Diisopropylethylamine → 1-(2-Hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [4-(2-phenyl-furo[3,2-b]pyridin-7-yloxy)-phenyl]-amide

Beteiligte Stoffe

Reaktionsschritte

To a 10 mL sealed tube with stirbar was added 1-(2-hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (57.62 mg; 0.20 mmol; 1.20 eq.), and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (63.15 mg; 0.25 mmol; 1.50 eq.). The tube was sealed and flushed with N2. To this mixture was added dioxane (3.00 ml) and N,N-diisopropylethylamine (0.14 ml; 0.83 mmol; 4.00 eq.) and the mixture was stirred at room temperature for 1 h. To the reaction mixture was then added 4-[(2-phenylfuro[3,2-b]pyridin-7-yl)oxy]aniline (50.00 mg; 0.17 mmol; 1.00 eq.) and stirred at room temperature overnight. The reaction mixture was concentrated on a rotary evaporator. The crude mixture was purified by Biotage chromatography (50% EtOAc/hex 10 column vol.; 50-100% 10 column vol.) to afford a beige solid (14 mg, 15%). (HPLC (method F): 88%, RT: 6.27 min); 1H NMR (400 MHz, DMSO-d6) δ [ppm] 10.84 (s, 1H), 8.35 (d, J=5.6, 1H), 7.98-7.90 (m, 2H), 7.73 (d, J=9.0, 2H), 7.70 (s, 1H), 7.60-7.50 (m, 4H), 7.49-7.43 (m, 2H), 7.35 (d, J=7.4, 2H), 7.30 (d, J=9.0, 2H), 6.71 (d, J=5.5, 1H), 4.85 (s, 1H), 3.86 (s, 2H), 2.80 (s, 3H), 0.97 (s, 6H); MS (m/z) 575 [M+H]+, RT: 3.7 min.

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