53234-56-3|6-Chloro-5-cyanopicolinic acid| Ambeed

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

Quality Control of [ 53234-56-3 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 53234-56-3 ]

CAS No. :	53234-56-3
Formula :	C₇H₃ClN₂O₂
M.W :	182.56
SMILES Code :	O=C(O)C1=NC(Cl)=C(C#N)C=C1
MDL No. :	MFCD18258363
InChI Key :	ROPFRDWKBGCDEZ-UHFFFAOYSA-N
Pubchem ID :	53433239

Safety of [ 53234-56-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Computational Chemistry of [ 53234-56-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.92
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	73.98 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.77
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	1.39
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.3
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.	-1.12
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	1.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.74

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.15
Solubility	1.29 mg/ml ; 0.00705 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.	-2.55
Solubility	0.518 mg/ml ; 0.00284 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	-2.1
Solubility	1.45 mg/ml ; 0.00793 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.	-6.43 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.	0.56

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)	1.79

Application In Synthesis of [ 53234-56-3 ]

* 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 [ 53234-56-3 ]

[ 53234-56-3 ] Synthesis Path-Downstream 1~11

1
[ 53234-56-3 ]
[ 78-81-9 ]
[ 1198296-76-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium fluoride; In 1-methyl-pyrrolidin-2-one; at 95.0℃; for 18.0h;	EXAMPLE 225-cyano-6-(isobufylamino)picolinic acid (70) A mixture of <strong>[53234-56-3]6-chloro-5-cyanopicolinic acid</strong> (30 mg, 0.16 mmol), isopropylamine (20 ul, 0.23 mmol), and KF (28 mg, 0.48 mmol) in N-methylpyrrolidinone (1 ml) was heated for 18 hrs at 95 C. The mixture was diluted with water (4ml) and standed overnight. The resulting precipitate was collected by filtration and dried under vacuum to afford 25 mg (75%) of the desired product 70. 1H NMR (600MHz, DMSOd6) delta 13.2 (s, IH), 8.03 (d, IH, J= 7.8 Hz), 7.25-7.21 (m, IH), 7.17 (d, IH, J= 7.8 Hz), 3.26-3.24 (m, 2H), 1.99-1.95 (m, IH), 0.89 (d, 6H, 6.6 Hz). MS: m/z Calcd 219.2 Found MH+ 220.1

References: [1]Patent: WO2009/145829,2009,A1 .Location in patent: Page/Page column 102.

2
[ 53234-56-3 ]
[ 6258-66-8 ]
[ 1198296-57-9 ]

Yield	Reaction Conditions	Operation in experiment
82%		Step 2Synthesis of 6-(4-chlorobenzylthio)-5-cyanopicolinic acid (52)A mixture of <strong>[53234-56-3]6-chloro-5-cyanopicolinic acid</strong> (30 mg, 0.16 mmol), 4-chlorophenyl methanethiol (24 ul, 0.18 mmol), and CsCO3 (156 mg, 0.48 mmol) in dimethylformamide (2 ml) was heated for 16 hrs at 45 0 C. After removal of the solvent, the residue was treated with water (2 ml) and acidified with IN-HCl to pH2. The precipitate was collected by filtration and dried under vacuum to afford 40 mg (82%) of the desired product 52. 1H NMR (600MHz, DMSO-d^) delta 13.6 (br s, IH), 8.46 (d, IH, J=7.8 Hz), 8.15 (d, IH, J=7.8 Hz), 7.55 (d, 2H, J=9 Hz), 7.47 (d, 2H, J= 9Hz). MS: m/z Calcd 304.8 Found MH+ 305.0

References: [1]Patent: WO2009/145829,2009,A1 .Location in patent: Page/Page column 98-99.

3
[ 1312772-66-9 ]
[ 53234-56-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 216-(4-chlorobenzylthio)-5-cyanopicolinic acid (52) <n="101"/> Step 1Synthesis of 6-chloro-5-cyanopicolinic acid (51) To a solution of 6-chloro-5-cyano-2-picoline 50 (3.0 g, 20 mmol) in COnC-H2SO4 (20 ml) was added CrO3 (4.9 g, 49 mmol) portionwise over 2 hr period while the reaction mixture was kept below 2O 0 C. After stirring overnight at room temperature, the mixture was poured into ice-water and the resulting solid was collected by filtration to give the crude 6-chloro-5-(aminocarbonyl)-2-picolinic acid which was dissolved in POCl3 (15 ml). After heating at reflux for 30 min, the reaction mixture was concentrated in vacuo and the residue was treated with ice water. The precipitate was collected by filtration to afford 2.5 g (71% for 2 steps) of the desired product 51. 1H NMR (600MHz, DMSO-d6) delta 8.65 (delta, IH, theta= 7.8 Hzeta), 8.17 (delta, IH, theta= 7.8 Hzeta)

References: [1]Patent: WO2009/145829,2009,A1 .Location in patent: Page/Page column 98-99.

4
[ 53234-56-3 ]
[ 1378870-53-1 ]

References: [1]Patent: WO2012/69366,2012,A1 .

5
[ 53234-56-3 ]
[ 1378870-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20.0℃; for 4.0h;	Example 18: Preparation of 6-Chloro-5-cyano-pyridine-2-carboxylic acid (2-methyl-5- pentafluoroethyl-4-trifluoromethyl-2H-pyrazol-3-yl)-amideTo a suspension of <strong>[53234-56-3]6-chloro-5-cyano-pyridine-2-carboxylic acid</strong> (5.6 g, 25.2 mmol)(commercially available) in dichloromethane (100 ml) was added N,N-dimethylformamide (0.2 ml) at ambient temperature, followed by oxalyl chloride (3.2 ml, 38 mmol). The reaction mixture was stirred for 4 hour at room temperature and then concentrated. The residue was was used for the next step.2-Methyl-5-pentafluoroethyl-4-trifluoromethyl-2H-pyrazol-3-ylamine (Example II, 6.66 g, 23.5 mmol) was dissolved in tetrahydrofuran (120 ml) and pyridine (2.7 ml, 34 mmol) was added. 6-Chloro-5-cyano-pyridine-2-carboxylic acid chloride was added portionwise. The reaction mixture was stirred at ambient temperature for 19 hours. Then aqueous sodium hydrogen carbonate (saturated) was added and the aqueous phase was extracted three times with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and concentrated. The residue was purified by columnchromatography on silica gel (eluent: heptane / ethyl acetate 3 : 1) to give 6-chloro-5-cyano- pyridine-2-carboxylic acid (2-methyl-5-pentafluoroethyl-4-trifluoromethyl-2H-pyrazol-3-yl)- amide (7.1 g, 71% yield). 1H- MR (400 MHz, CDC13): 9.4 (sb, 1H), 8.35 (d, 1H), 8.31 (d, 1H), 3.90 (s, 3H) ppm.

References: [1]Patent: WO2012/69366,2012,A1 .Location in patent: Page/Page column 102-103.

6
[ 53234-56-3 ]
[ 1378870-54-2 ]

References: [1]Patent: WO2012/69366,2012,A1 .

7
[ 28900-10-9 ]
[ 53234-56-3 ]