4-Aminocarbonylphenylboronic acid → 4-{8-[4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-benzamide

Participants

Reaction Steps

In the same way as described for Compound 178, step 4, using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenyl]-amine (40 mg, 0.0923 mmol), 4-(aminocarbonyl)phenylboronic acid (30.5 mg, 0.185 mmol) 1.5 M Na2CO3 (0.492 mL, 0.738 mmol), and Pd(PPh3)4 (26.7 mg, 0.023 mmol) in (2:1) DMF-dioxane (1.5 mL). The crude material is purified by Isolute FlashSilicaII Cartridge chromatography eluting with 98:2 DCM:NH3 (7M in MeOH) followed by 97:3 DCM:NH3 (7M in MeOH). The title compound is obtained as a white solid (23.5 mg, 54%). LCMS: Rt 2.67 min (95%) m/z (ES+) 474 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 7.41-7.47 (1H, d), 7.53 (1H, d), 7.66 (1H, br s), 7.81 (1H, s), 7.84-7.90 (2H, d), 7.96-8.07 (3H, m), 8.08-8.20 (5H, m), 8.36-8.44 (2H, d), 8.70 (1H, d), 9.30 (1H, s), 10.15 (1H, s).

Provenance & Evidence