Cyclopentylamine → HCID 44242731, compound

Participants

Reaction Steps

To a suspension of 5-(1-(4-fluorophenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-1,2,4-oxadiazole-3-carbonyl chloride (21 mg, 0.049 mmol) in DCE (5 mL) was added DIPEA (21 μL, 120 μmol) to form a clear solution. To that solution was added cyclopentyl amine (40 μL, 0.099 mmol) and saturated aqueous NaHCO3 (1 mL). The reaction was stirred for 72 hours. LCMS analysis of the reaction mixture indicated consumption of starting material. The reaction 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 to provide N-cyclopentyl-5-(1-(4-fluorophenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-1,2,4-oxadiazole-3-carboxamide (7.7 mg, 0.016 mmol, 32.2%) as a white solid. LCMS (+ESI) m/z=474.1 [M+H]+; 1H-NMR (CDCl3) δ 8.90 (d, 1H), 8.87 (d, 1H), 7.75 (m, 2H), 7.21 (m, 2H), 6.97 (m, 1H), 4.47 (m, 1H), 4.09 (dd, 2H), 3.92 (dd, 2H), 2.13 (m, 2H), 1.82-1.52 (m, 6H).

Provenance & Evidence