrogen and the catalyst was removed by filtration through celite. The solvent was removed and the residue was purified by preperative reverse phase HPLC to afford the title compound as a gum (18.6 mg, 47%); 1H NMR (CDCl3, 400 MHz) δ 0.97 (s, 9H), 1.69 (dd, 1H, J1=9.0, J2=14.5), 1.81 (dd, 1H, J1=3.4, J2=14.5), 2.71-2.90 (m, 2H), 3.04-3.16 (m, 1H), 3.19-3.31 (m, 2H), 3.40-3.50 (m, 1H), 3.66 (d, 1H, J=5.2), 4.13-4.21 (m, 1H), 4.38 (dd, 1H, J1=3.4, J2=9.0), 6.44-6.52 (m, 1H), 6.59-6.66 (m, 1H), 6.70-6.74 (m, 1H), 7.14 (dd, 1H, J1=J2=7.7), 7.23 (dd, 1H, J1J2=7.6), 7.30 (d, 1H, J=7.8), 7.33 (d, 1H, J=8.0); HPLC-MS calcd. for C25H31FN4O3 (M+H+) 455.2, found 455.5.

Provenance & Evidence