Pyridine → 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-[2-methyl-6-(4-morpholinyl)-3-pyridinyl]benzenesulfonamide

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A mixture of 2-methyl-6-(4-morpholinyl)-3-pyridinamine (170 mg, 0.880 mmol) and 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}benzenesulfonyl chloride (265 mg, 0.880 mmol) in dichloromethane (4 mL) and pyridine (0.142 mL, 1.759 mmol) was heated at 65° C. for 2 hours. The reaction mixture was allowed to cool and separated between dichloromethane and saturated sodium bicarbonate solution. The organic phase was passed through a hydrophobic frit and evaporated in vacuo. The crude was purified by flash silica (Si) chromatography (0-100% ethyl acetate-cyclohexane gradient) to give the title compound (271 mg) as an off-white solid. LCMS (2 min, formic) Rt 0.82 min, m/z (ES+) 459 (M+H).

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