180995-12-4|2,4-Dichloronicotinonitrile| Ambeed

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Quality Control of [ 180995-12-4 ] Purity: 98% SDS Specification

COA

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Product Details of [ 180995-12-4 ]

CAS No. :	180995-12-4
Formula :	C₆H₂Cl₂N₂
M.W :	173.00
SMILES Code :	N#CC1=C(Cl)N=CC=C1Cl
MDL No. :	MFCD09750302
InChI Key :	OQYZEFBWEXEOPL-UHFFFAOYSA-N
Pubchem ID :	21997828

Safety of [ 180995-12-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 180995-12-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	38.97
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	36.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.47
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	2.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.26
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.	1.0
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	2.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.72
Solubility	0.332 mg/ml ; 0.00192 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.	-2.56
Solubility	0.473 mg/ml ; 0.00274 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	-3.34
Solubility	0.0793 mg/ml ; 0.000458 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	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.	-5.82 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	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)	1.67

Application In Synthesis of [ 180995-12-4 ]

* 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 [ 180995-12-4 ]

[ 180995-12-4 ] Synthesis Path-Downstream 1~35

1
[ 180995-12-4 ]
[ 124-41-4 ]
[ 95689-37-5 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2457.
[2]Chemische Berichte,1923,vol. 56,p. 2457.

2
[ 70593-56-5 ]
[ 180995-12-4 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 523 - 525.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 386 - 390.
[3]Chemische Berichte,1923,vol. 56,p. 2457.

3
[ 89694-06-4 ]
[ 180995-12-4 ]

References: [1]Journal of the American Chemical Society,1956,vol. 78,p. 214,216.

4
[ 21642-98-8 ]
[ 180995-12-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; for 19.0h;Heating / reflux; Neat (no solvent);	2,4-dichloronicotinonitrile A solution of 5.0 g of commercial 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile in 50 ml of phosphorus oxychloride is refluxed for 19 hours. After cooling, the reaction medium is poured into a mixture of water and ice. The precipitate formed is filtered off and the filtrate is extracted twice with a 90/10 ethyl acetate/methanol solution. The combined organic phases and the precipitate are dried over magnesium sulfate and then concentrated under reduced pressure to give 6.76 g of a yellowish powder. The crude product is purified on a prepacked Biotage KP-Sil column of 60 A SiO2 32-63 muM (5/95 to 10/90 gradient ethyl acetate in cyclohexane) to give 2.08 g of a white powder of 2,4-dichloronicotinonitrile. MS-IE: 172=[M+] (base peak), 137=[M+]-Cl IR spectrum (KBr): 3072; 2236; 1559; 1539; 1445; 1368; 1220; 1197; 1069; 859; 818; 791 and 416 cm-1 1H NMR spectrum (400 MHz, (CD3)2SO, delta in ppm): 7.92 (d, J=5.5 Hz, 1H); 8.67 (d, J=5.5 Hz, 1H)

References: [1]Patent: US2008/39491,2008,A1 .Location in patent: Page/Page column 24.

5
[ 180995-12-4 ]
[ 380430-49-9 ]
[4-(4-chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 2.0h;	[4-(4-Chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester To a solution of 519 mg of <strong>[180995-12-4]2,4-dichloronicotinonitrile</strong> in 25.5 ml of dioxane are added 782 mg of (4-boc-aminophenyl)boronic acid, 693 mg of sodium bicarbonate in 8.5 ml of water and 347 mg of tetrakis(triphenyl-phosphine)palladium. The suspension is stirred at 100 C. for 2 hours under argon. After cooling, the reaction mixture is poured into water and extracted three times with a 90/10 ethyl acetate/methanol solution. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure. 1.58 g of crude product are chromatographed on a prepacked Biotage KP-Sil column of 60 A SiO2 32-63 mum (from 0.5/99.5 to 1/99 gradient of solution A in dichloromethane; solution A=38/17/2 dichloromethane/methanol/aqueous ammonia). 797 mg of [4-(4-chloro-3-cyanopyrid-2-yl)phenyl]carbamic acid tert-butyl ester are obtained, the characteristics of which are as follows: MS-EI: 329 (+) IR spectrum (CCl4): 3343; 2981; 2230; 1741; 1524; 1501; 1411; 1392; 1368; 1316; 1220; 1155; 1050 and 844 cm-1 1H NMR spectrum (400 MHz, (CD3)2SO, delta in ppm): 1.50 (s, 9H); 7.62 (d, J=9.0 Hz, 2H); from 7.78 to 7.84 (m, 3H); 8.83 (d, J=5.5 Hz, 1H); 9.67 (s, 1H).

References: [1]Patent: US2008/39491,2008,A1 .Location in patent: Page/Page column 24.

6
[ 180995-12-4 ]
[ 621-29-4 ]
[ 214360-73-3 ]
N-[4-(3-amino-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl]-N'-(3-methylphenyl)urea [ No CAS ]
N-[4-(3-amino-1H-pyrazolo[4,3-c]pyridin-4-yl)phenyl]-N'-(3-methylphenyl)urea [ No CAS ]