Bis-(1H-imidazol-2-YL)-methanone → HCID 178436415, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of (±)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester (0.55 g, 2.1 mmol) in tetrahydrofuran (6 mL) at 0° C. was treated with carbonyl diimidazole (0.37 g, 1.1 equiv). The reaction was stirred for 5 min at 0° C., warmed to room temperature, stirred 10 min, and treated with 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (0.53 g, 1.1 equiv). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to give 0.94 g (86%) as a white powder. 1H-NMR (DMSO-d6) δ 1.26 (t, J=7.5, 3H), 1.49 (m, 1H), 2.44 (s, 3H), 2.83 (dd, J=7.3, 7.6, 1H), 2.84 (dd, J=115.0, 7.6, 1H), 2.88-3.10 (m, 1.5H), 3.18 (d, J=5.5, 0.5H), 3.61 (s, 3H), 4.04-4.16 (m, 3H), 4.28 (m, 2H), 6.76 (d, J=7.9, 1H), 6.86 (m, 2H), 7.04-7.25 (m, 3H), 7.36 (s, 1H), 7.40 (s, 1H), 9.18 (s, 1H), 12.59 (s, 1H). Mass spec.: 519.37 (MH)+.

Provenance & Evidence