4-Nitrophenyl chloroformate → HCID 21073537, compound

Participants

Reaction Steps

A mixture of 3-aminomethyl-6-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-pyridin-2-ylamine (0.260 g, 0.61 mmol) in THF (10 mL) was treated with 4-nitrophenyl chloroformate (0.160 g, 0.79 mmol). The mixture was stirred at room temperature for 30 minutes, then cooled to 0° C. and treated with LDA (0.9 mL, 3.8 mmol, 2.0 M in heptane/THF/ethylbenzene). The brown mixture was stirred at room temperature for 1 hour, then quenched with water and extracted with EtOAc. The organic extracts were washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (10% MeOH/EtOAc) to afford the title compound as a light yellow solid (0.071 g, 25%). mp 166–167° C.; 1 H NMR (400 MHz, CDCl3): δ 7.25 (s, 1H), 7.19–7.14 (m, 2H), 7.14–7.09 (br s, 1H), 6.99–6.94 (m, 1H), 6.32 (d, 1H), 5.57–5.51 (br s, 1H), 4.45 (s, 2H), 4.24 (t, 2H), 3.16–3.02 (m, 4H), 2.75–2.58 (m, 4H), 2.49 (t, 2H), 1.84–1.64 (m, 4H). MS ES: m/z=450.03, 452.02.

Provenance & Evidence