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CAS No. : | 1876473-39-0 | MDL No. : | MFCD24540474 |
Formula : | C12H21BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OEIOIWLEZPKVFD-UHFFFAOYSA-N |
M.W : | 236.12 | Pubchem ID : | 66509544 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 69.74 |
TPSA : | 36.28 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.35 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.96 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | 0.87 |
Log Po/w (SILICOS-IT) : | 1.12 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.62 |
Solubility : | 0.561 mg/ml ; 0.00237 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.35 |
Solubility : | 1.06 mg/ml ; 0.0045 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.19 |
Solubility : | 0.151 mg/ml ; 0.000638 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.26 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In acetonitrile at 130℃; for 0.166667h; Inert atmosphere; Microwave irradiation; | 113.a 4-(1-ethyl-3-methyl-1H-pyrazol-5-yl)-2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H- pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridine A suspension of 100 mg (0.19 mmol) of 2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H- pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate, 90 mg (0.38 mmol) 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-d ioxaborolan-2-yl )-1H-pyrazole, 15 mg (0.019mmol) of [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1, Pd(dppf)C12) and 65 mg (0.47 mmol) of potassium carbonate in 2.0 ml of MeCN and 1.0 ml water was degased with argon. Under argon, the reaction mixture was stirred at 130°C for 10 minutes in a microwave reactor. After cooling the reaction mixture was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (2x). The combindedorganic phases were filtered using a Whatman filter and then concentrated to give the crude product that was used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a degassed solution of <strong>[1003845-06-4](2-chloropyrimidin-5-yl)boronic acid</strong> (Combi-Blocks, cat No.BB-5457: 82 mg, 0.52 mmol) and 3-bromo-5-methoxy-4-nitrobenzamide (143 mg, 0.520 mmol) in dioxane (1733 mul) and water (347 mul) was added dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (25.5 mg, 0.031 mmol) and sodium carbonate (110 mg, 1.040 mmol). The reaction was stirred at 100 C. for 2 h. Then, 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Enamine Ltd, cat No.EN300-207291; 123.0 mg, 0.520 mmol) was added. The reaction mixture was heated to 100 C. for another 1 h. H2O was added to the reaction mixture, and the reaction was extracted with DCM. The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on a silica gel column eluting with 0 to 8% MeOH in DCM to afford the desired product. LC-MS calculated for C18H19N6O4 (M+H)+: m/z=383.1; found 383.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; | 1.11 Step 11: 2-(1-ethyl-3-methyl-1H-pyrazol-5-yl)-9H-pyrimido[4,5-b]indole-6-carboxamide To a solution of 2-chloro-9H-pyrimido[4,5-b]indole-6-carboxamide (60.0 mg, 0.243 mmol), 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Enamine, cat No.EN300-207291: 57.4 mg, 0.243 mmol), and sodium carbonate (51.6 mg, 0.487 mmol) in dioxane (676 μl) and water (135 μl) was added dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (11.92 mg, 0.015 mmol). The vial was flushed with nitrogen, and the reaction was stirred at 100° C. for 1 h. The reaction mixture was quenched by NH4OH aqueous solution then extracted with DCM. The organic phases were combined and dried over MgSO4, then filtered. The crude residue was purified by flash chromatography on a silica gel column eluting with 0 to 8% MeOH in DCM to afford the desired product. LC-MS calculated for C17H17N6O (M+H)+: m/z=321.1; found 321.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 2 h / 100 °C 1.2: 1 h / 100 °C 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 3 h / 160 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 2 h / 100 °C 1.2: 1 h / 100 °C 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 3 h / 160 °C 3.1: water; ethanol / 4 h / 95 °C 3.2: pH 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 2 h / 100 °C 1.2: 1 h / 100 °C 2.1: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 3 h / 160 °C 3.1: water; ethanol / 4 h / 95 °C 3.2: pH 2 4.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 4.2: pH 2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a degasseed solution of 3-bromo-4-nitrobenzonitrile (J& W PharmLab, cat No.05R0293: 50 mg, 0.220 mmol) and <strong>[444120-94-9]2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine</strong> (Aldrich, cat No.659843: 52.8 mg, 0.220 mmol) in dioxane (587 mul) and water (147 mul) was added dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (8.99 mg, 0.011 mmol) and sodium carbonate (46.7 mg, 0.440 mmol). The reaction was stirred at 100 C. for 2 h. 1-Ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Enamine Ltd, cat No.EN300-207291: 52.0 mg, 0.220 mmol) was added. The reaction mixture was heated to 100 C. for another 1 h. H2O (2 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (2 mL*5). The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude product was used directly without further purification. LC-MS calculated for C18H16N5O2 (M+H)+: m/z=334.1; found 334.