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CAS No. : | 1188405-87-9 | MDL No. : | MFCD09951915 |
Formula : | C8H13BN2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IUEPVMMFUSDDBJ-UHFFFAOYSA-N |
M.W : | 212.01 | Pubchem ID : | 44118675 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 54.25 |
TPSA : | 84.58 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) : | -7.3 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.41 |
Log Po/w (WLOGP) : | -0.65 |
Log Po/w (MLOGP) : | -0.57 |
Log Po/w (SILICOS-IT) : | -2.11 |
Consensus Log Po/w : | -0.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.4 |
Solubility : | 8.53 mg/ml ; 0.0402 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.75 |
Solubility : | 3.75 mg/ml ; 0.0177 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.21 |
Solubility : | 132.0 mg/ml ; 0.621 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.73 |
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 |
---|---|---|
61% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pynmidine-2- carboxylate (XXXIII) A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1 ,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H20 (8 mL) was stirred under N2atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1 |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate (XXXIII ) A mixture of ethyl 5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine-2-carboxylate (1.0 g, 3.32 mmol), (1-(tert-butoxycarbonyl)-1 H-pyrazol- 4-yl)boronic acid (704 mg, 3.32 mmol), Na2CO3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H2O ( 8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure . The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), Rt = 4.20 min; [M+ H]+= 334.1 . |
61% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1 ,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CO3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H2O (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SO 4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), Rt = 4.20 min; [M+H]+= 334.1 . |
61% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1 ,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CO3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H2O (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SO 4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), Rt = 4.20 min; [M+H]+= 334.1 . |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2-carboxylate (XXXIII ) A mixture of ethyl 5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine-2-carboxylate (1.0 g, 3.32 mmol), (1-(tert-butoxycarbonyl)-1 H-pyrazol- 4-yl)boronic acid (704 mg, 3.32 mmol), Na2CO3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H2O ( 8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure . The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), Rt = 4.20 min; [M+ H]+= 334.1 . |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; lithium hydroxide monohydrate; anhydrous sodium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) [0337] A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1,4-dioxane (40 mL) and H20 (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1) to give the desired product (525 mg, 61%) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1. |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; lithium hydroxide monohydrate; anhydrous sodium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) [0337] A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1,4-dioxane (40 mL) and H20 (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1) to give the desired product (525 mg, 61%) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1. |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; lithium hydroxide monohydrate; anhydrous sodium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) [0337] A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1,4-dioxane (40 mL) and H20 (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1) to give the desired product (525 mg, 61%) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1. |
61% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; lithium hydroxide monohydrate; anhydrous sodium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-2- carboxylate (XXXIII) [0337] A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1,4-dioxane (40 mL) and H20 (8 mL) was stirred under N2 atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1) to give the desired product (525 mg, 61%) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1. |
61% | With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; Inert atmosphere; | 71.6 Step 6: ethyl 5-chloro-3-isopropyl-7-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pynmidine-2- carboxylate (XXXIII) A mixture of ethyl 5, 7-dichloro-3-isopropylpyrazolo[1 ,5-a]pyrimidine- 2-carboxylate (1.0 g, 3.32 mmol), (1 -(tert-butoxycarbonyl)-1 H-pyrazol-4-yl)boronic acid (704 mg, 3.32 mmol), Na2CC>3 (704 mg, 6.64 mmol) and Pd(dppf)2Cl2 (243 mg, 0.39 mmol) in degassed 1 ,4-dioxane (40 ml.) and H20 (8 mL) was stirred under N2atmosphere at 80 °C overnight. The mixture was poured into water and extracted with DCM (20 mL x 3). The organics were washed with water and brine, dried over Na2SC>4, filtered and concentrated under reduced pressure. The reside was purified by silica gel column chromatography (DCM:MeOH, 100:1 ) to give the desired product (525 mg, 61 %) as a yellow solid. LCMS (Method A), R, = 4.20 min; [M+H]+= 334.1 |
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