120686-00-2|Methyl 6-hydroxy-2-methoxy-7,8-dihydroquinoline-5-carboxylate| Ambeed

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Quality Control of [ 120686-00-2 ] Purity: 95% SDS Specification

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Product Details of [ 120686-00-2 ]

CAS No. :	120686-00-2
Formula :	C₁₂H₁₃NO₄
M.W :	235.24
SMILES Code :	O=C(C1=C(O)CCC2=C1C=CC(OC)=N2)OC
MDL No. :	MFCD26406741
InChI Key :	OPTRBDFGSOAYQF-UHFFFAOYSA-N
Pubchem ID :	54696199

Safety of [ 120686-00-2 ]

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

Computational Chemistry of [ 120686-00-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	3
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	60.95
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.65 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.14
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	1.76
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.48
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.	0.49
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	1.72
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.47
Solubility	0.796 mg/ml ; 0.00339 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.	-2.82
Solubility	0.357 mg/ml ; 0.00152 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	-2.74
Solubility	0.427 mg/ml ; 0.00182 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.	-6.49 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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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)	2.94

Application In Synthesis of [ 120686-00-2 ]

* 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 [ 120686-00-2 ]

[ 120686-00-2 ] Synthesis Path-Downstream 1~29

1
[ 78-85-3 ]
[ 120686-00-2 ]
[ 120686-01-3 ]

References: [1]Heterocycles,1997,vol. 46,p. 27 - 30.
[2]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 97 - 105.

2
[ 78-85-3 ]
[ 120686-00-2 ]
[ 120686-01-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h;	General procedure: To a solution of beta-ketoester 10a (1 mmol), 1,1,3,3-tetramethylguanidine (26 muL, 0.2 mmol) in dichloromethane (2.5 mL) was added alpha,beta-unsaturated aldehyde 11a (10 mmol). The reaction mixture was stirred at room temperature for 12 h and then the solvent was removed under vacuum. The residue was purified by silica gel chromatography to yield the bridged product 12a. To a solution of the alcohol 12a (0.5 mmol) and trimethylamine (690 muL, 5 mmol) in 2.5 mL of dichloromethane was added dropwise mesyl chloride (154 muL, 2 mmol) and a catalytic amount of DMAP at room temperature. The solution was stirred for 12 h at room temperature, and then diluted with dichloromethane, washed with satd aq NH4Cl, dried and concentrated. The above crude product was dissolved in HOAc (10 mL), and NaOAc (48 mg, 0.6 mmol) was added. The solution was heated to reflux for 24 h. After concentration in vacuum, the residue was treated with satd aq NaHCO3, and extracted with ethyl acetate. The combined organic extracts was washed with brine and dried. After concentration in vacuum, the residue was purified by silica gel chromatography to give rac-13a.
	With N,N,N',N'-tetramethylguanidine; In dichloromethane; at 20℃; for 12h;	rac-4 To a solution of beta-keto ester 2 (0.5 mmol),1,1,3,3-tetramethyl guanidine (13 mL, 0.1 mmol) in dryDCM (2 mL) was added methacrolein 3 (5 mmol). Thereaction mixture was stirred at room temperature for 12 hand then the solvent was removed under vacuum. Theresidue was purified by silica gel chromatography to yieldthe rac-9. To a solution of the alcohol rac-9 (0.25 mmol)and triethylamine (340 muL, 2.5 mmol) in 2 mL of DCMwas added dropwise mesyl chloride (77 muL, 1 mmol) and DMAP (3 mg, 0.025 mmol) at room temperature. Thesolution was stirred for 12 h at room temperature, andthen diluted with DCM, washed with saturated aq NH4Cl,dried and concentrated. The above crude product was dissolvedin HOAc (5 mL), and NaOAc (24 mg, 0.3 mmol)was added. The solution was heated to reflux for 24 h.After concentration in vacuum, the residue was dissolvedin ethyl acetate, was washed with saturated Na2CO3 andbrine, dried over Na2SO4. Evaporation of the ethyl acetateand flash chromatography of the residue (20 % and then40 % ethyl acetate in hexanes) gave 79 mg of rac-4 in 55 %yield.

