Triethylamine → HCID 69480863, compound

Participants

Reaction Steps

To a cold (0° C.) solution of ethyl 3-[(2-aminoethyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (90 mg, 0.284 mmol) and triethylamine (59 μL, 0.426 mmol) in dichloromethane (1 mL) was added methanesulfonyl chloride (26 μL, 0.341 mmol) in dichloromethane (1 mL) dropwise. The reaction mixture was warmed to room temperature and stirred one hour. The reaction mixture was quenched with ice and diluted with dichloromethane. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) provided ethyl 5-[(4-fluorophenyl)methyl]-3-({2-[(methylsulfonyl)amino]ethyl}amino)-2-pyridinecarboxylate as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1 H), 7.87 (t, J=5.6 Hz, 1 H), 7.13 (dd, J=8.3, 5.5 Hz, 2 H), 6.97 (t, J=8.7 Hz, 2 H), 6.89 (s, 1 H), 4.93 (m, 1 H), 4.39 (q, J=7.1 Hz, 2 H), 3.91 (s, 2 H), 3.38 (m, 2 H), 3.33 (m, 2 H), 2.94 (s, 3 H), 1.41 (t, J=7.1 Hz, 3 H); MS m/z 396 (M+H)+.

Provenance & Evidence