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CAS No. : | 97305-12-9 | MDL No. : | MFCD11041490 |
Formula : | C11H10F2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GLRNJDWFZNOBHC-UHFFFAOYSA-N |
M.W : | 228.19 | Pubchem ID : | 13550002 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 52.26 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 2.19 |
Log Po/w (WLOGP) : | 2.94 |
Log Po/w (MLOGP) : | 2.43 |
Log Po/w (SILICOS-IT) : | 3.19 |
Consensus Log Po/w : | 2.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.58 |
Solubility : | 0.597 mg/ml ; 0.00262 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.73 |
Solubility : | 0.421 mg/ml ; 0.00184 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.8 |
Solubility : | 0.0363 mg/ml ; 0.000159 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.84 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; at 20℃; for 18h; | Ethyl 3-(2,6- difiuorophenyl)-3-oxopropanoate (12.3 g, 53.8 mmol) and triethylaroine (22.5 mL, 0.161 mol, 3.0 equiv) were dissolved in acetonitrile (160 mL) and treated with 4-acetamidobenzenesuifonyl azide. The mixture was stirred for 18 hours at ambient temperature, concentrated in vacuo and the residue was purified by silica gel chromatography (eluting with chloroform), providing the titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 2,6- difluorobenzoic acid (15 g, 0.095 mol) and carbonyldiimidazole (18 g, 0.14 mol, 1.5 equiv) in anhydrous tetrahydrofuran (150 mL) was stirred at ambient temperature for 6 hours. In a separate flask, a suspension of anhydrous magnesium(II) chloride (9.0 g, 0.095 mol, 1.0 equiv) and potassium ethyl malonate (22 g, 0.13 mol, 1.4 equiv) in tetrahydrofuran (225 mL) was stirred at 50-60 0C for 6 hours, cooled to ambient temperature, which was then added via syringe to the solution of activated acid, and the mixture was stirred for an additional 18 hours at ambient temperature. The mixture was refluxed for 3 hours, cooled to ambient temperature, poured into water and acidified with hydrochloric acid (12 N aqueous) to pH <; 2. The aqueous layer was extracted with ethyl acetate and the organic extract was washed with water, dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 50℃; for 4h; | To a solution of ethyl 3~(2,6-difluorophenyl)-3-oxopropanoate (3.60 g, 15.8 mmoi) in 30 mL of dichloromethane was added l5l-diethoxy-N,N-dimethylmethanamme (3.10 mL, 18.1 mmol). The reaction mixture was stirred at 50 0C for 4 hours, then cooled to room temperature and concentrated in vacuo to provide ethyl (22)-2-(2,6-difluorobenzoyl)-3-(dimethylamino)acrylate. To a solution of the above compound (0.500 g, 1.76 mmol) in 10 mL of dioxane was added ten- butyl [4-(aminomethyl)phenyl]carbamate (0.392 g, 1.76 mmol), and potassium phosphate (0.922 g, 5.30 mmol). The reaction mixture was stirred at 70 0C for 3 hours, then at 130 0C for 40 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate and brine. The organic fractions were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography eluted with 10-70% EtOAc in hexanes to provide ethyl -{4-[tert- butoxycarbonyi)amino]benzy.}-5-fluoro-oxo-l,4-dihydroquinoline-3-carboxyIate that gave a mass ion (ES+) of 441.1 for M+H+. To a solution of this yellow solid in 10 mL of dichloromethane was added 4 N HCl in dioxane (3.53 mL, 14.1 mmol). After 5 hours, the reaction mixture was concentrated in vacuo to provide 4-[3-ethoxycarbonyl)-5-fluoro-4- oxoquinolin-l(4H)-yl]methyl}benzenaminium chloride which gave a mass ion (ES+) of 341.2 for M+Eta+.To a suspension of the above salt in 1 mL of dichiorom ethane at 0 0C was added triethylamine (0.048 mL, 0.34 mmol) and 2-methy.propanoyl chloride (0.022 mg, 0.21 mmol). After 1 hour, the reaction mixture was warmed to room temperature and additional triethylamine (0.048 mL, 0.34 mmol) and 2-methylpropanoyl chloride (0.022 mg, 0.21 mmol) were added. After 1 hour, 1 N NuaOEta (0.50 mL, 0.50 mmol) and 0.3 mL of DSvISO were added. The dichloromethane was removed in vacuo, and 2 mL DMSO, and 1 N NuaOEta (0.50 mL, 0,50 mmol) were added to the mixture. After 2 hours, the reaction mixture was filtered and purified via reverse phase EtaPLC to provide the title compound which gave a proton NuMR spectrum consistent with theory and a mass ion (ES+) of 383.2 for M+Eta+: 1H NuMR (400 MHz, d6-DMSO) 8 9.87 (s, H), 9.23 (s, IH), 7.86-7.80 (m, IH), 7.65 (d, J= 8.7 Hz, IH), 7.58 (d, J- 8.4 Hz, 2H), 7.39-7.34 (m, IH), 7.22 (d, J = 8.4 Hz, 2H), 5.76 (s, 2H), 2.57-2.50 (m, IH), 1.07 (d, J= 6.8 Hz, 6H). |
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