1,10-Phenanthroline → 1-(3-{[2-(4-amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-6-yl]oxy}phenyl)-4-(4-methyl-1-piperazinyl)-4-oxo-1-butanone

Participants

Reaction Conditions

Reaction Steps

Under argon, to a suspension of 4-(6-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-furazan-3-amine (prepared by the method of Example 8, Steps 3-7, substituting ethylamine for aniline in Step 3) (80 mg, 0.26 mmol) in toluene (4 mL) and DME (4 mL), was added the product of Step 2 (145 mg, 0.52 mmol), CuI (50 mg, 0.26 mmol), 1,10-phenanthroline (94 mg, 0.52 mmol), and Cs2CO3 (210 mg, 0.65 mmol). This mixture was then heated to 170° C. by microwave for 25 min. The reaction mixture was added DMSO (2.0 mL), diluted with EtOAC/MeOH, sonicated for 10 min, then filtered and concentrated. The residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA), to afford the title compound as a pale yellow solid (7.3 mg, 5%). 1H NMR (400 MHz, MeOD) δ ppm 8.75 (s, 1H), 7.91 (d, 1H, 7.6 Hz), 7.73-7.75 (m, 1H), 7.59 (td, 1H, 8.0 Hz, 2.0 Hz), 7.45 (dt, 1H, 8 Hz, 0.8 Hz), 7.36 (s, 1H), 4.77 (q, 2H, 7.2 Hz), 3.40-3.58 (m, 8H), 2.86-3.14 (m, 4H), 2.98 (s, 3H), 1.50 (t, 3H, 7.2 Hz). MS (ES+) m/e 505 [M+H]+.

Provenance & Evidence