Cesium carbonate → HCID 57933062, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-chloro-5-iodo-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.65 mmol), 1H-triazole (0.047 g, 0.69 mmol), CuI (0.0062, 0.033 mmol), Cs2CO3 (0.45 g, 1.37 mmol) and DMF (3 mL) is added (1S,2S)-(+)-N,N′-dimethylcyclohexane-1,2-diamine (0.014 mL, 0.098 mmol). The solution is heated at 112° C. overnight, diluted with CH2Cl2 (10 mL) and filtered thru Celite® and concentrated. The residue is purified by ISCO flash chromatography (30%-40% EtOAc gradient furnish the title compound (0.028 g, 0.070 mmol, 11%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.75-1.92 (m, 4H), 2.51 (s, 3H), 2.52 (s, 3H), 3.26-3.35 (m, 1H), 6.72 (s, 1H), 7.22 (s, 1H), 8.10 (s, 1H), 8.50 (s, 1H). LC/MS (m/z): calcd. for C19H21ClN6S (M+H)+: 401.1; found: 401.2.

Provenance & Evidence