Diisopropylethylamine → HCID 89784119, compound

Participants

Reaction Steps

Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (AK Scientific, Inc., Union City, Calif.) (415 mg, 0.80 mmol) was added to a solution of 2-(aminomethyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (301c) (255 mg, 0.61 mmol) and DIPEA (Sigma-Aldrich) (0.43 mL, 2.45 mmol) in CH2Cl2 (15 mL) and DMF (15 mL) at RT. After 30 min the reaction mixture was concentrated. EtOAc and H2O were added and the layers were separated. The aq. layer was extracted with EtOAc (2×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude material was absorbed onto a plug of silica gel and purified by silica gel chromatography (0-5% MeOH in CH2Cl2), to provide a yellow solid. The combined fractions were triturated with CH2Cl2 and the solid was collected by filtration and washed with CH2Cl2 and Et2O to provide 2-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (301) (48 mg, 0.13 mmol, 22% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.97 (br. s., 1H), 7.89 (d, J=7.04 Hz, 1H), 7.74 (t, J=6.55 Hz, 1H), 7.67 (d, J=8.22 Hz, 1H), 7.52 (br. s., 1H), 7.39-7.47 (m, 1H), 6.97 (s, 1H), 4.33-4.46 (m, 2H), 4.25 (br. s., 2H), 2.59 (s, 3H). 19F NMR (376 MHz, DMSO-d6) δ ppm −69.44 (s, 3F). m/z (ESI, +ve) 362.0 (M+H)+.

Provenance & Evidence