p-Toluenesulfonic acid → HCID 68992316, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrazin-2-yl]-propionamide (685 mg, 1.26 mmol) in methanol (12.6 mL, 0.1 M) and methylene chloride (5 mL) was treated with para-toluenesulfonic acid (36 mg, 0.18 mmol). The reaction stirred at 25° C. overnight. At this time, the reaction was diluted with ethyl acetate (100 mL) and washed with a saturated aqueous sodium bicarbonate solution (150 mL), water (150 mL), and a saturated aqueous sodium chloride solution (150 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[5-((R)-1,2-dihydroxy-ethyl)-pyrazin-2-yl]-propionamide as an off-white solid (0.50 g, 81%); ES+-HRMS m/e calcd for C24H25N5O5F2 [M+H+] 502.1897 found 502.1894. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04-1.21 (m, 1H), 1.27-1.85 (m, 8H), 1.91-2.08 (m, 1H), 2.22-2.41 (m, 1H), 3.50-3.62 (m, 1H), 3.62-3.73 (m, 1H), 4.62 (q, J=5.1 Hz, 1H), 4.72 (t, J=5.7 Hz, 1H), 5.52-5.64 (m, 2H), 6.07 (d, J=2.5 Hz, 1H), 7.33-7.56 (m, 3H), 8.31 (d, J=2.5 Hz, 1H), 8.45 (s, 1H), 9.13 (s, 1H), 11.25 (br. s., 1H).

Provenance & Evidence