Ethylamine hydrochloride → (S)-N-ethyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide

Participants

Reaction Steps

(S)-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinic acid (87 mg, 0.213 mmol) and ethanamine hydrochloride (17.4 mg, 0.213 mmol) were suspended in DMF (1.065 mL) and treated with DIPEA (0.186 mL, 1.065 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (162 mg, 0.426 mmol). The reaction mixture was stirred at room temperature for 3 h and purified using HPLC (10-95% acetonitrile in water, NH4HCO3 buffered) to afford (S)—N-ethyl-6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinamide (26.4 mg, 0.061 mmol, 28.5% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1.09 (t, J=7.20 Hz, 3 H) 1.82-2.02 (m, 3 H) 2.18 (d, J=2.27 Hz, 1H) 2.41 (t, J=4.80 Hz, 5 H) 3.20-3.29 (m, 2 H) 3.34-3.44 (m, 3 H) 3.51-3.63 (m, 5 H) 3.95-4.03 (m, 1 H) 6.82 (d, J=9.09 Hz, 1 H) 6.99 (d, J=1.77 Hz, 1 H) 7.61 (d, J=1.77 Hz, 1 H) 7.93 (dd, J=9.09, 2.53 Hz, 1 H) 8.23 (t, J=5.31 Hz, 1 H) 8.57 (d, J=2.27 Hz, 1H) 10.44 (s, 1 H); [M+H] calc'd for C23H29N7O2, 422; found, 422.

Provenance & Evidence