59718-84-2|Methyl 3-methylpicolinate| Ambeed

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Quality Control of [ 59718-84-2 ] Purity: 98% SDS Specification

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Product Details of [ 59718-84-2 ]

CAS No. :	59718-84-2
Formula :	C₈H₉NO₂
M.W :	151.16
SMILES Code :	COC(=O)C1=NC=CC=C1C
MDL No. :	MFCD03789583
Boiling Point :	No data available
InChI Key :	CCQFKEITVOTHIW-UHFFFAOYSA-N
Pubchem ID :	12264487

Safety of [ 59718-84-2 ]

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

Computational Chemistry of [ 59718-84-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	40.48
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.	1.83
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	1.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.18
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.	0.66
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	1.64
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.93
Solubility	1.77 mg/ml ; 0.0117 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.	-1.83
Solubility	2.25 mg/ml ; 0.0149 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	-2.47
Solubility	0.512 mg/ml ; 0.00339 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.	-6.23 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)	1.53

Application In Synthesis of [ 59718-84-2 ]

* 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 [ 59718-84-2 ]

[ 59718-84-2 ] Synthesis Path-Downstream 1~35

1
[ 59718-84-2 ]
[ 116986-09-5 ]

Yield	Reaction Conditions	Operation in experiment
80.6%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90℃; for 16h;Inert atmosphere;	A mixture of methyl 3-methylpicolinate (4.1 g, 27.1 mmol), NBS (5.8 g, 32.5 mmol), and AIBN (100 mg, 0.61 mmol) in carbon tetrachloride (55 mL) was stuffed at 90 C for 16 h under nitrogen. The mixture was filtered and concentrated before being purified by column chromatography to give the desired product (5.0 g, 80.6%). ?H NMR (400 MHz, CDC13, ): 8.67 (dd, J= 1.6, 4.6 Hz, 1 H), 7.91 (dd, J= 1.5, 7.9 Hz, 1 H), 7.48 (dd, J= 4.6, 7.9 Hz, 1 H), 4.95 (s, 2 H), 4.07 - 4.03 (m, 3 H). LCMS (mlz): 229.9 (M+1).

References: [1]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00472; 00473.
[2]Journal fur praktische Chemie (Leipzig 1954),1987,vol. 329,p. 557 - 562.
[3]Organic Letters,2017,vol. 19,p. 3895 - 3898.

2
[ 594-27-4 ]
[ 157865-84-4 ]
[ 59718-84-2 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 459 - 462.

3
[ 59718-84-2 ]
(2S,3R)-3-Methyl-piperidine-2-carboxylic acid methyl ester; hydrochloride [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 459 - 462.

4
[ 67-56-1 ]
[ 1071068-55-7 ]
[ 59718-84-2 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 7840 - 7850.

5
[ 583-61-9 ]
[ 67-56-1 ]
[ 55589-47-4 ]
[ 59718-84-2 ]

References: [1]Organic Preparations and Procedures International,1999,vol. 31,p. 120 - 123.

8
[ 937782-76-8 ]
[ 59718-84-2 ]
methyl 2-[2-(3-benzyloxy-4-methoxyphenyl)oxazol-4-ylmethyl]-3-(3-methylpyridin-2-yl)-3-oxopropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In 1,2-dimethoxyethane; for 4h;Heating / reflux;	5 g quantity of methyl 3- [2- (3-benzyloxy-4-methoxy phenyl) oxazol-4-yl] propionate obtained in Reference Example 48 <n="118"/>and 3.2 g of <strong>[59718-84-2]methyl 3-methylpicolinate</strong> were dissolved in 150 ml of dimethoxyethane. While stirring the solution with ice cooling 1.2 g of sodium hydride was added thereto and further stirred. The reaction mixture was heated and refluxed for 4 hours. At the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the mixture while stirring with ice cooling, and the mixture was further stirred. After stirring the reaction mixture for 30 minutes, water was added thereto and ethyl acetate extraction was performed. The organic layer was washed twice with water, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n- hexane: ethyl acetate = 2:1), thereby yielding 5.5 g of colorless oily substance methyl 2- [2- (3-benzyloxy-4-methoxyphenyl) oxazol-4- ylmethyl] -3- (3-methylpyridin-2-yl) -3-oxopropionate. 1H-NMR (CDCl3) δ: 8.49 (IH, dd, J = 4.8, 1.2 Hz), 7.59-7.28 (1OH, m), 6.91 (IH, d, J = 9.0 Hz), 5.23-5.16 (3H, m) , 3.91 (3H, s) , 3.65 (3H, s), 3.37-3.18 (2H,m,) 2.59 (3H, s)

