Triethylamine → HCID 24888597, compound

Participants

Reaction Steps

To a mixture of N-(4-(2-aminoethoxy)-3-(1-methyl-1H-pyrazol-5-yl), phenyl)-3-methoxybenzamide (50 mg, 136 μmol) and triethylamine (0.038 mL, 0.27 mmol) in dichloromethane was added benzyl chloroformate (26 mg, 150 μmol), dropwise at room temperature. The mixture was stirred at room temperature overnight. The reaction was quenched with water, extracted with dichloromethane (3×20 mL) and dried over anhydrous MgSO4. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography. (EtOAc/Hexane=50-90%). {2-[4-(3-Methoxy-benzoylamino)-2-(2-methyl-2H-pyrazol-3-yl)-phenoxy]-ethyl}-carbamic acid benzyl ester was obtained as white solid in 37% yield. LCMS m/z (%)=501 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ ppm 3.5 (q, J=5.4 Hz, 2H), 3.7 (s, 3H), 3.9 (s, 3H), 4.0 (t, J=5.1 Hz, 2H), 4.9 (t, J=5.8 Hz, 1H), 5.1 (s, 2H), 6.3 (d, J=2.0 Hz, 1H), 7.0 (d, J=8.6 Hz, 1H), 7.1 (m, 1H), 7.3 (m, 5H), 7.4 (m, 1H), 7.5 (m, 2H), 7.7 (dd, J=8.8, 2.8 Hz, 1H), 7.8 (s, 1H).

Provenance & Evidence