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Chemical Structure| 720702-41-0 Chemical Structure| 720702-41-0

Structure of 720702-41-0

Chemical Structure| 720702-41-0

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Product Details of [ 720702-41-0 ]

CAS No. :720702-41-0
Formula : C4H7BN2O2
M.W : 125.92
SMILES Code : OB(C1=CC=NN1C)O
MDL No. :MFCD11053031
InChI Key :MGNBKNBEZGLHNF-UHFFFAOYSA-N
Pubchem ID :11182610

Safety of [ 720702-41-0 ]

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

Computational Chemistry of [ 720702-41-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 5
Fraction Csp3 0.25
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 33.31
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

58.28 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.83
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-1.9
Log Po/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.

-1.79
Log Po/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

-2.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.32

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.44
Solubility 45.4 mg/ml ; 0.361 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

0.09
Solubility 154.0 mg/ml ; 1.22 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

0.35
Solubility 285.0 mg/ml ; 2.26 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
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

No
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

No
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

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.66 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

2.0
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<1.0
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)

2.0

Application In Synthesis of [ 720702-41-0 ]

* 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 [ 720702-41-0 ]

[ 720702-41-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 121554-10-7 ]
  • [ 720702-41-0 ]
  • [ 1159186-42-1 ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 1h; 5-Bromo-2-iodobenzonitrile (0.30 g, 1.0 mmol), (1 -methyl -1 H-pyrazol -5- yl)boronic acid (188 mg, 1.5 mmol), dichloro[1 ,1 '- bis(diphenylphosphino)ferrocene] palladium(ll) dichoromethane adduct (26 mg, 0.05 mmol) and cesium carbonate (651 mg, 2.00 mmol) were stirred together at 80 degrees Celsius in a solvent mixture of 3:1 dioxane/water (5 ml_), respectively, for one hour. The reaction mixture was allowed to cool to room temperature and water (25 ml_) and 1 N HCI (5 ml_) were added. The product was extracted into methyene chloride. The organic mixture was concentrated by rotary evaporation to a small volume which was applied to a 40 g cartridge of silica gel. The cartridge was eluted with a 70:30 mixture of hexanes-acetone, respectively. The fractions containing the product were combined and concentrated to give a white solid as product. (210 mg, 80 %)
  • 2
  • [ 175205-81-9 ]
  • [ 720702-41-0 ]
  • 2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 48h;Sealed tube; Inert atmosphere; To a heat dried flask, (2-methylpyrazol-3-yl)boronic acid (2 g, 1.2 equiv., 15.9 mmol), cesium carbonate (8.65 g, 2 equiv., 26.550 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]-dichloropalladium(ii) DCM complex (0.558 g, 0.05 equiv., 0.66375 mmol) were added. The flask was sealed and vacuumed and backfilled with nitrogen 3 times. 1,4-dioxane (66.4 mL, 0.2 M) and water (22.1 mL, 0.6M) were added, followed by <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (3 g, 13.275mmol), and the reaction was heated to 100C. The reaction was ran for 48h and full conversion was seen. The reaction was cooled to room temperature, was filtered through silica gel (isopropyl acetate eluting). The crude reaction was concentrated and purified by column chromatography to give a pale yellow oil (2.59 g, 86percent yield). 1H NMR (400 MHz, Chloroform-d) delta 8.85 (d, J = 5.2 Hz, 1H), 7.81 - 7.75 (m, 1H), 7.54 (d, J= 2.0 Hz, 1H), 7.45 (dd, J= 5.2, 1.5 Hz, 1H), 6.68 (d, J= 2.0 Hz,1H), 4.25 (s, 3H).
  • 3
  • [ 133627-45-9 ]
  • [ 720702-41-0 ]
  • 4-methyl-2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 100℃; for 3h; A mixture of <strong>[133627-45-9]2-chloro-4-methylpyridin-3-amine</strong> (5.0 g, 35 mmol), (1-methyl-1H-pyrazol-5-yl)boronic acid (13.25 g, 105.2 mmol), K3PO4 (22.33 g, 105.20 mmol), and Pd(dppf)Cl2 (2.57 g, 3.51 mmol) in 10:1 dioxane/ water (110 mL) was heated at 100 C. After 3 h, the solids were filtered, and the filtrate was concentrated in vacuo. Purification of the resulting residue by flash column chromatography (3:2 petroleum ether/ethyl acetate) afforded 4-methyl-2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-amine (2.0 g, 30% yield) as a brown solid. LCMS (ESI) [M+H]+=189
 

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