4-Methylmorpholine → HCID 86661691, compound

Participants

Reaction Steps

Into a 8-dram vial, Prop-2-ynylamine (0.0643 g, 0.00117 mol) was dissolved in N,N-Dimethylformamide (1.75 mL), and 1-Hydroxybenzotriazole hydrate (0.0429 g, 0.000280 mol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (53.7 mg, 0.280 mmol) were added. After stirring for 5 min, 3-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzoic acid (100 mg, 0.233 mmol) was added followed by 4-Methylmorpholine (0.0308 mL, 0.280 mmol). The reaction was stirred at rt for 1 hour. The reaction mixture was diluted with NaHCO3 and the resulting ppt was filtered, washed with NaHCO3 and water. The solid was dried under vacuum to give 3-{2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-N-prop-2-ynyl-benzamide as a yellow solid (37 mg, 34%). LCMS (E/I+) 466.19 (M+H). MP 185-187° C. NMR 1H (DMSO-d6)-9.25 (s, 1H), 9.03 (t, 1H, J=4.84 Hz), 8.96 (s, 1H), 8.57 (s, 1H), 8.39 (d, 1H, J=8.02 Hz), 7.84 (d, 1H, J=8.02 Hz), 7.65 (d, 1H, J=8.02 Hz), 7.62 (d, 2H, J=8.32 Hz), 7.20 (d, 1H, J=4.75 Hz), 6.95 (d, 1H, J=4.75 Hz), 6.89 (d, 2H, J=8.00 Hz), 4.11 (s, 2H), 3.14 (s, 1H), 3.06 (bs, 4H), 2.46 (bs, 4H), 2.22 (s, 3H).

Provenance & Evidence