Condensed 5-oxazolidinone derivative
A compound and alkyl technology, applied in the introduction of heterocyclic compound isotopes, drug combination, blood diseases, etc., can solve problems such as serious adverse reactions that hinder hemostasis
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[0898] The present invention will be described in further detail below in relation to Reference Examples, Examples, and Test Examples, but the present invention is not limited thereto at all. Note that not all the compound names described in the following Reference Examples and Examples are named according to the International Union of Pure and Applied Chemistry (IUPAC). Note that abbreviations may be used herein to simplify the description and have the same meanings as those described above.
[0899] The following abbreviations may be used here.
[0900] The following abbreviations can be used in the NMR data of Reference Examples and Examples.
[0901] Me:methyl
[0902] Et: ethyl
[0903] Bu: Butyl
[0904] tert-: tert
[0905] Boc: tert-butoxycarbonyl
[0906] Tf: Trifluoromethanesulfonyl
[0907] THF: Tetrahydrofuran
[0908] DMF:N,N-Dimethylformamide
[0909] TFA: Trifluoroacetic acid
[0910] DBU:1,8-Diazabicyclo[5.4.0]undec-7-ene
[0911] WSC·HCl: 1-ethyl-3-...
reference example 1
[0952] (1S)-1-[trans-4-({(2S,3S)-3-cyclohexyl-2-[(3,3-dimethyl-1-oxo-1H-[1,3] Azolo[3,4-a]indol-7-yl)carbamoyl]piperidin-1-yl}carbonyl)cyclohexyl]-2-fluoroethyl}carbamate tert-butyl
[0953]
[0954] At room temperature, stir the compound of reference example 1-8 (77.4mg, 0.179mmol), the compound of reference example 1-3 (57.0mg, 0.200mmol), 1-hydroxybenzotriazole (41.1mg, 0.269mmol), WSC. A mixture of HCl (51.5 mg, 0.269 mmol), triethylamine (62.3 μl, 0.448 mmol), and DMF (3 mL) was carried out for 3 hours. To the reaction mixture was added saturated aqueous ammonium chloride, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated aqueous ammonium chloride solution and once with saturated aqueous sodium bicarbonate solution and saturated brine solution, then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to...
reference example 1-2
[0962] Methyl trans-4-(fluoroacetyl)cyclohexanecarboxylate
[0963]
[0964] To a solution of the compound of Reference Example 1-1 (7.00 g, 24.62 mmol) in acetonitrile (50 mL) was added Selectfluor (13.08 g, 36.92 mmol) at room temperature and the resulting mixture was stirred at 40° C. for 4 hours and then at room temperature 13 hours. To the reaction solution was added saturated aqueous sodium thiosulfate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, saturated aqueous ammonium chloride solution, and saturated brine solution, then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product (6.78 g).
[0965] To a solution of the obtained crude product (6.64 g, 21.96 mmol) in chloroform (30 mL) was added trifluoroacetic acid (15.02 g, 131.7 mmol) at room temperature, and the resulting mixture was stirred at 40°C for ...
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