Sulfatase inhibiting agent
A compound, -R3 technology, applied in the field of inhibitors of the enzyme steroid sulfatase, new sulfamic acid benzothiophene derivatives, and can solve problems such as sulfamic acid cleavage
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Embodiment 1
[0067] Example 1: 6-Methoxybenzothiophene (3)
[0068]Bromoacetaldehyde diethyl acetal (16.50ml, 0.11mol) was added dropwise to m-methoxythiophenol (1) (15ml, 0.12mol) and K in acetone (150ml) at room temperature 2 CO 3 (16.60g, 0.12mol) in a mixture. The reaction mixture was stirred for 16 hours, then filtered. The solid was washed with acetone, and the combined filtrates were concentrated in vacuo. The residue was washed with water, washed with Et 2 O extraction. The organic phase was washed with 0.5M KOH, water and brine, washed with Na 2 SO 4 Drying, filtration and concentration in vacuo yielded 27.40 g of compound (2) as a dark yellow oil.
[0069] 1 H-NMR (CDCl 3 ): 1.18(t, 6H), 3.13(d, 2H), 3.43-3.73(m, 4H), 3.77(s, 3H), 4.67(t, 1H), 6.60-7.27(m, 4H).
[0070] Under nitrogen atmosphere and room temperature, (2) (13.00 g, 0.051 mol) was dissolved in CH 2 Cl 2 (100ml) was added dropwise to BF 3 .Et 2 O (6.70ml, 0.054mol) in CH 2 Cl 2 (1000ml) in solution. ...
Embodiment 2
[0072] Example 2: 2-bromo-6-methoxybenzothiophene (4)
[0073] N-Bromosuccinimide (14.70 g, 82.59 mmol) and p-toluenesulfonic acid (2.70 g, 15.68 mmol) were added to benzothiophene (3) (15.10 g, 92.07 mmol) in 1,2-dichloroethane (300ml) in solution. The mixture was kept at 70°C for 35 minutes, cooled in an ice bath, and the succinimide was removed by filtration. The solution was extracted with saturated sodium bicarbonate solution, and Na 2 SO 4 Dry, filter and concentrate in vacuo to give 22.00 g of an oil. Crystallization from pentane gave a white solid (16.50 g, 74%), melting point 62°C.
[0074] 1 H-NMR (CDCl 3 ): 3.85(s, 3H), 6.9(dd, 1H), 7.50(m, 2H), 7.65(d, 1H)
[0075] Preparation of monosubstituted benzothiophene (5)
Embodiment 3
[0076] Example 3: 2-cyclohexyl-6-methoxybenzothiophene
[0077] under argon atmosphere to the Et 2 To Mg (0.22g, 9.05mmol) in O (20ml) was added dropwise bromide (4) (2.00g, 8.23mmol) in Et 2 solution in O (20ml). The mixture was refluxed for 2 hours, cyclohexanone (1.00ml, 9.87mmol) was added in Et 2 solution in O (5ml). The mixture was refluxed and poured into water. The solution was extracted with ethyl acetate, and Na 2 SO 4 Dry, filter and concentrate in vacuo to give 8.00 g of an oil. Trituration from diisopropyl ether gave 2-(1-hydroxycyclohexyl)-6-methoxybenzothiophene as a white powder (0.90 g, 65%).
[0078] 1 H-NMR (DMSOd 6 ): 1.20-2.00(m, 10H), 3.80(s, 3H), 5.30(s, 1H), 6.93(dd, 1H), 7.10(s, 1H), 7.42(d, 1H), 7.60(d, 1H).
[0079] To 2-(1-hydroxycyclohexyl)-6-methoxybenzothiophene (0.30 g, 1.14 mmol) in dichloromethane (10 ml) was added triethylsilane (0.22 ml) dropwise under argon atmosphere , 1.37mmol). The solution was then stirred at 0°C and triflu...
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