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CAS No. : | 1095080-54-8 | MDL No. : | MFCD03419491 |
Formula : | C5H9BN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZMKALWZRSCXBEY-UHFFFAOYSA-N |
M.W : | 139.95 | Pubchem ID : | 49964170 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 38.12 |
TPSA : | 58.28 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) : | -7.53 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | -0.53 |
Log Po/w (WLOGP) : | -1.42 |
Log Po/w (MLOGP) : | -1.38 |
Log Po/w (SILICOS-IT) : | -1.88 |
Consensus Log Po/w : | -1.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.61 |
Solubility : | 34.2 mg/ml ; 0.244 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.23 |
Solubility : | 83.3 mg/ml ; 0.596 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.07 |
Solubility : | 120.0 mg/ml ; 0.861 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In water; acetonitrile; at 130.0℃; for 0.166667h;Inert atmosphere; Microwave irradiation; | 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, 53 mg (0.38 mmol) <strong>[1095080-54-8](1-ethyl-1H-pyrazol-5-yl)boronic acid</strong>, 15 mg (0.02 mmol) 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 ml MeCN and 1 ml water was degased with argon. Under argon, the reaction mixture was stirred at 130C for 10 mm in a microwave reactor. After cooling the reaction mixture was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (2x). The combinded organic phases werefiltered using a Whatman filter and concentrated to give the crude product that was used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100.0℃; for 3.0h;Inert atmosphere; | 3- bromo-4-(2,6-difluoro-4-nitrophenoxy)-1 -[2-(trimeth^ H-pyrrolo[2,3- b]pyridine (1.00 g, 2.00 mmol, intermediate 16), [1 ,1 '-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) (146 mg, 0.20 mmol), (1 -ethyl-1 H-pyrazol-5-yl)boronic acid (559 mg, 4.00 mmol, CAS No. [1095080-54-8]), and potassium carbonate (1 .38 g, 9.99 mmol), were dissolved in a mixture of 1 ,4-dioxane (20 ml_), and water (10 ml_). The resulting mixture was degassed with argon for 10 min, after which time it was heated to 100C for 3h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water was added. The layers were separated, and the aqueous phase was extracted two times with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness to give the crude product. The crude produt was purified by flash column chromatography to afford 4-(2,6-difluoro-4-nitrophenoxy)-3-(1 -ethyl-1 H- pyrazol-5-yl)-1 -[2-(trimethylsilyl)ethoxy]methyl}-1 H-pyrrolo[2,3-b]pyridine (260 mg, 20% Yield). LC-MS (Method 2): Rt = 1 .52 min; MS (ESIpos): m/z = 516 [M+H]+ 1H NMR (400 MHz, DMSO-d6) delta ppm -0.10 (s, 9 H), 0.80 - 0.88 (m, 2 H), 1 .25 (t, 3 H), 3.56 - 3.65 (m, 2 H), 4.10 (q, 2 H), 5.71 (s, 2 H), 6.30 (d, 1 H), 6.66 (d, 1 H), 7.45 (d, 1 H), 7.90 (s, 1 H), 8.25 (d, 1 H), 8.32 - 8.38 (m, 2 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A vial was charged with 3-(5-amino-2-(benzo[i/|isoxazol-3-yhnethyl)-8-bromo- [l ,2,4jtriazolo[l ,5-cjpyrimidin-7-yl)benzonitrile (24 mg, 0.054 mmol), (1 -ethyl- LH-pyrazol- 5-yl)boronic acid (17 mg, 0.12 mmol), XPhos Pd G2 (4 3 mg, 0.0054 mmol), K3PO4 (23 mg, 0.11 mmol), dioxane (1 mL) and water (0.2 mL). The reaction mixture was then heated and stirred at 80 C for 1 h, cooled to r.t, diluted with saturated NH4CI solution (1 mL), and extracted with EtOAc (5 mL). The organic phase was separated, dried over NaiSCL, concentrated, and purified by preparative LC-MS (pH 2, acetonitrile/water with TFA) to afford the product as a TFA salt. LCMS calculated for C25H20N9O (M+H)1 : 462.2. Found; 462.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); In 1,4-dioxane; water; at 90.0℃; for 1.0h; | To the crude 3-(5-amino-8-bromo-2-(hydroxymethyl)-[l,2,4]triazolo[L5- c]pyrimidin-7-yl)benzonitrile from previous step was added (1-ethyl- l//-pyrazol-5-yl)boronic acid (47 mg, 0.34 mmol), XPhos Pd G2 (13 mg, 0.017 mmol), K3PO4 (71 mg, 0.34 mmol), dioxane (3 mL) and water (0.6 mL). The reaction mixture was heated and stirred at 90 C for 1 h, cooled to r.t, diluted with saturated NH4CI solution (3 mL), and extracted with EtOAc (15 mL). The organic phase was separated, dried over Na2S04, concentrated, and purified by flash chromatography (0 to 70% EtOAc in diehloromethane) to give the desired product (40 mg, 55%). LCMS calculated for CI8HI7N80 (M+H)+: 361.1. Found: 361.