Structure of 2239-31-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 2239-31-8 |
Formula : | C7H15NO |
M.W : | 129.20 |
SMILES Code : | NCC1(CO)CCCC1 |
MDL No. : | MFCD09864390 |
InChI Key : | WUROIEARWDBJIO-UHFFFAOYSA-N |
Pubchem ID : | 22379517 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15.9 g | With triethylamine; In tetrahydrofuran; at 20℃; | To a stirred solution of [1-(aminomethyl)cyclopentyl]methanol (50.7 g) in THF (304 mL) was added triethylamine(60.2 mL) under ice-cooling. Di-tert-butyl dicarbonate (94.2 g) in THF (101 mL) was added dropwise to this solution.After the addition, the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted withwater and ethyl acetate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturatedsaline, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The residuewas extracted with ethyl acetate-hexane (1:9) (700 mL), and the extract was stirred at room temperature for 3 hours.Insolubles were collected by filtration, washed with hexane, and dried to afford the title compound (49.2 g). For thefiltrate, the solvent was removed under the reduced pressure, and the residue was purified by silica gel column chromatographyto afford the title compound (15.9 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2-hydroxypyridin; triethylamine; at 80℃; for 18.0h; | General procedure: 2-Hydroxypyridine (38.3 mg, 0.404 mmol) was added to a solution of 17a (205 mg, 0.404 mmol) and 3-amino-2,2-dimethylpropanamide (140 mg, 1.21 mmol) in triethylamine (4 mL), and the mixture was stirred at 80 C for 4 h. The reaction mixture was concentrated under reduced pressure, and then stirred at 80 C for an additional 14 h. After cooling, water was added to the reaction mixture, followed by extraction with CH2Cl2. The organic layer was driedover anhydrous MgSO4. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, CH2Cl2/MeOH = 40:3) to obtain tert-butyl {(2S,3S,5S)-5-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-3-hydroxy-6-methylheptan-2-yl}carbamate (167 mg, 66%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15 mg | With N-ethyl-N,N-diisopropylamine; In ethanol; at 140℃; for 0.333333h;Sealed tube; Microwave irradiation; | General procedure: A3: To a solution of the appropriate methylated TTZD (1 eq.) in EtOH (1.5 mL) was added the requisite amine (1.5 eq.) and diisopropylethyl amine (2.5 eq.). The vial was sealed and heated in a microwave at 140 C for 20 min. The reaction was cooled to room temperature, diluted with water and left to stand at room temperature until a precipitate formed, which was filtered, washed with water, ice-cooled EtOH and Et2O. The solid was collected and dried under vacuum to give the desired product. |
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