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CAS No. : | 4027-57-0 | MDL No. : | MFCD00233455 |
Formula : | C7H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BOTXQJAHRCGJEG-UHFFFAOYSA-N |
M.W : | 154.17 | Pubchem ID : | 77645 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.64 |
TPSA : | 54.98 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) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 1.57 |
Log Po/w (XLOGP3) : | 1.17 |
Log Po/w (WLOGP) : | 0.89 |
Log Po/w (MLOGP) : | 0.33 |
Log Po/w (SILICOS-IT) : | 1.52 |
Consensus Log Po/w : | 1.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.67 |
Solubility : | 3.29 mg/ml ; 0.0213 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.92 |
Solubility : | 1.85 mg/ml ; 0.012 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.09 |
Solubility : | 1.26 mg/ml ; 0.00817 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
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 |
---|---|---|
82.4% | With diisobutylaluminium hydride In toluene at -78℃; | Reference 4 Preparation of 3-formyl-5-methylpyrazole; Under nitrogen environment, 3-ethoxycarbonyl-5-methylpyrazole (1.0 g, 4.34 mmol) was dissolved in 15 ml of purified toluene, and DIBAL (8.68 ml, 8.62 mmol) was slowly added and stirred at -78°C. The reaction progress and completion were confirmed using TLC (hexane : EtOAc = 6 : 1). Upon completion of the reaction, MeOH and water were slowly added to the reaction mixture and the resulting mixture was filtered through a celite bed, and the aqueous layer was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane : EtOAc : CH2Cl2 = 3 : 1 : 1) to obtain the title compound. Yield: 82.4percent 1H NMR (300 MHz, CDCl3) δ 9.92 (s, 1H), 6.68 (s, 1H), 2.82 (s, 3H) |
82.4% | Stage #1: With diisobutylaluminium hydride In toluene at -78℃; Stage #2: With methanol; water In toluene |
Reference 4; Preparation of 3-formyl-5-methylpyrazole; Under nitrogen environment, 3-ethoxycarbonyl-5-methylpyrazole (1.0 g, 4.34 mmol) was dissolved in 15 ml of purified toluene, and DIBAL (8.68 ml, 8.62 mmol) was slowly added and stirred at -78° C. The reaction progress and completion were confirmed using TLC (hexane:EtOAc=6:1). Upon completion of the reaction, MeOH and water were slowly added to the reaction mixture and the resulting mixture was filtered through a celite bed, and the aqueous layer was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:1) to obtain the title compound. Yield: 82.4percent 1H NMR (300 MHz, CDCl3) δ 9.92 (s, 1H), 6.68 (s, 1H), 2.82 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | for 1 h; Heating / reflux | To a solution of 5-methylpyrazole-3-carboxylic acid ethyl ester (4.94 g, 32.0 mmol) in abs. EtOH (80 mL) was added NaOH (6.4 g, 160 mmol). The mixture was heated at reflux for 1 h and cooled to 20 C. The mixture was acidified with HC1 (aq., 2 M, 85 mL, 170 mmol) and the pH adjusted to 3 withNaOH (aq., 2 M). The mixture was extracted with EtOAc (200 mL). The organic phase was washed with NaCI (aq, sat, 50 mL) and concentrated to give the title compound (3.54 g, 88 percent) as a white solid. 5 ^ NMR (DMSO-ds, 400 MHz) S 12.83 (br. s, 1H). 6.43 (s, 1H), 2.22 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: With hydrazine In acetic acid; ethyl acetate at 0 - 20℃; for 15 h; Stage #2: With sodium hydrogencarbonate In water; acetic acid; ethyl acetate |
Hydrazine monohydrate (5.4 ml_, 110.68 mmol) was added to a 00C cooled solution of ethyl 2,4-dioxopentanoate (11.67 g, 73.79 mmol) in EtOH/AcOH (100/1 ml_). The reaction mixture was stirred at room temperature, for 15 h, poured into H2O (50 ml_) and NaHCO3 (saturated aqueous solution, 5 ml_) and extracted with EtOAc (3x50 ml_). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated, to furnish ethyl 5-methyl-1 H-pyrazole- 3-carboxylate, which was submitted to next step without further purification (8.41 g, white solid, yield: 74percent). 1H NMR (CDCI3, 250 MHz): δ ppm 6.55 (s, 1 H), 4.34 (c, J = 7.13 Hz, 2H,), 2.35 (s, 3H), 1.33 (t, J = 7.13 Hz, 3H). El MS: m/z = 155 (M+1 ). |
57% | With hydrazine In ethanol; water for 2 h; Heating / reflux | The title compound is commercially available (Maybridge), but has been prepared as follows (J. Med. Chem. 2002, 45, 1035): Hydrazine monohydrate (25.6 g, 162 mmol) was added to a solution of ethyl 2,4-dioxovalerate (7.85 mL, 162 mmol) in absolute EtOH. The mixture was heated at reflux for 2 h and concentrated to give a yellow oil. Crystallisation from EtOH:water (1:3) gave the title compound (14.225 g, 57 percent) as colourless needles. 1NMR (DMSO-de, 400 MHz) 5 13.2 (br. s, 1H), 6.47 (s, 1H), 4.22 (q, 2H), 2.23 (s, 3H), 1.25 (t, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With sodium hydride In tetrahydrofuran at 50℃; for 1 h; Cooling with ice Stage #2: at 50℃; for 2 h; |
