Potassium Fluoride → HCID 53374176, compound

Participants

Reaction Steps

A solution of (35)-1-[2-(3-methylquinoxalin-2-yl)-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-3-yl methanesulfonate (50 mg, 0.0955 mmol) 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane (108 mg, 0.286 mmol), and potassium fluoride (17 mg, 0.286 mmol) in acetonitrile (2.0 mL) was refluxed for 15 min. After being cooled to ambient temperature, the reaction mixture was concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=97:3) to give 5-(2,5-dihydro-1H-pyrrol-1-yl)-2-(3-methylquinoxalin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (the compound of Example 1.009 listed in the Table of Examples as described hereinafter). 1H-NMR (400 MHz, CDCl3): δ 1.73-1.82 (2H, m), 2.13-2.16 (2H, m), 3.04 (3H, s), 3.59 (2H, dt, J=11.8, 2.1 Hz), 3.68-3.78 (1H, m), 4.09 (2H, dt, J=11.8, 3.6 Hz), 4.38 (4H, br), 5.17 (1H, s), 5.98 (2H, s), 6.17 (1H, d, J=7.9 Hz), 6.67 (1H, s), 7.69-7.77 (2H, m), 8.03-8.06 (1H, m), 8.17-8.19 (1H, m).

Provenance & Evidence