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CAS No. : | 4434-13-3 | MDL No. : | MFCD01704358 |
Formula : | C7H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HWMYXZFRJDEBKC-UHFFFAOYSA-N |
M.W : | 137.14 | Pubchem ID : | 199575 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.16 |
TPSA : | 50.19 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) : | -6.37 cm/s |
Log Po/w (iLOGP) : | 0.98 |
Log Po/w (XLOGP3) : | 1.08 |
Log Po/w (WLOGP) : | 1.09 |
Log Po/w (MLOGP) : | -0.78 |
Log Po/w (SILICOS-IT) : | 1.17 |
Consensus Log Po/w : | 0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.75 |
Solubility : | 2.45 mg/ml ; 0.0178 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.73 |
Solubility : | 2.58 mg/ml ; 0.0188 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.76 |
Solubility : | 2.41 mg/ml ; 0.0175 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.39 |
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 |
---|---|---|
59% | With hydrogenchloride In 1,4-dioxane at 20 - 70℃; | 15 ml (60 mmol) of a 4M solution of hydrogen chloride in dioxane were added dropwise to 3.00 g (21.9 mmol) of 5-methylpyridine-2-carboxylic acid in 40 ml of methanol, and the mixture was stirred at room temperature overnight. 10 ml (40 mmol) of a 4M solution of hydrogen chloride in dioxane were then added dropwise, and the mixture was initially stirred at room temperature overnight and then at 70° C. overnight. Methanol and a further 20 ml (80 mmol) of a 4M solution of hydrogen chloride in dioxane were added and the mixture was stirred at reflux overnight. The mixture was then concentrated under reduced pressure, and water and dichloromethane were added to the residue. After phase separation, the aqueous phase was washed twice with dichloromethane and the combined organic phases were washed with sodium chloride solution and then dried over sodium sulphate. After filtration, the filtrate was concentrated under reduced pressure and the residue was dried under high vacuum. This gave 2.08 g (59percent of theory) of the desired product. LC-MS (Method 1A): Rt=0.55 min; MS (ESIpos): m/z=152 [M+H]+ |
2.08g | With hydrogenchloride In 1,4-dioxane at 20 - 70℃; Reflux | The 15ml (60mmol) in dioxane was added dropwise a 4M solution of hydrogen chloride in 40ml of methanol 3.00g (21.9mmol) of 5-methyl-pyridine-2-carboxylic acid, and the mixture was stirred overnight at room temperature .Then added dropwise 10ml (40mmol) in dioxane solution of 4M hydrogen chloride, and the mixture was stirred first overnight at room temperature and then stirred overnight at 70 .The methanol and additional 20ml (80mmol) of 4M solution of hydrogen chloride in dioxane was added and the mixture was stirred overnight at reflux.The mixture was then concentrated under reduced pressure, and water and dichloromethane were added to the residue.After the phases were separated, the aqueous phase was washed with dichloromethane and washed twice and the combined organic phases were washed with sodium chloride solution and then dried over sodium sulfate.After filtration, the filtrate was concentrated and the residue was dried under high vacuum under reduced pressure.The thus obtained 2.08g (59percent, based on the theoretical value) of the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.4 g | Stage #1: for 17 h; Reflux; Inert atmosphere Stage #2: at 0 - 20℃; for 2 h; Inert atmosphere |
To a mixture of 5-methylpicolinic acid (13.7 g) and thionyl chloride (150 mL) was added sodium bromide (20.6 g) by small portions, and the mixture was heated under reflux under a nitrogen atmosphere for 1 hr. DMF (2 mL) was added and the mixture was further heated under reflux under a nitrogen atmosphere for 16 hr. An operation to add toluene (100 mL) to the reaction mixture and evaporate the solvent under reduced pressure was repeated twice, and toluene (100 mL) was added to the obtained residue. To a mixture thereof were added DIPEA (25.8 g) and methanol (20 mL) under a nitrogen atmosphere at 0°C, and the mixture was further stirred at 20°C for 2 hr. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.40 g). 1H NMR (400 MHz, CDCl3) δ2.43 (3H, s), 3.99 (3H, s), 8.10 (1H, s), 8.54 (1H, s). |
220 mg | Stage #1: at 72℃; for 12 h; Stage #2: at 30℃; for 2 h; |
To a stirred solution of 5-methylpicolinic acid (2.5 g, 18 mmol) in 50C12 (10 mL) was slowly added DMF (21.3 mg, 3 mmol). The resulting solution was heated to 72 oC for 12h. After cooling to room temperature, the mixture was diluted with toluene and concentrated to near dryness in vacuo. MeOH was added to the obtained oily residue. The contents were stirred for 2 h at 30 oC. After filtration, aq.15percent Na2CO3 was added to the filter cake to adjust its pH to 7, and then washed with cold MeOH to afford the title compound (220 mg). MS (ES) m/z 186 (M+H). |
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