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[ CAS No. 1188405-87-9 ] {[proInfo.proName]}

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Chemical Structure| 1188405-87-9
Chemical Structure| 1188405-87-9
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Product Details of [ 1188405-87-9 ]

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 :

Calculated chemistry of [ 1188405-87-9 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 1188405-87-9 ]

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:

Application In Synthesis of [ 1188405-87-9 ]

* 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.

  • Downstream synthetic route of [ 1188405-87-9 ]

[ 1188405-87-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1188405-87-9 ]
  • [ 2760415-25-4 ]
  • [ 2760415-26-5 ]
YieldReaction ConditionsOperation 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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