Bis-(1H-imidazol-2-YL)-methanone → HCID 11444467, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1-([1,2,4]triazolo[4,3-a]pyridine-3-yl)-2-(7-methyl-1H-indazol-5-yl)ethanamine (30 mg, 0.1 mmol) in dimethylformamide (1.0 mL) at 0° C. was treated with carbonyl diimidazole (17.5 mg, 1.1 equiv). The reaction was stirred for 5 min at 0° C., warmed to room temperature, stirred for 10 min, and treated with 8-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (26.0 mg, 1.1 equiv). The mixture was then stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to afford 30 mg (53%). 1H-NMR (CD3OD, 300 MHz) δ 1.25-1.60 (m, 5H), 2.50 (s, 3H), 2.67-2.81 (m, 2H), 3.60 (s, 1H), 3.62 (s, 1H), 3.12-4.18 (m, 4H), 4.25-4.45 (m, 1H), 5.80 (dd, J=8.1, 8.1, 1H), 6.08-7.04 (m, 4H), 7.10 (s, 1H), 7.35-7.44 (s, 1H), 7.49 (s, 1H), 7.70 (m, 1H), 7.96 (s, 1H), 8.41 (d, J=7.0, 1H). Mass spec.: 568.10 (MH)+.

Provenance & Evidence