82257-15-6|4-Methoxynicotinaldehyde| Ambeed

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Quality Control of [ 82257-15-6 ] Purity: 95% SDS Specification

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Product Details of [ 82257-15-6 ]

CAS No. :	82257-15-6
Formula :	C₇H₇NO₂
M.W :	137.14
SMILES Code :	O=CC1=CN=CC=C1OC
MDL No. :	MFCD04112505
InChI Key :	QWUFIMUCFQUBOT-UHFFFAOYSA-N
Pubchem ID :	11332503

Safety of [ 82257-15-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 82257-15-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	36.12
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.	1.36
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	0.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.9
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.	-0.48
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	1.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.71

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.18
Solubility	8.96 mg/ml ; 0.0653 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.	-0.68
Solubility	29.0 mg/ml ; 0.211 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	-2.07
Solubility	1.16 mg/ml ; 0.00849 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.	-6.93 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	1.0 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)	1.15

Application In Synthesis of [ 82257-15-6 ]

* 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 [ 82257-15-6 ]

[ 82257-15-6 ] Synthesis Path-Downstream 1~35

1
[ 620-08-6 ]
[ 33513-42-7 ]
[ 82257-15-6 ]

Yield	Reaction Conditions	Operation in experiment
61%		Example 2 Preparation of 4-Methoxypyridine-3-carboxaldehyde tert-Butyllithium (90.6 mL, 154 mmol ; 1.7 M in pentane) was added via cannula to a stirred solution of tetrahydrofuran (380 mL) under an atmosphere of nitrogen at room temperature. The reaction mixture was cooled to-78 C before adding 2-bromomesitylene (11.3 mL, 74.1 mmol) dropwise. The reaction mixture was allowed to stir for 1 hour at-78 C. To the reaction mixture at-78 C was added 4- methoxypyridine (5.79 mL, 57 mmol) dropwise, and the resulting mixture was stirred at- 23 C for 3 hours. The reaction mixture was then re-cooled to-78 C and dimethylformamide (6.62 mL, 85.5 mmol) was added and stirring was continued for 1 hour at-78 C. The reaction mixture was quenched slowly at-78 C with saturated aqueous sodium chloride solution (100 mL) and allowed to warm to room temperature slowly. To the reaction mixture was added diethyl ether (200 rnL) and the layers were separated. The aqueous layer was extracted with diethyl ether (2 x 150 mL) and the combined organic layers were dried over potassium carbonate (20 g). The potassium carbonate was removed by filtration and washed with diethyl ether (100 mL) and the solvent removed under reduced pressure. The resulting crude 4-methoxy-3- pyridinecarboxaldehyde was purified by column chromatography (SiO2, 5: 95 ethanol: ethyl acetate) to give 4.79 g of the title intermediate as a yellow solid (61 % yield; >98% purity by'H NMR).
47.6%		To a solution of t-butyllithium in THF (1.7 M, 9.7 mL, 16.5 mmol, 2.1 eq) in THF (40 mL) maintained at -78 C was added 2-bromomesitylene (1.6 g, 8.0 mmol, 1.3 eq) dropwise. The resulting solution was stirred for 1 h at -78 C, then 4-methoxypyridine (681 mg, 0.63 mL, 6.2 mmol) was added and the mixture was warmed to -20 C in an ice-salt bath. After stirring for 3 h at -20 C, the mixture was cooled back to -78 C and DMF (1.17 g, 16.0 mmol, 2.0 eq) was added. The reaction mixture was stirred for 1 h, quenched with brine at -78 C and extracted with diethyl ether (3 × 100 mL). The combined organic extracts were dried over K2CO3, filtered and evaporated to yield a crude oil that was purified by silica gel chromatography using 1:1 EtOAc:hexanes to yield 405 mg (47.6%) of product as a pale yellow oil: Rf 0.25 (1:1 hexane:EtOAc); 1H NMR (300 MHz, CDCl3) δ 10.43 (s, 1H), 8.87 (s, 1H), 8.62 (d, 1H), 6.92 (d, 1H), 4.1 (s, 3H).
		A flask is charged with 1.7M tert-butyllithium in pentane (47.1 ml_, 80.1 mmol) and THF (20 ml_), and cooled to -78 0C. 2-Bromomesitylene (6.0 ml_, 39 mmol) is added dropwise. The mixture is stirred for 1 h, and 4-methoxypyridine (3.0 ml_, 30 mmol) is added dropwise. The mixture is warmed to -23 C and stirred for 3 h. The mixture is <n="128"/>cooled again to -78 C and dimethylformamide (3.5 ml_, 45 mmol) is added. After 1 h, brine (50 ml.) is added to the mixture at -78 C and warmed to room temperature. The mixture is extracted with ether and the combined organic layer is dried over Na2SO4. Concentration followed by silica gel chromatography eluting with a O to 6% methanol- dichloromethane gradient gives 4-methoxy-pyridine-3-carbaldehyde. 1H NMR (400 MHz, CDCI3) δ ppm 4.01 (s, 3 H), 6.94 (d, J=5.8 Hz, 1 H), 8.65 (d, J=5.8 Hz, 1 H), 8.90 (s, 1 H), 10.46 (s, 1 H).

