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

Participants

Reaction Conditions

Reaction Steps

Neat (3-aminopyridin-2-yl)methanol (may be prepared as described in Description 80; 68 mg, 0.55 mmol) was added in one charge to a stirred suspension of 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoic acid (may be prepared as described in Description 79; 120 mg, 0.393 mmol), EDC (151 mg, 0.786 mmol), HOBT (120 mg, 0.79 mmol) and triethylamine (0.11 ml, 0.79 mmol) in N,N-dimethylformamide (1.5 ml) in air at 15° C. The reaction mixture was stirred at 15° C. overnight. Water (30 ml) was added and the reaction mixture extracted with ethyl acetate (30 ml×3). The organic phases were dried with Na2SO4 and concentrated. The residue was purified by pre-HPLC (instrument: Gilson-281, Column: WATERS XBRIDGE 30-100 MM 5 UM, Mobile Phase: A: 0.04% NH3H2O B: CH3CN, Flow rate: 30.0 ml/L, Gradient: 0-10 min, B=30-38% RT=P1: 7.0 min; P2: 9.5 min) to yield the title compound as a white solid. 20 mg.

Provenance & Evidence