Sodium Carbonate → 5-(8-(4-(2-Morpholinoethoxy)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 the methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine (80 mg, 0.19 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (74 mg, 0.29 mmol), and Pd(PPh3)4 (55 mg, 0.047 mmol) in 1.5M Na2CO3 (1.02 mL, 1.53 mmol) and dioxane (3 mL). The reaction mixture is purified by silica gel column chromatography eluting with DCM and a 97:3 mixture DCM:NH3 (7M in MeOH). After trituration using diethyl ether, the title compound is isolated as a solid (61.9 mg, 69%). Conversion of the material into the mesylate salt, using 1M methanesulfonic acid (0.134 mL) in MeOH, affords the title compound (57.1 mg). 1H-NMR (400 MHz, d6-DMSO) δ(ppm) 2.40 (3H, s, MsOH), 3.25-3.38 (2H, m), 3.60-3.78 (4H, m), 3.84 (2H, t), 4.09 (2H, d), 4.45 (2H, m), 4.56 (2H, s), 7.14 (2H, d), 7.90 (1H, d), 8.05-8.19 (4H, m), 8.28 (1H, s), 8.76 (1H, br s), 8.79 (1H, s), 10.00 (1H, br s), 10.16 (1H, s). LCMS: Rt 1.98 min (99.1%), m/z (APCI) 472 (M+H)+.

Provenance & Evidence