References: [1]Tetrahedron Letters,2006,vol. 47,p. 39 - 41.
[2]Tetrahedron Letters,2000,vol. 41,p. 4777 - 4780.
[3]Patent: WO2005/42514,2005,A2 .Location in patent: Page/Page column 25.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 419 - 434.
[5]Journal of Organic Chemistry,1990,vol. 55,p. 69 - 73.
[6]Tetrahedron Letters,1988,vol. 29,p. 773 - 776.
[7]Patent: WO2009/156462,2009,A2 .Location in patent: Page/Page column 126-127.
[8]Biochemistry,2010,vol. 49,p. 10421 - 10439.

2
[ 141-82-2 ]
[ 82257-15-6 ]
[ 116922-79-3 ]

References: [1]Organic Letters,2017,vol. 19,p. 984 - 987.
[2]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 81 - 87.

3
[ 82257-15-6 ]
[ 135397-32-9 ]
5-Ethyl-3-[(4-methoxy-pyridin-3-ylmethyl)-amino]-6-methyl-1H-pyridin-2-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 249 - 255.

4
[ 124-41-4 ]
[ 114077-82-6 ]
[ 82257-15-6 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 81 - 87.

5
[ 82257-15-6 ]
[ 74-88-4 ]
[ 123506-70-7 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 69 - 73.

6
[ 82257-09-8 ]
[ 82257-15-6 ]
[ 82257-21-4 ]

References: [1]Journal of Chemical Research, Miniprint,1982,p. 912 - 942.

7
[ 82257-15-6 ]
[ 158588-34-2 ]
4-iodo-N,N-diisopropyl-3-(4-methoxypyrid-3-yl)hydroxymethyl-2-pyridinecarboxamide [ No CAS ]

References: [1]Synthesis,1995,p. 321 - 324.

8
[ 637-81-0 ]
[ 82257-15-6 ]
[ 290332-96-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium ethanolate; In ethanol; at -15℃; for 4h;	EXAMPLE 7: SYNTHESIS OF AZAINDOLE AND AZAINDOLE RELATED COMPOUNDS [024O] In this example, various preferred azaindole and azaindole-related compounds are prepared. <n="83"/>p c -[0241] Ethyl α-Azido-β-(4-methoxypyrid-3-yl)-acrylate 2. A homogeneous mixture of 3- formyl-4-methoxypyridine 1 (7.0 g, 54.7 mmol) and ethyl azidoacetate (5.0 g, 36.4 mmol) in anhydrous EtOH (50 mL) was added through a dropping funnel to a well-stirred solution containing Na (0.1.24 g, 54.7 mmol) in anhydrous EtOH (30 mL) under N2 at -15 0C. The mixture was stirred at that temperature for 4 h. During this time the precipitated solid was filtered and washed with ice cooled ethanol (30 mL). The compound was dried under vacuum oven for 3 h to get pure title compound 2 as white crystalline solid. Mp 92-95 C; Yield: 4.8 g, 53%; ESI MS: m/z 248.9 (M+1).
53%	With sodium ethanolate; In ethanol; at -15℃; for 4h;	<n="227"/>LiAIH4, THF reflux [00567] Ethyl α-Azido-β-(4-methoxypyrid-3-yl)-acrylate 2. A homogeneous mixture of <strong>[82257-15-6]3-formyl-4-methoxypyridine</strong> 1 (7.0 g, 54.7 mmol) and ethyl azidoacetate (5.0 g, 36.4 mmol) in anhydrous EtOH (50 mL) was added through a dropping funnel to a well-stirred solution containing Na (0.1.24 g, 54.7 mmol) in anhydrous EtOH (30 mL) under N2 at -15 0C. The mixture was stirred at that temperature for 4 h. During this time the precipitated solid was filtered and washed with ice cooled ethanol (30 mL). The compound was dried under vacuum oven for 3 h to get pure title compound 2 as white crystalline solid. Mp 92-95 0C; Yield: 4.8 g, 53%; ESI MS: m/z 248.9 (M+1).
53%	With sodium ethanolate; In ethanol; at -15℃; for 4h;	A homogeneous mixture of <strong>[82257-15-6]3-formyl-4-methoxypyridine</strong> 1 (7.0 g, 54.7 mmol) and ethyl azidoacetate (5.0 g, 36.4 mmol) in anhydrous EtOH (50 mL) was added through a dropping funnel to a well-stirred solution containing Na (0.1.24 g, 54.7 mmol) in anhydrous EtOH (30 mL) under N2 at -15 C. The mixture was stirred at that temperature for 4 h. During this time the precipitated solid was filtered and washed with ice cooled ethanol (30 mL). The compound was dried under vacuum oven for 3 h to get pure title compound 2 as white crystalline solid. Mp 92-95 C.; Yield: 4.8 g, 53%; ESI MS: m/z 248.9 (M+1).

References: [1]Tetrahedron Letters,2000,vol. 41,p. 4777 - 4780.
[2]Journal of Organic Chemistry,2003,vol. 68,p. 489 - 499.
[3]Patent: WO2007/56184,2007,A2 .Location in patent: Page/Page column 82.
[4]Patent: WO2007/56279,2007,A2 .Location in patent: Page/Page column 226.
[5]Patent: US2007/135385,2007,A1 .Location in patent: Page/Page column 120-121.

9
[ 82257-15-6 ]
[ 2688-84-8 ]
(4-methoxy-pyridin-3-ylmethyl)-(2-phenoxy-phenyl)-amine [ No CAS ]