Triethylamine → N-[5-isopropoxy-1-(4-fluorophenyl)pyrazol-4-yl]-2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanamide

Participants

Reaction Steps

A mixture of crude 1-(4-fluorophenyl)-5-isopropoxy-pyrazol-4-amine (prepared in step b, 0.032 g, 0.13 mmol), 2-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propanoic acid (0.031 g, 0.13 mmol), HATU (0.057 g, 0.13 mmol), and 100 μL of Et3N in 1 mL of CH2Cl2 was stirred at room temperature. After 30 min, the reaction mixture was diluted with 10 mL of aqueous saturated sodium bicarbonate and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) provided the title compound as a colorless solid (0.030 g, 0.068 mmol, 52% for 3 steps). 1H NMR (400 MHz, CD3OD) δ 7.81 (s, 1H), 7.70 (s, 1H), 7.68-7.57 (m, 2H), 7.30-7.19 (m, 2H), 5.16 (q, J=6.5 Hz, 1H), 4.26 (he, J=6.1 Hz, 1H), 2.47 (s, 3H), 1.80 (d, J=6.5 Hz, 3H), 1.14 (d, J=6.1, 6 H). MS: (ES) m/z calculated for C20H21F4N5O2 [M+H]+ 439.2, found 439.4.

Provenance & Evidence