Acetylenic sulfonamide thiol TACE inhibitors
A technology of butynyloxy and alkyl groups, applied in the preparation of thiols, active ingredients of amides, anti-inflammatory agents, etc., can solve the problems of bioavailability and pharmacokinetics.
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Embodiment 1
[0170] 4-(2-Butynyloxy)-benzenesulfonic acid sodium salt
[0171] In a solution formed by 52.35g (0.225mol) of 4-hydroxybenzenesulfonic acid sodium salt in 1L of isopropanol and 225mL of 1.0N sodium hydroxide solution, add 59.96g (0.45mol) of 1-bromo-2-butane alkyne. The resulting mixture was heated to 70° for 15 hours, then the isopropanol was removed by evaporation in vacuo. The resulting white precipitate was collected by filtration, washed with isopropanol and diethyl ether, and dried in vacuo to yield 56.0 g (100%) of butynyl ether as a white solid.
Embodiment 2
[0173] 4-(2-Butynyloxy)-benzenesulfonyl chloride
[0174] 6.77mL (0.087mol) of DMF (N,N-dimethylformamide ), then add 7.24g (0.029mol) embodiment 1 product. The reaction mixture was stirred at 0° for 10 minutes, then allowed to warm to room temperature and stirred for 2 days. The reaction mixture was then poured into ice and extracted with 150 mL of hexane. The organics were washed with water and brine, washed with Na 2 SO 4 Drying, filtration, and concentration in vacuo yielded 6.23 g (88%) of yellow solid of sulfonyl chloride; mp 63-65° C., EI (electron impact) mass spectrometry: 243.9 (M + ).
Embodiment 3
[0176] 2-butynyloxy-benzene
[0177] In a solution formed by dissolving 6.14 g of triphenylphosphine (0.023 mol) in 100 mL of benzene and 40 mL of THF (tetrahydrofuran), 1.75 mL (0.023 mol) of 2-butyn-1-ol was added. After 5 minutes a solution of 2.00 (0.023 mol) phenol in 10 mL THF was added to the reaction mixture, followed by 3.69 mL (0.023 mol) of diethyl azodicarboxylate. The resulting reaction mixture was stirred at room temperature for 18 hours, then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate / hexanes to give 2.18 g (70%) of butynyl ether as a clear liquid. EI (electron impact) mass spectrometry: 146.0MH + .
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