51498-37-4|4-Hydroxypyridine-3-sulfonic 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 [ 51498-37-4 ] 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 [ 51498-37-4 ]

CAS No. :	51498-37-4
Formula :	C₅H₅NO₄S
M.W :	175.16
SMILES Code :	O=S(C1=C(O)C=CN=C1)(O)=O
MDL No. :	MFCD02093473
InChI Key :	AZRCSTMIVMQIPR-UHFFFAOYSA-N
Pubchem ID :	3016673

Safety of [ 51498-37-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Computational Chemistry of [ 51498-37-4 ] 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	5.0
Num. H-bond donors	2.0
Molar Refractivity	36.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	95.87 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	-0.32
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	-0.2
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.11
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.	-1.09
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	-0.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.14
Solubility	12.8 mg/ml ; 0.0728 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.36
Solubility	7.7 mg/ml ; 0.044 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.8
Solubility	28.0 mg/ml ; 0.16 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.	-7.51 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)	1.97

Application In Synthesis of [ 51498-37-4 ]

* 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 [ 51498-37-4 ]

[ 51498-37-4 ] Synthesis Path-Downstream 1~37

1
[ 51498-37-4 ]
[ 33263-44-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With phosphorus pentachloride; trichlorophosphate; at 125℃; for 1.0h;	4-chloropyridine-3-sulfonyl chloridePentachlorophosphorane (7.29 g, 35 mmol), phosphoryl trichloride (1.86 ml_, 20 mmol) were added to <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (1.75 g, 10 mmol). The mixture was stirred at 125 C for 1 h. The solution was allowed to cool to 23 C and then concentrated to remove excess POCI3, diluted with Et20 and poured onto ice. The residue was stirred for 5 min and then was neutralized with solid NaHC03, the mixture was extracted with EtOAc and combined extracts were dried (Na2S04) and concentrated giving 2.02 g (95%) of the title compound. LC-MS m/z 211.8 (M+H)+, 0.74 (ret. time).
84%	With phosphorus pentachloride; at 0 - 120℃; for 1.0h;	To a suspension of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (17 .5 g, 1 00 mmol) at 0 oc wasadded PCis (72.8 g, 350 mmol) and POCb (18.62 ml, 200 mmol). It was heated at 120 oc10 for 1 h. The reaction mixture was cooled to ambient temperature and concentrated. It wasdiluted with EtOAc and poured over ice. Solid NaHC03 was added and extracted withEtOAc. The organic layer was dried over anhydrous Na2S04 and filtered. The filtrate wasconcentrated to give the title compound (18 g, 84 mmol, 84 % yield) as pale yellow liquid.LC/MS m/z = 211.96 (M+Ht, 1.94 min (ret. time).
68.6%	With phosphorus pentachloride; trichlorophosphate; at 0 - 120℃; for 1.0h;	To a suspension of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (25 g, 143 mmol) was added PCI5 (104 g, 500 mmol) and POCI3 (26.6 ml, 285 mmol) at 0 C and stirred at 120 C for 1 h. The reaction mixture was cool to ambient temperature, the reaction mass was concentrated. The residue was diluted with EtOAc and poured in to ice. Solid NaHC03 was added and the aqueous phase was extracted with EtOAc. The organic layer was dried over anhydrous Na2S04 and filtered to afford the title compound (25 g, 98 mmol, 68.6% yield). LCMS mfz 212 (M+H)+, 1.93 min (ret. time).

