Morpholine → (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-morpholin-4-yl-isonicotinamide

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 100 mg (0.22 mmol) (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide, 145 mg (0.44 mmol) cesium carbonate and a few crystals of 2,6-di-tert-butyl-p-cresol in 0.39 ml (4.44 mmol) morpholine in a thick-walled glass pressure tube fitted with a teflon cap was heated at 100° C. for 16 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. Flash chromatography (1/1 acetone/hexane) followed by trituration in ether afforded 35 mg (35%) (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-morpholin-4-yl-isonicotinamide as a white solid. [α]D20=+63.7° (c=0.63, CHCl3), ES-MS m/e (%): 457 (M+H+, 100).

Provenance & Evidence