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

참여 물질

반응 단계

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 (118 mg, 0.28 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxamide (142 mg, 0.56 mmol), and Pd(PPh3)4 (81 mg, 0.07 mmol) in 1.5M Na2CO3 (1.5 mL, 2.24 mmol) and dioxane (4.5 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 (33 mg, 25%). LCMS: Rt 2.66 min (99%). Conversion into the mesylate salt using 0.1M methanesulfonic acid in MeOH (0.569 mL) affords the title compound (24 mg, 86%). 1H-NMR (400 MHz, d6-DMSO) δ(ppm) 2.37 (3H, s, MsOH), 3.25 (2H, m), 3.50-3.64 (4H, m), 3.76 (2H, t), 4.05 (2H, d), 4.40 (2H, m), 7.09 (2H, d), 7.51 (1H, br s), 7.87 (1H, d), 7.99-8.05 (3H, m), 8.11 (1H, br s), 8.37 (1H, s), 8.84 (1H, s), 9.92 (1H, br s), 10.21 (1H, s). LCMS: Rt 1.95 min (98.8%), m/z (APCI) 466 (M+H)+.

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