37669-78-6|Ethyl 2,4-dimethylnicotinate| Ambeed

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Quality Control of [ 37669-78-6 ] Purity: 98% SDS Specification

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Product Details of [ 37669-78-6 ]

CAS No. :	37669-78-6
Formula :	C₁₀H₁₃NO₂
M.W :	179.22
SMILES Code :	O=C(OCC)C1=C(C)N=CC=C1C
MDL No. :	MFCD00051962
InChI Key :	DIZHKKYVLBSXAW-UHFFFAOYSA-N
Pubchem ID :	736245

Safety of [ 37669-78-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 37669-78-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	50.26
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	39.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.26
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	1.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.88
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.	1.28
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	2.47
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.999 mg/ml ; 0.00557 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.	-2.28
Solubility	0.933 mg/ml ; 0.00521 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	-3.28
Solubility	0.0943 mg/ml ; 0.000526 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.	-6.09 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)	1.74

Application In Synthesis of [ 37669-78-6 ]

* 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 [ 37669-78-6 ]

[ 37669-78-6 ] Synthesis Path-Downstream 1~35

1
[ 37669-78-6 ]
[ 141-78-6 ]
[ 38059-38-0 ]

References: [1]Chemische Berichte,1947,vol. 80,p. 502,505.

2
[ 37669-78-6 ]
[ 80-48-8 ]
[ 104094-94-2 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 704,707.

3
[ 37669-78-6 ]
[ 55314-30-2 ]

Yield	Reaction Conditions	Operation in experiment
99%		A mixture of <strong>[37669-78-6]ethyl 2,4-dimethylnicotinate</strong> (3.58 g, 20 mmol) and an aqueous solution of NaOH (10M, 20 ml) in ethanol (20 ml) was stirred at room temperature for 24 hours. The mixture was cooled to 0 C. and methanol (200 ml) was added follow by aqueous HCl (10 M) to adjust pH to 7. The resulting precipitated (NaCl) was filtered off.The filtrated was concentrated to remain approximately 20 ml and methanol (100 ml) was added again to precipitate the remaining sodium chloride. The precipitation (NaCl) was repeated until all NaCl was removed from methanolic solution of the reaction mixture. The mixture was concentrated to dryness to yield 1a (3.01 g, 19.9 mmol, 99%).

References: [1]Patent: US2008/318979,2008,A1 .Location in patent: Page/Page column 19-20.
[2]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.
[3]Chemische Berichte,1885,vol. 18,p. 2022.

4
[ 52199-37-8 ]
[ 37669-78-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.
[2]Roczniki Chemii,1973,vol. 47,p. 1871 - 1874.
[3]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

5
[ 37669-78-6 ]
1-oxido-2,4-dimethyl-pyridine-3-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3343 - 3346.

6
[ 37669-78-6 ]
[ 193889-71-3 ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 1815 - 1820.

7
[ 37669-78-6 ]
[ 193889-74-6 ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 1815 - 1820.

8
[ 37669-78-6 ]
[ 168072-32-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

9
[ 37669-78-6 ]
2,4-dimethyl-3-<(2'-carbbiphenyl-4-yl)methyl>pyridine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

10
[ 37669-78-6 ]
[ 1027913-91-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

11
[ 37669-78-6 ]
[ 1026431-90-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

12
[ 37669-78-6 ]
[ 1027899-64-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.

13
[ 626-34-6 ]
[ 37669-78-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849.
[2]Journal of Organic Chemistry,1956,vol. 21,p. 800.

14
[ 37669-78-6 ]
[ 82776-25-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.

15
[ 37669-78-6 ]
[ 101947-94-8 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.

16
[ 37669-78-6 ]
((1R,3S,4S)-3-Bromo-1,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-7-yl)-methanesulfonate3-diethylcarbamoyl-1,2,4-trimethyl-pyridinium; [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.

17
[ 37669-78-6 ]
((1R,3R,4S)-3-Bromo-1,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-7-yl)-methanesulfonate3-diethylcarbamoyl-1,2,4-trimethyl-pyridinium; [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1982,vol. 101,p. 191 - 192.

