1-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Cat.NO.:A122729 Purity:97%

Product Details of [ 1002334-13-5 ]

CAS No. :	1002334-13-5
Formula :	C₁₅H₁₉BN₂O₂
M.W :	270.13
SMILES Code :	CC1(C)C(C)(C)OB(C2=NN(C3=CC=CC=C3)C=C2)O1
MDL No. :	MFCD16659786
InChI Key :	UBYYGXCGPBWGKO-UHFFFAOYSA-N
Pubchem ID :	70700444

Safety of [ 1002334-13-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 1002334-13-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	11
Fraction Csp3	0.4
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	80.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.28 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.17
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.67
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.62
Solubility	0.0643 mg/ml ; 0.000238 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.33
Solubility	0.126 mg/ml ; 0.000465 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.53
Solubility	0.00805 mg/ml ; 0.0000298 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.88 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12’782’590 molecules and tested on 40 external molecules (r² = 0.94)	3.03

Application In Synthesis of [ 1002334-13-5 ]

* 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.

Upstream synthesis route of [ 1002334-13-5 ]
Downstream synthetic route of [ 1002334-13-5 ]

[ 1002334-13-5 ] Synthesis Path-Upstream 1~2

1
[ 508191-77-3 ]
[ 347389-74-6 ]
[ 1002334-13-5 ]
[ 1002334-12-4 ]

References:

[1] Journal of the American Chemical Society, 2009, vol. 131, p. 7762 – 7769.

[2] Angewandte Chemie – International Edition, 2007, vol. 46, # 45, p. 8656 – 8658.

[3] Journal of the American Chemical Society, 2009, vol. 131, p. 7762 – 7769.

2
[ 347389-74-6 ]
[ 1002334-13-5 ]
[ 1002334-12-4 ]

References:

[1] Angewandte Chemie – International Edition, 2007, vol. 46, # 45, p. 8656 – 8658.

[ 1002334-13-5 ] Synthesis Path-Downstream 1~8

1
N-phenyl syndone [ No CAS ]
[ 347389-74-6 ]
[ 1002334-13-5 ]
[ 1002334-12-4 ]

References: [1]Angewandte Chemie – International Edition,2007,vol. 46,p. 8656 – 8658.

2
[ 508191-77-3 ]
[ 347389-74-6 ]
[ 1002334-13-5 ]
[ 1002334-12-4 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 7762 – 7769.
[2]Angewandte Chemie – International Edition,2007,vol. 46,p. 8656 – 8658.
[3]Journal of the American Chemical Society,2009,vol. 131,p. 7762 – 7769.

3
[ 1008-79-3 ]
[ 1002334-13-5 ]

References: [1]Patent: US2019/51845,2019,A1 .

4
[ 92-43-3 ]
[ 1002334-13-5 ]

References: [1]Patent: US2019/51845,2019,A1 .

5
[ 1190837-93-4 ]
[ 73183-34-3 ]
[ 1002334-13-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium acetate; potassium bromide; In 1,4-dioxane; for 16.0h;Reflux;	(44) (10 g, 34.2 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (9.56 g, 37.6 mmol), Pd(PPh3)4 (3.16 g, 2.74 mmol), potassium bromide (4.48 g, 37.6 mmol), and potassium acetate (10.08 g (103 mmol) were combined in dioxane (171 ml) and heated at reflux for 16 hours. The mixture was partitioned between EtOAc and water and the organics were washed with brine, dried, vacuumed down, and purified by column chromatography, yielding (45) as a yellow oil, 7.84 g (85%).

References: [1]Patent: US2019/51845,2019,A1 .Location in patent: Paragraph 0198.

6
[ 1002334-13-5 ]
1,4-bis(3-(1-phenyl-1H-pyrazol-3-yl)phenyl)but-2-ene [ No CAS ]

References: [1]Patent: US2019/51845,2019,A1 .

7
[ 1002334-13-5 ]
1,4-bis(3-(1-phenyl-1H-pyrazol-3-yl)phenyl)butane [ No CAS ]

References: [1]Patent: US2019/51845,2019,A1 .

8
[ 18257-89-1 ]
[ 1002334-13-5 ]
3-(3-allylphenyl)-1-phenyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With dicyclohexyl-(2′,6′-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane-d8; for 16.0h;Reflux;	(45) (7.20 g, 26.7 mmol), potassium phosphate (9.44 g, 44.5 mmol), Pd2(dba)3 (0.407 g, 0.445 mmol), (46) (4.38 g, 22.23 mmol) and S-Phos (0.730 g, 1.778 mmol) were combined in dioxane (123 ml) and the reaction mixture was heated at reflux for 16 hours. Water was added and the mixture was extracted with EtOAc. The organics were washed with brine and solvent was evaporated. The resulting residue was purified by column chromatography to yield (47) as a pale yellow oil, 2.41 g (42%).

References: [1]Patent: US2019/51845,2019,A1 .Location in patent: Paragraph 0200.

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