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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.
5,5-Dimethyl-2,4-oxazolidinedione is a cathepsin K inhibitor, it's an anticonvulsant.
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CAS No. : | 695-53-4 |
Formula : | C5H7NO3 |
M.W : | 129.11 |
SMILES Code : | O=C(N1)OC(C)(C)C1=O |
MDL No. : | MFCD00005379 |
InChI Key : | JYJFNDQBESEHJQ-UHFFFAOYSA-N |
Pubchem ID : | 3081 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
22% | With sodium; In tetrahydrofuran; for 3h;Reflux; | 5,5-Dimethyloxazolidine-2,4-dione (0.15 g, 1.16 mmol) and sodium (catalytic amount) were added to a stirred solution of 4-methylbenzenesulfonyl chloride (0.17 g, 0.89 mmol) in dry THF (3 mL). The resulting mixture was refluxed for 3h and the reaction progress was followed by TLC. After the addition of DCM (15 mL) to the flask, the mixture was filtered and the solvents were removed. The resulting residue was purified by recrystallization from DCM-light petroleum to give 4h as white crystals (22%); m.p. 119-121C; numax 3049, 2971, 1811, 1772, 1587, 1389, 1300, 1172 cm-1; 1H-NMR delta 1.56 (6H, s, CH3), 2.50 (3H, s, ArCH3), 7.43 (2H, d, J=8.4, ArH), 8.06 (2H, d, J=8.4, ArH); 13C-NMR delta 21.9, 23.6, 83.4, 128.8, 130.3, 133.7, 147.3, 148.1, 170.8; MS-EI m/z 283 (M+); Anal. calcd for C12H13NO5: C 50.88, H 4.62, N 4.94; found C 50.95, H 4.68, N 4.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
applying a pharmaceutically effective amount of a cationic derivative of Minoxidil to said skin, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of; ... 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); and | ||
...cally effective amount of a cationic derivative of Minoxidil to a positive donor electrode of an iontophoresis apparatus having a negative receiver electrode, said cationic derivative of Minoxidil formed by mixing solutions of Minoxidil with an organic acid selected from the group consisting of: ... 3,4-dihydroxybenzoic acid (also known as protocatechuic acid); 2,3,4-trihydroxybenzoic acid; 3,4,5-trihydroxybenzoic acid (also known as gallic acid); 5-nitro-2-furoic acid; and 5,5-dimethyloxazolidine-2-4-dione (also known as dimethadione); | ||
As the compound represented by the formula (XXIV), there are given for example acid imides corresponding to the compounds represented by the foregoing formula (XXIII) and the compounds described below: ... 5,5-Dimethyl-4-thioxo-2-oxazolidinone 5,5-Dimethyl-2,4-thiazolidinedione 2-Thioxo-4-imidazolidinone 2,4-Imidazolidinedione 5,5-Dimethyl-2,4-oxazolidinedione 5,5-Dimethyl-2-thioxo-4-imidazolidinone 5,5-Dimethyl-2,4-imidazolidinedione 5,5-Dimethyl-2-thioxo-4-thiazolidinone ... |
Consequently, the purity of purified 5,5-dimethyl-2,4-oxazolidinedione was 99.3%; 5,5-dimethyl-2,4-oxazolidinedione was 11.2 g, 2-hydroxyisobutyric acid amide was 7.7 g, methyl carbamate was 1.0 g in the filtrate; 5,5-dimethyl-2,4-oxazolidinedione was 8.1 g, 2-hydroxyisobutyri c acid amide was 1.7 g, and methyl carbamate was 0.2 g in the wash liquid. The net yield of 5,5-dimethyl-2,4-oxazolidinedione which was provided in consideration of the purity of purified 5,5-dimethyl-2,4-oxazolidinedione based on starting urea was 65.5%. | ||
As the compound represented by the formula (XXIV), there are given for example acid imides corresponding to the compounds represented by the foregoing formula (XXIII) and the compounds described below: ... 2-Thioxo-4-imidazolidinone 2,4-Imidazolidinedione 5,5-Dimethyl-2,4-oxazolidinedione 5,5-Dimethyl-2-thioxo-4-imidazolidinone ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; In hexane; water; | 13-1) Production of 5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione A mixture of <strong>[695-53-4]5,5-dimethyloxazolidine-2,4-dione</strong> (1.9 g, 15 mmol), 2-nitrobenzylchloride (2.6 g, 15 mmol), potassium carbonate (2.5 g, 18 mmol) and N, N-dimethylformamide (15 ml) was heated at 80C for 2 hours while stirring. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate, and the organic layer was washed with water (twice), then with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. After concentrated under reduced pressure, the organic layer was mixed with hexane, and precipitated solid material was collected by filtration to obtain 5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione (3.7 g). Yield: 93% Properties: melting point 133.5-134.5C |