53052-06-5|Oxazolo[4,5-b]pyridine-2(3H)-thione| Ambeed

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Quality Control of [ 53052-06-5 ] Purity: 98% SDS Specification

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Product Details of [ 53052-06-5 ]

CAS No. :	53052-06-5
Formula :	C₆H₄N₂OS
M.W :	152.17
SMILES Code :	S=C1OC2=CC=CN=C2N1
MDL No. :	MFCD01089040
InChI Key :	BRSZJWYJYOGBGK-UHFFFAOYSA-N
Pubchem ID :	658727

Safety of [ 53052-06-5 ]

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

Computational Chemistry of [ 53052-06-5 ] 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	2.0
Num. H-bond donors	1.0
Molar Refractivity	39.19
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	73.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
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	1.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.89
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.	0.07
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	3.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.08
Solubility	1.27 mg/ml ; 0.00833 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.	-2.14
Solubility	1.1 mg/ml ; 0.00723 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	-2.63
Solubility	0.353 mg/ml ; 0.00232 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.	-6.52 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)	2.37

Application In Synthesis of [ 53052-06-5 ]

* 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 [ 53052-06-5 ]

[ 53052-06-5 ] Synthesis Path-Downstream 1~35

1
[ 6959-48-4 ]
[ 53052-06-5 ]
[ 88594-61-0 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 547 - 551.

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[ 53052-06-5 ]
[ 60832-72-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 167 - 170.

3
[ 16867-03-1 ]
[ 140-89-6 ]
[ 53052-06-5 ]

Yield	Reaction Conditions	Operation in experiment
86.95%	With pyridine; at 110.0℃;	Step 1: Preparation of oxazolo[4,5-b]pyridine-2-thiol A solution of 2-aminopyridin-3-ol (5.0g, 45.45 mmol) and potassium ethyl xanthate (8.0g, 49.99 mmol) in pyridine (50mL) was heated at 110C overnight. The reaction mixture was cooled to 0C, added ice water and acidified with Cone. HCl. The solid was filtered and dried under vacuum to afford the title compound (6.0g, 86.95%). 1HNMR (DMSO-d6, 300MHz): delta 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: m/z: 153.0 (M+l) +.
86.95%	With pyridine; at 110.0℃;	A solution of 2-aminopyridin-3-ol (5.0 g, 45.45 mmol) and potassium ethyl xanthate (8.0 g, 49.99 mmol) in pyridine (50 mL) was heated at 1100 C. overnight. The reaction mixture was cooled to 00 C., added ice water and acidified with Conc. HC1. The solid was filtered and dried under vacuum to afford the title compound (6.0 g, 86.95%). 10206] ?HNMR (DMSO-d5, 300 MHz): oe 8.24-8.22 (d, 1H), 7.90-7.87 (d, 1H), 7.30-7.26 (m, 1H). LCMS: mlz:153.0 (M+1).
74%	In ethanol; for 24h;Reflux;	A mixture of 2-amino-pyridin-3-ol (1) (2.00 g, 18.16 mmol) and potassium ethyl xanthate (2.91 g, 18.16 mmol) in ethanol (40 mL) was heated under reflux for 24 h. The solvent was removed in vacuo and water (30 mL) was added. The mixture was acidified with AcOH to pH 5. The resultant precipitate was filtered, washed with water (20 mL) and dried to give oxazolo[4,5-b]pyridine-2-thiol (2) (2.05 g, 74% yield). 300 MHz 1H-NMR (DMSO-d6, ppm): 8.21 (dd, J=5.2, 1.3 Hz, 1H) 7.85 (dd, J=8.1, 1.3 Hz, 1H) 7.25 (dd, J=8.1, 5.2 Hz, 1H).

With hydrogenchloride; In pyridine; water;

(1) 2-Amino-3-hydroxypyridine (5.51 g) was dissolved in pyridine (100 mL), and potassium ethylxanthate (8.82 g) was added thereto. The mixture was refluxed for 2 hr. Iced water (400 mL) was added to the reaction mixture, and concentrated hydrochloric acid (40 mL) was added thereto. The mixture was extracted with chloroform and the extract was washed with brine and concentrated under reduced pressure to give 1,3-oxazolo[4,5-b]pyridine-2-thiol (5.13 g) as a pale-brown powder.

References: [1]Patent: WO2015/104688,2015,A1 .Location in patent: Page/Page column 36.
[2]Patent: US2016/340366,2016,A1 .Location in patent: Paragraph 0205; 0206.
[3]Monatshefte fur Chemie,2011,vol. 142,p. 895 - 899.
[4]Patent: US2019/367499,2019,A1 .Location in patent: Paragraph 0166.
[5]Journal of Organic Chemistry,1995,vol. 60,p. 5721 - 5725.
[6]European Journal of Medicinal Chemistry,2005,vol. 40,p. 15 - 23.
[7]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 114 - 125.
[8]Patent: EP1308439,2003,A1 .

4
[ 53052-06-5 ]
[ 74-88-4 ]
[ 169205-95-2 ]

Yield	Reaction Conditions	Operation in experiment
93.75%	With potassium carbonate; In ethyl acetate; at 20.0℃;	Step 2: Preparation of 2-(methylthio)oxazolo[4,5-b]pyridine To a stirred solution of <strong>[53052-06-5]oxazolo[4,5-b]pyridine-2-thiol</strong> (3.0g, 19.73 mmol) in ethyl acetate (30mL) was added potassium carbonate (3.81g, 27.62 mmol) and methyl iodide (3.08g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100ml), extracted with ethyl acetate (2x50mL), dried over sodium sulphate and concentrated to afford the title compound (3.0g, 93.75%). 1HNMR (CDCI3, 300MHz): delta 8.46-8.44 (d, 1H), 7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS: m/z: 167.0(M+1) +.
93.75%	With potassium carbonate; In ethyl acetate; at 20.0℃;	To a stirred solution of oxazolo[4,5-b]pyridine-2- thiol (3.0 g, 19.73 mmol) in ethyl acetate (30 mL) was added potassium carbonate (3.81 g, 27.62 mmol) and methyl iodide (3.08 g, 21.71 mmol) and stirred at RT overnight. The reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (2x50 mL), dried over sodium sulphate and concentrated to afford the title compound (3.0 g, 93 .75%).10208] ?HNMR (CDC13, 300 MHz): oe 8.46-8.44 (d, 1H),7.71-7.68 (d, 1H), 7.20-7.15 (m, 1H), 2.81 (s, 3H). LCMS:mlz: 167.0 (M+1)+.

References: [1]Patent: WO2015/104688,2015,A1 .Location in patent: Page/Page column 36.
[2]Patent: US2016/340366,2016,A1 .Location in patent: Paragraph 0207; 0208.
[3]Journal of Organic Chemistry,1995,vol. 60,p. 5721 - 5725.
[4]Ultrasonics Sonochemistry,2010,vol. 17,p. 783 - 788.
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2075 - 2078.
[6]Advanced Synthesis and Catalysis,2017,vol. 359,p. 1837 - 1843.
[7]European Journal of Medicinal Chemistry,2005,vol. 40,p. 15 - 23.
[8]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 114 - 125.

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[ 300672-18-8 ]