2-(4-Hydroxyphenyl)acetohydrazide → 4-(6-Thiazol-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

Participants

Reaction Conditions

Reaction Steps

3-Chloro-6-thiazol-2-yl-pyridazine (20 mg, 0.10 mmol) and (4-Hydroxy-phenyl)-acetic acid hydrazide (20 mg, 0.12 mmol) were combined in butanol (5 mL), fitted with water filled condenser and heated to 120° C. overnight. The reaction was concentrated in vacuo followed by purification by HPLC (10-80% CH3CN over 25 min) resulting in the title compound (11.5 mg, 37%) as a white solid. 1H-NMR (CD3OD/CDCl3): δ 8.26-8.24 (1H, d, J=9.6 Hz), 8.17-8.15 (1H, d, J=9.6 Hz), 8.05-8.04 (1H, d, J=3.2 Hz), 7.82-7.81 (1H, d, J=3.0 Hz), 7.32-7.30 (2H, t, J=8.6 Hz), 6.77-6.74 (2H, d, J=8.3 Hz), 4.53 (2H, s). ESI-MS (m/z): Calcd. For C15H11N5OS: 309.07; found: 310.2 (M+H).

Provenance & Evidence