HCID 59807136, compound → HCID 178483724, compound

Participants

Reaction Steps

To a stirred solution of 9-amino-1-(2-(dimethylamino)ethyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (85 mg, 0.344 mmol) in EtOH (6 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (196 mg, 0.687 mmol). The resulting suspension was stirred overnight at room temperature. The reaction mixture was then diluted with Na2CO3 (aq, sat) and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 2-5% 2M NH3/MeOH in dichloromethane, giving the desired product. Yield: 87 mg, 71%. 1H NMR (DMSO-d6) δ 7.75 (d, 1H, J=3.3 Hz, 7.61 (d, 1H, J=4.5 Hz), 7.16 (d, 1H, J=7.8 Hz), 7.10 (m, 1H), 6.82 (s, 1H), 6.66 (d, 1H, J=8.1 Hz), 6.46 (brs, 2H), 2.65 (m, 3H), 2.28 (m, 3H), 2.17 (m, 2H), 1.9-2.15 (m, 8H). ESI-MS (m/z, %): 357 (MH+, 100), 312 (48), 156 (38), 148 (31).

Provenance & Evidence