Diisopropylethylamine → HCID 18617839, compound

Participants

Reaction Steps

4-(6-Oxo-piperidin-3-yl)-benzoic acid (190 mg, 0.87 mmol, reference example 65) and 5-(2-amino-ethyl)-1H-indole-3-carbonitrile (161 mg, 0.87 mmol, reference example 2) is dissolved in anhydrous DMF (3 mL). To this solution is added diisoproplyethylamine (330 μl, 1.9 mmol), followed by HBTU (330 mg, 0.87 mmol) and allowed to stir at room temperature overnight (16 hours). The product is isolated by Reverse-Phase chromatography of the crude reaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes, A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.26 (m, 2H), 2.92 (t, J=7.1, 2H), 3.19 (m, 1H), 3.48 (m, 2H), 3.46 (m, 2H), 7.13 (d, J=8.4, 1H), 7.15 (d, J=1.4, 2H), 7.36 (d, J=8.3, 2H), 7.43 (d, J=8.5, 1H), 7.46 (s, 1H), 7.55 (d, J=2.5, 1H), 7.73 (d, J=8.3, 2H), 8.17 (d, J=3.0, 1H), 8.47 (t, J=5.5, 1H). MS (Ion spray) m/z 387 (M+H)+.

Provenance & Evidence