62226-18-0|6-Chlorothieno[2,3-b]pyridine| Ambeed

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Quality Control of [ 62226-18-0 ] Purity: 95% SDS Specification

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Product Details of [ 62226-18-0 ]

CAS No. :	62226-18-0
Formula :	C₇H₄ClNS
M.W :	169.63
SMILES Code :	ClC1=NC2=C(C=CS2)C=C1
MDL No. :	MFCD18253768
InChI Key :	FBLJMPADHWBVBA-UHFFFAOYSA-N
Pubchem ID :	11636880

Safety of [ 62226-18-0 ]

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

Computational Chemistry of [ 62226-18-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	44.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.13 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.02
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	3.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.95
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.	2.11
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	3.83
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.82

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.55
Solubility	0.0473 mg/ml ; 0.000279 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.	-3.7
Solubility	0.0335 mg/ml ; 0.000197 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	-3.58
Solubility	0.0447 mg/ml ; 0.000264 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.	-5.08 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)	1.95

Application In Synthesis of [ 62226-18-0 ]

* 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 [ 62226-18-0 ]

[ 62226-18-0 ] Synthesis Path-Downstream 1~20

1
[ 62226-16-8 ]
[ 62226-18-0 ]

References: [1]Journal of Heterocyclic Chemistry,1976,vol. 13,p. 1197 - 1200.

2
[ 110651-85-9 ]
[ 62226-18-0 ]
[ 62226-17-9 ]

References: [1]Journal of Heterocyclic Chemistry,1976,vol. 13,p. 1197 - 1200.

3
[ 62226-18-0 ]
[ 104-78-9 ]
[ 72411-47-3 ]

References: [1]Journal of Heterocyclic Chemistry,1979,vol. 16,p. 1289 - 1291.

4
[ 68236-35-1 ]
[ 62226-18-0 ]

References: [1]Synthesis,2006,p. 1295 - 1300.
[2]Journal of the Chemical Society. Perkin transactions I,1981,p. 2509 - 2517.

5
[ 62226-18-0 ]
[ 124-41-4 ]
6-methoxythieno<2,3-b>pyridine [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

6
[ 99429-80-8 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

8
[ 62226-18-0 ]
pyridin-2-ylzinc(II) bromide [ No CAS ]
[ 890402-83-2 ]

References: [1]Synthesis,2006,p. 1295 - 1300.

9
[ 68236-26-0 ]
[ 62226-18-0 ]

References: [1]Synthesis,2006,p. 1295 - 1300.

10
[ 59739-05-8 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

11
[ 99429-78-4 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

12
[ 99429-68-2 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

13
[ 99429-66-0 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

14
[ 99429-79-5 ]
[ 62226-18-0 ]

References: [1]Journal of Chemical Research, Miniprint,1985,p. 2501 - 2523.

15
[ 25557-50-0 ]
[ 62226-18-0 ]

References: [1]Journal of Heterocyclic Chemistry,1976,vol. 13,p. 1197 - 1200.

16
[ 62226-18-0 ]
[ 205055-23-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 70 <strong>[62226-18-0]6-Chloro-thieno[2,3-b]pyridine</strong>-2-sulfonyl chloride <strong>[62226-18-0]6-Chloro-thieno[2,3-b]pyridine</strong> (0.73 g, 4.3 mmol) is to subjected to the three step sequence sequence described in EXAMPLE 8, Part A. Flash chromatography (15 % EtOAc/Hexane) of the crude product gives the title compound (0.75 g, 2.8 mmol): 1H NMR (CDCl3, 300 MHz) delta8.19 (d, 1H), 8.07 (s, 1H), 7.47 (d, 1H). EI MS M+=267, 269, 271.

References: [1]Patent: US6281227,2001,B1 .

17
[ 62226-18-0 ]
[ 91419-52-2 ]
[ 1196973-50-8 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 6303 - 6306.

18
[ 62226-18-0 ]
[ 1431869-49-6 ]

References: [1]Patent: WO2013/62900,2013,A1 .

19
[ 62226-18-0 ]
[ 1431869-34-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-iodo-succinimide; In trifluorormethanesulfonic acid; at 20℃; for 4.0h;	Step A: 6-Chloro-2-iodothieno[Z3-b1pyridine: To a flask charged with 6-Chlorothieno[2,3- b]pyridine (500 mg, 3.0 mmol) and a stir bar was added NIS (800 mg, 3.5 mmol) and Triflic acid (5 mL). The mixture was monitored by TLC and allowed to stir at RT for 4 hours. The reaction was poured into ice, neutralized with aqueous sodium carbonate, extracted with DCM, dried over sodium sulfate, concentrated and purified by flash chromatography (Hex: EtOAc gradient) to obtain the title product. LC-MS (IE, tn/z): 296 [M + 1]+.

References: [1]Patent: WO2013/62900,2013,A1 .Location in patent: Page/Page column 26; 27.

20
[ 62226-18-0 ]
[ 1431869-33-8 ]

References: [1]Patent: WO2013/62900,2013,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 62226-18-0 ]

Chlorides

A137163 [99429-80-8]

4,6-Dichlorothieno[2,3-b]pyridine

Similarity: 0.84

A150933 [18368-64-4]

2-Chloro-5-methylpyridine

Similarity: 0.63

A319798 [18740-39-1]

2,4-Dichlorothieno[2,3-d]pyrimidine

Similarity: 0.61

A105037 [43088-67-1]

4-Chloro-5-methylthieno[2,3-d]pyrimidine

Similarity: 0.61

A222387 [90196-32-0]

2-Chloro-5-ethylpyridine

Similarity: 0.60

Related Parent Nucleus of
[ 62226-18-0 ]

Other Aromatic Heterocycles

A137163 [99429-80-8]

4,6-Dichlorothieno[2,3-b]pyridine

Similarity: 0.84

A148552 [272-23-1]

Thieno[2,3-b]pyridine

Similarity: 0.82

A319798 [18740-39-1]

2,4-Dichlorothieno[2,3-d]pyrimidine

Similarity: 0.61

A105037 [43088-67-1]

4-Chloro-5-methylthieno[2,3-d]pyrimidine

Similarity: 0.61

A105167 [59207-24-8]

4-Chloro-2-methylthieno[3,2-c]pyridine

Similarity: 0.60

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 62226-18-0

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