25391-60-0|2-Chloro-3-iodo-5-nitropyridine| Ambeed

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Structure of 25391-60-0

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Quality Control of [ 25391-60-0 ] Purity: 95% SDS Specification

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Product Details of [ 25391-60-0 ]

CAS No. :	25391-60-0
Formula :	C₅H₂ClIN₂O₂
M.W :	284.44
SMILES Code :	O=[N+](C1=CN=C(Cl)C(I)=C1)[O-]
MDL No. :	MFCD12028701
InChI Key :	KUMMEUQAQSZVOD-UHFFFAOYSA-N
Pubchem ID :	11140639

Safety of [ 25391-60-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H318
Precautionary Statements:	P280-P305+P351+P338
Class:	8
UN#:	1759
Packing Group:	Ⅲ

Computational Chemistry of [ 25391-60-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	50.79
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.71 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.37
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	2.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.25
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.	1.63
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	0.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.69

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.38
Solubility	0.118 mg/ml ; 0.000413 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.	-3.16
Solubility	0.197 mg/ml ; 0.000691 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	-2.97
Solubility	0.307 mg/ml ; 0.00108 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.	-6.41 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	4.0 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)	2.44

Application In Synthesis of [ 25391-60-0 ]

* 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 [ 25391-60-0 ]

[ 25391-60-0 ] Synthesis Path-Downstream 1~35

1
[ 25391-58-6 ]
[ 25391-60-0 ]

Yield	Reaction Conditions	Operation in experiment
94.4%	With trichlorophosphate; at 80℃; for 3h;	2-Hydroxy-3-iodo-5-nitropyridine (1.0 g, 3.76mmol) and phosphorus oxychloride (3.5 g, 11.28mmol) were charge, and the temperature was raised to 80C. The reaction was carried out at 80C for 3 hours and the mixture was poured into ice water. The precipitated crystals were filtered to give the title compound (1.01 g, 94.4%).
81%	With trichlorophosphate; In quinoline; at 120℃; for 2h;	Synthesis of 2-Chloro-3-iodo-5-nitro-pyridine (CXXII): To a solution of CXXI (14 g, 52.6 mmol) in quinoline (5 mL) was added phosphorous oxychloride (4.8 mL, 52.2 mmol). The resulting mixture was heated at 120 C for 2 h. Progress of the reaction was monitored by 15 TLC. After cooling to room temperature the reaction mixture was poured onto ice cold water (75 mL) and the precipitate that formed was collected by filtration. The filtered solid was washed with water and allowed to dry to obtain CXXII (12 g, 81%) as a brown solid.1H NMR (400 MHz, CDCl3): delta 9.12 (d, J= 2.3 Hz, 1H), 8.84 (d, J= 2.4 Hz, 1H).
69%	With phosphorus pentachloride; trichlorophosphate; at 140℃; for 0.75h;Product distribution / selectivity;	Intermediate 1; 6-Phenyl-5-(trifluoromethyl)pyridin-3-amineA. 2-Chloro-3-iodo-5-nitropyridineA mixture of <strong>[25391-58-6]3-iodo-5-nitropyridin-2-ol</strong> (37.60 mmol, 10 g), POCI3 (86.47 mmol, 7.94 ml) and PCI5 (48.87 mmol, 10.2 g) was heated at 14O0C for 45 minutes under argon atmosphere. The mixture was cooled at room temperature, poured slowly over iced-water and extracted with dichloromethane. The organic phase was washed with water, NaHCO3 aqueous solution and brine. The solvent was evaporated and the crude mixture was purified by chromatography over SiO2 eluting hexane/DCM mixtures affording 7.32 g (yield 69%) of the expected product. <n="39"/>1H NMR (300 MHz, CDCI3) delta ppm: 8.90 (s, 1 H), 9.19 (s, 1H). Intermediate 4A. 2-Chloro-3-iodo-5-nitropyridineA mixture of <strong>[25391-58-6]3-iodo-5-nitropyridin-2-ol</strong> (37.6 mmol, 10 g), POCI3 (86.47 mmol, 7.94 ml) and PCI5 (48.87 mmol, 10.2 g) was heated at 14O0C for 1h, under argon atmosphere. The crude mixture was poured into a mixture of ice and water and extracted with DCM. The solid residue was purified by chromatography over SiO2 eluting with hexane/dichloromethane mixtures affording 2-chloro-3-iodo-5-nitropyridine (7.32 g, yield69%) of the expected product. 1H NMR (300 MHz, CDCI3) delta ppm: 8.91 (d, J=2.47 Hz, 1H) 9.19 (d, J=2.47 Hz, 1H). Intermediate 606-Chloro-5-(trifluoromethyl)pyridin-3-amineA. 2-Chloro-3-iodo-5-nitropyridine A mixture of <strong>[25391-58-6]3-iodo-5-nitropyridin-2-ol</strong> (37.60 mmol, 10 g), POCI3 (86.47 mmol, 7.94 ml) and PCI5 (48.87 mmol, 10.2 g) was heated at 14O0C for 45 minutes under argon atmosphere. The mixture was cooled at room temperature, poured slowly over iced-water and extracted with dichloromethane. The organic phase was washed with water, NaHCO3 aqueous solution and brine. The solvent was evaporated and the crude mixture was purified by chromatography over SiO2 eluting hexane/DCM mixtures affording 7.32 g (yield 69%) of the expected product. delta 1H NMR (300 MHz, CDCI3): 8.90 (s, 1H), 9.19 (s, 1H).

