Soluble epoxide hydrolase inhibitors
A compound, cycloalkyl technology, applied in the field of medicinal chemistry, can solve the problem of low activity
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[0327] In the examples below and throughout the application, the following abbreviations have the following meanings. If not defined otherwise, said terms have their commonly accepted meanings.
[0328] aq. = aqueous solution
[0329] brs = broad singlet
[0330] d = doublet
[0331] DCM = dichloromethane
[0332] DMAP = dimethylaminopyridine
[0333] DMF = dimethylformamide
[0334] DMSO = dimethyl sulfoxide
[0335] EtOAc = ethyl acetate
[0336] g = gram
[0337] LCMS = Liquid Chromatography Mass Spectrometry
[0338] m = multiplet
[0339] MHz = megahertz
[0340] mL = milliliter
[0341] m.p. = melting point
[0342] N = equivalent
[0343] RT = room temperature
[0344] s = singlet
[0345] t = triplet
[0346] TEA = Triethylamine
[0347] TLC = thin layer chromatography
example 1
[0349] 4-(3-Adamantan-1-yl-ureido)-benzenesulfonamide (1)
[0350]
[0351] Adamantyl isocyanate (0.07 mL, 0.745 mmol) was added to a stirred solution of 4-aminobenzenesulfonamide (150 mg, 0.850 mmol) in ethanol (15 mL) at room temperature overnight. The precipitated solid was filtered, washed with petroleum ether and pentane and recrystallized in acetone to give the title compound (100 mg, 49%) as a white solid; mp 270-275 °C; LC / MS purity 99.7%; mass: 350[ M+1]; 1 HNMR: (300MHz; DMSO-D 6 )δ: 1.60-2.20 (m, 15H CH 2 ); 7.23-7.65 (4H, ArCH); 9.26 (brs, 2H, NH).
example 2
[0353] 3-(3-Adamantan-1-yl-ureido)-benzenesulfonamide (2)
[0354]
[0355] To a stirred solution of 3-nitrobenzenesulfonamide (300 mg, 0.95 mmol) in methanol (10 mL) was added Pd-C (100 mg) and stirred at room temperature under hydrogen atmosphere overnight. The solution was filtered and the filtrate was concentrated under vacuum to give 3-aminobenzenesulfonamide as a yellow solid (yield 250 mg); mass: 172 [M+1].
[0356] To a stirred solution of 3-aminobenzenesulfonamide (150 mg, 0.872 mmol) in ethanol (15 mL) was added adamantyl isocyanate (0.12 mL, 0.855 mmol) at room temperature overnight. The precipitated solid was filtered, washed with petroleum ether and pentane and recrystallized in acetone to give the title compound (180 mg, 45%) as an off-white solid; mp 158-162 °C; LC / MS purity 99.4%; mass: 360[M+1]; 1 HNMR: (300MHz; DMSO-D 6 )δ: 1.60-2.19 (15H, adamantyl CH 2 ); 7.20-7.45 (4H, ArCH); 9.26 (brs, 2H, NH).
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