Hydrochloric Acid → HCID 135518301, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-{2-[(6-chloropyrimidin-4-yl)oxy]ethyl}morpholine (0.116 g, 0.47 mmol), 2-oxoindoline-6-carbonitrile (0.075 g, 0.47 mmol) and cesium carbonate (0.46 g, 1.42 mmol) in butyronitrile (3 mL), was heated in a microwave oven at 160° C. for 10 min. The crude product was purified using preparative HPLC (XTerra®PrepMS C8 column 10 μm, 30×150 mm; 0.1 M NH4OAc buffer/acetonitrile, (80:20-20:80), as the eluent). The acetonitrile was evaporated and the remaining aqueous phase was extracted with chloroform and evaporated in vacuo to give a yellow solid. The solid was dissolved in dichloromethane/methanol, (9:1), and treated with HCl in diethyl ether (1 M) at 0° C. The resulting yellow crystals were collected by filtration, washed with diethyl ether, and dried to obtain 0.036 g (17% yield) of the title compound: 1H NMR (D2O, 400 MHz) δ 8.31 (s, 1H), 7.15 (dd, J=8, 2 Hz, 1H), 6.96 (d, J=8 Hz, 1H), 6.93 (d, J=2 Hz, 1H), 6.01 (s, 1H), 4.67 (m, 2H), 4.17 (m, 2H), 3.94 (m, 2H), 3.75 (m, 2H), 3.66 (m, 2H), 3.40 (m, 2H); MS (ESP) m/z 366 (M++1).

Provenance & Evidence