Triethylamine → 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]ethanone

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Reaction Steps

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.023 g, 0.11 mmol), 2-[3-(trifluoromethyl)-4,5,6,7-tetrahydroindazol-1-yl]acetic acid (0.027 g, 0.11 mmol) and NEt3 (0.050 mL, 0.36 mmol) in DMF (0.6 mL) was added HATU (0.050 g, 0.13 mmol). The mixture was stirred at rt for 30 min. It was then quenched with water. The mixture was partitioned between IPA/CHCl3 (1:2, 50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.027 g, 55%). 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 7.42 (dd, J=8.8, 4.4 Hz, 2H), 7.17 (dd, J=9.2, 8.0 Hz, 2H), 5.15 (s, 2H), 3.87 (m, 2H), 2.82 (t, J=6.2 Hz, 2H), 2.61 (m, 4H), 2.11 (m, 2H), 1.87 (m, 2H), 1.79 (m, 2H); MS: (ES) m/z calculated for C22H21F4N5O [M+H]+ 448.1, found 448.1.

Provenance & Evidence