Acetonitrile → HCID 56971122, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottomed flask was placed 4-(4-chlorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4,5,6,7-tetrahydro-1,3-benzothiazole (250 mg, 0.66 mmol) along with 1,4-dioxane (15 mL) and acetonitrile (15 mL). To the mixture were added a solution of copper (II) sulfate pentahydrate (670 mg, 2.7 mmol) in water (10 mL) and a solution of potassium persulfate (770 mg, 2.8 mmol) in water (10 mL). The mixture was stirred for 6 hr at 90° C. The mixture was allowed to cool to rt and then insoluble materials were removed by filtration through a celite pad. The celite pad was washed with water and EtOAc. The aqueous phase was separated from the filtrate and then extracted with EtOAc (50 mL×2). The combined organic phases were washed with a 10% aqueous solution of NaHSO3 (50 mL), then a saturated aqueous solution of NaHCO3 (50 mL), then a saturated aqueous solution of NH4Cl (50 mL), and then dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (12 g) column chromatography, eluting with 0% to 50% EtOAc/hexane to yield the title compound (100 mg; 40%) as a yellow crystalline solid. LCMS: (FA) ES+ 394, 396; 1H NMR (400 MHz, d6-DMSO) δ ppm 8.42 (dt, 1H), 8.15 (dt, 1H), 7.32-7.35 (m, 3H), 7.17 (d, 2H), 6.90 (td, 1H), 4.45 (dd, 1H), 2.57-2.75 (m, 5H), 2.29-2.37 (m, 1H), 2.00-2.15 (m, 1H).

Provenance & Evidence