13578-51-3|1-Tosyl-1H-1,2,4-triazole| Ambeed

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Quality Control of [ 13578-51-3 ] Purity: 97% SDS Specification

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Product Details of [ 13578-51-3 ]

CAS No. :	13578-51-3
Formula :	C₉H₉N₃O₂S
M.W :	223.25
SMILES Code :	O=S(N1N=CN=C1)(C2=CC=C(C)C=C2)=O
MDL No. :	MFCD00458591
InChI Key :	GFWABQNSSIQCLB-UHFFFAOYSA-N
Pubchem ID :	3505424

Safety of [ 13578-51-3 ]

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

Computational Chemistry of [ 13578-51-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	11
Fraction Csp3	0.11
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	54.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	73.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.46
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	1.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.9
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.	1.31
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	0.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.64
Solubility	0.508 mg/ml ; 0.00228 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.	-2.75
Solubility	0.398 mg/ml ; 0.00178 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	-2.87
Solubility	0.298 mg/ml ; 0.00134 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.	-6.53 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	0.0 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)	2.68

Application In Synthesis of [ 13578-51-3 ]

* 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 [ 13578-51-3 ]

[ 13578-51-3 ] Synthesis Path-Downstream 1~35

1
[ 6002-45-5 ]
[ 13578-51-3 ]
[ 62116-95-4 ]
C₁₇H₂₁O₃PS₂ [ No CAS ]

References: [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 8,p. 375 - 378.

2
[ 4923-86-8 ]
[ 13578-51-3 ]
[ 82220-42-6 ]
triazolium trifluoromethanesulfonate [ No CAS ]

References: [1]Chemische Berichte,1982,vol. 115,p. 1636 - 1643.

3
[ 18293-54-4 ]
[ 98-59-9 ]
[ 75-77-4 ]
[ 13578-51-3 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1986,vol. 26,p. 321 - 326.

4
[ 288-88-0 ]
[ 30955-05-6 ]
[ 13578-51-3 ]

References: [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1067 - 1071.

5
[ 13578-51-3 ]
5-(Toluene-4-sulfonyl)-1H-[1,2,4]triazole [ No CAS ]

References: [1]Heterocycles,1998,vol. 48,p. 155 - 159.

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; triethylamine; In dichloromethane; water; at 20℃; for 12h;	General procedure: Step 1: Preparation of 1- (p-toluenesulfonyl) imidazole: 150 mL of dichloromethane and 250 mL of aqueous sodium bicarbonate were added to the reaction flask, stirred and stirred, followed by the addition of 12.75 g of imidazole, 38.25 g of p-toluenesulfonyl chloride After 3 g of triethylamine was added to the above solution, the mixture was stirred at room temperature for 12 hours. The separated aqueous phase was extracted with methylene chloride and the organic phase was dried over anhydrous magnesium sulfate. The filtrate was collected by suction filtration and concentrated to 50 mL 13mL low polarity organic solvent, put it overNight to give the crude product which was filtered, washed twice with a low polarity organic solvent and the resulting crystals were dried in vacuo at 30 C for 6 hours to give 1- (p-toluenesulfonyl) imidazole;

7
[ 288-88-0 ]
[ 98-59-9 ]
[ 13578-51-3 ]

Yield	Reaction Conditions	Operation in experiment
83.7%	With triethylamine; In dichloromethane;	1-(p-toluenesulfonyl)-1,2,4-triazole (10) 1,2,4-triazole (9.28 g) was suspended in dichloromethane (110 mL) dried over molecular sieves. Triethylamine (13.6 g) was added; the triazole dissolved after triethylamine addition. Tosylchloride (25.62 g;) was added to the reaction mixture over approx. 30 min. The reaction mixture was stirred overnight. Precipitated salt was filtered off. Filtrate was washed with water and dried with Na2SO4. The drying agent was filtered off and filtrate was evaporated on rotary evaporator. Cyclohexane (300 mL) was added to the residue and the mixture was allowed to crystallise overnight. Product was separated by filtration, washed with cyclohexane (50 mL), and dried in oven at 50 C. to give the title compound as white crystalline powder, 25.1 g (83.7% of theoretical yield; m.p. 105-107 C.
		General procedure: The appropriate N-heterocycle (0.01 mol) and KOH (0.01 mol) wasadded in DMSO (15 mL) to a round bottom flask (50 mL) and the mixture was cooled to 0 C. Then, the appropriate sulfonyl chloride(0.012 mol) was added portionwise and the reaction mixture wasstirred at 0 C for 1-2 h (TLC control). After completion of thereaction, the mixture was poured into water (100 mL) and extracted with CHCl3 or EtOAC (100 mL). The organic layer was then washed with water (4 × 100 mL), dried over anhydrous sodium sulfateand evaporated. The crude product was purified by short column chromatography on silica gel eluting with n-hexane:EtOAc.

