Tricyclic substituted piperidine diketones
A technology of compound and cycloalkyl, applied in the field of derivative compounds represented by the formula or their pharmaceutically acceptable salts, to achieve the effect of excellent pharmacokinetic properties
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Embodiment 1
[0117] Example 1: WX001
[0118]
[0119] Step 1: Synthesis of intermediate WX001–2
[0120] WX001-1 (11 g, 79.64 mmol) was dissolved in dichloromethane (100 mL) at room temperature, followed by the addition of diisopropylethylamine (36.03 g, 278.74 mmol, 48.55 mL). The reaction mixture was cooled to 0°C, then chloromethyl ether (10.7 g, 132.90 mmol, 10.09 mL) was added, the reaction mixture was warmed to room temperature and stirred for 2 hours. After the reaction was completed, water (100 mL) was added for dilution, and the organic phase was collected after liquid separation, and the aqueous phase was extracted with dichloromethane (50 mL×2). Combine the organic phases, dry the organic phase with anhydrous sodium sulfate, filter and concentrate under reduced pressure to obtain a residue, and the resulting residue is separated by column chromatography (eluent: petroleum ether / ethyl acetate=100 / 0–9 / 1, volume ratio), to obtain intermediate WX001–2. 1 H NMR (400MHz, CDCl ...
Embodiment 2
[0131] Example 2: WX002
[0132]
[0133] Step 1: Synthesis of intermediate WX002–2
[0134] At room temperature, WX002-1 (5g, 34.68mmol) was dissolved in dichloromethane (70mL), and then N-iodosuccinimide (7.80g, 34.68mmol) and p-toluenesulfonic acid (1.98g , 10.40mmol), the reaction mixture was stirred at room temperature for 30 minutes. After the reaction was completed, water (50 mL) was added for dilution, and the organic phase was collected after liquid separation, and the aqueous phase was extracted with dichloromethane (50 mL×2). The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain the target intermediate WX002–2. 1 HNMR (400MHz, CDCl 3 )δ: 7.96 (d, J = 8.4Hz, 1H), 7.76 (dd, J = 3.2, 8.4Hz, 2H), 7.58 (t, J = 7.7Hz, 1H), 7.46–7.37 (m, 1H), 7.32–7.24(m,1H),4.95(s,1H).
[0135] Step 2: Synthesis of intermediate WX002–3 Intermediate WX002–2 (9 g, 33.33 mmol) wa...
Embodiment 3
[0140] Embodiment 3: the hydrochloride of WX003
[0141]
[0142] Step 1: Synthesis of intermediate WX003–2
[0143] At room temperature and under nitrogen protection, WX003-1 (9.5g, 65.45mmol) and tert-butyl 2-bromoacetate (14.04g, 71.99mmol, 10.64mL) were dissolved in N,N-dimethylformamide (100mL) , then slowly added potassium carbonate (9.05g, 65.45mmol) in batches, the reaction mixture was heated to 60°C and stirred for 12 hours, then the reaction system was cooled to 30°C, and sodium hydrogen (2.62g, 65.45mmol, purity : 60%), was heated to 60 ℃ again and continued stirring reaction for 2 hours. After the reaction was completed, it was cooled to room temperature, quenched by adding water (100 mL), and extracted with ethyl acetate (200 mL×2). The organic phases were combined, washed with half-saturated brine (150 mL×3), dried over anhydrous sodium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The obtained residue was separate...
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