Methyl iodide → HCID 58529823, compound

Participants

Reaction Steps

A solution of 5-(2-benzyl-2H-indazol-6-yl)-7-morpholin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (65 mg, 0.12 mmol) in DMF (2 mL) was cooled to −40° C. and treated with methyl iodide (20.5 mg, 0.145 mmol) as a solution in DMF (1 mL) and potassium carbonate (33 mg, 0.24 mmol). The reaction was allowed to warm slowly to rt over 1 h. The reaction was diluted with EtOAc and washed 3 times with water. The organic layer was dried with sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with CH2Cl2:MeOH:NH3 to provide 17.9 mg (34%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1 H), 7.89 (s, 1 H), 7.79 (d, 1 H, J=9 Hz), 7.65 to 7.73 (m, 1H), 7.59 (s, 1H), 7.26 to 7.41 (m, 5H), 7.13 (d, 1 H, J=9 Hz), 6.76 (s, 1H), 5.65 (s, 2H), 4.98 (dd, 1H, J=11, 2 Hz), 4.08 (dd, 1H, J=6, 2 Hz), 3.85 to 3.94 (m, 1H), 3.15 to 3.23 (m, 1H), 2.98 to 3.08 (m, 1H), 2.80-2.96 (m, 2H), 2.11 (s, 3H); ES-MS m/z 440.4 [M+H]+, HPLC RT (min) 2.07.

Provenance & Evidence