72716-80-4|5,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile| Ambeed

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Quality Control of [ 72716-80-4 ] Purity: 95% SDS Specification

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Product Details of [ 72716-80-4 ]

CAS No. :	72716-80-4
Formula :	C₈H₈N₂O
M.W :	148.16
SMILES Code :	CC1=C(C)C=C(C#N)C(=O)N1
MDL No. :	MFCD03004855
InChI Key :	BUGNNHLZTBPABI-UHFFFAOYSA-N
Pubchem ID :	590532

Safety of [ 72716-80-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 72716-80-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	41.71
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	56.65 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.39
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	0.42
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.86
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.	0.31
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	2.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.43
Solubility	5.54 mg/ml ; 0.0374 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.	-1.18
Solubility	9.86 mg/ml ; 0.0666 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	-2.77
Solubility	0.25 mg/ml ; 0.00169 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	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.	-6.91 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	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)	1.8

Application In Synthesis of [ 72716-80-4 ]

* 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.

Upstream synthesis route of [ 72716-80-4 ]
Downstream synthetic route of [ 72716-80-4 ]

[ 72716-80-4 ] Synthesis Path-Upstream 1~1

1
[ 72716-80-4 ]
[ 113124-09-7 ]

References: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 351 - 355.

[ 72716-80-4 ] Synthesis Path-Downstream 1~31

1
[ 72716-80-4 ]
[ 113124-06-4 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 351 - 355.

2
[ 143193-92-4 ]
[ 107-91-5 ]
[ 72716-80-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine; pyridine; acetic acid; In water; at 20℃; for 20h;Reflux;	To a solution of 480mL of water (E / Z) -2- methyl-3-oxo-1-ene-1-ol Sodium (77.6g, 0.64mol) was added cyanoacetamide (49.0g, 0.70mol). To this mixture was added a solution of piperidine-acetic acid(From acetic acid (9.16g, 8.75mL, 0.15mol),21.2mL of water and pyridine (13.0g, 15.1mL, 0.15mol) was obtained), and the mixture was heated at reflux through 4h, then stirred at room temperature for 16h. Acetic acid (75.5g, 72mL, 1.26mol) was added to the reaction mixture, the precipitated pale yellow solid. The latter was filtered off with suction, washed with water and dried under reduced pressure at 2h at 55 . To give 66.4 g of (70% of theory) of a pale yellow solid.

References: [1]Patent: CN105530814,2016,A .Location in patent: Paragraph 0328; 0329; 0330.
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 351 - 355.
[3]New Journal of Chemistry,2020,vol. 44,p. 2247 - 2255.

3
[ 72716-80-4 ]
[ 74-88-4 ]
[ 98042-65-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 2313 - 2322.

4
[ 5720-05-8 ]
[ 72716-80-4 ]
5,6-dimethyl-1-(4-methylphenyl)-2-oxo-1,2-dihydropyridin-3-carbonitrile [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 12757 - 12770.

5
[ 132247-74-6 ]
[ 107-91-5 ]
[ 72716-80-4 ]

References: [1]Nucleosides and Nucleotides,1999,vol. 18,p. 2335 - 2343.

6
[ 72716-80-4 ]
[ 27992-31-0 ]

Yield	Reaction Conditions	Operation in experiment
94.3%	With hydrogenchloride; In water; at 135℃; for 72h;Heating / reflux;	To a suspension of <strong>[72716-80-4]3-cyano-5,6-dimethyl-2-pyridone</strong> (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 C)1H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d,J = 9.0 Hz, 1H), 13.17 (br s, 1H).
94.3%	With hydrogenchloride; water; at 135℃; for 72h;Heating / reflux;	To a suspension of <strong>[72716-80-4]3-cyano-5,6-dimethyl-2-pyridone</strong> (1-013-02) (12.0 g) in water (293 mL) was added conc. hydrochloric acid (293 mL), and the reaction mixture was reflux with stirring in oil-bath at 135 DEG C. After 3 days, the reaction mixture was cooled, and evaporated under reduced pressure. To the residue (24.75 g) were added chloroform (300 mL) and methanol (15 mL), and the reaction mixture was heated in a water bath at 65 DEG C, and the dissolble material was filtered off. Furthermore, the dissolble material was treated by chloroform (200 mL) and methanol (10 mL) in a similar manner to described above. The combined filtrates were evaporated under reduced pressure. To the obtained residue (13.26 g) were added methanol (150 mL) and potassium carbonate (10 g). After stirred at room temperature for 30 min, the dissolble material was filtered off. The filtrate was evaporated under reduced pressure. To the obtained residue (14.7 g) was added chloroform (200 mL), and the dissolble material was filtered off again. The filtrate was evaporated under reduced pressure to give 5,6-dimethyl-2-pyridone (1-013-03) (9.41 g, 94.3%, m.p.: 202-207 DEG C)<1>H NMR (300 MHz, CDCl3): delta 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J = 9.0 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 13.17 (br s, 1H).
		To a suspension of 5,6-dimethyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (5.90 g) in Eta2O(145 ?iL) was added cone. HCl (145 mL) dropwise and the mixture was stirred at ambient temperature for 15 min and at reflux for 60.5 h and concentrated under reduced pressure. The residue was suspended with CHCl3 (150 mL) and MeOH (7.5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The insoluble material was suspended in CHCl3 (100 mL) and MeOH (5 mL) and the mixture was heated at 65 0C on a water bath and filtered. The combined filtrate was concentrated under reduced pressure. To the residue were added MeOH (75 mL) and K2CO3 (5 g) and the mixture was stirred at ambient temperature for 30 min. The insoluble material was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in CHCl3 (100 mL) and the insoluble material was filtered. The filtrate was concentrated under reduced pressure to give 5,6- dimethylpyridin-2(lH)-one (2.19 g) as a yellow solid.1HNMR (300 MHz, CDCl3, delta): 2.05 (s, 3H), 2.31 (s, 3H), 6.38 (d, J= 9.2 Hz, IH), 7.26 (d, J= 9.2Hz, IH); ESI MS m/z 124 (M+H-I, 100%).

References: [1]Patent: EP1477186,2004,A1 .Location in patent: Page/Page column 29.
[2]Patent: EP1357111,2003,A1 .Location in patent: Page/Page column 46-47.
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 1948 - 1964.
[4]Patent: WO2006/35967,2006,A1 .Location in patent: Page/Page column 89.

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[ 72716-80-4 ]
[ 847740-87-8 ]