Triethylamine → (R)-N-Benzyl-2-chloro-N-(2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-ylamino)ethyl)propanamide

Participants

Reaction Steps

Sequentially treat a solution of N1-benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine (4.90 g, 13.98 mmol) in CH2Cl2 (70 mL) with (R)-(+)-2-chloropropionic acid (1.84 mL, 20.97 mmol), triethylamine (2.92 mL, 20.97 mmol), HOBT (3.21 g, 20.97 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.02 g, 20.97 mmol). Stir the resulting mixture at ambient temperature overnight. Wash the reaction mixture with saturated aqueous NaHCO3. Extract the aqueous layer with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (20% EtOAc in hexanes) to afford the title compound as a yellow foam (4.59 g, 74%). ES/MS m/z 441.2 (M+1).

Provenance & Evidence