反应详情

温度

70 °C

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyrazin-2-yl)-3-(tetrahydro-pyran-4-yl)-propionamide (prepared as in Example 22, 151 mg, 0.34 mmol) in ethanol (2 mL) and water (1 mL) was treated with hydroxylamine hydrochloride (28 mg, 0.40 mmol) and sodium carbonate (35 mg, 0.34 mmol). The reaction was heated at 70° C. for 3 h. At this time, the reaction was concentrated in vacuo and then extracted with 10% methanol/chloroform (3×30 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 20/80 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-N-[5-(N-hydroxycarbamimidoyl)-pyrazin-2-yl]-3-(tetrahydro-pyran-4-yl)-propionamide (110 mg, 68%) as a white solid: mp 137.2–140.5° C.; (ES)+-HRMS m/e calcd for C20H24ClN5O5S (M+H)+ 482.1260, found 482.1263.

1. concentrationAt this time, the reaction was concentrated in vacuo
2. extractionextracted with 10% methanol/chloroform (3×30 mL)
3. dry with materialThe organics were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo