HCID 22252596, compound → HCID 22252599, compound

Participants

Reaction Steps

To a stirred solution of compound 3d (37 mg, 0.088 mmol) in ethanol (8 mL) was added 1 pinch of Raney Nickel and 5 drops of hydrazine hydrate, and the mixture was stirred at ambient temperature for 2 h. The mixture was filtered through Celite and the filtrate was evaporated. The residue was dissolved in chloroform (25 mL) and washed with brine (25 mL), dried (MgSO4), and evaporated, giving 28 mg (81%) as a yellow solid; mp 239-241° C.; 1H NMR (CDCl3) δ 1.80 (s, 6H), 2.10 (m, 2H), 4.05 (s, 3H), 4.13 (s, 3H), 4.48 (m, 3H), 5.07 (m, 1H), 6.79 (dd, 1H, J=6.3, J=2.5), 7.52 (m, 2H), 7.64 (s, 1H), 7.87 (s, 1H), 9.38 (s, 1H); 13C NMR (CDCl3) δ 45.1, 50.5, 56.3, 56.4, 57.4, 102.0, 109.1, 109.6, 111.3, 112.6, 118.7, 119.5, 127.7, 130.0, 141.0, 142.6, 144.8, 149.8, 150.0, 154.3, 164.5; HRMS calcd for C22H24O3N4H: 393.1927; found: 393.1925.

Provenance & Evidence