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CAS No. : | 153888-45-0 | MDL No. : | MFCD09835081 |
Formula : | C6H5BrN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VFWZQRFZMKHGOY-UHFFFAOYSA-N |
M.W : | 233.02 g/mol | Pubchem ID : | 52911253 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.49 |
TPSA : | 67.82 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.13 cm/s |
Log Po/w (iLOGP) : | 1.15 |
Log Po/w (XLOGP3) : | 0.84 |
Log Po/w (WLOGP) : | 1.06 |
Log Po/w (MLOGP) : | 0.28 |
Log Po/w (SILICOS-IT) : | -0.53 |
Consensus Log Po/w : | 0.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.12 |
Solubility : | 1.78 mg/ml ; 0.00762 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.85 |
Solubility : | 3.31 mg/ml ; 0.0142 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.73 |
Solubility : | 4.3 mg/ml ; 0.0185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.14 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
77% | Stage #1: With hydrogenchloride; water; iron In ethanol at 60℃; for 2 h; Stage #2: With water; potassium carbonate In ethanol |
3-Amino-5-bromo-1-methylpyridin-2-one (42); A 1-L three-neck round-bottomed flask equipped with a mechanical stirrer and reflux condenser was purged with nitrogen and charged with 41 (21.7 g, 93.3 mmol), ethanol (305 mL), iron powder (-325 mesh, 52.1 g, 933 mmol) and 2N hydrochloric acid (50 mL, 100 mmol), and the mixture was heated for 2 h at 60° C. After this time, the reaction was cooled to room temperature, and potassium carbonate was added to pH 8 as determined by a pH paper. The resulting suspension was filtered and the filter cake washed with ethanol (4.x.100 mL). The filtrate was concentrated under reduced pressure to yield a brown solid. This solid was purified by column chromatography on silica gel to afford 42 in 77percent yield (14.5 g) as an off-white powder: mp 104-105° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.15 (d, 1H, J=2.5 Hz), 6.46 (d, 1H, J=2.5 Hz), 5.45 (bs, 2H), 3.40 (s, 3H); MS (ESI+) m/z 203 (M+H). |
34% | With iron; ammonium chloride In ethanol; water-d2 at 95℃; for 3 h; Inert atmosphere | Iron powder (1 g, 18 mmol, 4.2 equivalents) and ammonium chloride (0.964 g, 18 mmol, 4.2 equivalents) were added to a solution of 1-methyl-3-nitro-5-bromo-pyridin-2-one (1 g, 4.3 mmol, 1 equivalent) in ethanol (8 mL) and water (6 mL) and stirred at 95 °C for 3 hours. The solution was then filtered through a pad of celite and concentrated. The residue was then taken up in water (20 mL) and extracted with EtOAc (3 x 30 mL). The organic layers were dried over magnesium sulfate and concentrated to give a brown oil that solidified upon standing. The residue was purified by SCX to give the desired product as a dark red solid (300 mg, 34percent). |
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