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CAS No. : | 65515-39-1 | MDL No. : | MFCD00124716 |
Formula : | C9H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WEJLKGQPSKTCBR-UHFFFAOYSA-N |
M.W : | 162.19 | Pubchem ID : | 595276 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.38 |
TPSA : | 45.91 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) : | -6.12 cm/s |
Log Po/w (iLOGP) : | 2.2 |
Log Po/w (XLOGP3) : | 1.64 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 0.57 |
Log Po/w (SILICOS-IT) : | 2.22 |
Consensus Log Po/w : | 1.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.18 |
Solubility : | 1.06 mg/ml ; 0.00656 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.22 |
Solubility : | 0.984 mg/ml ; 0.00607 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.0 |
Solubility : | 0.161 mg/ml ; 0.000993 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.93 |
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 |
---|---|---|
100% | for 1 h; | Add a solution of NaOCH3 in MeOH (30 mass percent, 175 mL, 940 mmol) drop wise to a solution of 2-chloro-4,6-dimethyl-pyridine-3 -carbonitrile (75 g, 441.1 mmol) inMeOH (450 mL) in a water bath followed by another drop wise addition of NaOCH3 in MeOH (25 mass percent, 250 mL, 1090 mmol). Stir the resulting mixture for 1 hr, pour in ice cold water, stir for 30 mm, and filter the resulting solid. Wash filter cake with hexane and dry in a vacuum oven overnight. Extract the aqueous filtrate with DCM, dry the organic phase over Mg504, filter and concentrate in vacuo. Combine the filtered solid and theevaporated residue to afford title compound as a solid (71.8 g, quantitative yield). ES/MS (mlz): 163 (M+H). |
99% | at 0℃; for 10 h; | 2-chloro-4,6-dimethyl-nicotinonitrile (2.5 g, 15.01 mmol) was dissolved in anhydrous methanol (70mL), added with sodium methoxide (4. 27 g, 75.03 mmol) at 0 °C and stirred for about 10 hours at nitrogen atmosphere. The above mixture was concentrated under reduced pressure and then neutrailized with a saturated solution of ammonium chloride and then extracted twice with 150 mL of methylenechloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (20percent EtOAc/Hexanes) was performed on the resulting residue and 2.41g (99percent) of 2- methoxy-4, 6-dimethyl-nicotinonitrile was obtained in white solid. 'H NMR (300 MHz, CDC13) 8 2.44 (s, 3H), 2.45 (s, 3H), 4.01 (s, 3H), 6.68 (s, 1H). |
65% | at 60℃; for 4 h; | Step 2: 3-Cyano-4,6-dimethyl-2-methoxypyridine: A solution of 2-chloro-3-cyano-4,6- dimethylpyridine (4.60 g, 27.7 mmol) in methanol (30 mL) is added to a stirred solution of sodium methoxide (2.09 g, 38.78 mmol) in methanol (20 mL) and the reaction mixture is heated at 60°C for 4 hr. After cooling, the reaction is diluted with water (150 mL) and the solids are collected by filtration, washed with water and dried to yield 3-cyano-4,6-dimethyl-2- methoxypyridine (2.90 g, 65percent) as an off-white solid containing the same impurity as the starting material. LC/MS: MS m/e = 163 (M + H) ; RT 3.29 min; 1H NMR (CDCl3, 8 ppm) 6.69, (1H, s), 4.00 (3H, s), 2.43 (6H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 70℃; for 4 h; | Sodium (23 g, 0.99 mol) was added to dry MeOH (800 mL) portion-wise. After the addition, the mixture was stirred for an hour until the sodium was mostly dissolved. To the reaction mixture was added 2-chloro-4,6-dimethylpyridine-3-carbonitrile (110 g, 0.66 mol). The resulting mixture was heated at 70° C. and stirred for four hours. The suspension was filtered and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc, 10:1) to give 2-methoxy-4,6-dimethylpyridine-3-carbonitrile (Cpd S, 103 g, 100percent) as a white solid. |
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