1-Methoxy-2-propanol → 2-(4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-fluoro-phenyl}-piperazin-1-yl)-acetamide

Participants

Reaction Steps

N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (0.092 g, 0.26 mmol), N-Phenylbis(trifluoromethanesulphonimide) (0.112 g, 0.314 mmol), N,N-Diisopropylethylamine (0.139 mL, 0.797 mmol) and 1-Methoxy-2-propanol (4.0 mL, 41 mmol) were combined in a tube and stirred at room temperature for 18 hours. 2-[4-(4-Amino-2-fluoro-phenyl)-piperazin-1-yl]-acetamide (0.087 g, 0.34 mmol) was added and the reaction was stirred at room temperature for 4 days to yield an orange solid, 2-(4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-2-fluoro-phenyl}-piperazin-1-yl)-acetamide; compound with 2 trifluoroacetic acids (35 mg, 16%). LCMS: m/z=581.25 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.59 (s, 1H), 8.98 (s, 1H), 8.41 (s, 1H), 8.33 (d, 1H, J=7.9 Hz), 7.95 (s, 1H), 7.80 (d, 1H, J=7.8 Hz), 7.66 (m, 2H), 7.54 (m, 3H), 7.14 (d, 1H, J=4.7 Hz), 7.07 (m, 1H), 6.96 (d, 1H, J=4.7 Hz), 3.95 (s, 2H), 3.5 (m, 2H), 3.31 (m, 4H), 3.09 (m, 2H), 1.05 (s, 9H).

Provenance & Evidence