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 120.0℃; for 1.5h;Inert atmosphere; | Cesium carbonate (23.04 mg, 0.071 mmol) was added to the mixture of 3-(4-amino- 7-bromo-2-(pyridin-2-ylmethyl)-2H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-fluorobenzonitrile (30 mg, 0.071 mmol) and <strong>[1095080-54-8](1-ethyl-1H-pyrazol-5-yl)boronic acid</strong> (19.79 mg, 0.141 mmol) in 1,4-dioxane (2.0 ml) and water (0.2 ml). The reaction was sparged with N2 for 2 min and chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'- biphenyl)]palladium(II)(7.07 µmol) was added. The reaction was stirred at 120 C for 1.5 h. Direct purification on prep. HPLC afforded the desired product. LC-MS calculated for C23H19FN9: 440.2 (M+H)+; found: 440.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 120.0℃; for 1.5h;Inert atmosphere; Microwave irradiation; | To the mixture of 3-(7-amino-4-bromo-2-(pyridin-2-ylmethyl)-2H-pyrazolo[3,4- c]pyridin-5-yl)benzonitrile (162 mg, 0.400 mmol) and <strong>[1095080-54-8](1-ethyl-1H-pyrazol-5-yl)boronic acid</strong> (55.9 mg, 0.400 mmol) 1,4-dioxane (2.0 mL) and water (0.2 mL) was added cesium carbonate (260 mg, 0.799 mmol). The resulting mixture was sparged with N2 for 2 min and chloro(2- dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'- biphenyl)]palladium(II) (0.040 mmol) was added. The reaction mixture was stirred at 120 C under microwave irradiation for 90 min. The reaction mixture was diluted with methanol. Direct purification on prep. HPLC afforded the desired product. LC-MS calculated for C24H21N8: 421.2 (M+H)+; found: 421.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 120.0℃; for 1.5h;Inert atmosphere; Microwave irradiation; | To the mixture of 3-(7-amino-4-bromo-2-((6-methylpyridin-2-yl)methyl)-2H- pyrazolo[3,4-c]pyridin-5-yl)benzonitrile (60 mg, 0.143 mmol) and (1-ethyl-1H-pyrazol-5- yl)boronic acid (20.03 mg, 0.143 mmol) in 1,4-dioxane (2.0 mL) and water (0.2 mL) was added cesium carbonate (93 mg, 0.286 mmol). The resulting mixture was sparged with N2 for 1 min and chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino- 1,1'-biphenyl)]palladium(II)(0.014 mmol) was added. The reaction mixture was stirred at 120 C under microwave irradiation for 90 min. The reaction mixture was diluted with methanol. Direct purification on prep. HPLC (pH=2) afforded the desired product. LC-MS calculated for C25H23N8: 435.2 (M+H)+; found: 435.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 120.0℃; for 1.5h;Inert atmosphere; Microwave irradiation; | Cesium carbonate (292 mg, 0.896 mmol) was added to the mixture of 3-(4-amino-7- bromo-2-(pyridin-2-ylmethyl)-2H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)benzonitrile (182 mg, 0.448 mmol) and <strong>[1095080-54-8](1-ethyl-1H-pyrazol-5-yl)boronic acid</strong> (62.7 mg, 0.448 mmol) in 1,4- dioxane (2 ml) and water (2 ml). The resulting reaction mixture was sparged with N2 for 2 min and then chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'- amino-1,1'-biphenyl)]palladium(II) (0.045 mmol) was added. The reaction mixture was stirred at 120 C for 1.5 h. The reaction mixture was diluted with methanol. Direct purification on prep. HPLC afforded the desired product. LC-MS calculated for C23H20N9: 422.2 (M+H)+; found: 422.3 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate; In 1,4-dioxane; water; at 50.0℃; for 2.0h;Inert atmosphere; | [00364] A mixture of 3-bromo-2-(3-cyanophenyl)-N-(2-hydroxy-2-methylpropyl)pyrazolo[1,5-a]pyrimidine-5-carboxamide (Intermediate B) (60 mg, 0.14 mmol), (2-ethylpyrazol-3-yl)boronic acid (22 mg, 0.16 mmol) and K2CO3 (40 mg, 0.29 mmol) in 1,4-dioxane (1 mL) and water (0.20 mL) was degassed under a flow of N2. Pd(tBu3P)2 (4 mg, 0.01 mmol) was added and the reaction mixture heated to 50 C for 2 h. Additional (2-ethylpyrazol-3-yl)boronic acid (11 mg, 0.08 mmol) was added and the mixture heated for a further hour. After cooling to room temperature, the resulting mixture was partitioned between H2O (15 mL) and EtOAc (20 mL), the organic portion was separated and the aqueous further extracted with EtOAc (2x25 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification by chromatography on silica eluting with 3% MeOH in DCM to afforded the title compound as a yellow solid. [00365] LC-MS (Method 8B): Rt 3.95 mins; MS m/z 430.3 = [M+H]+ [00366] 1H NMR (500 MHz, DMSO-d6) δ 9.44 (d, J = 7.2 Hz,1H), 8.21 (t, J = 6.2 Hz,1H),7.94 - 7.90 (m, 2H),7.84 (d, J = 8.0 Hz,1H),7.73 (d, J = 7.2 Hz,1H),7.67 (t, J = 8.0 Hz,1H),7.63 (d, J = 1.7 Hz,1H), 6.33 (d, J = 1.7 Hz,1H), 4.69 (s,1H), 3.94 (q, J = 7.2 Hz, 2H), 3.29 (d, J = 6.2 Hz, 2H),1.20 (t, J = 7.2 Hz, 3H),1.09 (s, 6H). |
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