3-Aminobenzonitrile → HCID 54523328, compound

Participants

Reaction Steps

To 2-(4-Adamantan-1-yl-phenoxy)-acetic acid (200.0 mg, 0.70 mmol), 3-amino-benzonitrile (124.1 mg, 1.05 mmol), N-(3-dimethylaminopropyl)-N-ethyl carbodiimide HCl (EDC) (201.3 mg, 1.05 mmol) and 1-hydroxybenzotriazole (HOBt) (142.9 mg, 1.05 mmol) in DMF (10 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (131.5 mg, 0.18 ml, 1.05 mmol). The mixture was stirred overnight; and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-(4-Adamantyl-1-yl-phenoxyl)-N-(3-cyano-phenylacetamide as a yellow solid (222.8 mg, 82.6% yield).

Provenance & Evidence