HCID 53741197, compound → HCID 44383311, compound

Participants

Reaction Steps

Hydrogen chloride gas is bubbled into an ice-cooled solution of 4-[4-(6-chloro-1H-benzoimidazol-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-benzonitrile (100 mg, 0.264 mmol), (prepared by deprotecting 4-(4-cyanobenzyl)-3-oxopiperazine-1-carboxylic acid benzyl ester, EXAMPLE 66, Part A, followed by alkylation with 6-chloro-2-chloromethylbenzimidazole) in 15 mL of methanol. The solution contained 3Å molecular sieves. The reaction mixture is stored at −30° C. The methanol is removed on the rotovap. Fresh methanol (20 ml) is added folowed by a stream of ammonia gas. The resulting mixture is heated to reflux for three hours. The reaction mixture is filtered at room temperature. The mother liquor is condensed and the resulting residue is purified by reverse phase HPLC (0-50% ACN/H2O). The product is isolated as a white solid with a melting point of 91-95° C. MS C20H21ClN6O m/z: 397, 399. Anal. cald. for C20H21ClN6O.3C2HF3O2: C, 42.26; H, 3.27; N, 11.37. Found C, 42.20; H, 3.44; N, 11.36.

Provenance & Evidence