Diisopropylethylamine → HCID 71731518, compound

Participants

Reaction Steps

To a 50-mL round-bottomed flask was added 2-(1-aminocyclopropyl)-5-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (283e; 0.30 g, 0.718 mmol), DIEA (Aldrich) (0.75 mL, 4.31 mmol) in DMF (1.8 mL) and DCM (1.8 mL). Then 1H-benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (Matrix innovation, Quebec City, Canada) (0.45 g, 0.86 mmol) was added into the reaction mixture. The overall mixture was stirred under inert atmosphere 40 min. The mixture was partially concentrated (removed DCM) in vacuo, then diluted with water and stirred 10 min. The precipitate was collected by filtration. The solids were triturated from hot EtOH in a sealed tube. The solids were collected by filtration, washed with Et2O, and dried in a reduced pressure oven (40° C.) overnight. This gave 2′-(3-(cyclopropylamino)-6-fluoro-2-methylquinoxalin-5-yl)-1′H-spiro[cyclopropane-1,6′-pyrrolo[3,4-b]pyrrol]-4′(5′H)-one (283) (0.13 g, 0.36 mmol, 50% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.61 (br. S, 1H), 7.74 (br. s, 1H), 7.62-7.70 (m, 2H), 6.92 (br. s, 1H), 1.38-1.45 (m, 2H), 1.35 (br. s, 3H), 0.75-0.84 (m, 2H), 0.72 (br. s, 4H). m/z (ESI, +ve) 364 (M+H).

Provenance & Evidence