Toluene → HCID 19919606, compound

Participants

Reaction Steps

In an analogous manner to example 3, the title compound (0.39 g) as a white solid, mp 267°-269° C., is prepared from ethyl-4-[4-[2-(4-chlorophenyl)ethyl]-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (1.60 g, 3.73 mmol, prepared in example 18), dry ammonium chloride (0.60 g, 11.2 mmol) and 2M trimethyl aluminum in toluene (5.6 mL, 11.2 mmol). The free base of the title compound is isolated by flash chromatography (ethyl acetate:hexane, 50:50, then ethyl acetate followed by ethanol:ethyl acetate, 50:50, Rf =0.4 in ethyl acetate:hexane, 40:60); 1H NMR (DMSO-d6) δ 11.35 (1H, bs), 8.50 (1H, s), 7.82 (1H, d, J=8.2 Hz), 7.57 (1H, t, J=8.0 Hz), 7.45 (2H, d, J=8.4 Hz), 7.36 (2H, d, J=8.4 Hz), 7.10 (1H, d, J=7.6 Hz), 3.63 (4H, m), 3.37 (6H, m), 3.17 (2H, m); 13C NMR (DMSO-d6) δ 148.02, 142.47, 136.12, 134.77, 131.45, 131.41, 130.58, 129.21, 128.58, 117.53, 114.72, 113.99, 107.10, 55.75, 51.10, 48.53, 28.61; IR (KBr) 2430, 2218, 1458, 958 cm-1 ; CI/MS (CH4) 382(100%). IC50 =13 nM (5HT1ABinding Affinity) IC50 =31 nM (5HT1DBinding Affinity) pA2 =7.37 (34%) (blocking of 5-HTl-like-mediated contraction in canine saphenous vein)

Provenance & Evidence