Sodium Carbonate → 5-(8-(4-(4-Isopropyl-2-oxopiperazin-1-yl)phenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)isoindolin-1-one

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Reaction Steps

This compound may be prepared using methods as described for Compound 6, step 4, using 1-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-4-isopropyl-piperazin-2-one (40 mg, 0.09 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (37 mg, 0.14 mmol), and Pd(PPh3)4 (31 mg, 0.027 mmol) in 1.5M Na2CO3 (aq) (0.5 mL, 0.75 mmol), and dioxane (1.2 mL). The reaction mixture is diluted with brine then toluene is added and a precipitate is formed and collected by filtration. The filtrate is washed with diethyl ether, petroleum ether and MeOH and then purified by silica gel column chromatography. Elution with 99:1 DCM:NH3 (7M in MeOH) followed by 98:2 and 95:5 DCM:NH3 (7M in MeOH) affords the title compound as a yellow solid (24 mg, 55%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 1.08 (6H, d), 2.73-2.87 (3H, m), 3.27 (2H, s), 3.62-3.68 (2H, m), 4.52 (2H, s), 7.36 (2H, d), 7.84 (1H, d), 8.07-8.10 (4H, m), 8.25 (1H, s), 8.70 (1H, br s), 8.77 (1H, s), 10.28 (1H, s). LCMS: Rt 1.94 min (95.2%), m/z (APCI) 483 (M+H)+.

Provenance & Evidence