References: [1]Carbohydrate Research,2003,vol. 338,p. 451 - 453.
[2]Journal of Organic Chemistry,2010,vol. 75,p. 2722 - 2725.
[3]Patent: US2008/76933,2008,A1 .Location in patent: Page/Page column 3-5.
[4]Patent: EP1258480,2002,A1 .Location in patent: Page 37.
[5]Journal of Chemical Research,2016,vol. 40,p. 101 - 106.

8
[ 13578-51-3 ]
cyclomaltoheptaose [ No CAS ]
2^I-O-p-tolylsulfonylcyclomaltoheptaose [ No CAS ]

References: [1]Carbohydrate Research,2003,vol. 338,p. 451 - 453.

9
[ 18293-54-4 ]
[ 98-59-9 ]
[ 13578-51-3 ]

References: [1]Pharmaceutical Chemistry Journal,2006,vol. 40,p. 145 - 148.

10
[ 98-59-9 ]
1-propyloxy-ethanol-⁽²⁾ [ No CAS ]
[ 13578-51-3 ]

References: [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1067 - 1071.

11
[ 13578-51-3 ]
[ 62116-95-4 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 8,p. 375 - 378.

12
[ 13578-51-3 ]
3-(4-toluenesulfonyl)-1H-1,2,4-triazole [ No CAS ]

References: [1]Patent: EP1258480,2002,A1 .Location in patent: Page 37.

13
[ 13578-51-3 ]
[ 124627-86-7 ]

Yield	Reaction Conditions	Operation in experiment
43%		(Example 32) (2R,3S)-2-(2,4-Difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol -1-yl)methyl]oxirane First, 0.21 g (5.10 mmol) of sodium hydride (60% content) was suspended in 3 mL of DMF, and the resulting suspension was cooled in ice. A solution of 0.53 g (2.19 mmol) of (2R,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diolin 5 mL of DMF was added thereto, and stirring was performed for 1 hour. A solution of 0.64 g (2.85 mmol) of <strong>[13578-51-3]1-(p-toluenesulfonyl)-1,2,4-triazole</strong> and 0.06 g (0.88 mmol) of triazole in 3 mL of DMF was added, and the reaction solution was stirred at 60C for 3 hours. Then, the resulting solution was cooled to room temperature, and 10 mL of water was added to stop the reaction. The resulting product was extracted with ethyl acetate (20 mL * 2), and concentration was performed under reduced pressure. A quantitative analysis was performed by HPLC. Thereby, the title compound was obtained in a yield of 43% (HPLC conditions, column: CAPCELL PAK C18 TYPE MG manufactured by Shiseido Co. Ltd., mobile phase: acetonitrile/20 mM (potassium) phosphate buffer solution (pH = 2.5) = 2/8, flow rate: 1.0 mL/min, column temperature: 30C, detector: UV 210 nm, retention time: 37 minutes). 1H-NMR (400 MHz, CDCl3) delta: 1.64 (d, 3H, J = 5.6 Hz), 3.19 (q, 1H, J = 5.6 Hz), 4.42 (d, 1H, J = 14.6 Hz), 4.87 (d, 1H, J = 14.6 Hz), 6.69-6.80 (m, 2H), 6.98-7.03 (m, 1H), 7.81 (s, 1H), 7. 98 (s, 1H).

References: [1]Patent: EP1647551,2006,A1 .Location in patent: Page/Page column 30.

14
[ 13578-51-3 ]
[ 106-95-6 ]
[ 960069-33-4 ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7685 - 7688.

15
bis(2,2,6,6-tetramethylpiperidine) zinc lithium magnesium chloride complex [ No CAS ]
[ 13578-51-3 ]
Zn(C₂HN₃SO₂C₆H₄CH₃)2 [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7685 - 7688.

16
[ 694-59-7 ]
[ 13578-51-3 ]
[ 25700-17-8 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 2722 - 2725.
[2]RSC Advances,2016,vol. 6,p. 58118 - 58124.

17
[ 17043-94-6 ]
[ 13578-51-3 ]
[ 36209-77-5 ]
[ 1342564-58-2 ]
[ 91159-94-3 ]