Cyclopropylamine → (S)-N-cyclopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

Participants

Reaction Steps

(S)-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzoic acid (87 mg, 0.214 mmol) and cyclopropanamine (18.29 mg, 0.320 mmol) were suspended in DMF (1 ml) and treated with DIPEA (0.186 ml, 1.068 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (162 mg, 0.427 mmol). The reaction mixture was stirred at room temperature for 3 h and purified using HPLC (25-95% acetonitrile in water, NH4HCO3 buffered) to afford (S)-N-cyclopropyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide (43.0 mg, 0.096 mmol, 45.1% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 0.46-0.59 (m, 2H) 0.59-0.71 (m, 2H) 1.82-2.02 (m, 3H) 2.10-2.25 (m, 1H) 2.46 (br. s., 4H) 2.74-2.83 (m, 1H) 3.21 (br. s., 4H) 3.34-3.46 (m, 3H) 3.53-3.64 (m, 1H) 3.94-4.02 (m, 1H) 6.91 (d, J=8.84 Hz, 2H) 6.98 (d, J=1.77 Hz, 1H) 7.61 (d, J=1.26 Hz, 1H) 7.68 (d, J=8.84 Hz, 2H) 8.13 (d, J=4.04 Hz, 1H) 10.44 (s, 1H); [M+H] calc'd for C25H30N6O2, 447; found, 447; melting point 265-268° C.

Provenance & Evidence