68.6%	With phosphorus pentachloride; trichlorophosphate; at 0 - 120℃; for 1.0h;	To a suspention of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (25 g, 143 mmol) was added PCl5 (104 g, 500 mmol) and POCl3 (26.6 ml, 285 mmol) at 0 C and stirred at 120 C for 1h. The reaction mixture was cool to ambient temperature, the reaction mass was concentrated. The residue was diluted with EtOAc and poured in to ice. Solid NaHCO3 was added and the aqueous phase was extractred with EtOAc.The organic layer was dried over anhydrous Na2SO4 and filtered to afford the title compound (25 g, 98 mmol, 68.6% yield). LCMS m/z 212 (M+H)+, 1.93 min (ret. time).
	With phosphorus pentachloride; trichlorophosphate;	(1) 80 g of phosphorus pentachloride, 80 g of phosphorus oxychloride and 20 g of <strong>[51498-37-4]4-hydroxy-3-pyridinesulfonic acid</strong> were mixed and reacted under reflux for 4.5 hours to obtain a reaction mixture containing 4-chloro-3-chlorosulfonylpyridine. From the obtained reaction mixture, excess phosphorus oxychloride was distilled off under reduced pressure. The residue was put into ice of about 200 g and extracted with dichloromethane. The obtained extract layer was washed with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and cooled with ice.
	With phosphorus pentachloride; In chlorobenzene; for 6.0h;Heating / reflux;	Example 2; 4-Chloro-3-pyridinesulfonamide [4]. "One-pot"procedure:; A mixture of <strong>[51498-37-4]4-hydroxy-3-pyridinesulfonic acid</strong> [5] (50.0 g, 0.29 mol), phosphorus pentachloride (130. 8 g, 0.63 mol) and chlorobenzene (580 g) was stirred under reflux conditions for 6 hours. The mixture of phosphorus oxychloride and chlorobenzene (590-610 g) were distilled off from the mixture at atmospheric pressure. The cooled (25-30 C) residue (-100 mL) was added dropwise to the stirred mixture of 25 % aqueous ammonia (116.5 g, 1.7 mol) and acetone (20 g) for 30-40 minutes maintaining the temperature at 0-5 C. The reaction mixture (pH 11-12) was stirred for 1 hour at the same temperature and for 1 hour at 25 C. Chlorobenzene (50 g) and water (150 g) were added to the stirred mixture at the same temperature. The reaction mixture was concentrated to 250-300 g (pH 7-8) under reduced pressure (20 - 100 mbar) at 30-40 C. The obtained suspension was stirred for 5 hours at 0- 5 C. The precipitated solids were filtered off, triturated with water (2 x 200 g) at 30 C and dried under reduced pressure at 40-50 C (water bath) to a constant weight to give 42.7 g (77.6 %) of 4-chloro-3-pyridinesulfonamide [4] with 99.6 % purity by HPLC, assay 99.9 % by HC104 titration, 0.06 % of water by KF titration and mp 146-148 C (dec. ).
	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In 1,2-dichloro-ethane; at 90℃; for 0.75h;	4-Chloro-N-(3,4-dimethoxyphenyl)pyridine-3-sulfonamide (IntDI ) A solution of <strong>[51498-37-4]4-hydroxypyridine-3-sulfonic acid</strong> (5.0 g, 28.5 mmol), N,N- di/'sopropylethylamine (9.2 g, 71.3 mmol), phosphorus(V) oxychloride (10.9 g, 71.3 mmol) in 1 ,2-dichloroethane (50 mL) was heated at 90C for 45 min with TLC monitoring (hexane:EtOAc, 1 :1). After cooling, the solution was added to 3,4- dimethoxyaniline (4.8 g, 31.0 mmol), A/./V-di/sopropylethylamine (7.35 g, 57.0 mmol) in 1 ,2-dichloroethane (50 mL) at -10C and the resulting mixture stirred for approximately 2 h at rt with TLC monitoring (hexane:EtOAc, 1 :1). The mixture was then added to saturated aqueous NaHC03 (200 mL), extracted with DCM (3 x 50 mL) and the combined organic layers dried over Na2S04 and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-20% EtOAc in hexane yielded the title compound (2.2 g, 6.69 mmol). Mass spectroscopy: (ESI +ve) 329.2, 331.2 [M+H]+1H NMR: (400 MHz, DMSO) delta 3.65 (s, 3H), 3.65 (s, 3H), 6.60 (dd, J=8.5, 2.4, 1 H), 6.72 (d, J=2.4, 1 H), 6.81 (d, J=8.9, 1 H), 7.78 (d, J=5.2, 1 H), 8.72 (d, J=5.2, 1 H), 8.96 (s, 1 H), 10.52 (br s, 1 H)

References: [1]Patent: WO2015/92713,2015,A1 .Location in patent: Page/Page column 299.
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 3583 - 3588.
[3]Patent: WO2018/109643,2018,A1 .Location in patent: Page/Page column 104; 105.
[4]Patent: WO2018/109649,2018,A1 .Location in patent: Page/Page column 84.
[5]Patent: WO2018/109647,2018,A1 .Location in patent: Page/Page column 121.
[6]Journal of Medicinal Chemistry,1993,vol. 36,p. 3211 - 3213.
[7]Tetrahedron,1995,vol. 51,p. 3221 - 3234.
[8]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1103 - 1108.
[9]Patent: US5869428,1999,A .
[10]Patent: WO2003/97603,2003,A1 .Location in patent: Page/Page column 31-32.
[11]Patent: WO2014/6402,2014,A1 .Location in patent: Page/Page column 100-101.

4
4-oxy-pyridine [ No CAS ]
[ 51498-37-4 ]

References: [1]Chemische Berichte,1924,vol. 57,p. 2082.

5
diazotized 4-amino-pyridine-sulfonic acid-⁽³⁾ [ No CAS ]
[ 51498-37-4 ]

References: [1]Chemische Berichte,1924,vol. 57,p. 2082.

6
[ 51498-37-4 ]
4-Chloro-pyridine-3-sulfonic acid {(S)-1-benzyl-2-[4-(2-fluoro-ethyl)-piperidin-1-yl]-2-oxo-ethyl}-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1103 - 1108.
[2]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 3583 - 3588.

7
[ 51498-37-4 ]
4-Chloro-pyridine-3-sulfonic acid [(S)-2-[4-(2-fluoro-ethyl)-piperidin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-amide [ No CAS ]