References: [1]Patent: WO2007/58338,2007,A2 .Location in patent: Page/Page column 116; 117.

9
[ 874-24-8 ]
[ 59718-84-2 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 459 - 462.

10
[ 62733-99-7 ]
[ 59718-84-2 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 459 - 462.

11
[ 59718-84-2 ]
[ 116985-98-9 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1987,vol. 329,p. 557 - 562.

12
[ 59718-84-2 ]
[ 116985-94-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1987,vol. 329,p. 557 - 562.

13
[ 59718-84-2 ]
[ 878207-91-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 4h;	To a solution of <strong>[59718-84-2]methyl 3-methylpicolinate</strong> (5.0 g, 33.1 mmol) in dichloromethane (100 ml) was added of m-chloroperbenzoic acid (8.9 g, 39.7 mmol) at 0oC. After being stirred for 4 h at room temperature, the reaction mixture was combined with 100 ml of water, extracted with dichoromethane (50 ml x 2), and washed with water and sat. sodium bicarbonate solution. The combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under reduced pressure, and the resulting residue was refined by silica gel column chromatography (5% MeOH/CH2Cl2) to give 5.3g (yield 98%) of the title compound. 1H NMR(300MHz, CDCl3) δ 8.09 (d, J = 6.3 Hz, 1H), 7.12 (m, 1H), 7.13 (d, J = 7.9 Hz, 1H), 4.03 (s, 3H), 2.30 (s, 3H).
96%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 45℃; for 4h;	A solution of <strong>[59718-84-2]methyl 3-methylpyridine-2-carboxylate</strong> (800 mg, 5.29 mmol, 1.00 equiv) and 3-chloroperoxybenzoic acid (1826 mg, 10.58 mmol, 2.00 equiv) in dichloromethane (20 mL) was stirred for 4 hours at 45 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (850 mg, 96%) as yellow oil. LC-MS (ES, m/z): 168 [M+H]+.
96%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 45℃; for 4h;	A solution of <strong>[59718-84-2]methyl 3-methylpyridine-2-carboxylate</strong> (800 mg, 5.29 mmol, 1.00 equiv) and 3-chloroperoxybenzoic acid (1826 mg, 10.58 mmol, 2.00 equiv) in dichloromethane (20 mL) was stirred for 4 hours at 45 C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:3). This resulted in the title compound (850 mg, 96%) as yellow oil. LC-MS (ES, mlz): 168 [M+H]+

