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CAS No. : | 25700-11-2 | MDL No. : | MFCD09033534 |
Formula : | C8H7N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XXTPHXNBKRVYJI-UHFFFAOYSA-N |
M.W : | 145.16 | Pubchem ID : | 5324086 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.36 |
TPSA : | 30.71 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) : | 1.8 |
Log Po/w (XLOGP3) : | 1.15 |
Log Po/w (WLOGP) : | 1.27 |
Log Po/w (MLOGP) : | 0.94 |
Log Po/w (SILICOS-IT) : | 1.09 |
Consensus Log Po/w : | 1.25 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.14 |
Solubility : | 1.06 mg/ml ; 0.00727 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.39 |
Solubility : | 5.92 mg/ml ; 0.0408 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.53 |
Solubility : | 0.427 mg/ml ; 0.00294 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 |
---|---|---|
87% | for 8 h; Reflux | (Pyr-N-PzH) Compound 3 To a 250 mL single-neck round bottomed flask were charged 15.0 g (95 mmol) of 2-bromopyridine, 25.0 g (367 mmol, 3.86 eq.) of pyrazole, and 45 mL of xylenes. The mixture was heated at reflux for eight hours, then was cooled to room temperature. The resulting mixture was dissolved in dichloromethane, and the organic layer washed four times with 250 mL of water (until no pyrazole was observed by GC). Drying over magnesium sulfate, filtering and rotary evaporation gave 12.0 g (82.6 mmol, 87percent) of the product as a white solid. 1H NMR (400 MHz, CDCl3) 8.59 (m, 1H, Pyridyl 6-H), 8.39 (s, 1H, Pyrazole 5-H), 7.90 (d, 1H, Pyridyl 3-H), 7.80 (m, 1H, Pyridyl 4-H), 7.73 (s, 1H, Pyrazole 3-H), 7.15 (s, 1H, Pyridyl 5-H), 6.45 (m, 1H, Pyrazole 4-H). |
75% | With potassium hydroxide In dimethyl sulfoxide at 120℃; for 24 h; | Dry DMSO (4 mL) was added to a mixture of 1H-pyrazole (340 mg, 5.00 mmol), 2-bromopyridine (790 mg, 5.00 mmol) and KOH (700 mg, 12.5 mmol) and heated at 120 °Cfor 24 h. The reaction mixture was quenched with saturated solution of NH4Cl and extractedwith EtOAc. The organic phase was dried over anhydrous Na2SO4, followed by evaporationunder reduced pressure to remove the solvent. Purification of the crude reaction mixture byflash column chromatography using 2.5percent acetone in petroleum ether afforded the titledcompound as low melting white solid (544 mg, 75percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24 h; Inert atmosphere | General procedure: The N-nucleophile (0.735mmol), Cu2O (0.0735mmol), Cs2CO3 (1.47mmol), DMSO (0.3mL) and heteroaryl halide (1.103mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100°C for 24h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of the products was confirmed by 1H, 13C NMR spectroscopic analysis and elemental analysis or mass spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With copper(l) iodide; manganese(II) fluoride; (1R,2R)-1,2-diaminocyclohexane; potassium hydroxide In water at 100℃; for 48 h; | General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999percent purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98percent purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With hydrogenchloride In ethanol; water | EXAMPLE 176 (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester To a stirring solution of 2-pyridylhydrazine (3.30 g, 30.2 mmol) and malonaldehyde bis (dimethylacetal) (4.96 g, 30.2 mmol) in absolute ethanol (60 mL) at room temperature was added concentrated HCl until the mixture was acidic (3 mL). The mixture was heated at reflux for 3 h, and was allowed to cool to room temperature. The mixture was concentrated with a rotary evaporator, and the residue was triturated with ether and filtered. The remaining solid was dissolved in water, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (sodium sulfate), and concentrated with a rotary evaporator to afford 3.10 g (70percent) of 1-(pyrid-2-yl)pyrazole. 1 H NMR (CDCl3) δ6.48 (dd, 1, J=1, 2), 7.20 (dd, 1, J=8, 10), 7.75 (d, 1, J=l), 7.82 (dt, 1, J=2, 10), 8.00 (d, 1, J=10), 8.42 (dd, 1, J=2, 8), 8.59 (d, 1, J=2). |
