Triethylamine → HCID 73336015, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetic acid (20 mg, 0.073 mmol) in DMF (2 mL) was added Et3N (50 μL, 0.219 mmol), HATU (55 mg, 0.145 mmol) followed by methyl 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine-5-carboxylate (20 mg, 0.073 mmol) at room temperature. The resulting solution was then stirred at 80° C. for 5 h. The reaction mixture was then cooled to room temperature, H2O (10 mL) was added and the mixture was extracted with EtOAc (2×15 mL). The combined EtOAc layers were dried (MgSO4), filtered, concentrated in vacuo and the resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the desired product as white powder (0.004 g, 0.008 mmol, 7%). 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 7.52 (2H, dd, J=5, 9 Hz), 7.26 (2H, t, 8.6, J=17.2 Hz), 5.3 (2H, dd, J=17.2, 69.2 Hz), 3.83 (s, 3H), 2.80-2.82 (m, 2H), 2.29 (s, 3H), 2.15-2.17 (m, 2H); MS: (ES) m/z calculated for C21H18ClF4N5O3 [M+H]+ 500.1, found 500.1.

Provenance & Evidence