To a solution of 5-amino-1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester (47 mg, 0.16 mind, 1.0 eq), EDCI (62 mg, 0.32 mmol, 2.0 eq), HOBt (44 mg, 0.32 mmol, 2.0 eq), and diisopropylethyl amine (119 μL, 0.32 mmol, 2.0 eq) in DMF (5 mL) which had been stirred at RT for 15 min was added cyclopropylamine (23 μL, 0.32 mmol, 2.0 eq). After stirring overnight, the solution was diluted with EtOAc and water and the organic layer was washed with water and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography on silica gel eluted with 8/2 EtOAc/hexanes to provide the product as a colorless oil (42 mg, 79%). HPLC (4 minute 10-95 gradient) tR1.84 min; MS m/z 329.09 [M+H]+; 1H NMR (CD3OD), δ 7.96 (s, 1H, NH), 7.88 (d, J=7.9 Hz, 1H), 7.78 (s, 1H), 7.75 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 4.28 (q, J=7.1 Hz, 2H), 2.83 (m, 1H), 2.16 (s, 3H), 1.35 (d, J=7.0 Hz, 3H), 0.78 (dd, J=12.3, 7.0 Hz, 2H), 0.63 (dd, J=7.0, 4.5 Hz, 2H) ppm; 13C NMR (CD3OD), δ 170.1, 165.8, 152.3, 142.1, 141.8, 137.2, 134.6, 132.8, 130.0, 128.2, 128.1, 95.8, 60.8, 24.1, 17.6, 14.9, 6.6 ppm.
