Triethylamine → HCID 73335730, compound

Participants

Reaction Steps

A mixture of 2-[(4-chloro-pyrazol-1-yl)]acetic acid (0.050 g, 0.31 mmol), (COCl)2 (0.060 mL, 0.70 mmol) and DMF (1 drop) in CH2Cl2 (1 mL) was stirred for 30 min at rt. It was then evaporated to dryness on a high vacuum pump. The obtained oil was added to a mixture containing 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine (0.020 g, 0.092 mmol) and NEt3 (0.070 mL, 0.50 mmol) in CH2Cl2 (1 mL). The resulting mixture was then stirred at rt for 30 min. It was then quenched with water and partitioned between EtOAc (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 (0.012 g, 36%). 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.60 (s, 1H), 7.51 (s, 1H), 7.44 (dd, J=8.8, 4.6 Hz, 2H), 7.17 (dd, J=9.2, 8.8 Hz, 2H), 5.16 (s, 2H), 3.82 (m, 2H), 2.85 (t, J=6.2 Hz, 2H), 2.09 (m, 2H); MS: (ES) m/z calculated for C17H15ClFN5O [M+H]+ 360.1, found 360.1.

Provenance & Evidence