Sodium hydride → HCID 66832542, compound

Participants

Reaction Steps

To a solution of (R)-6-(3-(3-(2-chloroethyl)ureido)piperidin-1-yl)-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (86 mg, 0.162 mmol) in DMF (1 mL) was added NaH (32.4 mg, 0.811 mmol) and stirred at rt for 1 h. The reaction mixture was quenched with water, extracted twice into CH2Cl2 twice. The combined organic extracts were washed with 10% LiCl and concentrated. The residue was purified by MPLC chromatography (ISCO, 6% NH4OH/MeOH/CH2Cl2, 40 g silica gel column) and further purified by HPLC. The product containing fractions were collected, basified with 1N NaOH, and extracted with CH2Cl2 twice. The combined organic layers were concentrated to give 13 mg of (R)-2-(4-(morpholine-4-carbonyl)phenylamino)-6-(3-(2-oxoimidazolidin-1-yl)piperidin-1-yl)nicotinamide as a light yellow solid. LCMS: (M+H)+=494.23. 1H NMR (400 MHz, CDCl3) δ ppm 11.17 (1H, s), 7.66-7.71 (2H, m), 7.52 (1H, d, J=8.79 Hz), 7.34-7.39 (2H, m), 6.07 (1H, d, J=8.79 Hz), 5.62-5.84 (2H, m), 4.54 (1H, s), 4.26-4.38 (2H, m), 3.76-3.88 (2H, m), 3.57-3.75 (8H, m), 3.43 (4H, d, J=4.39 Hz), 2.94-3.03 (1H, m), 1.92-2.02 (1H, m), 1.80-1.89 (1H, m), 1.68 (2H, m).

Provenance & Evidence