Hydrochloric Acid → HCID 66580977, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl oxo[4-oxo-7-(trifluoromethoxy)-3,4-dihydro-2H-thiochromen-3-yl]acetate (3.00 g; 8.61 mmol; 1 eq.) and tert-butyl 3-[2-(tert-butoxycarbonyl)hydrazino]piperidine-1-caroxylate (4.08 g; 12.92 mmol; 1.50 eq.) in EtOH (80 ml) is added HCl (4M in dioxane, 42.38 mL) were added in a dropwise fashion. Reaction mixture is heated at 75° C. for 5 h after which it is concentrated under vacuum, partitioned between NaHCO3 sat (pH 7-8) and EtOAc. Organic layer is washed NaHCO3 sat and brine, dried over MgSO4 to give 3.1 g (88%) of the title compound as a brown solid. 1H NMR (DMSO, 300 MHz): δ 7.77 (d, J=9.43 Hz, 1H), 7.62 (s, 1H), 7.39 (d, J=7.7 Hz, 1H), 4.61-4.46 (m, 1H), 4.40-4.26 (m, 2H), 4.17 (s, 1H), 4.09-3.98 (m, 1H), 3.19-3.06 (m, 1H), 2.97-2.82 (m, 2H), 2.17-2.05 (m, 2H), 1.99 (s, 1H), 1.80-1.67 (m, 1H), 1.67-1.45 (m, 1H), 1.32 (t, J=7.0 Hz, 3H), 1.18 (t, J=6.9 Hz, 1H).

Provenance & Evidence