18
[ 37669-78-6 ]
[ 405058-67-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 48h;	To a solution of <strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (1.79 g, 10.0 mmol) in CH2Cl2 (50 mL) was added 3-chloroperoxybenzoic acid (77% max., 4.48 g, 20.0 mmol). The mixture was stirred at room temperature for 2 days, and then concentrated under reduced pressure. The residual solid was purified by flash column chromatography on silica gel (EtOAc) to afford 2,4-dimethyl-1-oxy-nicotinic acid ethyl ester as a white solid (1.95 g, 100%). 1H NMR (CDCl3) delta 1.41 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 2.49 (s, 3H), 4.44 (q, 2H, J=7.2 Hz), 7.00 (d, 1H, J=6.6 Hz), 8.19 (d, 1H, J=6.6 Hz).
	With dihydrogen peroxide; In dichloromethane; acetic acid;	Preparation of 2,4-dimethyl-1-oxy-nicotinic acid ethyl ester: To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (2.0 g, 11.2 mmol) in AcOH (28 mL) was added H2O2 (34-37%, 1.1 mL, 11.2 mmol) and the resultant mixture was heated to 70 C. for 3 hours. A second aliquot of H2O2 (34-37%, 1.1 mL, 11.2 mmol) was added and the mixture heated at 70 C. overnight. The reaction mixture was concentrated under reduced pressure and the resulting syrup was dissolved in CH2Cl2 (150 mL) and washed with saturated NaHCO3 (225 mL). The aqueous layer was extracted with CH2Cl2 (2100 mL) and the combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford the desired N-oxide (2.07 g, 95%/o). 1H NMR (CDCl3) delta 1.41 (t, 3H, J=7.2 Hz), 2.30 (s, 3H), 2.49 (s, 3H), 4.44 (q, 2H, J=7.2 Hz), 6.99 (d, 1H, J=6.6 Hz), 8.19 (d, 1H, J=6.6 Hz).

References: [1]Patent: US2005/277668,2005,A1 .Location in patent: Page/Page column 16.
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6950 - 6954.
[3]Patent: US2002/147192,2002,A1 .

19
[ 37669-78-6 ]
[ 7732-18-5 ]
[ 194151-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Step 2. The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0 C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0 C. and quenched with EtOAc (2.5 mL), then H2 O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2 O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine.

References: [1]Patent: US5726172,1998,A .

20
[ 37669-78-6 ]
[ 1759-53-1 ]
[ 918144-21-5 ]

Yield	Reaction Conditions	Operation in experiment
18%		To a solution of <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (0.59 g, 3.29 mmol) and cyclopropane carboxylic acid (1.2 ml (15.1 mmol) in 10% aqueous H2SO4 (3 ml) was added AgNO3 (154 mg, 0.91 mmol) followed by a solution of ammonium persulfate (1.541 g, 6.75 mmol) in water (6 ml) and the mixture stirred at room temperature overnight. The reaction was neutralized to pH 10 with saturated aqueous NH4OH (5 ml) and extracted with EtOAc (3 x 20 ml). The combined organic extracts were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 96:4 then 1:1 then 0:100) to afford desired 6-cyclopropyl-<strong>[37669-78-6]2,4-dimethyl-nicotinic acid ethyl ester</strong> (133 mg, 18%) as a clear oil along with recovered starting <strong>[37669-78-6]ethyl 2,4-dimethylpyridine-3-carboxylate</strong> (0.31 g). 1H NMR (CDCl3) delta 0.93-0.97 (m, 4H), 1.38 (t, 3H, J= 6 Hz), 1.92-2.02 (m, IH), 2.28 (s, 3H), 2.47 (s, 3H), 4.39 (q, 2H, J= 6 Hz), 6.73 (s, IH).

References: [1]Patent: WO2006/138350,2006,A2 .Location in patent: Page/Page column 195.

21
[ 37669-78-6 ]
[ 86732-22-1 ]
C₂₁H₂₅N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		A 25 mL 3-neck flask equipped with stir bar, addition funnel, N2 inlet tube and reflux condenser was charged with 4a (l.Og, 4.94 mmol) and (dry) toluene (4 mL) and cooled to 0 C. Trimethylaluminum (2.5 mL of a 2.0 M toluene solutionn, 5.0 mmol) was added dropwise, then allowed to warm to RT. 2,4-Dimethyl-nicotinic acid ethyl ester (80, 0.93 g, 5.2 mmol) in toluene (1 mL) was added dropwise then heated at 120 C for 18 h. The reaction mixture was cooled in an ice bath and MeOH (2 mL) was added. The mixture was brought to RT, heated at reflux for 10 min then recooled to RT. The mixture was filtered through a CELITE pad. The filtrate was washed with brine, dried (MgS04) then concentrated in vacuo. The crude product was purified by flash chromatography on silica eluting with 7.5% MeOH (containing 2% NH40H) / DCM to afford 1.17 g, (71%) of 81 as a pale yellow liquid: ms (ES+) m/z 336 (M+H)+.

References: [1]Patent: WO2005/121145,2005,A2 .Location in patent: Page/Page column 177-178.

22
[ 62022-04-2 ]
[ 544-97-8 ]
[ 37669-78-6 ]