Sodium hydride → HCID 10128455, compound

Participants

Reaction Steps

To a stirred solution of 200 mg (0.52 mmol) 2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide in 1 ml DMF and 4 ml 1,2-dimethoxyethane was added 44 mg (1.04 mmol) sodium hydride (60% dispersion in mineral oil). After stirring for 15 min at room temperature, 90 mg (1.04 mmol) lithium bromide was added and stirring continued for a further 15 min. 95 mg (0.58 mmol) 4-(2-chloroacetyl)morpholine was then added and the mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with ethyl acetate, and washed sequentially with 0.5 M hydrochloric acid, saturated sodium bicarbonate solution and saturated brine. The combined aqueous phases were filtered, and the filter cake washed with ether, then resuspended in toluene and concentrated in vacuo. Flash chromatography (MeOH/CH2Cl2) followed by trituration in ethyl acetate afforded 83 mg (31%) 1-(2-morpholin-4-yl-2-oxo-ethyl)-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide as a yellow crystalline solid. ES-MS m/e (%): 536 (M+Na+, 25), 514 (M+H+, 100).

Provenance & Evidence