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CAS No. : | 22282-72-0 | MDL No. : | MFCD01318566 |
Formula : | C6H5NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BXHCJLRTXPHUGH-UHFFFAOYSA-N |
M.W : | 139.11 | Pubchem ID : | 280756 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 34.02 |
TPSA : | 70.16 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) : | -7.54 cm/s |
Log Po/w (iLOGP) : | 0.62 |
Log Po/w (XLOGP3) : | -0.55 |
Log Po/w (WLOGP) : | 0.07 |
Log Po/w (MLOGP) : | -0.15 |
Log Po/w (SILICOS-IT) : | 0.89 |
Consensus Log Po/w : | 0.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.73 |
Solubility : | 25.7 mg/ml ; 0.185 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.45 |
Solubility : | 48.9 mg/ml ; 0.352 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.28 |
Solubility : | 7.33 mg/ml ; 0.0527 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
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 |
---|---|---|
85% | With hydrogen; palladium(II) hydroxide In methanol at 20℃; for 18 h; Autoclave | To a stirred solution of 2-oxo-l,2-dihydropyridine-4-carboxylic acid (SMI) (500 g, 3.59 mol) in methanol (10 L) was added palladium hydroxide (150 g) into a 20 L autoclave under N2 atmosphere. The reaction mixture was stirred under atmosphere (5 kg/ cm2) at RT for 18 h. After consumption of the starting material (monitored by LCMS), the reaction mixture was filtered through a pad of celite and concentrated under reduced pressure. Obtained reside was triturated with diethyl ether (2.5 L) and dried under vacuum to afford compound 1 (450 g, 85 percent) as off white solid. 1H NMR (500 MHz, DMSO-d6): δ 12.37 (s, 1H), 7.44 (s, 1H), 3.16-3.12 (m, 2H), 2.78-2.71 (m, 1H), 2.33-2.21 (m, 2H), 1.98-1.92 (m, 1H), 1.74-1.63 (m, 1H). LCMS (m/z): 144.2 [M++1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38 g | With palladium 10% on activated carbon; hydrogen In methanol at 30℃; for 24 h; | A solution of 2-hydroxypyridine-4-carboxylic acid (40.0 g) and 10percent palladium hydroxide/carbon (8.0 g) in methanol (500 mL) was stirred at 30°C for 24 hr under a hydrogen atmosphere (50 psi) . The reaction mixture was filtered, the catalyst was removed, and the filtrate was concentrated under reduced pressure to give the title compound (38.0 g) .XH NMR (400 MHz, CDC13) δ 1.64-1.73 (1H, m) , 1.92-1.99 (1H, m) , 2.20-2.32 (2H, m) , 2.71-2.78 (1H, m) , 3.11-3.17 (2H, m) , 7.50 (1H, s) , 12.49 (1H, brs) .MS (ESI+) : [M-l]+ 142. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Stage #1: at 0 - 20℃; Stage #2: With hydrogenchloride In acetic acid methyl ester at 20℃; for 16 h; |
A. Methyl 2-oxo-l,2-dihydropyridine-4-carboxylate[0095] To MeOH (80 mL) at 00C was slowly added acetyl chloride (20.45 mL, 288 mmol) while stirring. The resulting solution was allowed to warm to RT and stirred for 30 min. To the resulting HCl/MeOH/MeOAc solution was added 2- hydroxyisonicotinic acid (4.00 g, 28.8 mmol) in one portion, and the mixture was stirred at ambient temperature for 16h. The mixture was concentrated and the residue was stripped from MeOH (10 mL). The crude product was purified by chromatography (silica gel 230-400 mesh, solvent gradient 0-20percent MeOH/CH2Cl2) to afford IA (3.40 g, 22.20 mmol, 77 percent yield) as a yellow solid. LC-MS, [M + H]+ = 154. |
3.5 g | at 0 - 20℃; | Example 170 1- (2-Cyclopropyl-3-methylimidazo [1, 2-a] pyridin-6-yl) -4- ( (4- fluorophenoxy) methyl) pyridin-2 ( 1H) -one A) Methyl 2-oxo-l, 2-dihydropyridine-4-carboxylate To a stirred solution of 2-hydroxypyridine-4-carboxylic acid (5.0 g) in MeOH (50 ml) was added acetyl chloride (26 ml) dropwise at 0°C over 15 min. The reaction mixture was slowly warmed to room temperature, and stirred for 20 h. The reaction mixture was concentrated in vacuo, and diluted with EtOAc and water. The organic layer was washed with saturated NaHCC>3 solution, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to afford the title compound (3.5 g) as an off-white solid. MS (ESI+) : [M+H]+ 154.0. |
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