	With quinoline; trichlorophosphate; at 20 - 120℃; for 2h;	K1 ) 2-Chloro-3-iodo-5-nitro-pyridine; :<strong>[25391-58-6]2-hydroxy-3-iodo-5-nitropyridine</strong> (2.0 g, 7.52 mmol) is added to a mixture of POCI3 (0.7 ml, 7.52 mmol) and quinoline (0.44 ml, 3.76 mmol) at room temperature. The <n="49"/>reaction mixture is heated at 120 0C for 2 h. The reaction mixture is then cooled to 96 0 C and is carefully quenched by the dropwise addition of water (32 ml). The reaction mixture is cooled to room temperature and filtered. The solid collected is dissolved in EtOAc and dried (MgSO4) then concentrated in vacuo to yield the title compound.
		Example 70: N-[6-methyl-5-(9H-pyrimido[4,5-b]indol-7-yl)pyridin-3-yl]-3- (trifluoromethyl)benzamide <n="80"/>Stepl : 2-chloro-3-iodo-5-nitropyridine3-Iodo-5-nitropyridin-2-ol (3.00 g, 0.0113 mol) was heated to reflux in phosphoryl chloride(15 mL, 0.1609 mol) for 4 hours. The reaction was quenched in ice/water and was neutralized with Na2CO3. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo to give the product, which was used in the next reaction without purification

References: [1]Australian Journal of Chemistry,2008,vol. 61,p. 438 - 445.
[2]Patent: EP2599771,2013,A1 .Location in patent: Paragraph 0505.
[3]Patent: WO2015/73528,2015,A1 .Location in patent: Page/Page column 191.
[4]Journal of Medicinal Chemistry,2002,vol. 45,p. 2841 - 2849.
[5]Patent: WO2009/21696,2009,A1 .Location in patent: Page/Page column 37-38; 41; 69.
[6]Patent: WO2007/65662,2007,A2 .Location in patent: Page/Page column 47-48.
[7]Patent: WO2008/79965,2008,A1 .Location in patent: Page/Page column 78-79.

2
[ 25391-60-0 ]
[ 444902-32-3 ]

References: [1]Australian Journal of Chemistry,2008,vol. 61,p. 438 - 445.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 2841 - 2849.

3
[ 5418-51-9 ]
[ 25391-60-0 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 2841 - 2849.
[2]Patent: WO2015/73528,2015,A1 .

4
[ 25391-60-0 ]
5-(2-(4-pyridinyl)ethylenyl)-6-chloro-3-(2-(S)-pyrrolidinylmethoxy)pyridine [ No CAS ]