Heteroaromatic ring compound and application thereof
A compound and heteroaromatic ring technology, applied in the field of heteroaromatic ring compounds, can solve the problems of strong drug-resistant bacteria, weakened antibiotic inhibitory effect, and increased side effects of antibiotics in medical costs
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Embodiment 1
[0192] The preparation of embodiment 1 compound I-A
[0193]
[0194] Step (1): Synthesis of Compound B2
[0195]
[0196] To a solution of compound B1 (2.0 g, 11.4 mmol) in THF (30 mL) was added isoindoline-1,3-dione (2.52 g, 17.1 mmol), PPh3 (4.49 g, 17.1 mmol) in an ice-water bath and DIAD (3.46 g, 17.1 mmol), the reaction mixture was stirred overnight at room temperature. Then the reaction mixture was washed with H 2 O (30 mL) was diluted and extracted with ethyl acetate (30 mL x 2). The combined organic layers were washed with brine (50 mL), Na 2 SO 4 Dry, filter and concentrate. The residue was purified by reverse-phase silica gel column chromatography (acetonitrile / H 2 O=5%-95%, 254nm, 30min), to obtain compound B2 (2.68g) as a white solid.
[0197] MS calculated: 304; MS found: 305 [M+H] + .
[0198] Step (2): Synthesis of Compound B3
[0199]
[0200] To a solution of compound B2 (2.68 g, 8.81 mmol) in ethanol (20 mL) was added HCl / ethanol (20 mL), ...
Embodiment 2
[0244] The preparation of embodiment 2 compound I-B
[0245]
[0246] Step (1): Synthesis of Compound 2
[0247]
[0248] SEM: (trimethylsilyl)ethoxymethyl.
[0249] Compound 1-2 (0.50 g, 4.7 mmol) and K were added to a solution of compound 1 (1.0 g, 3.1 mmol) in DMF (10 mL). 2 CO 3 (1.28 g, 9.3 mmol). The reaction mixture was stirred at 120 °C for 1 h. The reaction mixture was washed with H 2 O (30 mL) was diluted and extracted with ethyl acetate (30 mL x 2). The combined organic layers were washed with brine (50 mL), washed with Na 2 SO 4 Dry, filter and concentrate. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to obtain Compound 2 (0.6 g) as a yellow oil.
[0250] MS (mass spec) calculated: 426; MS found: 427 [M+H] + .
[0251] Step (2): Synthesis of Compound 3
[0252]
[0253] Jones reagent (2 mL) was added to compound 2 (0.55 g, 1.3 mmol) in acetone (10 mL), the reaction mixture was stirred at room...
Embodiment 3
[0276] The preparation of embodiment 3 compound I-C
[0277]
[0278] Step (1): Synthesis of Compound 2
[0279]
[0280] SEM: (trimethylsilyl)ethoxymethyl.
[0281] Compound 1-2 (0.29 g, 2.3 mmol) and K were added to a solution of compound 1 (0.5 g, 1.6 mmol) in DMF (10 mL). 2 CO 3 (0.66g, 4.8mmol), the reaction mixture was stirred at 120°C for 1h. Then the reaction mixture was washed with H 2 O (30 mL) was diluted and extracted with ethyl acetate (30 mL x 2). The combined organic layers were washed with brine (50 mL), Na 2 SO 4 After drying, filtering and concentrating, the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to obtain compound 2 (0.45 g) as a yellow solid.
[0282] MS calculated: 443; MS found: 444 [M+H] + .
[0283] Step (2): Synthesis of Compound 3
[0284]
[0285] To a solution of compound 2 (0.45 g, 1.0 mmol) in EtOH (10 mL) was added Fe (568.8 mg, 10.1 mmol) and NH 4 Cl (543.5mg, 10.1mmol), ...
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