9-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one → 2-(4-ethyl-1H-imidazol-1-yl)-9-(tetrahydrofuran-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

Participants

Reaction Steps

Example 111. A flask was charged with 9-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (250 mg, 0.67 mmol) in 20 mL THF and Raney-Nickel (100 mg, 0.67 mmol) was added. The flask was evacuated in vacuo and then filled with H2. The mixture was stirred at RT for 36 h. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue obtained was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) and the product obtained was recrystallized from heptane to give the title compound (63 mg; racemic) as beige solid. UPLC-MS: MS 377.3 (M+H+); UPLC rt 0.83 min. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.13 (t, J=7.62 Hz, 3H); 1.47-1.64 (m, 1 H); 1.81-2.00 (m, 2 H); 2.24-2.40 (m, 1 H); 2.40-2.55 (m, 2 H); 2.74-3.04 (m, 2 H); 3.59-3.74 (m, 1 H); 3.81 (q, J=7.56 Hz, 1 H); 3.86-3.97 (m, 1 H); 4.03 (q, J=7.17 Hz, 1 H); 4.21 (br. s., 2 H); 5.04 (t, J=7.04 Hz, 1 H); 7.06-7.17 (m, 1 H); 7.25-7.44 (m, 2 H); 7.52 (d, J=7.43 Hz, 1 H); 7.89 (d, J=8.21 Hz, 1 H); 8.12 (s, 1 H).

Provenance & Evidence