(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-hydrazine → 8-Bromo-2-[5-(2,4-difluoro-phenyl)-[1,2,4]-triazol-1-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Participants

Reaction Conditions

Reaction Steps

A suspension of (8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-hydrazine (312 mg, 1 mmol) and N-[1-dimethylamino-meth-(E)-ylidene]-2,4-difluoro-benzamide (232 mg, 1.1 mmol) in acetic acid (6 mL) was heated at 90° C. for 3 h, allowed to cool down to RT and filtered. The precipitate was washed with diethyl ether and dried to afford the title compound as a beige solid (300 mg, 65%). LCMS (Method B): RT=4.51 min, [M+H]+=461 and 463. 1H NMR (DMSO-d6): 8.50 (1 H, s), 7.82 (1 H, td, J=8.4, 6.4 Hz), 7.57 (1 H, ddd, J=10.4, 9.4, 2.5 Hz), 7.39-7.30 (2 H, m), 7.23 (1 H, d, J=2.0 Hz), 7.13 (1 H, dd, J=8.6, 2.0 Hz), 4.33 (2 H, t, J=5.0 Hz), 3.34 (2 H, t, J=5.0 Hz).

Provenance & Evidence