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 4116 - 4117.
[2]Tetrahedron,2012,vol. 68,p. 6240 - 6248.
[3]Journal of the Iranian Chemical Society,2016,vol. 13,p. 1481 - 1486.

3
[ 4432-63-7 ]
[ 120686-00-2 ]
10-Hydroxy-5-methoxy-13-oxo-11-phenyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 97 - 105.

4
[ 3775-29-9 ]
[ 120686-00-2 ]
[ 179105-08-9 ]

References: [1]Journal of the Chemical Society. Chemical communications,1993,p. 860 - 862.

5
[ 3775-29-9 ]
[ 120686-00-2 ]
(+/-)-7,8,9,10-Tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 7660 - 7669.
[2]Journal of the Chemical Society. Perkin transactions I,1996,p. 1287 - 1297.

6
[ 120686-00-2 ]
[ 57707-91-2 ]
[ 134757-76-9 ]

References: [1]Journal of the American Chemical Society,1991,vol. 113,p. 4695 - 4696.

7
[ 120686-09-1 ]
[ 616-38-6 ]
[ 120686-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; at 85 - 90℃; for 2h;Inert atmosphere;	Sodium hydride (50%, 27.7 g, 1.2 equivalents) and dimethyl carbonate (1,275 ml) were heated to 85-90 C. under nitrogen atmosphere, and the ketone of Formula (4) (85 g, 1.0 equivalent) diluted with dimethyl carbonate (1,275 ml) was added drop wise over a period of 1.5 hours. After addition, the reaction mixture was maintained at the same temperature for approximately 30 minutes. A sample for HPLC showed <1% of the ketone starting material remained. Dimethyl carbonate was then distilled off completely under vacuum at 40-45 C., and the residue was cooled to 10-15 C. Chilled water was added and dissolved completely. The pH was adjusted to 2-3 by adding 5 N HCl (160 ml) and extraction was performed with ethyl acetate (1 time with 340 ml and 2 times with 170 ml). The solvent was distilled off completely to get the crude beta-keto ester of Formula (5). The crude ester was dissolved in 800 ml 5% ethyl acetate:hexane mixture by heating at 60-65 C. The resulting mixture was allowed to cool to ambient temperature (20-25 C.) and filtered through filter paper. The solvent was distilled off completely under vacuum at 40-45 C. The resulting residue was stirred with hexane for 30 minutes at 20-25 C. The product was then collected by filtration and bed washed with portions of hexane. The product was dried under vacuum (740-750 mm/Hg) at 25-30 C. for 2 hours to yield pure product (80.2 g, 71% yield, HPLC purity-98%).

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 97 - 105.
[2]Patent: US2009/247754,2009,A1 .Location in patent: Page/Page column 10; 7.

8
[ 120685-99-6 ]
[ 616-38-6 ]
[ 120686-00-2 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 4116 - 4117.

9
[ 120686-00-2 ]
[ 107-02-8 ]
[ 137720-08-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3399 - 3402.

10
[ 120686-00-2 ]
[ 107-02-8 ]
[ 142142-12-9 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 2653 - 2656.

11
[ 120686-00-2 ]
[ 74-88-4 ]
[ 137720-02-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 3279 - 3284.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 3399 - 3402.

12
[ 3775-29-9 ]
[ 120686-00-2 ]
[ 185741-49-5 ]
[ 185741-71-3 ]

References: [1]Tetrahedron Asymmetry,1997,vol. 8,p. 829 - 832.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[3]Tetrahedron,1998,vol. 54,p. 5471 - 5484.

13
[ 78-85-3 ]
[ 120686-00-2 ]
[ 185741-40-6 ]
[ 191600-74-5 ]

References: [1]Heterocycles,1997,vol. 46,p. 27 - 30.
[2]Heterocycles,1997,vol. 46,p. 27 - 30.

