Ammonium → 6-[Amino-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one

Participants

Reaction Steps

A solution of 6-[Chloro-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one; hydrochloride (2.15 g, 3.7 mmol) in THF (40 mL) was treated with ammonium, stirred at ambient temperature for 2 hours, and concentrated in vacuo. The reaction mixture was diluted with ethyl acetate/H2O (1:1, 200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (200 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a crude yellow foam. Purification by flash column chromatography (silica, EtOAc:MeOH:NEt3 9:1:.01) gave 6-[Amino-(4-chloro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-chloro-phenyl)-1-cyclopropylmethyl-1H-quinolin-2-one (1.54 g, 79%) as a yellow foam.

Provenance & Evidence