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A kind of high-efficiency preparation method of sulfoxide sulfonylurea series compound

A sulfoxide sulfinyl urea and compound technology, which is applied in the field of high-efficiency preparation of sulfoxide sulfinyl urea series compounds, can solve the problems of highly toxic properties, unstable chemical properties of isocyanates, easy hydrolysis and deterioration, etc. Application prospect, beneficial to separation and purification, good reactivity effect

Inactive Publication Date: 2019-09-24
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this reaction is that the conditions are relatively harsh. In addition, the chemical properties of isocyanate are not very stable, highly toxic, and easy to hydrolyze and deteriorate. It needs to be synthesized in advance and stored under harsh conditions.

Method used

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  • A kind of high-efficiency preparation method of sulfoxide sulfonylurea series compound
  • A kind of high-efficiency preparation method of sulfoxide sulfonylurea series compound
  • A kind of high-efficiency preparation method of sulfoxide sulfonylurea series compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Dissolve 4-methoxybenzoyl azide (63.7mg, 0.36mmol) in organic solvent acetonitrile (1mL) under air atmosphere, add dropwise to diphenylsulfinimide at 80°C in a magnetic stirrer (65.1mg, 0.3mmol) in acetonitrile (1mL) solution, the reaction was continued for 3 hours under air atmosphere, and the reaction was monitored by TLC plate until complete reaction. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3a was separated by flash column chromatography. Yield: 96%. The following is the NMR experimental data of product 3a:

[0017] 1 H NMR (400MHz, d6-DMSO) δ9.50(s, 1H), 8.03(d, J=6.8Hz, 4H), 7.63(d, J=7.7Hz, 6H), 7.42(d, J=8.6Hz ,2H),6.81(d,J=8.2Hz,2H),3.68(s,3H).

[0018] 13 C NMR (100MHz, d6-DMSO) δ157.3, 154.8, 140.6, 133.8, 130.2, 127.9, 120.4, 120.0, 114.2, 55.6.

Embodiment 2

[0020]

[0021] Under air atmosphere, 4-methylbenzoyl azide (58 mg, 0.36 mmol) was dissolved in organic solvent acetonitrile (1 mL), and added dropwise to diphenylsulfinimide (65.1 mg, 0.3 mmol) in acetonitrile (1 mL) solution, the reaction was continued for 3 hours under the air atmosphere, and the reaction was monitored by TLC plate during the reaction until complete reaction. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3b was separated by flash column chromatography. Yield: 91%. The following is the NMR experimental data of product 3b:

[0022] 1H NMR(400MHz,d6-DMSO)δ9.55(s,1H),8.03(d,J=7.1Hz,4H),7.71-7.59(m,6H),7.39(d,J=8.3Hz,2H) ,7.02(d,J=8.1Hz,2H),2.21(s,3H).

[0023] 13 C NMR (100MHz, d6-DMSO) δ157.3, 140.5, 138.2, 133.8, 131.1, 130.2, 129.4, 128.0, 118.6, 20.8.

Embodiment 3

[0025]

[0026] Benzoyl azide (882mg, 6mmol) was dissolved in organic solvent acetonitrile (10mL) under air atmosphere, and added dropwise to diphenylsulfinimide (1.085g, 5mmol) in a magnetic stirrer at 80°C In an acetonitrile (10 mL) solution, the reaction was continued for 3 hours under an air atmosphere, and the reaction was monitored by a TLC plate during the reaction until complete reaction. After treatment, the pure product 1-sulfinyl-3-phenylurea compound 3c was separated by flash column chromatography, and the yield was 87%. The following is the NMR experimental data of product 3c:

[0027] 1 H NMR(400MHz,d6-DMSO)δ9.65(s,1H),8.04(d,J=7.2Hz,4H),7.69-7.62(m,6H),7.52(d,J=8.0Hz,2H) ,7.22(t,J=7.7Hz,2H),6.93(t,J=7.2Hz,1H).

[0028] 13 C NMR (100MHz, d6-DMSO) δ157.4, 140.7, 140.5, 133.9, 130.2, 129.0, 128.0, 122.3, 118.6.

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Abstract

The invention discloses a high-efficiency preparation method of sulfoxide sulfonylurea series compounds. The method adopts sulfoxide sulfimide and aralkyl acyl azide as reaction substrates, so that it can be prepared in the presence of no metal elements. The heating reaction is carried out under the conditions, the reaction temperature is 70-100° C., and the reaction time is 2 to 5 hours, and the sulfoxide sulfinyl urea series compounds are efficiently prepared. Through the method of the invention, the compound containing sulfinyl urea can be efficiently prepared. The method has high chemical selectivity, wide substrate applicability, simple operation, short reaction time, extremely high yield, and the only by-product is nitrogen, which is beneficial to separation and purification, and the product has high purity, and is applicable to large-scale preparation.

Description

technical field [0001] The invention relates to nitrogen-containing derivatives containing sulfoxide and urea structural skeletons, in particular to a high-efficiency preparation method for sulfoxide-sulfinylurea series compounds. Background technique [0002] Sulfoxide sulfoximine is a chemically stable compound containing both sulfur-oxygen and sulfur-nitrogen double bonds. Compared with sulfone compounds, sulfoximine is more polar and can effectively improve the dissolution of substances properties, and then construct more complex and diverse useful molecules. Compounds containing sulfinimide structures often have very obvious biological or pharmaceutical activities. For example, the sulfenimide-based drug BAY1000394, a CDK inhibitor, is used clinically in patients with advanced solid tumor cancer. AZD6738, a drug developed by AstraZeneca, is an effective ATR kinase inhibitor constructed on the basis of the sulfenimide structure (K.M.Foote, J.W.M.Nissink, P.Turner, Morp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/10
Inventor 陈知远周豪王秀梅
Owner JIANGXI NORMAL UNIV
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