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Preparation method and application of bicyclic borate compound

A technology of bicyclic boronic acid esters and compounds, which is applied in the field of preparation of bicyclic boronic acid ester compounds, can solve problems affecting research development, etc., and achieve the effects of improving synthesis yield, shortening synthesis steps, and simple preparation methods

Pending Publication Date: 2022-07-08
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthetic methods reported in the literature have many steps (11 steps) or focus on metal-catalyzed reactions (WO2019 / 075084; Org.Process Res.Dev.2022.26, 925-935, DOI: 10.1021 / acs.oprd.1c00285), Seriously affect the development of follow-up related research

Method used

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  • Preparation method and application of bicyclic borate compound
  • Preparation method and application of bicyclic borate compound
  • Preparation method and application of bicyclic borate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-19

[0062] Embodiment 1-19 provides a kind of bicyclic boronate ester compound respectively, and its general preparation method is as follows:

[0063]

[0064] 1.0 mL of DCM was added to a dry nitrogen-protected reaction tube, and after cooling at -60 °C, the BBr 3 (0.22 mmol, 1.1 equiv; 1.0 mol / L in DCM), base (0.22 mmol, 1.1 equiv, 2,6-di-tert-butylpyridine in Example 1-18, 2,3 in Example 19, 5,6-Tetramethylpyrazine) was dissolved and added dropwise to the solution. After 5 minutes, compound 1 (0.20 mmol, 1.0 equiv) was added dropwise, and the mixture was stirred at -60° C. for another 2.0 hours (in Example 19, it was at 0 °C stirring for 1.5h). Finally, the resulting reaction mixture was washed with base (1.0 equiv), methanol (1.0 mL) and H 2 O (0.2 mL) quenched. Most of the solvent was then spun off under reduced pressure and the crude product was purified by silica gel chromatography (PE / EA (5:1)) to give the desired product Compound A.

[0065] Substitute different s...

Embodiment 1

[0102]

[0103] Compound A1, white solid, 30 mg, 95% yield; mp 136-138°C; 1 H NMR (600MHz, MeOD) δ 7.63(d, J=7.9Hz, 1H), 7.38(s, 1H), 7.28–7.23(m, 1H), 7.17(s, 1H), 5.98(s, 1H) ,2.41(d,J=1.1Hz,3H); 13 C NMR (151MHz, MeOD) δ155.46, 152.49, 128.95, 124.95, 124.92, 121.88, 118.24, 20.84; 11 B NMR(193MHz,MeOD)δ27.02.HRMS(ESI): Calculated 159.0727, the measured value is 159.0726.

Embodiment 2

[0105]

[0106] Compound A2, white solid, 31 mg, 89% yield; melting point 150-152°C; 1 H NMR (600MHz, MeOD) δ 7.68 (d, J=6.6Hz, 1H), 7.39–7.35 (t, 1H), 7.27 (d, J=7.1Hz, 1H), 7.17 (t, J=7.0Hz) ,1H),6.00(s,1H),2.79(q,J=7.4,1.0Hz,2H),1.28(t,J=7.4Hz,3H); 13 C NMR (151MHz, MeOD) δ160.87, 152.72, 128.82, 124.48, 124.15, 121.84, 118.50, 26.80, 11.93; 11 B NMR (193 MHz, MeOD) δ 27.22.; HRMS (ESI): Calculated 213.1246, found 213.1242.

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Abstract

The invention provides a preparation method and application of a bicyclic borate compound, and the preparation method comprises the following steps: mixing a compound 1 with alkali and boron halide for reaction to obtain the bicyclic borate compound. The synthesis method provided by the invention has simple synthesis steps, realizes synthesis of p-bicyclo borate and QPX7728Li and intermediates thereof without metal participation, and provides a green and efficient synthesis method.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a preparation method and application of a bicyclic boronate compound, in particular to a preparation method and application of a bicyclic boronate compound with simple synthesis steps. Background technique [0002] The World Health Organization and other public health agencies have called for and encouraged the development of new antibiotics over the years since the hazard of Carbapenem-resistant Enterobacteriaceae was recognized. Although β-lactamase inhibitor combination therapy has played an important role in actual treatment in recent years, such as FDA-approved Avibactam (with Ceftazidime, 2015), Vaborbactam (with Meropenem, 2017), and Relebactam (with Imipenem and Cilastatin, 2019) ); but these drugs only address the class A serine carbapenemases, have no inhibitory activity against metallo-beta-lactamases such as NDM-1, and have no inhibitory activity against class D enzy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K31/69A61P43/00
CPCC07F5/025A61K31/69A61P43/00Y02P20/55
Inventor 田平李清华彭裴颖龚美玲张贵山林国强
Owner SHANGHAI UNIV OF T C M
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