Triethylamine → HCID 46222159, compound

Participants

Reaction Steps

The title compound was prepared according to general procedure B described in Scheme 1. N-Isopropylindole (150 mg, 0.94 mmol) was converted to 2-(1-isopropyl-1H-indol-3-yl)-2-oxoacetyl chloride as described in example 1 and treated with a solution of 2-(1-(2-aminoethyl)piperidin-4-yl)ethanol (236 mg, 1.13 mmol), triethylamine (1.3 mL, 9.4 mmol) in DCM (2 mL) and stirred at RT for 14 h. The reaction mixture was then washed with sat. NaHCO3 (1×3 mL), H2O (1×3 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica chromatography (Biotage, 10-50% MeOH/DCM, 30 min.) to provide N-(2-(4-(2-hydroxyethyl)piperidin-1-yl)ethyl)-2-(1-isopropyl-1H-indol-3-yl)-2-oxoacetamide and further purified using reverse phase HPLC. The purified material was converted to the HCl salt to afford (27 mg, 7% yield): 1H NMR (400 MHz, CDCl3): δ 9.11 (s, 1H), 8.45 (m, 1H), 7.93 (t, 1H), 7.44 (m, 1H), 7.34 (m, 2H), 4.71 (m, 1H), 3.71 (t, 2H), 3.47 (q, 2H), 2.92 (d, 2H) 2.55 (t, 2H), 2.01 (t, 2H), 1.70 (d, 2H), 1.62 (d, 6H), 1.53 (q, 3H), 1.33 (t, 3H); MS (ESI) m/z: Calculated for C22H31N3O3: 385.2. Found: 385.5 (M+H)+.

Provenance & Evidence