Triethylamine → HCID 73336017, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 2-[3-(trifluoromethyl)-5,6-dihydro-4H-cyclopenta[c]pyrazol-1-yl]acetic acid (83 mg, 0.35 mmol) in DMF (2 mL) was added Et3N (75 μL, 0.525 mmol), HATU (160 mg, 0.42 mmol), followed by 1-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine (77 mg, 0.35 mmol) at room temperature. The resulting solution was then stirred at 50° C. for 30 min. The reaction mixture was then cooled to room temperature, H2O (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined EtOAc layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the desired product as a white powder (0.011 g, 0.025 mmol, 7%). 1H NMR (400 MHz, DMSO-d6) δ 8.15 (s, 1H), 7.6 (m, 2H), 7.35 (t, 2H, J=8.6, 17.6 Hz), 5.38 (s, 2H), 3.77 (m, 2H), 2.85 (t, 2H, J=6.3, 12.5 Hz), 2.66 (m, 4H), 2.53 (m, 2H), 1.97 (m, 2H); MS: (ES) m/z calculated for C21H19F4N5O [M+H]+ 434.2, found 434.1.

Provenance & Evidence