Sodium Carbonate → 4-(8-(4-(2-Morpholinoethoxy)phenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl)thiophene-2-carboxamide

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Reaction Steps

This compound may be prepared using 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 (113 mg, 0.27 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxamide (136 mg, 0.537 mmol), and Pd(PPh3)4 (78 mg, 0.067 mmol) in 1.5M Na2CO3 (1.44 mL, 2.16 mmol) and dioxane (4.3 mL). The reaction mixture is purified by silica gel column chromatography eluting with 97:3 DCM:NH3 (7M in MeOH) to yield the title compound (65 mg, 52%). LCMS: Rt 1.98 min (98.9%). Conversion into the mesylate salt using 0.1M methanesulfonic acid in MeOH (1.1385 mL) affords the title compound (50 mg, 95%). 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.37 (3H, s, MsOH), 3.21-3.64 (6H, m), 3.76 (2H, t), 4.05 (2H, d), 4.40 (2H, m), 7.09 (2H, d), 7.61 (1H, br s), 8.02 (2H, d), 8.11 (2H, s), 8.48 (1H, s), 8.67 (1H, s), 8.82 (1H, s), 9.91 (1H, br s), 10.09 (1H, s). LCMS: Rt 1.98 min (97.7%), m/z (APCI) 466 (M+H)+.

Provenance & Evidence