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High-efficiency preparation method for sulfoxide sulfinyl urea compounds

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 unstable chemical properties of isocyanates, highly toxic properties, easy hydrolysis and deterioration, and the like. It is beneficial to separation and purification, good reactivity and good application prospect.

Inactive Publication Date: 2017-07-14
JIANGXI NORMAL UNIVERSITY
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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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  • High-efficiency preparation method for sulfoxide sulfinyl urea compounds
  • High-efficiency preparation method for sulfoxide sulfinyl urea compounds
  • High-efficiency preparation method for sulfoxide sulfinyl urea compounds

Examples

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 for sulfoxide sulfinyl urea compounds. According to the method, the sulfoxide sulfinyl urea compounds are efficiently prepared through carrying out a heated reaction on sulfoxide sulfinylimide and aralkyl acyl azide, which serve as reaction substrates, for 2 to 5 hours at the temperature of 70 DEG C to 100 DEG C in the absence of any metal element. By the method disclosed by the invention, sulfinyl-containing urea compounds can be efficiently prepared. The method is high in chemoselectivity, high in substrate applicability, simple and convenient in operation, short in reaction time and extremely high in yield, the unique byproduct is nitrogen gas, separation and purification are facilitated, and the product purity is high, so that the method can be applicable to relatively-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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IPC IPC(8): C07C381/10
Inventor 陈知远周豪王秀梅
Owner JIANGXI NORMAL UNIVERSITY
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