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Oxazolopyridine quaternary ammonium salt compound and preparation method and application thereof

A technology of oxazolopyridine and quaternary ammonium salts, which is applied in the transformation application field of oxazolopyridine quaternary ammonium salt compounds and synthetic intermediates, can solve the problem of low yield, achieve convenient post-processing, and good promotion and application value , The effect of high product yield

Active Publication Date: 2018-03-06
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the reaction of halogenated alkane compounds and pyridone compounds needs to be used in the preparation of nitrogen-substituted pyridone compounds in the previous step. The disadvantage of this method is that there is competition for reaction sites in the reaction of halogenated alkane compounds and pyridone compounds. , can generate nitrogen-substituted pyridone compound products, and can also generate oxygen-substituted pyridine compound by-products, resulting in low yield

Method used

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  • Oxazolopyridine quaternary ammonium salt compound and preparation method and application thereof
  • Oxazolopyridine quaternary ammonium salt compound and preparation method and application thereof
  • Oxazolopyridine quaternary ammonium salt compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0048] The preparation of embodiment 1 compound I-1

[0049]

[0050] Dissolve compound S-1 in dry toluene, add excess trifluoroacetic acid to it, heat to 50°C, keep dry, react overnight, spin dry excess acid and solvent, and wash with ether to obtain pure compound I-1 , and the yield was 86%. 1 HNMR (400MHz, chloroform-d) δ7.62 (dd, J = 7.0, 2.0Hz, 1H), 7.52 (ddt, J = 8.7, 6.6, 2.7Hz, 1H), 6.75 (d, J = 9.1Hz, 1H ),6.47(q,J=7.1Hz,1H),6.08–5.97(m,1H),3.78(q,J=11.5,9.8Hz,2H),3.37(s,3H). 13 C NMR (125MHz, CDCl 3 )δ159.91, 149.11, 137.12, 119.27, 110.64, 93.01, 75.74, 58.15. MS (EI): 265.

Embodiment 2

[0051] The preparation of embodiment 2 compound 1-2

[0052]

[0053] Compound S-2 was dissolved in dry anhydrous ether, and excessive concentrated hydrochloric acid was added thereto, and a large amount of yellow solid was precipitated immediately. After stirring for 3 hours, it was filtered and washed with anhydrous ether to obtain pure compound I-2. The yield was 92%. 1 H NMR (400MHz, chloroform-d) δ7.66 (d, J = 7.3Hz, 1H), 6.88 (dd, J = 1.9, 1.0Hz, 1H), 6.43 (dd, J = 7.3, 2.0Hz, 1H) ,6.07(dd,J=4.8,3.6Hz,1H),3.87–3.70(m,2H),3.45(s,3H). 13 C NMR (125MHz, CDCl 3 )δ160.93, 141.24, 140.97, 133.41, 122.63, 120.45, 117.99, 100.85, 84.91, 57.37, 43.98. MS(EI) 255.

Embodiment 3

[0054] The preparation of embodiment 3 compound 1-3

[0055]

[0056] The preparation method was the same as in Example 2, except that compound S-2 was replaced by compound S-3 to obtain compound I-3 with a yield of 99%. 1 HNMR (400MHz, chloroform-d) δ9.28(s, 1H), 8.60(dd, J=7.2, 2.2Hz, 1H), 7.77(dd, J=6.8, 1.9Hz, 1H), 6.56(t, J =6.9Hz,1H),6.22–6.09(m,1H),5.97(s,1H),3.93–3.69(m,2H),3.46(s,3H). 13 C NMR (125MHz, CDCl 3 )δ164.76, 161.45, 144.37, 135.61, 120.97, 106.16, 85.37, 57.49, 44.09. MS (ESI) 195.

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Abstract

The invention relates to an oxazolopyridine quaternary ammonium salt compound represented by formula 1 and a preparation method and a conversion application thereof as a synthesis intermediate. The preparation method of the oxazolopyridine quaternary ammonium salt compound represented by formula 1 mainly comprises the step of carrying out an intramolecular cyclization reaction of a 2-oxyacetal (orketal)yl-(substituted) pyridine compound under the action of an acid to obtain the oxazolopyridine quaternary ammonium salt compound. The conversion application of the oxazolopyridine quaternary ammonium salt compound represented by formula 1 as the synthesis intermediate mainly comprises that the oxazolopyridine quaternary ammonium salt compound is reacted with different nucleophilic reagents toobtain an N-substituted pyridone compound or a 2-substituted pyridine compound. (The formula I is shown in the description).

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular to oxazolopyridine quaternary ammonium salt compounds that can be used as organic synthesis intermediates and for treating tumors or cancer, diabetes, cardiovascular disease, central nervous system diseases, antibacterial and anti-inflammatory, etc. Methods and their transformational applications as synthetic intermediates. Background technique [0002] Quaternary ammonium salts (quaternary ammonium salts) are compounds in which all four hydrogen atoms in ammonium ions are replaced by hydrocarbon groups. The four hydrocarbon groups can be the same or different; the anions are mostly halogen anions (F, Cl, Br, I), or acid radicals (such as HSO 4 - 、RCOO - Wait). Quaternary ammonium salt compounds are widely used in medicine, chemical industry and other fields, such as fungicides, disinfectants, soft antistatic agents, flocculant demulsifiers, drilling flu...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D213/64C07D215/227C07D217/24C07D213/74C07D213/69C07D213/82A61P35/00A61P25/00A61P29/00A61P3/10A61P9/00
CPCC07D213/64C07D213/69C07D213/74C07D213/82C07D215/227C07D217/24C07D498/04Y02A50/30
Inventor 朱维良李波薛溯塑李小龙刘鹏张勇徐志建蔡婷婷陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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