70% | With hydrogenchloride In ethanol; water | EXAMPLE 176 (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester To a stirring solution of 2-pyridylhydrazine (3.30 g, 30.2 mmol) and malonaldehyde bis(dimethylacetal) (4.96 g, 30.2 mmol) in absolute ethanol (60 mL) at room temperature was added concentrated HCl until the mixture was acidic (3 mL). The mixture was heated at reflux for 3 h, and was allowed to cool to room temperature. The mixture was concentrated with a rotary evaporator, and the residue was triturated with ether and filtered. The remaining solid was dissolved in water, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (sodium sulfate), and concentrated with a rotary evaporator to afford 3.10 g (70percent) of 1-(pyrid-2-yl)pyrazole. 1 H NMR (CDCl3) δ6.48 (dd, 1, J=1, 2), 7.20 (dd, 1, J=8, 10), 7.75 (d, 1, J=1), 7.82 (dt, 1, J=2, 10), 8.00 (d, 1, J=10), 8.42 (dd, 1, J=2, 8), 8.59 (d, 1, J=2). |
70% | With hydrogenchloride In ethanol; water | Example 176 (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester To a stirring solution of 2-pyridylhydrazine (3.30 g, 30.2 mmol) and malonaldehyde bis(dimethylacetal) (4.96 g, 30.2 mmol) in absolute ethanol (60 mL) at room temperature was added concentrated HCl until the mixture was acidic (3 mL). The mixture was heated at reflux for 3 h, and was allowed to cool to room temperature. The mixture was concentrated with a rotary evaporator, and the residue was triturated with ether and filtered. The remaining solid was dissolved in water, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (sodium sulfate), and concentrated with a rotary evaporator to afford 3.10 g (70percent) of 1-(pyrid-2-yl)pyrazole. 1 H NMR (CDCl3) δ6.48 (dd, 1, J=1, 2), 7.20 (dd, 1, J=8, 10), 7.75 (d, 1, J=1), 7.82 (dt, 1, J=2, 10), 8.00 (d, 1, J=10), 8.42 (dd, 1, J=2, 8), 8.59 (d, 1, J=2). |
70% | With hydrogenchloride In ethanol; water | EXAMPLE 176 (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester To a stirring solution of 2-pyridylhydrazine (3.30 g, 30.2 mmol) and malonaldehyde bis(dimethylacetal) (4.96 g, 30.2 mmol) in absolute ethanol (60 mL) at room temperature was added concentrated HCl until the mixture was acidic (3 mL). The mixture was heated at reflux for 3h, and was allowed to cool to room temperature. The mixture was concentrated with a rotary evaporator, and the residue was triturated with ether and filtered. The remaining solid was dissolved in water, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (sodium sulfate), and concentrated with a rotary evaporator to afford 3.10 g (70percent) of 1-(pyrid-2-yl)pyrazole. 1 H NMR (CDCl3) δ6.48 (dd, 1, J=1, 2), 7.20 (dd, 1, J=8, 10), 7.75 (d, 1, J=l), 7.82 (dt, 1, J=2, 10), 8.00 (d, 1, J=10), 8.42 (dd, 1, J=2, 8), 8.59 (d, 1, J=2). |
70% | With hydrogenchloride In ethanol; water | Example 176 (7R)-7-[(phenylacetyl)amino]-3-(1-(pyrid-2-yl)pyrazol-5-ylthio)-3-cephem-4-carboxylate, 4-methoxybenzyl ester To a stirring solution of 2-pyridylhydrazine (3.30 g, 30.2 mmol) and malonaldehyde bis(dimethylacetal) (4.96 g, 30.2 mmol) in absolute ethanol (60 mL) at room temperature was added concentrated HCl until the mixture was acidic (3 mL). The mixture was heated at reflux for 3 h, and was allowed to cool to room temperature. The mixture was concentrated with a rotary evaporator, and the residue was triturated with ether and filtered. The remaining solid was dissolved in water, basified with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were washed with water and brine, dried (sodium sulfate), and concentrated with a rotary evaporator to afford 3.10 g (70percent) of 1-(pyrid-2-yl)pyrazole. 1 H NMR (CDCl3) δ 6.48 (dd, 1, J=1, 2), 7.20 (dd, 1, J=8, 10), 7.75 (d, 1, J=1), 7.82 (dt, 1, J=2, 10), 8.00 (d, 1, J=10), 8.42 (dd, 1, J=2, 8), 8.59 (d, 1, J=2). |
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