Sodium Iodide → HCID 25207206, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[6-(2-oxo-1,2-dihydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl]-N-(2,2,2-trifluoroethyl)thiophene-2-carboxamide (0.140 g, 0.334 mmol), 1-(2-chloroethyl)piperidine hydrochloride (0.092 g, 0.5 mmol), Cs2CO3 (0.435 g, 1.34 mmol), and NaI (0.010 g, 0.067 mmol) was evacuated and flushed with argon. DMF (15 mL) was added. The mixture was stirred for 16 h at 65-70° C. and evaporated. The residue was washed on a filter with water, ether, and purified on HPLC. Yield of 4-{6-[2-oxo-1-(2-piperidin-1-ylethyl)-1,2-dihydropyridin-4-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-N-(2,2,2-trifluoro ethyl)thiophene-2-carboxamide (bis-TFA salt): 0.022 g. 1H NMR (400 MHz, DMSO-d6): 1.57-1.77 (4H, m), 1.82-1.92 (2H, m), 2.90-3.02 (2H, m), 3.40-3.50 m), 4.05-4.15 (2H, m), 4.33 (2H, dd, J=6.85 Hz, J=6.85 Hz), 6.98 (1H, dd, J=7.1 Hz, J=2.2 Hz), 7.13 (1H, d, J=2.2 Hz), 7.89 (1H, d, J=7.1 Hz), 8.25 (1H, d, J=1.2 Hz), 8.50 (1H, d, J=1.2 Hz), 8.73 (1H, s), 9.11 (1H, d, J=2.2 Hz), 9.17 (1H, br s), 9.23 (1H, dd, J=6.35 Hz, J=6.35 Hz), 9.70 (1H, J=2.2 Hz). LC-MS APCI: m/z 531.1 [M+H]+.

Provenance & Evidence