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CAS No. : | 30062-34-1 | MDL No. : | MFCD17015470 |
Formula : | C7H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJLWQAUHCDNAEK-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 12342664 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.34 |
TPSA : | 59.16 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) : | -7.04 cm/s |
Log Po/w (iLOGP) : | 1.54 |
Log Po/w (XLOGP3) : | 0.27 |
Log Po/w (WLOGP) : | 0.16 |
Log Po/w (MLOGP) : | 0.2 |
Log Po/w (SILICOS-IT) : | 1.34 |
Consensus Log Po/w : | 0.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.23 |
Solubility : | 8.99 mg/ml ; 0.0587 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.07 |
Solubility : | 12.9 mg/ml ; 0.0844 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.99 |
Solubility : | 1.56 mg/ml ; 0.0102 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
---|---|---|
90% | With hydrogenchloride In 1,4-dioxane at 20℃; for 48 h; | Step 1: Synthesis of methyl 6-hydroxypicolinate0OH MeOH. HCIrt,2dOHTo a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCI in dioxane (4N, 10 mL). The resulting mixture wasstirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid. |
90% | With hydrogenchloride In 1,4-dioxane at 20℃; for 48 h; | To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCl in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid. |
90% | With hydrogenchloride In 1,4-dioxane at 20℃; for 48 h; | To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCI in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid. |
90% | With hydrogenchloride In 1,4-dioxane at 20℃; for 48 h; | To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCl in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid. |
87% | for 20 h; Reflux | General procedure: 4-Hydroxypicolinic acid 3 (348 mg, 2.5 mmol) was added to methanol (25 mL), and then concentrated sulfuric acid (0.2 mL). The mixture was refluxed for 20 h, then the solvent was evaporated under vacuum. The residue was neutralized with saturated aqueous sodium bicarbonate solution, extracted with DCM/MeOH (10/1, 5×30 mL), dried over anhydrous Na2SO4, concentrated under vacuum to give compound 4 (196 mg, 51percent) as a white solid. 1H NMR (400 MHz, Methanol-d4) δ 7.92 (d, J = 7.0 Hz, 1H), 7.14 (s, 1H), 6.63 (d, J = 7.0 Hz, 1H), 3.99 (s, 3H). MS (ESI) m/z = 154.1 ([M+H]+). To a solution of compound 4 (77 mg, 0.5mmol) in DMF (2 mL) was added potassium carbonate (104 mg, 0.75 mmol), then 1,4-dibromobutane (325 mg, 1.5 mmol) at 0°C. The mixture was stirred at room temperature for 3 h, and then partitioned between water (30 mL) and ethyl acetate (EA, 30 mL). The organic phase was washed with water (3×30 mL), saturated brine (30 mL), dried over anhydrous Na2SO4, concentrated under vacuum, purified by column chromatography using DCM : MeOH (100:1) as eluent to give 5 (95 mg, 66percent) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (d, J = 5.6 Hz, 1H), 7.55 (d, J = 2.6 Hz, 1H), 7.22 (dd, J = 5.7, 2.6 Hz, 1H), 4.19 (t, J = 6.2 Hz, 2H), 3.62 (t, J = 6.5 Hz, 2H), 1.98 (p, J = 6.7 Hz, 2H), 1.92 – 1.83 (m, 2H). MS (ESI) m/z = 288.2 ([M+H]+). Corresponding arylpiperazine (arylpiperidine) (0.24 mmol), 5 (90 mg, 0.31 mmol), potassium carbonate (83 mg, 0.6mmol) and potassium iodide (40 mg, 0.24 mmol) were added to acetonitrile (5 mL). The reaction mixture was refluxed overnight, cooled to room temperature, partitioned between EA and water. The organic layer was dried over anhydrous Na2SO4, concentrated under vacuum to give 6a–6e which was used directly in the next step without further purification. |
36% | at 65℃; | A solution of 6-hydroxypyridine-2-carboxylic acid (5.00 g, 35.94 mmol, 1.00 equiv) in methanol (100 mL) and sulfuric acid (20 mL). was stirred overnight at 65 °C. The resulting reaction mixture was concentrated under reduced pressure, diluted with water (200 mL) and the solid precipitate was collected by filtration and washed with water and aqueous NaHC03. The filter cake was dissolved in ethyl acetate (20 mL) dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 2 g (36percent) of the product as a white solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | at 110℃; for 14 h; | (a) Methyl -chloro-pyridine^-carboxylate; <n="75"/>To -hydroxy-pyridine^-carboxylic acid methyl ester (10.0 g, 71.9 mmol) was added phosphorus oxychloride (138 niL). The mixture was heated in an oil bath at 110 0C for 14 h and the excess phosphorus oxychloride was removed in vacuo. The resulting residue was cooled in an ice bath and anhydrous methanol (146 mL) was slowly added. After 15 min, half of the methanol was removed in vacuo and water (208 mL) was added. The solution was cooled in an ice bath and the precipitate was collected. The solid was dissolved in ethyl acetate and this organic phase was washed with water and then a saturated sodium bicarbonate solution. The combined aqueous layers were extracted with ethyl acetate and diethyl ether. The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo generating 7.47 g (61percent yield, 43.5 mmol) of the title compound. 1H NMR (CDCl3) δ ppm 8.07 (IH), 7.82 (IH), 7.54 (IH), 4.01 (3H); MS (ESI) m/z 172 (M+l). |
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