2-(Dimethylamino)ethanol → {2-[4-(3-Methoxy-benzoylamino)-2-(2-methyl-2H-pyrazol-3-yl)-phenoxy]-ethyl}-carbamic acid 2-dimethylamino-ethyl Ester

Participants

Reaction Conditions

Reaction Steps

Trichloromethyl 2-(4-(3-methoxybenzamido)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (50.0 g, 94.74 mmol), 2-(dimethylamino)ethanol (14.50 g, 1.1 eq) and magnesium oxide (1.067 mL, 1.0 eq) were taken up in 2 mL of ethyl acetate in a round bottomed flask and stirred at 22° C. for 3 hr. The magnesium oxide was filtered off. The solvent was then evaporated and it was purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 31.3% yield. LCMS m/z (%)=482 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.82 (s, 3 H), 2.84 (s, 3 H), 3.34 (q, J=5.05 Hz, 4 H), 3.69 (s, 3 H), 3.84 (s, 3 H), 4.06 (t, J=5.56 Hz, 2 H), 4.25-4.29 (m, 2 H), 6.28 (d, J=1.52 Hz, 1 H), 7.14-7.22 (m, 2 H), 7.40 (t, J=5.56 Hz, 1 H), 7.47 (d, J=2.02 Hz, 3 H), 7.51-7.55 (m, 1 H), 7.70 (d, J=2.53 Hz, 1 H), 7.84 (dd, J=8.84, 2.78 Hz, 1 H), 9.48-9.62 (m, 1 H).

Provenance & Evidence