N,N-Dimethylglycine → HCID 66621381, compound

Participants

Reaction Steps

To a solution of 2-(dimethylamino)acetic acid (648 mg, 2.02 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (186 mg, 0.97 mmol), 1-hydroxybenzotriazole (131 mg, 0.97 mmol) in N,N′-dimethylformamide (50 ml) was added diisopropylethylamine (280 mg). The mixture was stirred at room temperature for 0.5 h. 2-(4-(Piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (260 mg, 0.81 mmol) was added to the reaction mixture at 0° C. Then the mixture was stirred at room temperature for 4 h. Then ethyl acetate and water was added to the mixture and extracted. The organic phase was washed with water (50 mL×3), brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give crude product which was purified by chromatography (silica gel, dichloromethane/methanol=10:1) to give 2-(4-(1-(2-(dimethylamino)acetyl)piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (50 mg, Yield: 15%). 1H-NMR (400 MHz, DMSO-d6) δ: 1.41-1.58 (m, 1H), 1.76-1.84 (m, 2H), 1.96-1.98 (m, 1H), 2.10 (s, 6H), 2.54-2.88 (m, 2H), 2.93-3.09 (m, 2H), 3.14-3.26 (m, 2H), 4.11 (t, J=12 Hz, 1H), 4.44 (t, J=9.2 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 7.54-7.57 (dd, J1=8.0 Hz, J2=2.4 Hz, 2H), 7.81 (d, J=8.0 Hz, 1H), 7.87 (brs, 1H), 7.90 (brs, 1H), 7.95 (d, J=7.6 Hz, 1H), 8.24-8.26 (dd, J1=8.0 Hz, J2=5.6 Hz, 2H); LC-MS (ESI) m/z: 407 (M+1)+.

Provenance & Evidence