Sodium Azide → N-cyclopropyl-4-{6-[(E)-(1-methyl-5-oxopyrrolidin-2-ylidene)methyl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 23 mg (0.05 mmol) N-cyclopropyl-4-{6-[5-(methylamino)-5-oxopent-1-yn-1-yl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide in 1.00 mL NMP were added 6.5 mg (0.1 mmol) sodium azide and 0.5 mg (0.003 mmol) copper(I)iodide and the mixture was heated at 160° C. for 30 min in a microwave tube. The mixture was filtered and purified by HPLC to yield 4.3 mg (19%) of the title compound. UPLC-MS: RT=1.08 min; m/z (ES+) 459.6 [MH+]; required MW=458.6. 1H-NMR (300 MHz, CDCl3): δ=7.91 (2H, d), 7.59 (4H, m), 7.39 (1H, s), 6.31 (1H, tr), 6.28 (1H, s), 3.45 (1H, m), 3.40 (2H, t), 2.95 (1H, m), 2.82 (3H, s), 2.56 (1H, m), 2.33 (1H, s), 2.05 (1H, m), 1.95 (1H, m), 1.05 (6H, d), 0.92 (2H, m), 0.66 (2H, m) ppm.

Provenance & Evidence