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CAS No. : | 605-38-9 | MDL No. : | MFCD00186549 |
Formula : | C9H9NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YLGIBCYHQZTFQL-UHFFFAOYSA-N |
M.W : | 195.17 | Pubchem ID : | 69058 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.8 |
TPSA : | 65.49 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) : | -6.86 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 0.89 |
Log Po/w (WLOGP) : | 0.65 |
Log Po/w (MLOGP) : | 0.29 |
Log Po/w (SILICOS-IT) : | 1.1 |
Consensus Log Po/w : | 0.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.66 |
Solubility : | 4.23 mg/ml ; 0.0217 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.85 |
Solubility : | 2.76 mg/ml ; 0.0141 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.18 |
Solubility : | 1.28 mg/ml ; 0.00658 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.83 |
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 |
---|---|---|
95.8% | Stage #1: at 20℃; for 0.5 h; Stage #2: at 60℃; |
The compound of formula I (80g, 0.48mol) was dissolved in methanol (400ml), and stirred at rt for 30min, then a solution of concentrated sulfuric acid (94.1g, 0.96mol), the completion of the dropwise addition of about half an hour, heated to 60 , the reaction overnight.Spin dry methanol under reduced pressure, and the concentrate was slowly poured into aqueous sodium carbonate solution, there are a lot of gas evolution.PH was adjusted to 7-8, (1000ml * 2) and extracted with methylene chloride, dried over anhydrous sodium sulfate, and dried under reduced pressure to spin, to give a pale yellow solid was 89.7g, 99percent purity, yield 95.8percent. |
85.63% | at 60℃; for 10 h; | Concentrated sulfuric acid (17.61 g, 179.51 mmol, 9.57 mL, 1.50 eq) was added to a solution of pyridine-2,3-dicarboxylic acid (20.00 g, 119.67 mmol, 1.00 eq) in methanol (150.00 mL). The mixture was stirred at 60 °C for 10 hours. A sodium carbonate solution was added to adjust the pH to about 9 and the mixture was extracted with ethyl acetate (200 mL * 2). The combined organic layers were concentrated under reduced pressure and the residue was chromatographed on silica gel (SiO2, petroleum ether / ethyl acetate = 20/1 to 3: 1) to deliver dimethyl pyridine-2,3-dicarboxylate (20.00 g, 102.47 mmol, 85.63percent yield) as a white solid. |
75% | for 16 h; Reflux | Quinolinic acid (5, 15.6 g, 94.0 mmol, 1.00 eq.) was dissolved in MeOH (100 ml) and concentrated H2SO4 (10 ml) was added dropwise. The reaction mixture was heated to reflux for 16 h H2O (80 ml) was added and the mixture was adjusted to pH 8 by addition of NaOH platelets and extracted with CH2Cl2 (3 * 100 ml). The combined organic layers were dried (anhydr. Na2SO4) and the solvent was removed in vacuo. Yellow solid, yield 13.8 g (75percent). C9H9NO4 (195.2 g/mol). Mp = 55 °C. 1H NMR (600 MHz, CD3OD): δ = 3.96 (s, 3H, CH3), 3.99 (s, 3H, CH3), 7.70 (dd, J = 8.0, 4.9 Hz, 1H, 5-H), 8.35 (dd, J = 8.0, 1.6 Hz, 1H, 4-H), 8.78 (dd, J = 4.9, 1.6 Hz, 1H, 6-H). 13C NMR (151 MHz, CD3OD): δ = 55.1 (1C, CO2CH3), 55.5 (1C, CO2CH3), 126.7 (1C, 5-C), 127.5 (1C, 4-C), 139.4 (1C, 3-C), 152.0 (1C, 6-C), 152.9 (1C, 2-C), 168.2 (1C, C=O), 166.9 (1C, C=O). Exact MS (APCI): m/z = 196.0609 (calcd. 196.0604 for C9H10NO4+ [M + H+]). |
54% | Heating / reflux | To the solution of pyridine-2,3-dicarboxylic acid (50 g, 300 mmol) in MeOH (300 mL) was added SOCl2 (44 mL, 600 mmol), and the mixture was refluxed overnight. Volatiles were removed under vacuum, sat. Na2CO3 was added, and the mixture was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum to give dimethyl pyridine-2,3-dicarboxylate as a colorless oil. Yield 32 g, 54percent. |
45.7 g | for 24 h; Reflux | To a solution of pyridine-2,3-dicarboxylic acid (50.0 g, 0.299 mol) in methanol (500 ml) was added con. sulfuric acid (20 ml). After heated to reflux for 24 hours, the mixture wasbasified with saturate sodium carbonate solution until pH=8 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated to give D78 (45.7 g) as a white solid. 1H NMR (ODd3) 6 ppm = 3.95 (s, 3H), 4.01 (s, 3H), 7.51 (m, 1H), 8.18 (dd, J = 6.4, 1.6Hz, 1 H), 8.77 (dd, J = 6.8, 2.0 Hz, 1 H). |
45.7 g | for 24 h; Reflux | To a solution of pyridine-2,3-dicarboxylic acid (50.0 g, 0.299 mol) in methanol (500 ml) was added con. sulfuric acid (20 ml). After heated to reflux for 24 hours, the mixture was basified with saturate sodium carbonate solution until pH=8 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated to give D78 (45.7 g) as a white solid. 1H NMR (CDCl3) δ ppm=3.95 (s, 3H), 4.01 (s, 3H), 7.51 (m, 1H), 8.18 (dd, J=6.4, 1.6 Hz, 1H), 8.77 (dd, J=6.8, 2.0 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With dipotassium peroxodisulfate; silver trifluoromethanesulfonate In toluene at 80℃; for 6 h; Sealed tube | A mixture of propargylamine (1a, 1.0 mmol, 55.1 mg), dimethyl acetylenedicarboxylate (2a, 1.3 mmol, 185.0 mg), AgOTf (25.7 mg, 0.1 mmol) and K2S2O8 (270.0 mg, 1.0 mmol) in toluene (20 mL) in a thick-walled screw-capped Pyrex tube was stirred with a magnetic stirrer at 80 °C for 6 h. After removal of the solvent under reduced pressure, purification was performed by flash column chromatography on silica gel with petroleum ether/ethyl acetate (8:2) as eluent to afford 3aa in 93 percent yield (181.3 mg, 0.93 mmol). |
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