Hydrochloric Acid → HCID 47370290, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 2,6-dichloropyrazine (500 mg, 3.36 mmol), methyl 4-(aminomethyl)benzoate.HCl (744 mg, 3.69 mmol) and i-Pr2NEt (2.05 mL, 11.75 mmol) in a mixture of anhydrous THF/DMF (10 mL/2 mL) under nitrogen was heated at 90° C. for 24 h. The mixture was allowed to cool down to room temperature, was poured into saturated aqueous NH4Cl and extracted with AcOEt. The organic layer was washed with H2O and brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (AcOEt/CH2Cl2: 20/80→30/70) to afford the title compound 62 (300 mg, 1.08 mmol, 32% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.18 (t, J=6.0 Hz, 1H), 7.97 (s, 1H), AB system (δA=7.95, δB=7.49, JAB=8.5 Hz, 4H), 7.75 (s, 1H), 4.58 (d, J=5.9 Hz, 2H), 3.87 (s, 3H).

Provenance & Evidence