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Structure of 6268-43-5

Chemical Structure| 6268-43-5

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Product Details of [ 6268-43-5 ]

CAS No. :6268-43-5
Formula : C11H10N4O
M.W : 214.22
SMILES Code : O=C(NC1=NC=CC=C1)NC1=NC=CC=C1
MDL No. :MFCD00233705
Boiling Point : No data available
InChI Key :FOQXHWCMYZXOGZ-UHFFFAOYSA-N
Pubchem ID :80445

Safety of [ 6268-43-5 ]

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

Computational Chemistry of [ 6268-43-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 60.75
TPSA ?

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

66.91 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.59
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

1.26
Log Po/w (WLOGP)?

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

1.74
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.

0.72
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

0.73
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.21

Water Solubility

Log S (ESOL):?

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

-2.25
Solubility 1.2 mg/ml ; 0.00558 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.

-2.26
Solubility 1.17 mg/ml ; 0.00545 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

-4.23
Solubility 0.0126 mg/ml ; 0.000059 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

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

Yes
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.

-6.71 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

0.0 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)

2.15

Application In Synthesis of [ 6268-43-5 ]

* 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.

  • Downstream synthetic route of [ 6268-43-5 ]

[ 6268-43-5 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 504-29-0 ]
  • [ 57-13-6 ]
  • [ 6268-43-5 ]
YieldReaction ConditionsOperation in experiment
62% With iron(II,III) oxide; ferric hydroxide; In para-xylene; at 140℃; for 60.0h; 1 ,3-di(Pyridin-2-yl)urea (5a) was synthesised via the reaction of triphosgene (1 .0 g, 3.37 mmol) with 2-aminopyridine (6a) (1.576 g, 16.74 mmol) in the presence of DMAP (2.44 g, 20.01 mmol) in 0H2012(15.0 mL) at room temperature for 36 h. 5a was equally synthesised via Fe(OH)3Fe304-catalysed(0.060 g, 0.052 mmol) reaction of 2-aminopyridine (6a) (0.376 g, 4.0 mmol) with urea (3b) (0.120 g,2.0 mmol) in p-xylene at 140 00 for 2.5 days and obtained in 62% (0.266 g, 1.24 mmol) yield.26 White crystals; m.p. 175 c 130-NMR (100 MHz, DMSO-d6): : 152.4, 151.9, 147.3, 138.4, 118.1, 112.4.
  • 3
  • [ 13114-64-2 ]
  • [ 78-39-7 ]
  • [ 5255-67-4 ]
  • [ 6268-43-5 ]
  • 4
  • [ 13114-64-2 ]
  • [ 122-51-0 ]
  • [ 5255-67-4 ]
  • [ 6268-43-5 ]
  • 5
  • [ 6268-43-5 ]
  • [ 718-33-2 ]
  • 6
  • [ 6268-43-5 ]
  • <i>N</i>,<i>N</i>'-bis-(1-oxy-[2]pyridyl)-urea [ No CAS ]
  • 7
  • [ 1212-30-2 ]
  • [ 6268-43-5 ]
  • 8
  • [ 504-29-0 ]
  • [ 65478-59-3 ]
  • [ 6268-43-5 ]
  • 9
  • [ 504-29-0 ]
  • [ 24424-99-5 ]
  • [ 6268-43-5 ]
  • [ 38427-94-0 ]
  • 10
  • [ 504-29-0 ]
  • [ 88091-68-3 ]
  • [ 6268-43-5 ]
  • 2-(4-nitrophenyl)ethyl N-(pyridin-2-yl)carbamate [ No CAS ]
  • bis<2-(4-nitrophenyl)ethyl>carbonate [ No CAS ]
  • bis<2-(4-nitrophenyl)ethyl> N-(pyridin-2-yl)imidodicarbonate [ No CAS ]
  • 12
  • [ 88091-68-3 ]
  • [ 6268-43-5 ]
  • 2-(4-nitrophenyl)ethyl N-(pyridin-2-yl)carbamate [ No CAS ]
  • bis<2-(4-nitrophenyl)ethyl>carbonate [ No CAS ]
  • bis<2-(4-nitrophenyl)ethyl> N-(pyridin-2-yl)imidodicarbonate [ No CAS ]
  • 13
  • [ 65478-59-3 ]
  • [ 33471-48-6 ]
  • [ 6268-43-5 ]
  • 1-(2-oxido-3-pyridazinyl)-3-(2-pyridyl)urea [ No CAS ]
  • [ 18510-73-1 ]
  • 14
  • [ 17377-08-1 ]
  • [ 5255-67-4 ]
  • [ 6268-43-5 ]
YieldReaction ConditionsOperation in experiment
