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CAS No. : | 143355-56-0 | MDL No. : | MFCD00059082 |
Formula : | C12H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UDAQUPSJOGVPIX-UHFFFAOYSA-N |
M.W : | 218.21 | Pubchem ID : | 608330 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 59.42 |
TPSA : | 66.76 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.49 cm/s |
Log Po/w (iLOGP) : | 1.26 |
Log Po/w (XLOGP3) : | 3.02 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 1.72 |
Log Po/w (SILICOS-IT) : | 1.85 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.43 |
Solubility : | 0.0818 mg/ml ; 0.000375 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.09 |
Solubility : | 0.0179 mg/ml ; 0.0000818 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.01 |
Solubility : | 0.215 mg/ml ; 0.000984 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.17 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | 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 sulfuric acid; for 18.0h;Heating / reflux; | Example 3 5-(3 -Isopropyl-6-methoxy-naphthalen-2-yloxy)-pyrimidine-2,4-diamine The synthetic procedure used in this example is outlined below in Scheme E. Step 1 3-Hydroxy-7-methoxy-naphthalene-2-carboxylic acid methyl ester To a solution of <strong>[143355-56-0]3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid</strong> (2.5 g, 11.45 mmol) in 50 mL methanol was added 0.3 mL of concentrated sulfuric acid. The resulting mixture was heated at reflux for 18 hours, then cooled and diluted with diethyl ether. The organic phase was washed with water and saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered and concentrated under reduced pressure to give 2.51 g of <strong>[143355-56-0]3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid</strong> methyl ester, MP=129-131 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 25 5-(S)-(((3-Hydroxy-7-methoxy-naphthalene-2-carbonyl)amino)methyl)-2-(oxalyl-amino)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic Acid The title compound was prepared using <strong>[143355-56-0]3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid</strong> and 2-amino-5-(S)-aminomethyl-6-(1-(S)-phenyl-ethyl)4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as the starting material and Method A, B, C and D as described above. Calculated for C22H19N3O7S, 1xH2O, 0.7xC2HF3O2 C, 49.06%; H, 4.00%; N, 7.03%. Found: C, 49.30%; H, 4.37%; N, 6.66% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium bicarbonate; dimethyl sulfate; In N-methyl-acetamide; ice-water; | A. 6.55 g of <strong>[143355-56-0]3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid</strong> were dissolved in 20 ml of dimethylformamide, treated with 5.5 g of sodium hydrogen carbonate and 4.0 ml of dimethyl sulfate and stirred at 90 C. under argon for 10 minutes. Subsequently, the reaction mixture was poured on to ice-water and extracted with ether. The combined ether phases were washed with water, dried over magnesium sulfate and concentrated. The thus-obtained residue was recrystallized from ethyl acetate/hexane. Methyl 3-hydroxy-7-methoxy-naphthalene-2-carboxylate with m.p. 138 C. was thus obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With caesium carbonate; In N,N-dimethyl-formamide; at 23℃; for 1.5h; | A mixture of <strong>[143355-56-0]3-hydroxy-7-methoxy-2-naphthoic acid</strong> (75 g, 344 mmol) and cesium carbonate (336 g, 1031 mmol) in /V, /V- d i m c t h y I f r m a m i dc (687 mL) was rapidly stirred for 5 minutes at 23 C. Thereafter, benzyl bromide (84 mL, 705 mmol) was added. After 90 minutes, the mixture was poured into fLO (1 L) and extracted with ethyl acetate (4 x 300 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (3 x 100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford a brown solid. The crude solid was collected by filtration, slurried with teri-butyl methyl ether/heptanes (1:2, 3 x 100 mL), then dried in vacuo (12 mbar) at 40 C to afford the title compound (122.5 g, 307 mmol, 89% yield) as a beige solid. MS (APCI+) m/z 399 [M+H]+. |
