Hydrochloric Acid → HCID 178457365, compound

Participants

Reaction Steps

A solution of tert-butyl-isopropyl(2-(6-(thiophene-2-carboximidamido)-3,4-dihydro-quinolin-1(2H)-yl)ethyl)carbamate (compound 6, 50 mg, 0.113 mmol) in HPLC grade methanol (10 mL) was treated with 2N aq. HCl (0.565 mL, 1.13 mmol) and the mixture heated to reflux for 2 hours then cooled to room temperature overnight. The solution was concentrated and dried briefly on high-vac pump. The residue was taken up in 7.5% 2M NH3 in methanol/92.5% dichloromethane (5 mL), reconcentrated then purified directly on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane to yield a yellow solid, 61 (40 mg, quantitative). 1H-NMR (DMSO-d6) δ 7.66 (d, 1H, J=3.1 Hz), 7.54 (d, 1H, J=5.1 Hz), 7.06 (dd, 1H, J=5.0, 3.7 Hz), 6.61-6.50 (m, 2H), 6.47 (br s, 1H), 6.21 (br s, 2H), 3.30-3.18 (m, 4H), 2.79-2.70 (m, 1H), 2.70-2.61 (m, 4H), 1.88-1.80 (m, 2H), 0.97 (d, 6H, J=6.2 Hz). MS (ESI+): 343 (MH+, 100); ESI-HRMS calculated for C19H27N4S (MH+): 343.1950; observed: 343.1953.

Provenance & Evidence