With diethylene glycol dimethyl ether; cesium fluoride; at 100℃; for 20.0h;Schlenk technique; Glovebox; General procedure: In the glove box, add aniline (1mmol), CsF (2mol), and diglyme (3mL) to the 10ml Schlenk bottle, and replace the air with CO2. Connect the Schlenk bottle with a CO2 balloon, and then PMHS with a syringe (4.5 mmol) was poured into a reaction flask and placed in an oil bath and stirred at 100 C for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, and then poured into 30 mL of H2O, and a large amount of precipitate was immediately obtained, and then a large amount of solid powder was obtained by suction filtration. The solid powder was washed with n-hexane (3 x 5 mL) to remove unreacted raw materials, and then ethyl acetate was used. (3 x 10 mL) washed the solid powder. The ethyl acetate layer was collected, dried over anhydrous magnesium sulfate, and then subjected to vacuum rotary evaporation to obtain a pure product in an isolated yield of 96%.
  • 16
  • [ 504-29-0 ]
  • α-pyridyl urethane [ No CAS ]
  • [ 6268-43-5 ]
  • 17
  • N.N'-di-α-pyridyl-thiourea [ No CAS ]
  • [ 6268-43-5 ]
  • 18
  • [ 504-29-0 ]
  • [ 32315-10-9 ]
  • [ 6268-43-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; General procedure: To a stirred solution of various amines (2.0 equiv.) in 5 mLdichloromethane was added bis(trichloromethyl) carbonate (0.4 equiv.) andtriethylamine (2.0 equiv.). After stirring for 3 ~ 8 h atroom temperature, the solution was concentrated under reduced pressure andthe resulting residue was purified by flash chromatography on silica gel togive 39-40, 43-45 as whitesolids (44 ~ 87% yield).1,3-bis(4-morpholino-3-(trifluoromethyl)phenyl)urea 39 (81%yield).
With dmap; In dichloromethane; at 20℃; for 36.0h; 1 ,3-di(Pyridin-2-yl)urea (5a) was synthesised via the reaction of triphosgene (1 .0 g, 3.37 mmol) with 2-aminopyridine (6a) (1.576 g, 16.74 mmol) in the presence of DMAP (2.44 g, 20.01 mmol) in 0H2012(15.0 mL) at room temperature for 36 h. 5a was equally synthesised via Fe(OH)3Fe304-catalysed(0.060 g, 0.052 mmol) reaction of 2-aminopyridine (6a) (0.376 g, 4.0 mmol) with urea (3b) (0.120 g,2.0 mmol) in p-xylene at 140 00 for 2.5 days and obtained in 62% (0.266 g, 1.24 mmol) yield.26 White crystals; m.p. 175 c 130-NMR (100 MHz, DMSO-d6): : 152.4, 151.9, 147.3, 138.4, 118.1, 112.4.
  • 19
  • [ 504-29-0 ]
  • [ 57-13-6 ]
  • [ 6268-43-5 ]
  • 2,8-diaza-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one [ No CAS ]
  • 20
  • [ 504-29-0 ]
  • [ 5255-67-4 ]
  • [ 6268-43-5 ]
  • 21
  • [ 504-29-0 ]
  • [ 201230-82-2 ]
  • [ 6268-43-5 ]
YieldReaction ConditionsOperation in experiment
40% With 1-butyl-3-methyl-1H-imidazole-2(3H)-selenone; oxygen; at 90℃; under 9750.98 Torr; for 6.0h;Ionic liquid; Autoclave; General procedure: 5 mmol of aniline, 0.46 mmol of selenium-containing catalyst, and 0.25 g [BMIM]BF4 were sealed in a 100 mL stainless steel autoclave. The reactor was pressurized with 0.2 Mpa oxygen and 1.1 Mpa carbon monoxide and then placed in an oil bath preheated to 90 C; after 6 h of the reaction time, the apparatus was degassed, and the 1,3-diaryl urea was separated from [BMIM]BF4 by adding acetone and water to the reaction mixtures. Purification by column chromatography on silica gel or recrystallization gave the urea product. Products were identified by NMR measurements and/or comparison with authentic samples.
  • 22
  • [ 504-29-0 ]
  • [ 17717-92-9 ]
  • [ 6268-43-5 ]
  • 23
  • [ 6268-43-5 ]
  • [ 74-88-4 ]
  • 1-methyl-2-(3-(pyrid-2-yl)ureido)pyridinium iodide [ No CAS ]
  • 24
  • [ 504-29-0 ]
  • [ 4437-80-3 ]
  • 5,5-dimethyl-4-methylene-3-(2-pyridyl)oxazolidin-2-one [ No CAS ]
  • [ 6268-43-5 ]
  • 25
  • [ 504-29-0 ]
  • [ 170961-14-5 ]
  • [ 6268-43-5 ]
  • 26
  • [ 504-29-0 ]
  • methyl halide [ No CAS ]
  • [ 6268-43-5 ]
  • 27
  • [ 504-29-0 ]
  • 3-iodobenzyl 4-hydroxybenzoic acid coupled to N-methyl aminomethylated polystyrene [ No CAS ]
  • [ 6268-43-5 ]
  • 30
  • [ 6268-43-5 ]
  • [ 4589-12-2 ]
  • 31
  • [ 6268-43-5 ]
  • [ 157520-89-3 ]
  • 32
  • [ 6268-43-5 ]
  • [ 760214-97-9 ]
  • 33
  • [ 6268-43-5 ]
  • [ 56644-08-7 ]
  • 34
  • [ 6268-43-5 ]
  • <i>N</i>-[2]pyridyl-linolamide [ No CAS ]
  • 35
  • [ 6268-43-5 ]
  • (E)-N-(pyridin-2-yl)but-2-enamide [ No CAS ]
 

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Technical Information

Categories

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[ 6268-43-5 ]

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