3-Aminopyridine → 5,5-Dimethyl-2-[6-(pyridin-3-ylamino)-2,3-dihydrobenzo[1,4]oxazin-4-yl]-5,6-dihydro-4H-benzothiazol-7-one

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Reaction Steps

A mixture of Example 7 (50 mg, 0.14 mmol), 3-aminopyridine (0.171 g, 1.8 mmol), sodium tert-butoxide (0.041 g, 0.43 mmol), palladium(II) acetate (0.158 g, 0.70 mmol) and (But)3PBF4 (0.225 g, 0.78 mmol) in THF (3 mL) was heated to 140° C. under microwave irradiation for 80 min. After cooling to r.t., the mixture was concentrated in vacuo. The crude material was purified by prep HPLC to give the title compound as an off-white solid (5 mg, 8.7%). δH (CDCl3) 1.16 (6H, s), 2.44 (2H, s), 2.78 (2H, s), 4.12-4.22 (2H, m), 4.31-4.41 (2H, m), 5.75 (1H, br s), 6.84-6.89 (1H, m), 6.92-6.96 (1H, m), 7.20 (1H, dd, J 8.7, 5.1 Hz), 7.37-7.44 (1H, m), 7.87 (1H, d, J 2.6 Hz), 8.14 (1H, d, J 4.7 Hz), 8.33 (1H, d, J 2.8 Hz). LCMS (ES+) 407.0 (M+H)+.

Provenance & Evidence