Propionyl chloride → Methyl 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carboxylate

Participants

Reaction Steps

To a rapidly stirring biphasic solution of methyl 3-amino-6-(4-piperidyl)pyrazine-2-carboxylate (135 mg, 0.57 mmol) in 50% saturated sodium bicarbonate and dichloromethane (20 mL) at 25° C. was added propanoyl chloride (79 mg, 75 μL, 0.86 mmol) dropwise. The reaction was stirred at room temperature for 30 minutes. The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo to provide methyl 3-amino-6-(1-propionylpiperidin-4-yl)pyrazine-2-carboxylate (111 mg, 66%). 1H NMR (400 MHz, DMSO-d6) δ 8.25 (s, 1H), 7.19 (s, 2H), 4.51 (d, J=12.9 Hz, 1H), 3.95 (d, J=13.6 Hz, 1H), 3.84 (s, 3H), 3.08 (t, J=12.2 Hz, 1H), 2.88 (ddd, J=15.5, 7.9, 3.7 Hz, 1H), 2.61 (t, J=11.7 Hz, 1H), 2.34 (q, J=7.5 Hz, 2H), 1.80 (t, J=13.7 Hz, 2H), 1.69-1.39 (m, 2H), 1.00 (t, J=7.4 Hz, 3H). LC/MS m/z 293.5 [M+H]

Provenance & Evidence