23088-23-5|Methyl 6-Quinoxalinecarboxylate| Ambeed

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Quality Control of [ 23088-23-5 ] Purity: 98% SDS Specification

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Product Details of [ 23088-23-5 ]

CAS No. :	23088-23-5
Formula :	C₁₀H₈N₂O₂
M.W :	188.18
SMILES Code :	COC(=O)C1=CC2=C(C=C1)N=CC=N2
MDL No. :	MFCD00102618
InChI Key :	VFPWJISMXACHIG-UHFFFAOYSA-N
Pubchem ID :	2781239

Safety of [ 23088-23-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H335
Precautionary Statements:	P261

Computational Chemistry of [ 23088-23-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	50.82
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.04
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	1.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.42
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.	0.76
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	1.77
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.	-2.3
Solubility	0.934 mg/ml ; 0.00496 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.	-2.13
Solubility	1.4 mg/ml ; 0.00743 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	-3.41
Solubility	0.0739 mg/ml ; 0.000393 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.	-6.43 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)	1.57

Application In Synthesis of [ 23088-23-5 ]

* 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 [ 23088-23-5 ]

[ 23088-23-5 ] Synthesis Path-Downstream 1~25

1
[ 113-00-8 ]
[ 23088-23-5 ]
N-(Quinoxaline-6-carbonyl)-guanidine [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,1997,vol. 45,p. 1282 - 1286.

3
[ 131543-46-9 ]
[ 619-05-6 ]
[ 23088-23-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	In water; isopropyl alcohol; at 80.0℃; for 2.0h;	Step 1: Methyl quinoxaline-6-carboxylate (237a) [0385] To a stirred solution of 3, 4-DIAMINO-BENZOIC acid methyl ester (236,2 g, 12.03 mmol) in isopropanol (50 mL) was added oxaldehyde as a 40% solution in water (13.23 MMOL, 1.52 mL). The reaction mixture was heated at 80C for 2 hours, the solvent was removed under reduced pressure and the residue was dried under vacuum to yield 237a as a yellow solid (2.09 g, 93% yield NMR: (DMSO) 6 9.01 (s, 2H), 8.54 (d, J=1.6 Hz, 1H), 8.23 (dd, J=8.6, 2.0 Hz, 1H), 8.14 (dd, J=8. 6,0. 6 Hz, 1H), 3.35 (s, 3H).

References: [1]Patent: WO2005/30704,2005,A1 .Location in patent: Page/Page column 222.

4
[ 23088-23-5 ]
[ 6925-00-4 ]

Yield	Reaction Conditions	Operation in experiment
76.6%		Preparation Example I-1. Quinoxaline-6-carboxylic acid To a solution of quinoxaline-6-carboxylic acid methyl ester (2084mg, 11.07mmol) in ethanol (25mL) was added an aqueous solution of 1 N sodium hydroxide (25mL), and the solution was stirred for 4 hours under reflux. 1 N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, then, the precipitated solid was collected by filtration, washed with water and isopropanol, then dried to obtain the title compound (1477mg, 8.479mmol, 76.6%) as a solid. 1H-NMR Spectrum (DMSO-d6) δ (ppm): 8.18 (1 H, d, J=8.4Hz), 8.29 (1H, dd, J=8.4, 1.2Hz), 8.61 (1 H, d, J=1.2Hz), 9.00-9.07 (2H, m).
76.6%		To a solution of quinoxaline-6-carboxylic acid methyl ester (2084mg, 11.07mmol) in ethanol (25mL) was added an aqueous solution of 1 N sodium hydroxide (25mL), and the solution was stirred for 4 hours under reflux. 1 N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, then, the precipitated solid was collected by filtration, washed with water and isopropanol, then dried to obtain the title compound (1477mg, 8.479mmol, 76.6%) as a solid. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 8.18 (1H, d, J=8.4Hz), 8.29 (1H, dd, J=8.4, 1.2Hz), 8.61 (1 H, d, J=1.2Hz), 9.00-9.07 (2H, m).
		To a solution of <strong>[23088-23-5]methyl quinoxaline-6-carboxylate</strong> (500 mg, 2.66 mmol) in 10 mL of THF was added sodium hydroxide (5N, 2.5 mL, 12.5 mmol) followed by methanol (2.5 mL). The reaction was stirred at room temperature overnight and then concentrated in vacuo to remove THF/MeOH. The resulting aqueous mixture was acidified with IN HCl until the pH was slightly acidic (pH = 5). The resulting solution was extracted with EtOAc (3x), and the combined organic layers were then washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting white solid was used without further purification. LC-MS: 3.50 min. (M+H) = 175.16

References: [1]Patent: EP1782811,2007,A1 .Location in patent: Page/Page column 59.
[2]Patent: EP1669348,2006,A1 .Location in patent: Page/Page column 67.
[3]Patent: WO2006/14618,2006,A2 .Location in patent: Page/Page column 40.

