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Chemical Structure| 1072951-54-2 Chemical Structure| 1072951-54-2

Structure of 1072951-54-2

Chemical Structure| 1072951-54-2

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Product Details of [ 1072951-54-2 ]

CAS No. :1072951-54-2
Formula : C5H4BCl2NO2
M.W : 191.81
SMILES Code : OB(O)C1=CC(Cl)=NC(Cl)=C1
MDL No. :MFCD09751352
InChI Key :JFUQZFQJFYZZGY-UHFFFAOYSA-N
Pubchem ID :46739131

Safety of [ 1072951-54-2 ]

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

Computational Chemistry of [ 1072951-54-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 44.08
TPSA ?

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

53.35 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

1.68
Log Po/w (WLOGP)?

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

0.07
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.

-0.13
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

0.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.36

Water Solubility

Log S (ESOL):?

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

-2.43
Solubility 0.72 mg/ml ; 0.00376 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.

-2.41
Solubility 0.738 mg/ml ; 0.00385 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

-2.15
Solubility 1.35 mg/ml ; 0.00706 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

High
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.

-6.28 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

1.0
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

2.0 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)

1.87

Application In Synthesis of [ 1072951-54-2 ]

* 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 [ 1072951-54-2 ]

[ 1072951-54-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 98027-84-0 ]
  • [ 1072951-54-2 ]
YieldReaction ConditionsOperation in experiment
n-BuLi (3 mL, 2.5 M in hexane, 1.50 equiv) was added dropwise into a solution of 2,6- dichloro-4-iodopyridine (1.40 g, 5.112 mmol, 1.00 equiv) in tetrahydrofuran (20 mL) at -78C under nitrogen. The resulting solution was stirred for 30 mm at -78C. Trimethyl borate (580 mg, 5.582 mmol, 1.10 equiv) was added at -78C and the reaction was stirred for 1 h at -78C. The resulting solution was stirred for an additional 12 h at room temperature, quenched by 1.6 g of pinacol and then AcOH (0.6 mL). The solids were filtered out and the liquid was concentrated under vacuum. This resulted in the title compound (1 g, crude) as a yellow solid.
  • 2
  • [ 1072951-54-2 ]
  • [ 1187179-47-0 ]
  • 3
  • [ 1072951-54-2 ]
  • [ 1186403-14-4 ]
  • [ 1137639-40-7 ]
  • 4
  • [ 1072951-54-2 ]
  • [ 931-59-9 ]
  • [ 1393715-68-8 ]
YieldReaction ConditionsOperation in experiment
45% With Pd(2-[2-(benzylthio)phenyliminomethyl]-4-bromophenol-(H))Cl; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 5h;Sealed tube; Inert atmosphere; General procedure: A sealed tube was charged with sulfenyl chloride 2a (219mg, 1 mmol), phenylboronic acid (3a) (135 mg, 1 mmol),K2CO3 (254 mg, 2 mmol), catalyst 1a (2 mol%, 10 mg) andDMF (2 mL). The mixture was stirred at 90 C under an N2atm for 5 h. After completion of the reaction, the mixturewas cooled to r.t. and extracted with EtOAc (2 × 10 mL). The combined extracts were dried over anhydrous Na2SO4,filtered and the solvent removed under reduced pressure.The crude residue was purified by flash chromatographyover silica gel to provide product 4a (166 mg, 89%).
  • 5
  • [ 1072951-54-2 ]
  • 3,6’-dichloro-N-(4-(1-methyl-1H-pyrazol-4-yl)-2-nitrophenyl)[2,4'-bipyridin]-2'-amine [ No CAS ]
  • 6
  • [ 1072951-54-2 ]
  • 1-(3,6'-dichloro-[2,4'-bipyridin]-2'-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazole [ No CAS ]
  • 7
  • [ 1072951-54-2 ]
  • N-(3-chloro-6'-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)[2,4'-bipyridin]-2'-yl)cyclopropanesulfonamide [ No CAS ]
  • 8
  • [ 96424-68-9 ]
  • [ 1072951-54-2 ]
  • 2',3,6'-trichloro-2,4'-bipyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 2h;Inert atmosphere; Example 29.N-(3-chloro-6?-(S-( i-methyl-i H-pyrazol-4-yl)- 1 H-benzo[d}imidazol- l-yl)-[2,4?- bipyridinj-2?-yl)cyclopropanesulfonamidea) 2?,3,6?-Trichloro-2,4?-bipyridine A solution of <strong>[1072951-54-2](2,6-dichloropyridin-4-yl)boronic acid</strong> (0.76 g, 4 mmol) in 1,2- dimethoxyethane (15 ml) was degassed by N2 bubbling for 5 mm. 2-Bromo-3-chloro- pyridine (0.7 g, 3.63 mmol, 1.2 eq) was added and the mixture was degassed for another 5 mm. Pd(dppf)C12 (0.3 g, 0.36 mmol, 0.1 eq) and aqueous sodium carbonate (1.15 g,10.9 mmol, 3 eq) were added sequentially using the procedure of Intermediate Example1 and then heated at 90 C for 2 h. The reaction mixture was then quenched and extracted as in Intermediate Example 1. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 10 % ethyl acetate in hexane) to afford the title product in 74 % yield (0.7 g). ?H NMR (300 MHz,CDC13): oe 8.63 (dd, 1H),7.86 (m, III), 7.68 (s, 2H), 7.37 (dd, 1H).
  • 9
  • [ 1072951-54-2 ]
  • 2-chloro-6-fluoro-4-[5-(trifluoromethyl)pyridin-2-yl]pyridine [ No CAS ]
  • 10
  • [ 1072951-54-2 ]
  • 6-fluoro-4-[5-(trifluoromethyl)pyridin-2-yl]pyridine-2-carbonitrile [ No CAS ]
  • 11
  • [ 1072951-54-2 ]
  • [ 50488-42-1 ]
  • 2,6-dichloro-4-[5-(trifluoromethyl)pyridin-2-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 120℃; for 12h;Inert atmosphere; A mixture of 2-bromo-5-(trifluoromethyl)pyridine (800.00 mg, 3.54 mmol, 1.00 equiv), (2,6- dichloropyridin-4-yl)boronic acid (1 g, 5.21 mmol, 1.00 equiv), Pd(dppf)C12.CH2C12 (290 mg, 0.36 mmol, 0.10 equiv), and potassium carbonate (1.96 g, 14.18 mmol, 4.00 equiv) in 1,4-dioxane (40 mL) /water(2 mL) was stuffed for 12 h at 120C under nitrogen. The resulting solution was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (1:100). This resulted in the title compound (680 mg, 66%) as a white solid.
  • 12
  • [ 1072951-54-2 ]
  • ethyl 3-(5-(3-bromobenzyloxy)thiophen-2-yl)propanoate [ No CAS ]
  • 3-(5-(3-(2,6-dichloropyridin-4-yl)benzyloxy)thiophen-2-yl)propanoic acid [ No CAS ]
  • 13
  • [ 677-25-8 ]
  • [ 1072951-54-2 ]
  • C7H4Cl2FNO2S [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 1072951-54-2 ]

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Related Parent Nucleus of
[ 1072951-54-2 ]

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