Cesium carbonate → N-(4-(3-morpholinopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Participants

Reaction Steps

To a round bottomed flask was added 4-(2-chloropyridin-3-yl)morpholine (0.2076 g, 1.045 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (0.304 g, 1.254 mmol), and cesium carbonate (0.409 g, 1.254 mmol) in DMSO (3.48 mL) at 80° C. for two days. The reaction was allowed to cool to room temperature. The reaction mixture was diluted with a 50% sodium chloride solution and extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (25M), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide N-(4-(3-morpholinopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine. MS (ESI, pos. ion) m/z: 405 (M+1). IC50 (uM) +++++.

Provenance & Evidence