Home Cart Sign in  
Chemical Structure| 20265-35-4 Chemical Structure| 20265-35-4

Structure of 20265-35-4

Chemical Structure| 20265-35-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 20265-35-4 ]

CAS No. :20265-35-4
Formula : C6H6N2O3
M.W : 154.12
SMILES Code : O=[N+](C1=CC=CN=C1OC)[O-]
MDL No. :MFCD00023459
InChI Key :WZNQCVOSOCGWJG-UHFFFAOYSA-N
Pubchem ID :253219

Safety of [ 20265-35-4 ]

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

Computational Chemistry of [ 20265-35-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 39.55
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

67.94 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.14
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.99
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.0
Log Po/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.

0.25
Log Po/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

-0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.52

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.69
Solubility 3.14 mg/ml ; 0.0204 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.

-2.01
Solubility 1.52 mg/ml ; 0.00988 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

-1.52
Solubility 4.68 mg/ml ; 0.0303 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

No
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.

-6.54 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

2.0 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)

1.97

Application In Synthesis of [ 20265-35-4 ]

* 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 [ 20265-35-4 ]

[ 20265-35-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 5470-18-8 ]
  • [ 124-41-4 ]
  • [ 20265-35-4 ]
YieldReaction ConditionsOperation in experiment
90% In methanol; at 0℃; for 4h; A suspension of sodium methoxide (40.5 g, 0.750 mol) in 200 mL of methanol was slowly added to a solution of 2-chloro-3- nitro-pyridine (79.3 g, 0.500 mol) in 800 mL of methanol at 0 °C. The reaction mixture was stirred for 4 hours and then poured into 1000 g of ice. The resulting precipitate was filtered, washed with water, and dried to give 2-methoxy-3-nitro-pyridine (70. g, 0.45 mmol, 90 percent) as a white solid.
  • 2
  • [ 20265-35-4 ]
  • [ 20265-38-7 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen;palladium 10% on activated carbon; In methanol; for 4h; (1)10percent palladium-activated carbon (2.5 g) was added to a solution of commercially available <strong>[20265-35-4]2-methoxy-3-nitropyridine</strong> (50.5 g) in methanol (500 mL), and the mixture was stirred for four hours in a hydrogen atmosphere.The reaction solution was filtered through celite, and then the filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give 2-methoxypyridin-3-amine as a yellow powder (37.2 g, 92percent).1H NMR (300 MHz, CDCl3) delta ppm 3.64-3.88 (m, 2H), 3.92-4.05 (m, 3H), 6.67-6.76 (m, 1H), 6.84-6.92 (m, 1H), 7.54-7.62 (m, 1H).MS(+): 125 [M+H]+.
90% palladium-carbon; In ethanol; EXAMPLE 13 Synthesis of 2-methoxy-3-aminopyridine STR28 To a solution of the compound of Example 12 (17.12 g, 0.11 mol) in ethanol (180 mL) in a Parr bottle, was added 4percent Pd/C (3.43 g). The bottle was sealed, purged with nitrogen and was pressurized (5 psi) with hydrogen. After stirring at room temperature for 2 hr, the reaction vessel was vented, purged with nitrogen and filtered. The clear filtrate was concentrated to give the title compound (15.3 g, 90percent). 1 H NMR (CDCl3): 7.58 (dd, J=5, 2 Hz, 1H); 6.87 (dd, J=8, 2 Hz, 1H); 6.72 (dd, J=8, 5 Hz, 1H); 3.98 (s, 3H).
87% With hydrogen;palladium 10% on activated carbon; In methanol; for 15h; A solution of 2- methoxy-3-nitro-pyridine (70. g, 0.45 mol) in methanol (700 mL) containing palladium on carbon (7 g, 10 percent) was stirred under an atmosphere of hydrogen for 15 hours. The catalyst was filtered and washed with methanol. The filtrate was evaporated to dryness to give crude 2- methoxy-pyridin-3-ylamine (48 g, 0.39 mol, 87 percent), which was used directly in the next step.
74% With hydrogen;palladium 10% on activated carbon; In methanol; Compound 1 (20.8 g, 135 mmol) was dissolved in methanol (270 mL) and palladium on carbon (10percent Pd dry weight basis, Degussa type E101 NE/W, 50percent water content, 5.75 g, 2.7 mmol Pd) was added. The atmosphere was replaced with hydrogen (toggle between vacuum and hydrogen from a balloon five times), the mixture was stirred overnight, then filtered. The filtrate was concentrated under vacuum and the residue was taken up in a 1:1 hexanes:ethyl acetate mixture and washed with a 4:1 mixture of water and saturated NaHCO3, saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and filtered and the filtrate was concentrated under reduced pressure to give compound 2 (12.43 g, 74percent) as a white solid. This material was used without purification.
38.9 g With palladium 10% on activated carbon; hydrogen; In methanol; for 3h; A solution of <strong>[20265-35-4]2-methoxy-3-nitropyridine</strong> (50 g, 324.4 mmol) and 10percent Pd/C (5 g) in MeOH (500 ml_) was stirred under an atmosphere of H2 for 3 h. The mixture was filtered through celite and the filter was washed with MeOH. The filtrate was concentrated in vacuo to yield 2-methoxypyridin-3-amine as a brown solid (38.9 g, 313.4 mmol). 1H NMR: (300 MHz, CDCI3) delta: 3.74 (br. s, 2H), 3.96 (s, 3H), 6.72 (m, 1 H), 6.86 (m, 1 H), 7.56 (d, J=1.8, 1 H)

