Hydrochloric Acid → 4,5-Dimethyl-furan-2-carboxylic Acid [4-(2-amino-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-amide

Participants

Reaction Steps

4,5-dimethylfuran-2-carboxylic acid (12.65 mg, 1.2 eq), triethylamine (26.21 μL, 3.0 eq) and HATU (34.32 mg, 1.2 eq) were dissolved in 1 mL of dichloromethane and stirred at room temperature for 20 minutes. At this time tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (25.0 mg, 75.2 μmol) dissolved in 0.5 mL of dichloromethane was added and the reaction was stirred at room temperature for 18 hr. The solvent was evaporated under a stream of nitrogen and the residue was dissolved in 0.5 mL of ethyl acetate. To this was added 2.0M hydrochloric acid in ether (376 μL, 5 eq) and the reaction was stirred at room temperature overnight. The solvent was evaporated under a stream of nitrogen and the residue was dissolved in 1 mL of dimethylsulfoxide and purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a pale yellow solid in 47.3% yield. LCMS m/z (%)=355 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.98 (s, 3H), 2.30 (s, 3H), 3.11-3.20 (m, 2H), 3.71 (s, 3H), 4.16 (t, J=5.31 Hz, 3H), 6.36 (s, 1H), 7.10 (s, 1H), 7.21 (d, J=9.09 Hz, 1H), 7.49 (d, J=2.02 Hz, 1H), 7.49 (d, J=2.02 Hz, 1H), 7.68 (d, J=3.03 Hz, 1H), 7.84 (dd, J=9.09, 2.53 Hz, 1H), 7.86-7.98 (m, 2H), 10.01 (s, 1H).

Provenance & Evidence