Ammonium Chloride → HCID 178519310, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[5-(3-Hydroxy-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-benzoimidazol-1-yl]-propionitrile (250 mg, 0.7 mmol) in DMF (5 mL) was added sodium azide (184 mg, 2.83 mmol) and ammonium chloride (152 mg, 2.83 mmol) and heated to 100° C. for 12 h. The solvent was evaporated completely; methanol (20 mL) was added and filtered. The filtrate was concentrated and the residue purified by preparative HPLC to give 36 mg (13%) of 3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)-{1-[2-(1H-tetrazol-5-yl)-ethyl]-1H-benzoimidazol-5-yl}-methanone. MS-ESI m/z 368 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 1.3-2.0 (m, 8H), 3.15 (s, 1H), 3.5 (t, 2H), 3.9-4.0 (m, 2H), 4.6 (br, 1H), 4.75 (t, 2H), 7.4 (dd, 1H), 7.6-7.7 (m, 2H), 8.25 (s, 1H).

Provenance & Evidence