Triethylamine → HCID 136252349, compound

Participants

Reaction Steps

To a mixture of 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.050 g, 0.23 mmol), 2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridine-1-yl]acetic acid (0.050 g, 0.21 mmol) and Et3N (0.15 mL, 1.07 mmol) in DMF (0.7 mL) was added HATU (0.130 g, 0.33 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, 100 mL) and sat. NaHCO3 (40 ml). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by reverse phase HPLC to afford the desired product (0.090 g, 96%). 1H NMR (TFA salt) (400 MHz, CD3OD) δ 8.73 (dd, J=4.8, 1.6 Hz, 1H), 8.69 (dd, J=8.0, 1.6 Hz, 1H), 8.14 (s, 1H), 7.72 (s, 2H), 7.55 (m, 3H), 7.28 (dd, J=9.2, 8.4 Hz, 2H), 5.89 (s, 2H), 4.06 (m, 2H), 2.92 (t, J=6.2 Hz, 2H), 2.20 (m, 2H); MS: (ES) m/z calculated for C23H19FN8O [M+H]+ 443.1, found 443.1.

Provenance & Evidence