Diisopropylethylamine → HCID 73335227, compound

Participants

Reaction Steps

Dimethylformamide (0.7 mL) was added to a mixture containing 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]butyric acid (50.5 mg, 0.214 mmol) and HATU (84.1 mg, 0.221 mmol). Diisopropylethylamine (92 μL, 0.53 mmol) was added at room temperature and the reaction mixture was stirred for 1 minute. 1-(4-Fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (44.1 mg, 0.203 mmol) was then added all at once and the reaction mixture was stirred at room temperature overnight. Ethyl acetate and water were added and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 17-33% ethyl acetate in hexanes) to afford the desired product as a white solid (80.9 mg, 0.186 mmol, 92%). 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.44 (ddd, J=8.8, 5.2, 2.0 Hz, 2H), 7.15 (ddd, J=8.4, 8.4, 2.0 Hz, 2H), 6.30 (s, 1H), 5.32 (dd, J=8.4, 6.8 Hz, 1H), 3.78 (ddd, J=12, 7.2, 2.8 Hz, 1H), 3.47 (ddd, J=12, 8.8, 3.2 Hz, 1H), 2.69-2.81 (m, 2H), 2.31 (s, 3H), 2.18-2.38 (m, 2H), 1.88-1.97 (m, 1H), 1.74-1.83 (m, 1H), 0.98 (t, J=7.2 Hz, 3H); MS: (ES) m/z calculated for C21H21N5OF4 [M+H]+ 436, found 436.

Provenance & Evidence