N-methyl-2-pyrrolidone → [5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine

Participants

Reaction Conditions

Reaction Steps

Into a 30 mL vial, [A] 5-Bromo-2-methanesulfinyl-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.14 g, 0.00034 mol), 4-(4-morpholino)aniline (0.181 g, 0.00101 mol), and N-Methylpyrrolidinone (0.22 mL, 0.0023 mol) were added. The mixture was heated at 150° C. for 3 hours. The mixture was purified via ISCO column chromatography with DCM and MeOH as eluant (0 to 15% methanol). The collected fractions afforded [5-Bromo-7-(4-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine as a yellow solid (120 mg, 67%). MP 242-244° C. LCMS (E/I+) 451.23 (M+H). NMR 1H (DSMO-d6)-9.43 (s, 1H), 8.86 (s, 1H), 8.16 (d, 2H, J=7.76 Hz), 7.62 (d, 2H, J=8.93 Hz), 7.54 (t, 1H, J=7.77 Hz), 7.41 (t, 1H, J=7.16 Hz), 7.34 (s, 1H), 6.93 (d, 2H, J=8.97 Hz), 3.74 (t, 4H, J=4.29 Hz), 3.06 (t, 4H, J=4.64 Hz).

Provenance & Evidence