With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24.0h; | The 5.0g (21.7mmol) 3-hydroxy-7- methoxy naphthalene -2-carboxylic acid, 9.29g (54.3mmol) benzyl bromide and 9.01g (65.2mmol) potassium carbonate in 25mLDMF in the mixture in 60 C stirring 24 hours. After cooling to room temperature, the mixture is lean in a water, in extraction into EtOAc. For water and 3×1 × saturated NaCl wash the organic phase. Organic phase is dried with sodium sulfate, solvent is removed under reduced pressure. The residual solid crystallization from dichloromethane/ethanol, to obtain the title compound, as a tan solid, mp96-98. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24.0h; | Example 1; 5-(3-Hydroxy-7-methoxynaphthalen-2-yl)-1 ,1-dioxo-[1 ,2,5]thiadiazolidin-3-one potassium salt; Step i; S-Benzyloxy-T-methoxynaphthalene^-carboxylic acid benzyl ester; A mixture of 5.0 g (21.7 mmol) of <strong>[143355-56-0]3-hydroxy-7-methoxynaphthalene-2-carboxylic acid</strong>, 9.29 g (54.3 mmol) of benzyl bromide, and 9.01 g (65.2 mmol) of potassium carbonate in 25 ml_ of DMF is stirred at 60 C for 24 h. After allowing to cool to room temperature the mixture is poured into water and is extracted into EtOAc. The organic phase is washed 3x with water <n="21"/>and 1 x with saturated NaCl. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. The residual solid is crystallized from methylene chloride/ethanol to give the title compound as a tan solid, mp 96 - 98. 1H-NMR (CDCI3):delta 8.25 (s, 1 H), 7.61 (d, J = 8.83 Hz, 1 H), 7.49 (d, J = 7.35 Hz, 2H), 7.46 - 7.30 (m, 7H), 7.24 (d, J = 5.88 Hz, 2H), 7.18 (dd, J = 9.20 and 2.58 Hz, 1 H), 7.12 (m, 1 H), 5.40 (s, 2H), 5.23 (s, 2H), 3.89 (s, 3H). Anal. Calcd for C26H22O4: C, 78.38; H, 5.57. Found: C, 78.28; H, 5.56. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With trichlorophosphate; In toluene; for 6.0h;Reflux; | A mixture of 3-hydroxy-2-naphthoic acid 5 (3.3 g, 15 mmol), POCl3 (3 mL, 30 mmol) and toluene (40 mL) was heated under reflux for 6 h. After cooling the reaction mixture to room temperature, water was added. The crystals deposited were separated by filtration and washed with water and aq NaHCO3 solution. The crystalline solid was purified by silica gel column chromatography using AcOEt as eluent to give 3b as pale yellow solid. Yield 48% (1.5 g); mp>300 C; IR (Nujol) 1742 cm-1 (CO); 1H NMR (CDCl3, 400 MHz) delta 8.12 (d, J=8.8 Hz, 4H, Ar), 7.98-7.73 (m, 12H, Ar), 7.60-7.51 (m, 8H, Ar); 13C NMR (CDCl3, 67.8 MHz) delta 162.9, 157.9, 144.6, 132.7, 131.7, 130.9, 128.7, 122.3, 121.4, 121.0, 107.3, 55.4. Anal. Calcd for C48H32O12: C 72.00, H 4.03; found: C 71.72, H 4.09; MS (ESI) m/z: 807.32 [M+Li]; 839.41 [M+K]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone; for 6.0h;Reflux; | Example 2b: 3,7-dimethoxy-2-naphthoic acid3 -hydroxy-7-methoxy-2 -naphthoic acid (1.00 g, 4.58 mmol) was dissolved in anhydrous acetone (lOOmL) and potassium carbonate (4.00 g, 29.8 mmol) was added follow by dimethyl sulfate (1.50 g, 11.9 mmol). The mixture was refluxed for 6 h and cooled own to room temperature. Water (2mL) was added and the mixture was stirred at room temperature for 2 h. Insoluble material were removed by filtration. After removing acetone from the filtrate, the residue was dissolved in DCM and washed with water, dried over MgSC^ and concentrated under vacuum to give a yellow solid that was used in the next step without furtherpurification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 25 - 60℃; for 12.0h; | To a solution of <strong>[143355-56-0]3-hydroxy-7-methoxynaphthalene-2-carboxylic acid</strong> (5 g, 22.91 mmol) in /V,/V-dimcthylformamidc (50 mL) was added sodium bicarbonate (3.85 g, 45.8 mmol) and benzyl bromide (4.09 mL, 34.4 mmol) in order at 25 C. The mixture was heated to 60 C and stirred for 12 hours at 60 C. The reaction was quenched with water (100 mL). The mixture was extracted with ethyl acetate (3 x 150 mL). The combined organic layers were washed with brine (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (7 g, 20.43 mmol, 89% yield). JH NMR (400 MHz, D SO-cL) d ppm 10.10 (s, 1H), 8.40 (s, 1H), 7.68 (s, 1H), 7.54 (s, 2 H), 7.43 (br d, / = 7.50 Hz, 4 H), 7.31 (s, 1H), 7.19 - 7.24 (m, 1H), 5.44 (s, 2 H), 3.82 (s, 1H); MS (ESI+) m/z 309 (M+H)+. |
Tags: 143355-56-0 synthesis path| 143355-56-0 SDS| 143355-56-0 COA| 143355-56-0 purity| 143355-56-0 application| 143355-56-0 NMR| 143355-56-0 COA| 143355-56-0 structure
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