31872-64-7|3-Chloro-5-nitropyridin-4-ol| 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 [ 31872-64-7 ] Purity: 97% 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 [ 31872-64-7 ]

CAS No. :	31872-64-7
Formula :	C₅H₃ClN₂O₃
M.W :	174.54
SMILES Code :	OC1=C(Cl)C=NC=C1[N+]([O-])=O
MDL No. :	MFCD11044290
InChI Key :	VEOKYVSPRSTYHS-UHFFFAOYSA-N
Pubchem ID :	11850826

Safety of [ 31872-64-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 31872-64-7 ] 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	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.95
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	1.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
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.	-0.7
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	-0.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.51

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.2
Solubility	1.09 mg/ml ; 0.00624 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.	-2.77
Solubility	0.3 mg/ml ; 0.00172 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	-1.44
Solubility	6.29 mg/ml ; 0.0361 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.	-6.3 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	2.0 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)	1.99

Application In Synthesis of [ 31872-64-7 ]

* 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 [ 31872-64-7 ]

[ 31872-64-7 ] Synthesis Path-Downstream 1~35

2
[ 31872-64-7 ]
[ 56809-84-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trichlorophosphate; In toluene; at 20 - 100℃;	To a suspension of 9-b (35 g, 147.52 mol) in toluene (50 mL) was added POCI3 (50 mL) at room temperature. The mixture was slowly heated to 100C and stirred overnight at that temperature. The mixture was cooled to room temperature and concentrated. To the resulting residue ice-water was carefully added then the resulting mixture was extracted with ethyl acetate. The organic layers were separated, washed with water and brine, dried over anhydrous Na2S04 and evaporated. The intermediate 9-c was obtained (25 g, 90%).
90%	With trichlorophosphate; In toluene; at 100℃;	To a suspension of 18-a (35 g, 147.52 mol) in toluene (50 mL) was added POCI3 (50 mL) at room temperature. The mixture was slowly heated to 100C and stirred overnight at that temperature. The mixture was cooled to room temperature and concentrated. To the resulting residue ice-water was carefully added then the resulting mixture was extracted with ethyl acetate. The organic layers were separated, washed with water and brine, dried over anhydrous Na2S04 and evaporated. The intermediate 18-b was obtained (25 g, 90%).
		Step 2. 3,4-Dichloro-5-nitropyridine; To a mixture of <strong>[31872-64-7]3-chloro-4-hydroxy-5-nitropyridine</strong> (3.45 g, 19.8 mmol) in 20 mL ofDMF at room temperature is added phosphorus oxychloride (1.8 mL, 19.8 mmol). The resulting solution is heated to 1200C for 30 min., and then cooled to 00C. The reaction mixture is neutralized to pH=7 with sat. aqueous NaHCO3 and extracted with EtOAc (2 x 100 mL). The combined organic extracts are dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by column chromatography (gradient from hexane to 10% EtOAc/hexane) affords the title compound as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.94 (s, IH), 8.83 (s, IH).

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.
[2]Patent: WO2013/186332,2013,A1 .Location in patent: Page/Page column 51.
[3]Patent: WO2013/186335,2013,A1 .Location in patent: Page/Page column 76.
[4]Patent: WO2009/108551,2009,A2 .Location in patent: Page/Page column 66.

