Benzenesulfonamide derivative and application thereof
A compound and solvate technology, applied in the field of benzenesulfonamide derivatives and its applications, can solve problems such as cell cycle arrest and programmed cell death
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[0090] In certain embodiments, some or all of the compounds disclosed herein 1 H atoms are 2 H atom substitution. Synthetic methods of deuterium-containing compounds are known in the art and include the following synthetic methods by way of non-limiting example only.
[0091]Deuterium substituted compounds were synthesized using various methods such as in: Dean, Dennis C.; Ed. Recent Advances in the Synthesis and Applications of Radiolabeled Compounds for Drug Discovery and Development. [Curr., Pharm.Des., 2000; 6( 10)] 2000, p. 110; George W.; Varma, Rajender S. The Synthesis of Radiolabeled Compounds via Organometallic Intermediates, Tetrahedron, 1989, 45(21), 6601-21; and Evans, E. Anthony. Synthesis of radiolabeled compounds, Described in J. Radioanal. Chem., 1981, 64(1-2), 9-32.
[0092] Deuterated starting materials are readily available, and the synthetic methods described herein can be performed to provide the synthesis of deuterium-containing compounds. A number o...
Embodiment
[0330] I. Chemical synthesis
[0331] In some embodiments, the benzenesulfonamide derivative compounds disclosed herein are synthesized according to the following examples. As used hereinafter and throughout the description of the present disclosure, unless otherwise stated, the following abbreviations shall be understood to have the following meanings:
[0332] ℃ degrees Celsius
[0333] δ H Chemical shifts in parts per million downfield from tetramethylsilane
[0334] DCM dichloromethane (CH 2 Cl 2 )
[0335] DMF Dimethylformamide
[0336] DMSO dimethyl sulfoxide
[0337] EA ethyl acetate
[0338] ESI electrospray ionization
[0339] Et ethyl
[0340] g grams
[0341] hours
[0342] HPLC high performance liquid chromatography
[0343] Hz Hertz
[0344] J coupling constant (in NMR spectroscopy)
[0345] LCMS liquid chromatography-mass spectrometry
[0346] μ Micro
[0347] m multiplet (spectrum); meter; millimeter
[0348] M Moore
[0349] m + parent mol...
Embodiment A1
[0395] Example A1 (R)-1-(1-((perfluorophenyl)sulfonyl)piperidin-3-yl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3, 4-d] Synthesis of pyrimidin-4-amine (I-A1)
[0396]
[0397] The title compound I-A1, (R)-1-(1-((perfluorophenyl)sulfonyl)piperidin-3-yl)-3-(4-phenoxyphenyl) was prepared by general synthetic route A -1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1 H NMR (400MHz, chloroform-d) δ 1.96 (dt, J=12.8, 7.4Hz, 1H), 2.02–2.14(m, 1H), 2.22–2.31(m, 2H), 2.86(t, J=12.0 Hz, 1H), 3.40(t, J=11.3Hz, 1H), 4.05(d, J=12.3Hz, 1H), 4.19(dd, J=12.0, 4.5Hz, 1H), 5.05(tt, J=10.4 ,5.0Hz,1H),5.70(s,2H),7.06–7.13(m,2H),7.13–7.24(m,3H),7.39–7.47(m,2H),7.60–7.69(m,2H), 8.39(s,1H). 19 F NMR (376 MHz, chloroform-d) δ -159.32 - -157.72 (m), -145.32 (tt, J = 21.2, 6.5 Hz), -134.36 (qd, J = 13.8, 7.8 Hz).
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