4-Methylmorpholine → HCID 22736990, compound

Participants

Reaction Steps

To a stirred solution of 99 mg (0.49 mmol) 2-bromo-isonicotinic acid in 3 ml THF were added 195 mg (0.51 mmol) HATU and 0.11 ml (0.98 mmol) N-methylmorpholine and stirring continued at 30° C. for 5 h. 75 mg (0.24 mmol) 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine was then added and stirring continued at 40° C. for 16 h. The reaction mixture was then diluted with ethyl acetate and washed sequentially with 0.5 N hydrochloric acid, saturated sodium bicarbonate solution and brine. The organic phase was dried over sodium sulfate and concentrated in vactio. Flash chromatography (methanol/dichloromethane) followed by trituration in ether/hexane afforded 17 mg (14%) 2-bromo-N-{4-methoxy-7-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino)-benzothiazol-2-yl}-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 493 (M{81Br}+H+, 100), 491 (M{79Br}+H+, 95).

Provenance & Evidence