14
[ 78-85-3 ]
[ 120686-00-2 ]
[ 185741-41-7 ]
[ 191600-72-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of (2R)-catalyst 8b(18 mg, 0.03 mmol) and benzoic acid (12 mg, 0.1 mmol)and the beta-keto ester 2 (47 mg, 0.2 mmol) in dry DCM(2 mL) was added methacrolein 3 (84 mg, 1.2 mmol) at0 C. The reaction mixture was refluxed for 4 days, then thesolvent was removed under vacuum, the residue was dissolvedin DCM (2 mL), and then DBU (42 muL, 0.3 mmol)was added. The reaction mixture was stirred at room temperaturefor 2 h, and the solvent was removed under vacuum,then ethyl acetate and saturated NaCl were added. Theorganic phase was separated and the aqueous phase wasextracted with ethyl acetate. The combined organic layerswere dried over Na2SO4 and concentrated to give the crudeproduct. Purification of the residue by flash column chromatography(silica gel) eluting with 20 % ethyl acetate in hexanesgave 50 mg of 9 (82 %) as a mixture of diastereomers.1H NMR (400 MHz, CDCl3) (main diastereomer): delta 7.07 (d,J = 8.8 Hz, 1H), 6.62 (d, J = 8.4 Hz, 1H), 3.89 (s, 3 H),3.73 (s, 3 H), 3.70-3.78 (m, 1H), 3.43 (dd, J = 5.2, 17.6 Hz,1H), 3.43 (dd, J = 2.0, 18.0 Hz, 1H), 3.17 (dd, J = 6.8,13.2 Hz, 1H), 2.77-2.80 (m, 1H), 2.18 (brs, 1H), 1.71-1.78(m, 1H), 1.61-1.66 (m, 1H), 0.88 (d, J = 6.8 Hz, 3H); 13CNMR (100 Hz, CDCl3): delta 207.01, 171.77, 163.26, 149.88,138.74, 128.39, 110.45, 80.28, 60.28, 54.66, 53.70, 53.01,41.85, 39.20, 34.56, 17.58; ESI-MS m/z: 306.1 [M + H]+;ESI-HRMS calcd for C16H20NO5+ [M + H]+ 306.1339,found 306.1336

References: [1]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[2]Tetrahedron,1998,vol. 54,p. 5471 - 5484.
[3]Journal of the Iranian Chemical Society,2016,vol. 13,p. 1481 - 1486.

15
[ 4746-97-8 ]
[ 120686-00-2 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 4116 - 4117.

16
[ 120685-98-5 ]
[ 120686-00-2 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 4116 - 4117.

17
[ 3775-29-9 ]
[ 120686-00-2 ]
[ 185741-49-5 ]

Yield	Reaction Conditions	Operation in experiment
50%		A chiral ligand according to Formula (13) (2.13 g, 2 mol %), allyl palladiumchloride dimer (0.56 g, 1 mol %), and acetone (140 ml) were combined and stirred at 20-25 C. for 1 hour under a nitrogen atmosphere. To the mixture was added 2-methylene-1,3-propanediol diacetate (26.2 ml, 1.0 equivalent) and 35 ml of acetone and the new mixture was maintained at the same temperature for 1 hour. A mixture of the purified keto ester of Formula (5) (35 g, 1.0 equivalent), 1,1,3,3-tetramethyl guanidine (42 ml, 2.2 equivalents), and acetone (175 ml) was added to the above solution in lots over a period of 30 minutes at 20-25 C. The resulting mixture was then stirred at the same temperature for 1 hour under a nitrogen atmosphere. A sample for chiral HPLC indicated <1% starting material (keto ester) remained. Acetone was then distilled off under vacuum at 40-45 C. to obtain a crude material. The Crude material was passed through silica gel column and eluted with hexane and ethyl acetate mixtures to remove catalyst and ligand. The fractions containing product were collected and the solvent was distilled completely to yield pure product of the compound of Formula (6) (35 g, 82% yield, HPLC purity of 78%). This crude product (35 g) was stirred with isopropyl alcohol (140 ml) at 20-25 C. for 30 minutes. The obtained solid was filtered and washed with isopropyl alcohol (17.5 ml), and the material was dried under vacuum for 2-3 hours at 35-40 C. to get pure product as a white solid (21 g, 50% yield, HPLC purity of 97.5%).

References: [1]Patent: US2009/247754,2009,A1 .Location in patent: Page/Page column 10-11; 7.

18
[ 4417-80-5 ]
[ 120686-00-2 ]
C₁₈H₂₃NO₅ [ No CAS ]