Pyrrolidone derivative
A technology of drugs and compounds, applied in the field of pyrrolidone derivatives and pharmaceutical compositions containing them, can solve the problems of low efficacy, poor pharmacokinetics, side effects, etc.
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Embodiment 1
[0104] Preparation 3- (5- (3,5-difluorophenyl) -1,2,4-oxadazole-3-yl) -3-hydroxy-1- (1H-indole-5-yl)
[0105] Pyrrolidine-2-ketone (Compound 1)
[0106]
[0107] The reaction formula of this Example 1 is as follows:
[0108]
[0109]Step 1: Potassium t-butoxide (720.72 mg, 6.435 mmol, 1.5 equivalents) was added to the compound 1-1 (700 mg, 4.29 mmol, 1.0 equivalents) of tetrahydrofuran (10 mL) solution. The mixture was stirred at room temperature for 30 minutes, and Compound 1-2 (0.64 mL, 5.15 mmol, 1.2 equivalents) were added to the mixture. The mixture was continued for 2 hours at room temperature. The TLC analysis of the reaction mixture showed completely converted to the desired product. The mixture was then diluted with water (10 mL), extracted with ethyl acetate (2 × 10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether: ethyl a...
Embodiment 2 and 3
[0119] Preparation (S) -3- (5- (3,5-difluorophenyl) -1,2,4-oxadazole-3-yl) -3-hydroxy-1- (1H-indole-5- Base) pyrrolidine-2-ketone (Compound 2) and (R) -3- (5- (3,5-difluoroyl) -1, 2, 4-oxazole-3-yl) -3- Hydroxy-1- (1H-indole-5-yl) pyrrolidine-2-ketone (Compound 3).
[0120]
[0121] The reaction formula of this Example 2 and 3 is as follows:
[0122]
[0123] Squiped compound 3-5-3, 5-difluoroenzyl) -1,2,4-malodazole-3-yl) -3-hydroxy-1- (1H-indole-5-yl) pyrrolidine -2-ketone (Compound 1) (50 mg) was separated by the following method: a solvent system using a Chiralcel OD column (5 × 25 cm, 20% U03BCM) and n-heptane / ethanol (70:30), and 100 mL / min. After collecting the enantiomer of the first elution, it was concentrated to give (S) -3- (3- (3,5-difluoroyl) -1,2,4-oxadiazole-5- Base) -3-hydroxy-1- (1H-indole-5-yl) pyrrolidine-2-ketone (Compound 2). Collect the enantiomer in the second part, concentrate it, resulting in (R) -3- (3- (3,5-difluorophenyl) -1, 2, 4-oxadiazole-3-...
Embodiment 4
[0125] Preparation 3- (5- (3,5-difluoro) -1,3,4-oxadazole-2-yl) -3-hydroxy-1- (1H-indole-5-yl) pyrrolidine -2-ketone (Compound 4).
[0126]
[0127] The reaction formula of this Example 4 is as follows:
[0128]
[0129]Step 1: Potassium t-butoxide (10.4 g, 92.5 mmol, 1.5 equivalents) and compound 4-2 (13 g, 74.07 mmol, 1.2 equivalents) were added to compound 4-1 (10 g, 61.7 mmol, 1.0 equivalents) of tetrahydrofuran ( 100 mL) solution. The mixture was stirred at room temperature overnight. The TLC analysis of the reaction mixture showed completely converted to the desired product. The mixture was then diluted with water (100 mL), extracted with ethyl acetate (2 × 100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give Compound 4-3 (13.2 g, 71%) to white solid. TLC Condition: Petroleum ether: ethyl acetate = 5: 1, UV 254 nm. Compound 4-1 R f = 0...
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