3
[ 5435-54-1 ]
[ 31872-64-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With chlorine; acetic acid; In water; at 20℃; for 20.0h;	To a solution of 3-nitropyridin-4-ol 8-a (20 g, 142.76 mmol, 1 eq.) in 50 % aqueous acetic acid (250 mL) chlorine was bubbled for 20 h at room temperature. The resulting precipitate was filtered and washed with water. The intermediate 9-b was obtained (24 g, 97%).
97%	With chlorine; acetic acid; In water; at 20℃; for 20.0h;	To a solution of 3-nitropyridin-4-ol 17-a (20 g, 142.76 mmol, 1 eq.) in 50 % aqueous acetic acid (250 mL) chlorine was bubbled for 20 h at room temperature. The resulting precipitate was filtered and washed with water. The intermediate 18-a was obtained (24 g, 97%).
	With N-chloro-succinimide; In acetonitrile; at 70℃;Reflux;	EXAMPLE 11; 4-Chloro-N-(\| l-r(3S)-3-methylpiperazin-l-yllcyclohexyljmethyl)-l-pyrimidin-2-yl-lH- pyrrolo [2 ,3 -c 1 pyridine- 3 -carboxamide; Step 1. 3-Chloro-4-hydroxy-5-nitropyridine; A solution of N-chlorosuccinimide (4.6 g, 34.5 mmol) in 25 mL of acetonitrile is added dropwise to a mixture of 4-hydroxy-3-nitropyridine (4.4 g, 31.4 mmol) in 50 mL of acetonitrile.The reaction mixture is then heated to reflux and stirred for 2 days. After cooling to room temperature, the mixture is filtered. The solid is taken up in 100 mL of EtOH and stirred at 700C <n="67"/>for 30 min. The hot mixture is filtered, and the solid is dried in vacuo to afford the title compound as a white powder. 1H NMR (300 MHz, DMSOd6) delta 8.82 (s, IH), 8.28 (s, IH). Mass spec. (174.80, M+H).

References: [1]Patent: WO2013/186332,2013,A1 .Location in patent: Page/Page column 51.
[2]Patent: WO2013/186335,2013,A1 .Location in patent: Page/Page column 76.
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.
[4]Patent: WO2009/108551,2009,A2 .Location in patent: Page/Page column 65-66.

4
[ 31872-64-7 ]
[ 908355-84-0 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

5
[ 31872-64-7 ]
9-butyl-8-(7-chlorothiazolo[4,5-c]pyridin-2-ylsulfanyl)-9H-purin-6-ylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

6
[ 31872-64-7 ]
acetic acid 3-[6-amino-8-(7-chlorothiazolo[4,5-c]pyridin-2-ylsulfanyl)-purin-9-yl]-propyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

7
[ 31872-64-7 ]
{2-[6-amino-8-(7-chlorothiazolo[4,5-c]pyridin-2-ylsulfanyl)-purin-9-yl]-ethyl}-phosphonic acid diethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

8
[ 31872-64-7 ]
[ 89284-39-9 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5352 - 5362.

9
[ 31872-64-7 ]
7-chloro-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one [ No CAS ]

References: [1]Patent: WO2013/186332,2013,A1 .
[2]Patent: WO2013/186335,2013,A1 .

10
[ 31872-64-7 ]
3-chloro-N-cyclopropyl-5-nitropyridin-4-amine [ No CAS ]

References: [1]Patent: WO2013/186332,2013,A1 .
[2]Patent: WO2013/186335,2013,A1 .

11
[ 31872-64-7 ]
5-chloro-N<SUP>4</SUP>-cyclopropylpyridine-3,4-diamine [ No CAS ]

References: [1]Patent: WO2013/186332,2013,A1 .
[2]Patent: WO2013/186335,2013,A1 .

12
[ 31872-64-7 ]
[ 89284-28-6 ]

References: [1]Patent: WO2013/186332,2013,A1 .

13
[ 31872-64-7 ]
7-chloro-3-((5-chloro-1-(3-(methylsulfonyl)-propyl)-1H-benzo[d]imidazol-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one [ No CAS ]

References: [1]Patent: WO2013/186332,2013,A1 .

14
[ 31872-64-7 ]
3-amino-5-chloropyridin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen; In methanol; under 760.051 Torr; for 8.0h;	Asolution of <strong>[31872-64-7]3-chloro-4-hydroxy-5-nitropyridine</strong> (7.31 g, 42 mmol) in MeOH (400mL) was treated with RaneyNi (1 teaspoon) and hydrogenated for 8 hrs atatmospheric pressure. The mixture was filtered through Celite carefully withoutdrying out the celite/residue and the filtrate evaporated to dryness to afford3-amino-5-chloro-4- hydroxy-pyridine as a dark purple solid (5.8 g at 95%purity, 96% yield); H NMR (500 mHz, DMSO) delta 4.79 (bs, 2H), 7.13 (s, 1H), 7.76(s, 1H), 1 1.50 (bs, 1H).

References: [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 99; 100.

15
[ 31872-64-7 ]
N-(5-chloro-4-hydroxypyridin-3-yl)-6-(trifluoromethyl)pyridine-3-sulfonamide [ No CAS ]