1,2-Dichloroethane → N-(4-Methyl-3-pyridinyl)-2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 110 mg, 0.33 mmol), EDC (126 mg, 0.66 mmol) and HOBT (101 mg, 0.66 mmol) in dimethylformamide (2 ml) stirred in air at room temperature for 1 h. 4-Methylpyridin-3-amine (35.6 mg, 0.33 mmol) was then added in one charge. The reaction mixture was stirred at 25° C. overnight. The reaction mixture was diluted with water (25 ml), and then extracted with ethyl acetate (60 ml×3). The organic phases were combined, washed with brine (50 ml×3), dried over anhydrous MgSO4 and concentrated. The residue was purified by Prep-HPLC (instrument: Gilson GX-281, Column: Shimadzu 15 μm, 250×20 mm×2, Mobile Phase: A=10 mmol NH4HCO3/water B=CH3CN, Flow rate: 30.0 ml/L method: B=55%-65%, 0.0-7.2 min; B=65%-95%, 7.2-7.5 min; B=95%-95%, 7.5 min-11.5 min, the RT=10.0 min) to yield the title compound as a pink solid. 94 mg.

Provenance & Evidence