Dichloromethane → HCID 89783863, compound

Participants

Reaction Steps

1-(3-carboxy-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrolo-2-yl)cyclopropanaminium chloride (381b, 800 mg, 1.81 mmol) was treated with DCM (15 mL) and DMF (15.00 mL) followed by DIEA (1.27 mL, 7.24 mmol) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (1131 mg, 2.17 mmol). The reaction mixture was then stirred at RT for 15 min. It was diluted with EtOAc (100 mL) and washed with a saturated solution of NaHCO3, and brine (3×50 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (0-20% MeOH in DCM) twice to give 2′-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1′H-spiro[cyclopropane-1,6′-pyrrolo[3,4-b]pyrrol]-4′(5′H)-one (381) (62 mg, 0.16 mmol, 9% yield) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.60 (1H, s), 7.87 (1H, d, J=6.8 Hz), 7.72 (1H, t, J=6.3 Hz), 7.62-7.70 (2H, m), 7.44 (1H, t, J=7.8 Hz), 6.90-6.97 (1H, m), 4.31-4.45 (2H, m), 2.59 (3H, s), 1.36-1.45 (2H, m), 1.26 (2H, d, J=5.9 Hz). 19F NMR (376 MHz, DMSO-d6) δ ppm −69.21 (1F, s), −69.64 (1F, s), −71.10 (1F, s). m/z (ESI, +ve ion) 388.0 (M+H)+.

Provenance & Evidence