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; | 1.3 Step 3: 3-(2-(1-ethyl-3-methyl-1H-pyrazol-5-yl)pyrimidin-5-yl)-5-methoxy-4-nitrobenzamide To a solution of (2-chloropyrimidin-5-yl)boronic acid (82 mg, 0.52 mmol), 3-bromo-5-methoxy-4-nitrobenzamide (143 mg, 0.520 mmol), and sodium carbonate (110 mg, 1.040 mmol) in dioxane (2 mL) and water (0.4 mL) was added dichloro[1,11-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (25.5 mg, 0.031 mmol). The vial was flushed with nitrogen, and the reaction mixture was stirred at 100° C. for 1 h. The reaction mixture was then cooled to room temperature, and 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Enamine Ltd, catNo.EN300-207291: 123 mg, 0.520 mmol) was added. The reaction mixture was flushed with nitrogen, and heated to 100° C. for another 1 h. The reaction mixture was quenched by NH4OH (aqueous solution), and extracted with DCM. The organic phases were combined and dried over MgSO4, then filtered. The crude residue was purified by flash chromatography on a silica gel column eluting with 0 to 8% MeOH in DCM to afford the desired product. LC-MS calculated for C18H19N6O4 (M+H)+: m/z=383.1; found 383.2. | |
In 1,4-dioxane; water at 100℃; for 1h; | 1.15 Step 15: 3-(2-(l-ethyl-3-methyl-lH-pyrazol-5-yl)pyrimidin-5-yl)-5-methoxy-4-nitrobenzamide To a degassed solution of (2-chloropyrimidin-5-yl)boronic acid (Combi-Blocks, catBB-5457: 82 mg, 0.52 mmol) and 3-bromo-5-methoxy-4-nitrobenzamide (143 mg, 0.520 mmol) in dioxane (1733 m) and water (347 m) was added dichloro[l,l'- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (25.5 mg, 0.031 mmol) and sodium carbonate (110 mg, 1.040 mmol). The reaction was stirred at 100 °C for 2 h. Then, l-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (Enamine Ltd, catEN300-207291: 123.0 mg, 0.520 mmol) was added. The reaction mixture was heated to 100 °C for another 1 h. EhO was added to the reaction mixture, and the reaction was extracted with DCM. The combined organic layers were dried with NaaSCE, fdtered, and concentrated. The crude residue was purified by flash chromatography on a silica gel column eluting with 0 to 8% MeOH in DCM to afford the desired product. LC-MS calculated for CisHigNgCE (M+H)+: m/z = 383.1; found 383.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: 1-ethyl-3-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at 0 - 25℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 2.16667h; Inert atmosphere; | 14 Example 14. Synthesis of 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyrazole n-Butyllithium solution (0.4mL, 1mmol) was added to a stirred solution of 1-ethyl-3- methyl-pyrazole (0.1mL, 0.91mmol) and THF (5mL) at 0°C under a nitrogen atmosphere. The mixture was allowed to warm to 25°C for 1 hour and then cooled back to -78°C.2-Isopropoxy- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.22mL, 1.09mmol) was added; after 10 mins at - 78°C the reaction was allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with water and the resulting mixture reduced in vacuo. The residue was azeotroped with toluene to give 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyrazole (214mg, 0.91mmol, 100% yield) as an off white solid. The compound was used in the next step without further purification. UPLC-MS (ES+, Short acidic): 0.83 min, m/z 154.6 [M+H]+. |
100% | Stage #1: 1-ethyl-3-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at 0 - 25℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 2.16667h; Inert atmosphere; | 14 Example 14. Synthesis of 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyrazole n-Butyllithium solution (0.4mL, 1mmol) was added to a stirred solution of 1-ethyl-3- methyl-pyrazole (0.1mL, 0.91mmol) and THF (5mL) at 0°C under a nitrogen atmosphere. The mixture was allowed to warm to 25°C for 1 hour and then cooled back to -78°C.2-Isopropoxy- 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.22mL, 1.09mmol) was added; after 10 mins at - 78°C the reaction was allowed to warm to room temperature and stir for 2 hours. The reaction was quenched with water and the resulting mixture reduced in vacuo. The residue was azeotroped with toluene to give 1-ethyl-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyrazole (214mg, 0.91mmol, 100% yield) as an off white solid. The compound was used in the next step without further purification. UPLC-MS (ES+, Short acidic): 0.83 min, m/z 154.6 [M+H]+. |