89.9%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 16.25h;	To a solution of <strong>[59718-84-2]methyl 3-methylpyridine-2-carboxylate</strong> (13.0 g, 0.086 mol) in CH2CI2 (130 mL) is added meta-chloroperoxybenzoic acid (89.05 g, 0.258 mol, 50 % w/w) portionwise at 0 C. The reaction mixture is stirred for 15 minutes at 0C and then gradually warmed to ambient temperature. After 16 hours, saturated NaHC03 solution (100 mL) is added. The mixture is stirred for 30 minutes and is extracted with CH2CI2. The combined organic layers are washed with 0.5M NaOH aqueous solution (2 χ 50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give methyl 3 -methyl- 1 -oxido-pyridin- 1 -ium-2-carboxylate as an off- white solid (13.0 g, 89.9%). The residue is used in the next step without further purification. Mass spectrum (m z): 168.2 (M+H)+.
85%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	To a solution of ethyl 2-methyl-3-pyridinecarboxylate (1.86 ml_, 12.1 mmol) in DCM (50 ml_) mCPBA was added (4.18 g, 24.2 mmol) at RT. The solution was stirred at RT for 24 hrs. The solution was filtered and concentrated. The residue was purified by FC on silica (eluent: DCM to 15% MeOH) to a solid still containing mCBA that was dissolved with DCM and washed with NaHC03, the organic phase was dried and evaporated to afford 2- (methoxycarbonyl)-3-methylpyridin-N oxide (p134, 1.9 g, y=85%). MS (m/z): 168.1 [M]+.
79%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	A mixture of <strong>[59718-84-2]methyl 3-methylpicolinate</strong> (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8 mmol) in DCM (35 mL) was stirred at RT overnight. Then the mixture was washed with NaHSC (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM : MeOH = 200 : 1) to give the product of 2-(methoxycarbonyl)-3- methylpyridine 1-oxide (1.89 g, yield: 79%). -NMR (CDC13> 400 MHz) δ 8.05 (d, J= 6.0 Hz, 1H), 7.18 (t, J= 8.4 Hz, 1H), 7.10 (d, J= 8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H)+: 168.
79%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25℃;	A mixture of <strong>[59718-84-2]methyl 3-methylpicolinate</strong> (2 g, 14.8 mmol) and m-CPBA (3 g, 17.8mmol) in DCM (35 mE) was stirred at RT overnight. Then the mixture was washed with NaHSO3 (a.q.) and concentrated in vacuum. The residue was purified by column chromatography (DCM:MeOH = 200: 1) to give the product of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (1.89 g, yield: 79%). ‘H-NMR (CDC13, 400 MHz) 8.05 (d, J 6.0 Hz, 1H), 7.18 (t, J 8.4 Hz, 1H), 7.10 (d, J= 8.0 Hz, 1H), 3.95 (s, 3H), 2.23 (s, 3H). MS (M+H): 168.
	With dihydrogen peroxide; In water; acetic acid; at 20 - 60℃;	Example 716-[4-Chloro-3-[[(tricyclo[3.3.1.13'7]dec-l-ylmethyl)amino]carbonyl]phenyl]-3-methyl-2-pyridinecarboxylic acidCla) 3-Methyl-2-pyridinecarboxyIic acid 1-oxide, methyl esterA solution of 3-methyl 2-pyridinecarboxylic acid, methyl ester (340 mg) in acetic acid (5mL) and 35% aqueous hydrogen peroxide (5 mL) was heated at 60C for 5 hours beforebeing stirred at room temperature overnight. The reaction mixture was quenched bypouring into a sodium sulfite/ ice water mixture (50 mL) and then extracted intodichloromethane (3 x 25 mL). The organics were dried over magnesium sulphate, filteredand concentrated to dryness to give the sub-title compound as a colourless oil (300 mg).MS: APCI(+ve) 168 (M+H4).

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1736 - 1739.
[2]Patent: WO2016/202253,2016,A1 .Location in patent: Page/Page column 452.
[3]Patent: US2015/57260,2015,A1 .Location in patent: Paragraph 1232; 1233.
[4]Patent: WO2015/25026,2015,A1 .Location in patent: Page/Page column 268.
[5]Patent: WO2015/94912,2015,A1 .Location in patent: Page/Page column 11.
[6]Patent: WO2016/67043,2016,A1 .Location in patent: Page/Page column 124.
[7]Patent: WO2014/209727,2014,A1 .Location in patent: Page/Page column 69.
[8]Patent: WO2014/205593,2014,A1 .Location in patent: Page/Page column 72; 73.
[9]Heterocycles,2013,vol. 87,p. 1279 - 1287.
[10]Heterocycles,2013,vol. 87,p. 2071 - 2079.
[11]Patent: WO2006/25783,2006,A1 .Location in patent: Page/Page column 152-153.
[12]Advanced Synthesis and Catalysis,2020,vol. 362,p. 5777 - 5782.
[13]Organic Letters,2021,vol. 23,p. 6099 - 6104.

14
[ 59718-84-2 ]
[ 1400664-29-0 ]