5
[ 107-83-5 ]
[ 23088-23-5 ]
[ 6925-00-4 ]
[ 258503-93-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In methanol; water; ethyl acetate;	The 6-quinoxalinylcarbonyl chloride used as a starting material was prepared as follows: A 2N aqueous sodium hydroxide solution (7.95 ml) was added to a solution of <strong>[23088-23-5]methyl quinoxaline-6-carboxylate</strong> (1 g) in a mixture of methanol (30 ml) and water (5 ml) and the mixture was stirred at ambient temperature for 16 hours. The reaction mixture was evaporated and the residue was dissolved in water. The solution was acidified to pH3.5 by the addition of dilute aqueous hydrochloric acid and extracted with ethyl acetate. The organic extracts were evaporated and the residue was triturated under a mixture of ethyl acetate and isohexane. There was thus obtained quinoxaline-6-carboxylic acid a solid (0.5 g); NMR Spectrum: (DMSOd6) 8.16 (d, 1H), 8.28 (d, 1H), 8.59 (s, 1H), 9.02 (s, 2H).

References: [1]Patent: US6432949,2002,B1 .

6
[ 91367-09-8 ]
[ 677-22-5 ]
[ 23088-23-5 ]
[ 1246383-16-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran; diethyl ether; water;	Step 1: 2-(2-Chloro-4-methoxy-phenyl)-1-quinoxalin-6-yl-ethanone A 2M solution of tert-butylmagnesium chloride (CAS Reg. No. 677-22-5) in diethyl ether (5.9 ml) was added to 2-chloro-4-methoxyphenylacetic acid (1.173 g, CAS Reg. No. 91367-09-8) in THF (10 ml). The mixture was stirred at room temperature for 30 min. A solution of methyl 6-quinoxalinecarboxylate (1 g, CAS Reg. No. 23088-23-5) in THF (3 ml) was added and the resulting mixture was stirred overnight. Aqueous HCl (25%, 1.5 ml) and water (30 ml) were added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (480 mg) as a light brown solid. MS (m/e)=313.2 [M+H+].

References: [1]Patent: US2010/249139,2010,A1 .

7
[ 4845-50-5 ]
[ 36692-49-6 ]
[ 23088-23-5 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	In N,N-dimethyl-formamide; at 90.0℃; for 8.0h;	Take a 100ml single-mouth bottle,Add 3,4-diaminobenzoic acid methyl ester (2) 3.32 g (0.02 mol),And added 30 ml of N,N-dimethylformamide, and dissolved by stirring.Then, [1,4]dioxane-2,3-diol (a) 3.6 g (0.03 mol) was added.Stir at 90 C for 8 hours.Then extracted, washed,Drying to give methyl quinoxaline-6-carboxylate (3)3.64 g, yield 96.7%.

References: [1]Patent: CN108997229,2018,A .Location in patent: Paragraph 0015; 0019; 0015; 0026; 0028; 0029; 0031; 0032.

8
[ 619-05-6 ]
[ 23088-23-5 ]

References: [1]Patent: CN108997229,2018,A .

9
[ 23088-23-5 ]
[ 90918-37-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium tetrahydridoborate; In methanol; at 90.0℃; for 2.0h;	Take a 100 ml single-mouth bottle, add quinoxaline-6-carboxylic acid methyl ester (3) 3.76 g (0.02 mol), add 50 ml of methanol, stir to dissolve,Then, 3.02 g (0.08 mol) of sodium borohydride was slowly added.The reaction was carried out at 90 C for 2 hours.After the reaction is completed, excess methanol is distilled off under reduced pressure.Then, it is extracted and dried to obtain 3.24 g of methyl 1,2,3,4-tetrahydroquinoxaline-6-carboxylate (4).The yield was 87%.

References: [1]Patent: CN108997229,2018,A .Location in patent: Paragraph 0015; 0022; 0025; 0027; 0028; 0030; 0031; 0033.
[2]ChemCatChem,2022.

10
[ 131543-46-9 ]
[ 36692-49-6 ]
[ 23088-23-5 ]

References: [1]Journal of the American Chemical Society,2019,vol. 141,p. 14870 - 14877.

11
[ 23088-23-5 ]
[ 75-05-8 ]
3-oxo-3-(quinoxalin-6-yl)propanenitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 14664 - 14701.

12
[ 23088-23-5 ]
4-((1-methylpiperidin-4-yl)amino)-N-(3-(quinoxalin-6-yl)-1H-pyrazol-5-yl)benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 14664 - 14701.

13
[ 23088-23-5 ]
3-(quinoxalin-6-yl)-1H-pyrazol-5-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 14664 - 14701.

14
[ 23088-23-5 ]
S-(5-(quinoxalin-6-yl)-1,3,4-oxadiazol-2-yl)2-phenylethanethioate [ No CAS ]