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

Participants

Reaction Conditions

Reaction Steps

Neat (3-aminopyridin-4-yl)methanol (may be prepared as described in Description 81; 103 mg, 0.83 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; 180 mg, 0.59 mmol), EDC (226 mg, 1.18 mmol), HOBT (181 mg, 1.179 mmol) and triethylamine (0.16 ml, 1.18 mmol) in N,N-dimethylformamide (1.5 ml) in air at 15° C. The reaction mixture was stirred at 15° C. overnight. 100 ml of water was added. The solid was filtered, and then purified by prep-HPLC (instrument: Gilson-281, Column: Shimadzu 15 um: 250*20 mm*2, Mobile Phase: A: 10 mMol/LNH4HCO3, B: CH3CN, Flow rate: 30.0 ml/L, Gradient: B: 43-55% in 0-7.2 RT=7.5 min, 10.5) to yield the title compound as a white solid. 57 mg.

Provenance & Evidence