Hydrochloric Acid → HCID 178464379, compound

Participants

Reaction Steps

A solution of tert-butyl ethyl(2-(6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (compound 8, 115 mg, 0.268 mmol) in HPLC grade methanol (10 mL) was treated with 2N aq. HCl (1.35 mL, 2.7 mmol) and the mixture heated to reflux for 90 minutes. After cooling to room temperature, the solution was concentrated and dried briefly on high-vac pump. The residue was purified directly on silica gel eluting with 10% 2M NH3 in methanol/90% dichloromethane to yield a yellow solid, 9 (78 mg, 88%). 1H-NMR (DMSO-d6) δ 7.66 (d, 1H, J=3.0 Hz), 7.54 (dd, 1H, J=5.0, 0.9 Hz), 7.06 (dd, 1H, J=5.0, 3.7 Hz), 6.59-6.52 (m, 2H), 6.47 (br s, 1H), 6.21 (br s, 2H), 3.32-3.20 (m, 4H), 2.70-2.64 (m, 4H), 2.56 (q, 2H, J=7.1 Hz), 1.88-1.80 (m, 2H), 1.04 (t, 3H, J=7.0 Hz). MS (ESI+): 329 (MH+, 100), 258 (100); ESI-HRMS calculated for C18H25N4S (MH+): 329.1794; observed: 329.1798.

Provenance & Evidence