Reaction Steps
To a solution of tert-butyl 4-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)-amino)butylcarbamate, 10 (0.85 g, 1.80 mmol) in methanol (20 mL) was added thionyl chloride (1.27 g, 10.7 mmol) at room temperature. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo yielding 790 mg (85%) of Z: 1H NMR (400 MHz, d6-DMSO) δ 10.78, (bs, 1H), 8.93, (s, 1H), 8.51 (d, J=4.4 Hz, 1H), 8.25-8.06 (m, 3H), 7.84, (d, J=7.6 Hz, 2H), 7.71, (d, J=7.2 Hz, 2H), 7.62-7.55 (m, 2H), 7.52-7.46, (m, 1H), 7.40-7.35, (m, 1H), 4.77, (m, 1H), 4.50-4.38, (m, 2H), 3.32-3.22, (m, 1H), 3.15-3.02 (m, 1H), 2.88-2.66 (m, 4H), 2.50-2.39 (m, 1H), 2.15-2.00, (m, 2H), 1.95-1.68, (m, 3H), 1.64-1.50, (m, 2H), ESI+ MS: m/z (rel intensity) 377 (100, M+H).
