Home Cart Sign in  
Chemical Structure| 854044-51-2 Chemical Structure| 854044-51-2

Structure of 854044-51-2

Chemical Structure| 854044-51-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 854044-51-2 ]

CAS No. :854044-51-2
Formula : C10H16BrN3OSi
M.W : 302.24
SMILES Code : N#CC1=CN(COCC[Si](C)(C)C)C(Br)=N1
MDL No. :MFCD12964153
InChI Key :XDLFZSWZSHTGJY-UHFFFAOYSA-N
Pubchem ID :57920578

Safety of [ 854044-51-2 ]

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

Computational Chemistry of [ 854044-51-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 5
Fraction Csp3 0.6
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 68.89
TPSA ?

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

50.84 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.7
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

3.17
Log Po/w (WLOGP)?

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

2.68
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.

0.5
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

0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.97

Water Solubility

Log S (ESOL):?

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

-3.61
Solubility 0.0738 mg/ml ; 0.000244 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.

-3.91
Solubility 0.0373 mg/ml ; 0.000123 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

-3.56
Solubility 0.0838 mg/ml ; 0.000277 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

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

Yes
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.

-5.89 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)

3.23

Application In Synthesis of [ 854044-51-2 ]

* 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 [ 854044-51-2 ]

[ 854044-51-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 76513-69-4 ]
  • [ 57090-88-7 ]
  • [ 854044-51-2 ]
YieldReaction ConditionsOperation in experiment
1.24 g lH-<strong>[57090-88-7]imidazole-4-carbonitrile</strong> (1 g, 10.74 mmol) and potassium carbonate (2.97 g, 21.49 mmol) were added to a round bottomed flask and placed under an atmosphere of nitrogen by evacuation-refill. Acetone (10 mL) was added, evacuation-refill of the vessel repeated, and the mixture stirred prior to addition of (2- (chloromethoxy)ethyl)trimethylsilane (2.091 mL, 11.82 mmol). The reaction vessel was placed under an atmosphere of nitrogen and stirred at RT for 48 h. The solvent was removed under reduced pressure, and the residue redissolved in 30 mL EtOAc and washed sequentially with 20 mL water and 20 mL brine. The combined aqueous layers were extracted with further EtOAc (2 x 30 mL). The organic layers were combined and passed through a hydrophobic frit, and the solvent was removed under reduced pressure. The sample was dissolved in DCM and purified by column chromatography using a silica cartridge (120 g) with an ethyl acetate-cyclohexane solvent system [3CV, 10-20percent; 3CV, 20percent; 5CV, 20-50percent; 9CV, 50percent]. The appropriate fractions were combined and the solvent removed in vacuo to afford the title compound in a 2: 1 ratio of the l-((2-(trimethylsilyl)ethoxy)methyl)-lH-<strong>[57090-88-7]imidazole-4-carbonitrile</strong> and l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-5-carbonitrile regioisomers, as a pale yellow oil (1.71 g, 7.66 mmol, 71percent). LCMS (System B): tRET = 1.08 min; MH+ 224 (both regioisomers). l-((2-(Trimethylsilyl)ethoxy)methyl)-lH-<strong>[57090-88-7]imidazole-4-carbonitrile</strong> (for an example preparation, see Intermediate 15, 1.68 g, 7.52 mmol (2: 1 ratio of l-((2- (trimethylsilyl)ethoxy)methyl)-lH-<strong>[57090-88-7]imidazole-4-carbonitrile</strong> and H(2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-5-carbonitrile)) was added to a round bottomed flask containing THF (40 mL). Once dissolved, /V-bromosuccinimide (1.473 g, 8.27 mmol) was added, and the flask placed under an atmosphere of nitrogen. The reaction mixture was stirred at 60 °C overnight. Further 0.2 equivalents of /V-bromosuccinimide (0.268 g, 1.504 mmol) was added to the reaction mixture and the reaction left stirring at 60 °C for a further 8h. The reaction mixture was quenched with saturated sodium hydrogencarbonate solution (40 mL) and brine (40 mL) and extracted with EtOAc (3 x 40 mL). The combined organic layers were passed through a hydrophobic frit and the solvent removed under reduced pressure. The sample was loaded as a neat liquid and purified by column chromatography using a silica cartridge (80 g) with an ethyl acetate-cyclohexane solvent system [3CV, 0percent; 7CV, 0-10percent; 3CV, 10percent]. The appropriate fractions were combined and the solvent removed in vacuo to give the crude product. The crude product was dissolved in diethyl ether and filtered through Celite®, the solvent was removed from the filtrate under reduced pressure to afford the title compound as a pale yellow oil, (1.24 g, 4.10 mmol, 55percent). LCMS (System A): tRET = 1.23 min; MH+ 302, 304.
 

Historical Records

Technical Information

Categories