Tert-Butylamine → HCID 44242652, compound

Participants

Reaction Steps

To a biphasic mixture of 1-(piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride (38 mg, 0.110 mmol) in DCM (2 mL) and saturated aqueous NaHCO3 (2 mL) was added tert-butylamine (50 μL, 0.472 mmol). The reaction was stirred at room temperature for 16 h. The biphasic mixture was extracted with DCM (3×2 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting solid was purified by flash column chromatography using a gradient elution of hexanes with 10-70% EtOAc to provide N-tert-butyl-1-(piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxamide (27.7 mg, 0.072 mmol, 65.2% yield over 2 steps) as a white solid. LCMS (+ESI) m/z=383.1 [M+H]+; 1H-NMR (CDCl3) δ 8.27. (d, 1H), 8.17 (d, 1H), 5.86 (br s, 1H), 4.49 (dd, 2H), 3.78 (dd, 2H), 3.29 (dd, 4H), 1.67-1.53 (m, 6H), 1.46 (s, 9H).

Provenance & Evidence