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CAS No. : | 1174046-84-4 | MDL No. : | MFCD18911742 |
Formula : | C10H13NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CKTIVXCUXUFKSO-UHFFFAOYSA-N |
M.W : | 211.22 | Pubchem ID : | 53393185 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.45 |
TPSA : | 68.39 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) : | -7.1 cm/s |
Log Po/w (iLOGP) : | 1.92 |
Log Po/w (XLOGP3) : | 0.69 |
Log Po/w (WLOGP) : | 0.95 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | 2.06 |
Consensus Log Po/w : | 1.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.55 |
Solubility : | 5.95 mg/ml ; 0.0282 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.7 |
Solubility : | 4.18 mg/ml ; 0.0198 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.95 |
Solubility : | 0.235 mg/ml ; 0.00111 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
67% | Reflux | [01 03j A mixture of ethyl 2-cyano-5 -(dimethylamino)-3 -ethoxypenta-2,4-dienoate (15 Og, 0.63 mol) and HOAc (600 mL) was refluxed overnight. The mixture was cooled to RT, concentrated to dryness, treated with water and washed with EtOAc (2x). The aqueous layer was made basic (pH=9-10) with NaHCO3, extracted with DCM (3x) and the combined organics were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo- 1 ,2-dihydropyridine-3 -carboxylate (90 g, 67percent yield). |
66.6% | Stage #1: Reflux Stage #2: With sodium hydrogencarbonate In water |
A mixture of ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate (150g, 0.63 mol) and HOAc (600 mL) was refluxed overnight. The mixture was concentrated to dryness under high vacuum and the residue treated with water (300 mL). The mixture was extracted with EtOAc (2 x 250 mL) to remove the impurities. The pH of the aqueous was adjusted with NaHC03 to pH - 9- 10. The mixture was extracted with CH2C12 (3 x 300 mL). The combined organics were washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo- l ,2- dihydropyridine-3-carboxylate (90 g, 66.6percent yield). |
90 g | Reflux | A mixture of ethyl 2-cyano-5-(dimethylamino)-3-ethoxypenta-2,4-dienoate (150g, 0.63 mol) and HOAc (600 mL) was refluxed overnight. The mixture was concentrated to dryness under high vacuum, treated with water (300 mL) and washed with EtOAc (2 x 250 mL) to remove the impurities. The pH of the aqueous was adjusted with NaHC03 to pH - 9-10. The mixture was extracted with DCM (3 x 300 mL). The combined organics were washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography to afford ethyl 4-ethoxy-2-oxo-l ,2-dihydropyridine-3-carboxylate (90 g, 66.6percent yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | Stage #1: at 120℃; for 12 h; Stage #2: at 70℃; for 2 h; |
Ethyl cyanoacetate 70.5 mL (0.66 mol) of triethyl ortho-acetate in 249.6 mL (1.32 mmol), acetic acid 19.6 mL (0.33 mol) into a 120 after 12 hours stirring. Concentrating the solvent of the reaction mixture, it was added DEA-DMF (N, N- dimethylformamide diethyl acetal) 141 mL (0.55 mol). At 70 was stirred for at least 2 hours. To the reaction mixture Place 500 mL of distilled water and 60 mL of acetic acid was refluxed for 12 hours or more. The reaction mixture was cooled to ambient temperature, it was added a saturated aqueous solution of sodium hydrogen carbonate and water. Of dichloromethane and methanol, 9: 1 and extracted with a mixed solvent. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Add 100 mL ethyl acetate and concentrated. At this time, the generated gas by filtration to give the compound methyl 4-methoxy-2-oxo-1,2-dihydropyridine-3-carboxylate 37 g (26percent). |
26% | Stage #1: at 120℃; for 12 h; Stage #2: at 70℃; for 2 h; Stage #3: With acetic acid In water for 12 h; Reflux |
Ethyl cyanoacetate (70.5 mL, 0.66 mol) was added with triethyl orthoacetate (249.6 mL, 1.32 mmol) and acetic acid (19.6 mL, 0.33 mol) and stirred at 120°C for at least 12 hours. The solvent of the reaction mixture was concentrated and added with N,N-dimethylformamide diethylacetal (DMF-DEA) (141 mL, 0.55 mol) and stirred at 70°C for at least 2 hours. The reaction mixture was added with acetic acid (500 mL) and distilled water (60 mL) and refluxed for at least 12 hours. The reaction mixture was cooled to room temperature and added with a saturated aqueous solution of sodium hydrogen carbonate and water. The resultant was extracted using a mixed solvent (dichloromethane : methanol = 9 : 1). The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resultant was added with ethyl acetate (100 mL) and concentrated. The thus-obtained solid was filtered to obtain 37 g (26percent) of ethyl 4-ethoxy-2-oxo-1,2-dihydropyridin-3-carboxylate. |
26% | Stage #1: at 120℃; for 12 h; Stage #2: at 70℃; for 2 h; Stage #3: With acetic acid In water for 12 h; Reflux |
Ethyl cyanoacetate (70.5 mL, 0.66 mol) was added with triethyl orthoacetate (249.6 mL, 1.32 mmol) and acetic acid (19.6 mL, 0.33 mol) and stirred at 120° C. for at least 12 hours. The solvent of the reaction mixture was concentrated and added with N,N-dimethylformamide diethylacetal (DMF-DEA) (141 mL, 0.55 mol) and stirred at 70° C. for at least 2 hours. The reaction mixture was added with acetic acid (500 mL) and distilled water (60 mL) and refluxed for at least 12 hours. The reaction mixture was cooled to room temperature and added with a saturated aqueous solution of sodium hydrogen carbonate and water. The resultant was extracted using a mixed solvent (dichloromethane:methanol=9:1). The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resultant was added with ethyl acetate (100 mL) and concentrated. The thus-obtained solid was filtered to obtain 37 g (26percent) of ethyl 4-ethoxy-2-oxo-1,2-dihydropyridin-3-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ 11.61 (bs, 1H), 7.46 (d, J=7.6 Hz, 1H), 6.21 (d, J=7.6 Hz, 1H), 4.++14 (m, 4H), 1.22 (m, 6H) MS: 212 [M+H]+ |
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