406719-76-4|Methyl 4-cyano-2-methoxybenzoate| Ambeed

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Quality Control of [ 406719-76-4 ] Purity: 97% SDS Specification

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Product Details of [ 406719-76-4 ]

CAS No. :	406719-76-4
Formula :	C₁₀H₉NO₃
M.W :	191.18
SMILES Code :	O=C(OC)C1=CC=C(C#N)C=C1OC
MDL No. :	MFCD18399095
InChI Key :	JFCISGMVSHCQBL-UHFFFAOYSA-N
Pubchem ID :	57426183

Safety of [ 406719-76-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 406719-76-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	48.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.32 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.12
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.	1.35
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.	1.0
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	1.59

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	1.07 mg/ml ; 0.00558 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.	-2.62
Solubility	0.455 mg/ml ; 0.00238 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	-2.69
Solubility	0.39 mg/ml ; 0.00204 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.	-6.22 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)	1.78

Application In Synthesis of [ 406719-76-4 ]

* 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.

Downstream synthetic route of [ 406719-76-4 ]

[ 406719-76-4 ] Synthesis Path-Downstream 1~27

Yield	Reaction Conditions	Operation in experiment
71%		To the stirred mixture of CuCl (653 mg, 6.6 mmol) in 3 mL water at 0 C. was added NaCN (841 mg, 17 mmol, dissolved in 3 mL water). The mixture was stirred in ice bath. At the same time, commercial methyl 4-amino-2-inethoxybenzoate (1 g, 5.5 mmol) was stirred in 5 mL conc. HCl in ice bath. To it was added dropwise an ice-cold solution of NaNO2 (457 mg, 6.6 mmol, in 3 mL water). The mixture was stirred in the ice bath for 1 hr. A dark orange solution was got. To it was added solid K2CO3 till no more CO2 was released (pH=7). To the stirred cold suspension of freshly-prepared CuCN were added 5 mL toluene and then dropwise the neutralized diazonium slurry. The mixture was stirred in the ice bath for 20 min and then at room temperature for 1 hr. The mixture was diluted with 300 mL EtOAc, washed with water and brine, dried, purified by flash column to afford methyl 4-cyano-2-methoxybenzoate (71%). MS found for C10H9NO3 (M+H)+ 192.

2
[ 406719-76-4 ]
[ 89469-52-3 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 8124 - 8134.

3
[ 27492-84-8 ]
[ 544-92-3 ]
[ 406719-76-4 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 8124 - 8134.

4
[ 406719-76-4 ]
[ 1289571-14-7 ]

References: [1]Patent: US2011/86854,2011,A1 .

5
[ 406719-76-4 ]
[ 1027035-76-2 ]

Yield	Reaction Conditions	Operation in experiment
34.7%	With hydrogen;Raney-nickel; In methanol; water; under 2585.81 Torr; for 16.0h;	A mixture of <strong>[406719-76-4]4-cyano-2-methoxy-benzoic acid methyl ester</strong> (1.01 g, 5.28 mmol) in methanol (50 mL) was added to Raney-nickel 2800 slurry in water (a few grams washed with methanol to remove the water, Aldrich) and it was put under a 50 psi hydrogen atmosphere for 16 hrs. The mixture was filtered through Celite under an argon atmosphere and concentrated and then purified by flash chromatography to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 34.7%).

References: [1]Patent: US2011/86854,2011,A1 .Location in patent: Page/Page column 42.

6
[ 406719-76-4 ]
[ 1289570-73-5 ]
[ 1289570-74-6 ]

References: [1]Patent: US2011/86854,2011,A1 .

7
[ 406719-76-4 ]
rac-4-([(2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-(2,2-dimethylpropyl)pyrrolidine-1-carbonyl]amino}methyl)-2-methoxybenzoic acid methyl ester [ No CAS ]

References: [1]Patent: US2011/86854,2011,A1 .

8
[ 406719-76-4 ]
rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid [ No CAS ]

References: [1]Patent: US2011/86854,2011,A1 .

9
[ 67-56-1 ]
[ 89469-52-3 ]
[ 406719-76-4 ]

Yield	Reaction Conditions	Operation in experiment
96.4%	With toluene-4-sulfonic acid; In water; for 16.0h;Reflux; Inert atmosphere;	To a mixture of 4-cyano-2-methoxybenzoic acid (1.00 g, 5.648 mmol, Biogene) in methanol (15.0 mL) was added p-toluenesulfonic acid monohydrate (286 mg, 1.48 mmol, Aldrich) and it was heated to reflux under an argon atmosphere for 16 hrs. The solvent was removed and the reaction mixture was extracted with EtOAc, washed with saturated Na2CO3, water, and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-cyano-2-methoxy-benzoic acid methyl ester (1.04 g, 96.4%).

References: [1]Patent: US2011/86854,2011,A1 .Location in patent: Page/Page column 42.

10
[ 139102-34-4 ]
[ 406719-76-4 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 4786 - 4797.

11
[ 406719-76-4 ]
[ 1432496-19-9 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 4786 - 4797.

12
[ 81245-24-1 ]
[ 406719-76-4 ]

References: [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 2439 - 2445.
Angewandte Chemie,2020,vol. 133,p. 2469 - 2475,7.

13
[ 406719-76-4 ]
6-[(2,6-dimethylpyrimidin-4-yl)amino]-4-[[2-methoxy-4-(5-methyl-4H-1,2,4-triazol-3-yl)benzoyl]amino]-N-methylpyridine-3-carboxamide [ No CAS ]