Ethyl 5-methyl-1-hydro-pyrazolecarboxylate (30.8 g, 200 mmol) was dissolved in 200 mL of dry tetrahydrofuran solution. Sodium hydride (4.8 g, 200 mmol) was slowly added under ice-cooling and sodium hydride was added completely. After the temperature was raised to 50°C, the mixture was stirred for 1 hour and cooled to room temperature. Methyl iodide (28.2 g, 200 mmol) was then dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction. The addition was complete and heating to 50°C was continued for 2 hours. After the reaction is complete, cool to room temperature, remove tetrahydrofuran under reduced pressure, then add 100 mL of water, extract with ethyl acetate (100 mL x 3), combine the organic layers, dry, and remove the ethyl acetate under reduced pressure to give 5-methyl-1-carbonitrile. Ethyl 2-pyrazolecarboxylate 26.6 g, 85percent.Lithium aluminum hydride (3.8 g, 100 mmol) was added to a dry three-necked flask, 200 mL of dry tetrahydrofuran, and then ethyl 5-methyl-1-methyl-pyrazolecarboxylate (16.8 g, 100 mmol) was dissolved in 100 mL of dry. Tetrahydrofuran was slowly added dropwise to the three-necked flask, and stirring was continued for 4 hours after completion of the addition. After the reduction is completed, absolute ethanol is added dropwise to remove the remaining lithium tetrahydroaluminum, the tetrahydrofuran is removed under reduced pressure, 500 mL of methanol is added, the pH is adjusted to neutral, the mixture is heated to reflux for 6 hours, and the filtrate is filtrated. The filtrate is concentrated and dissolved in 100 mL of dichloromethane. And washed twice with 50 mL of saturated aqueous sodium chloride, and the organic layer was dried and concentrated to give 5-methyl-1-methyl-pyrazolemethanol 8.8 g, 70percent.5-methyl-1-carbonitrileThe base-pyrazole methanol (6.3 g, 50 mmol) was dissolved in 20 mL of methylene chloride. Thionyl chloride (6 g, 50 mmol) was slowly added dropwise. After the addition was complete, stirring was continued for 2 hours. After the reaction was complete, saturated sodium bicarbonate was added slowly. The aqueous solution was adjusted to pH neutral and then extracted with 200 mL of dichloromethane. The organic layers were combined, dried and concentrated to give 3-chloromethyl-1-methyl-5-methylpyrazole (6.5 g, 90percent).In a 50 mL round bottom flask was added 3-chloromethyl-1-methyl-5-methylpyrazole (1.44 g, 10 mmol) and N-(2,4,6-trimethylphenyl)imidazole (1.86 g) (10 mmol), 20 mL of acetonitrile, and the mixture was heated under reflux for 6 hours, cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained solid was dissolved in water and filtered. The filtrate was saturated with aqueous solution of ammonium hexafluorophosphate, and the solid precipitated and was dried to give 3.8. g imidazolium salt ligand (HL1PF6), yield 88percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.8% | With caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 140℃; for 8 h; | 0.1 mol of 3-methyl-5-pyrazolecarboxylic acid ethyl ester, 0.055 mol of dimethyl carbonate (DMC), 100 mL of xylene and 2.0 gCs2CO3, 130 ~ 140 reaction 8h; reaction Bi, cooled to room temperature, spin off the solvent, the oil-like 1,3-dimethyl-5-pyrazole formate, by liquid chromatography quantitative analysis of 97.7percent Yield 85.8percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9 g | at 60 - 70℃; | 3-methylpyrazole-5-carboxylic acid ethyl ester (65 mmol) and dimethyl sulfate (78 mmol) in N, N-dimethylformamide , 120 mL) and stirred at 60-70 ° C for 2-4 hours. The reaction solution was cooled and extracted with ethyl acetate. The resulting organic phase was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound 9. 0. g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium carbonate In acetonitrile for 3 h; Reflux | 154.1 g (1 mol) of intermediate A was added to a 1000 ml flask.Add 500 ml of acetonitrile and 138 g of potassium carbonate, Then add 1 mol of diethyl sulfate, and the system is stirred and heated to reflux.The plate chromatography was traced for about 3 hrs, the system was filtered, and the mother liquor was evaporated to dryness using a rotary evaporator.The residue was distilled under reduced pressure to give 140 g of Intermediate B (yield: 77.0percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20 g | With lithium hydroxide In tetrahydrofuran; water at 100℃; for 1 h; | Step C 3-methyl-1H-pyrazole-5-carboxylic acid (5c) To a stirred solution of 5b (28 g, 181.8 mmol) in THF (560 mL) was added LiOH (10.04 g, 454.5 mmol) dissolved in water (453 mL). The reaction mixture was heated at 100 °C for 1h. After the completion, the reaction mixture was cooled to room temperature. The volatiles were removed under reduced pressure and the crude mass was acidified with citric acid solution. The product was extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to yield 5c (20 g). 1H NMR (300 MHz, DMSO-d6): δ 6.45 (d, J=0.7 Hz, 1H), 2.23 (s, 3H). Molecular Formula: C5H6N2O2; LCMS purity: 98.1percent; Expected: 126; Observed: 127 (M+1). |
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