Hydrochloric Acid → HCID 25165895, compound

Participants

Reaction Steps

To a solution of (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.45 mmol) in DCM (5 mL) was added 4M HCl in dioxane (1.7 mL, 6.8 mmol). After 2 hours the reaction mixture was concentrated and the residue taken up in DCM (5 mL). DIPEA (0.32 mL, 1.70 mmol) and ethyl isocyanate (42 μL, 0.53 μmol) were added and the reaction mixture stirred at room temperature overnight. Solids were filtered off and washed with DCM to give (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-1-carboxylic acid ethylamide as white crystals (88 mg, 47%). M.p.=278-279° C.; 1H NMR (400 MHz, DMSO-d6) δ: 10.80 (s, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.39 (d, J=7.6 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 7.17 (s, 1H), 7.02 (t, J=8.0 Hz, 1H), 6.93 (t, J=7.2 Hz, 1H), 6.85 (t, J=7.6 Hz, 1H), 6.77 (d, J=6.8 Hz, 1H), 6.14 (t, J=5.6 Hz, 1H), 4.03-3.94 (m, 6H), 3.41-3.32 (m, 2H), 3.11-3.04 (m, 2H), 2.84 (t, J=6.0 Hz, 2H), 2.04 (t, J=5.2 Hz, 2H), 1.03 (t, J=7.2 Hz, 3H). LCMS: m/e 413.16 [M+H].

Provenance & Evidence