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CAS No. : | 86604-78-6 | MDL No. : | MFCD01076195 |
Formula : | C9H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PSEPRWKZZJWRCB-UHFFFAOYSA-N |
M.W : | 167.21 | Pubchem ID : | 737823 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.44 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 46.79 |
TPSA : | 42.35 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) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 1.91 |
Log Po/w (XLOGP3) : | 0.7 |
Log Po/w (WLOGP) : | 1.05 |
Log Po/w (MLOGP) : | 0.26 |
Log Po/w (SILICOS-IT) : | 2.09 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.56 |
Solubility : | 4.65 mg/ml ; 0.0278 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.17 |
Solubility : | 11.4 mg/ml ; 0.0681 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.75 |
Solubility : | 0.298 mg/ml ; 0.00178 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
83% | With potassium iodide; sodium hydroxide In methanol; water for 4 h; Reflux | Take 80 g of 2- (chloromethyl) -4-methoxy-3,5-dimethylpyridine hydrochloride,Add 300 mL of methanol,150 mL water,5.4 g Potassium iodide,40.4 g sodium hydroxide,Stirring heated to reflux, the reaction 4 h.Remove the methanol by rotary evaporation, add 300 mL of drinking water and extract with methylene chloride (150 mL × 3). Combine the organic phases. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated,50.0 g red oily liquid. Yield 83.0percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With sodium methylate In <i>N</i>-methyl-acetamide; methanol; water | EXAMPLE 8 Synthesis 2-hydroxymethyl-4-Methoxy-3,5-Lutidine In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes). Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100.image. C.). At the end of the reaction the solvent was distilled under vacuum. Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2*4 volumes). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55percent yield. In another work-up method, after evaporation of the dimethylformamide/methanol, water (2 volumes was added to the residue and the product was extracted with toluene (3*4 volumes). The organic extracts were combined and while cooling and stirring HCl gas (1.2 eq.) was bubbled into solution. The product 2-hydroxymethyl-4-Methoxy-3,5-lutidine hydrochloride salt was filtered and washed with toluene. The crude product was obtained as a white solid in 50percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With thionyl chloride In dichloromethane at 20℃; for 1 h; | To a solution [OF 4-METHOXY-3, 5-DIMETHYLPYRIDINEMETHANOL] (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0. [158] mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100percent) of the title compound as a white solid. |
100% | With thionyl chloride In dichloromethane at 20℃; for 1 h; | To a solution of 4-methoxy-3,5-dimethylpyridinemethanol (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100percent) of the title compound as a white solid. |
98% | With bis(trichloromethyl) carbonate; Triphenylphosphine oxide In toluene at 20 - 60℃; for 6 h; | Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel,BTC was added dropwise at room temperature,After the drop, the temperature is raised to 60 ° C.After incubation for 4 hours,2-hydroxymethyl-4-methoxy-3,5-dimethylpyridine (25.05 g, 150 mmol)Dissolved in toluene 75mL, at 40 ° C added to precipitate a white solid, incubation reaction 2 hours after stopping the reaction,The product was obtained by filtration to obtain a white solid which was dried to give 32.49 g of 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride, the product yield was 98percent |
86% | With thionyl chloride In <i>N</i>-methyl-acetamide; dichloromethane; ethyl acetate | EXAMPLE 3 2-CHLOROMETHYL-3,5-DIMETHYL-4-METHOXYPYRIDINE HYDROCHLORIDE 27.17 g (0.163 mole) of 2-hydroxymethyl-3,5-dimethyl-4methoxypyridine were dissolved in 48 ml of methylene chloride, 1.7 ml of dimethylformamide were added and thereafter 17.3 ml (0.238 mole) of thionyl chloride were added over 25 minutes, while holding the temperature to 25°-28° C. Stirring was continued for a further 15 minutes at 20°-25° C. and the CH2 Cl2 was removed by distillation until a thick paste was formed. 96 ml of ethyl acetate were added, the temperature was allowed to reach room temperature and stirring was continued for 15 minutes. The mixture was filtered and washed with ethyl acetate, to give 31.06 g of a white solid. Yield 86percent. |
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