Heterocyclic compounds and their use in the prevention or treatment of bacterial infections
A technology for bacterial infections, compounds, applied in the field of prevention or treatment of bacterial infections, β-lactamase inhibitors and/or antimicrobials, capable of solving problems such as inefficiency of bacterial strains
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Embodiment 1
[0325] Example 1: (5-methyl-4,9-dioxo-3-thia-5,8,10-triazatricyclo[6.2.1.0 2,6 ] Eleven-2 Synthesis of (6)-en-10-yl)sodium sulfate
[0326]
[0327] Step 1: Preparation of intermediate tert-butyl 4-bromo-3,5-dioxo-piperidine-1-carboxylate (1a)
[0328] At 0°C under an inert atmosphere, NBS (2.5 g, 14,07 mmol) and ACHN (0.223 g, 0.91 mmol) were added sequentially to tert-butyl 3,5-dioxopiperidine-1-carboxylate (3 g, 14.07 mmol) in anhydrous DCM (60 mL). The reaction mixture was stirred at 0°C for 2 hours. The resulting solution was washed with water followed by aqueous NaCl. use Na 2 SO 4 The organic layer was dried and evaporated under vacuum to give an off-white solid tert-butyl 4-bromo-3,5-dioxo-piperidine-1-carboxylate (1a) (4.11 g, 14.07 mmol, quantitative yield ).
[0329] MS m / z ([M+H-tertbutyl] + )236 / 238.
[0330] MS m / z ([M-H] - )290 / 292.
[0331]1 H NMR (400MHz, CDCl 3 ): δ (ppm) 1.48 (s, 9H), 4.35 (bs, 4H).
[0332] Step 2: Intermediate tert-...
Embodiment 2
[0377] Example 2: [5-(2-methoxy-2-oxo-ethyl)-4,9-dioxo-3-thia-5,8,10-triaza-tricyclic [6.2.1.0 2,6 Synthesis of ]undec-2(6)-en-10-yl]sodium sulfate
[0378]
[0379] Step 1: Intermediate tert-butyl 2,7-dioxo-4,6-dihydro-3H-thiazolo[4,5-c]pyridine-5-carboxylate (2a) preparation
[0380] 12N HCl (2.50 mL) was added dropwise to 2-methoxy-7-oxo-6,7-dihydro-4H-thiazolo[4,5-c]pyridine-5-carboxy tert-butyl ester (1d ) (7.19g, 25.31mmol) in anhydrous dioxane (193mL) solution. The reaction mixture was stirred at 70°C for 4 hours, then concentrated under vacuum. The residue was diluted with EtOAc and washed with water. use Na 2 SO 4 The organic layer was dried, filtered and concentrated under vacuum to give tert-butyl 2,7-dioxo-4,6-dihydro-3H-thiazolo[4,5-c]pyridine-5-carboxylate as an orange solid (2a) (3.43g, 12.70mmol, 50%).
[0381] MS m / z([M-tBu+H] + )215.
[0382] MS m / z ([M-H] - )269.
[0383] Step 2: Intermediate 3-(2-methoxy-2-oxo-ethyl)-2,7-dioxo-4,6-di...
Embodiment 3
[0408] Example 3: [5-(2-(tert-butoxycarbonylamino)ethyl)-4,9-dioxo-3-thia-5,8,10-triaza-tri ring [6.2.1.0 2,6 Synthesis of ]undec-2(6)-en-10-yl]sodium sulfate
[0409]
[0410] Step 1: Intermediate 3-(2-hydroxyethyl)-2,7-dioxo-4,6-dihydrothiazolo[4,5-c]pyridine-5-carboxylic acid tertiary Preparation of butyl ester (3a)
[0411] Under an inert atmosphere, the K 2 CO 3 (7.3g, 52.90mmol) and iodoethanol (12.7mL, 162mmol) were added to 2,7-dioxo-4,6-dihydro-3H-thiazolo[4,5-c]pyridine-5-carboxylic acid tert Butyl ester (2a) (11 g, 40.70 mmol) in anhydrous ACN (90 mL), and the mixture was stirred at 70° C. for 7 hours and concentrated in vacuo. The residue was diluted with EtOAc and water. The aqueous layer was acidified (pH 2) with 1N hydrochloric acid solution and extracted twice with EtOAc. The organic layers were combined, washed with water and aqueous NaCl, washed with NaCl 2 SO 4 Dry, filter and concentrate in vacuo to give a yellow oil 3-(2-hydroxyethyl)-2,7...
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