  • 3
  • [ 20893-30-5 ]
  • [ 20265-35-4 ]
  • [ 22018-90-2 ]
  • 4
  • [ 617-35-6 ]
  • [ 20265-35-4 ]
  • [ 112777-38-5 ]
  • 5
  • [ 20265-35-4 ]
  • [ 5878-19-3 ]
  • [ 112777-36-3 ]
  • 6
  • [ 20265-35-4 ]
  • [ 67-64-1 ]
  • [ 112777-37-4 ]
  • 7
  • [ 20265-35-4 ]
  • [ 58819-89-9 ]
  • 8
  • [ 20265-35-4 ]
  • 3-hydroxyamino-2-methoxypyridine [ No CAS ]
  • 9
  • [ 20265-35-4 ]
  • [ 5470-18-8 ]
  • 12
  • [ 74-88-4 ]
  • silver-salt of 3-nitro-pyridin-2-ol [ No CAS ]
  • [ 20265-35-4 ]
  • [ 32896-91-6 ]
  • 13
  • [ 20265-35-4 ]
  • [ 1826-67-1 ]
  • [ 160590-40-9 ]
YieldReaction ConditionsOperation in experiment
21.27% In tetrahydrofuran; at -78 - -20℃; To a mixture of 2-methoxy-3- nitropyridine (5 g, 0.032 mol) in tetrahydrofuran (100 mL) at -78°C was added dropwise vinylmagnesium bromide (100 mL, 1 M). The reaction mixture was stirred at -20°C overnight then quenched with saturated aqueous NH4CI and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford the desired product (1 g, 21.27percent yield) as black solid. LC-MS: 149 (M+H)+.
100 mg In tetrahydrofuran; methanol; at -78 - -20℃; for 6h; Method 4 Synthesis of 7-methoxy-1H-pyrrolo[2,3-c]pyridine (Intermediate 5) A solution of R-4 (500 mg, 3.24 mmol) in anhydrous THF (20 mL) is cooled to -78° C. and vinylmagnesium bromide (9.73 mL of a 1 M solution in THF, 9.73 mmol) added. The reaction is stirred at -20° C. for 6 h then quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The organic phase is concentrated in vacuo and the crude material purified by flash chromatography (SiO2, 2percent to 10percent MeOH in DCM) to give the title intermediate I-5 (100 mg) m/z 148.9 [M+H].
  • 14
  • [ 20265-35-4 ]
  • [ 125867-19-8 ]
  • 15
  • [ 20265-35-4 ]
  • 4-deutero-2-methoxy-3-pivaloylaminopyridine [ No CAS ]
  • 16
  • [ 20265-35-4 ]
  • 3-amino-4-benzylpyridin-2(1H)-one [ No CAS ]
  • 17
  • [ 20265-35-4 ]
  • [ 197229-82-6 ]
  • 19
  • [ 20265-35-4 ]
  • [ 112777-47-6 ]
  • 20
  • [ 20265-35-4 ]
  • [ 112777-27-2 ]
  • 21
  • [ 20265-35-4 ]
  • [ 112777-41-0 ]
  • 22
  • [ 20265-35-4 ]
  • [ 112797-19-0 ]
  • 23
  • [ 20265-35-4 ]
  • [ 112777-28-3 ]
  • 24
  • [ 20265-35-4 ]
  • [(2-Methoxy-1-methyl-ethyl)-(2-methoxy-pyridin-3-yl)-amino]-oxo-acetyl chloride [ No CAS ]
  • 25
  • [ 20265-35-4 ]
  • [ 112777-48-7 ]
  • 26
  • [ 20265-35-4 ]
  • [ 112777-43-2 ]
  • 27
  • [ 20265-35-4 ]
  • [ 112777-45-4 ]
  • 28
  • [ 20265-35-4 ]
  • [ 112777-42-1 ]
  • 29
  • [ 20265-35-4 ]
  • [ 112777-33-0 ]
  • 30
  • [ 20265-35-4 ]
  • [ 112777-44-3 ]
  • 31
  • [ 6332-56-5 ]
  • [ 20265-35-4 ]
  • 32
  • [ 5470-18-8 ]
  • [ 20265-35-4 ]
YieldReaction ConditionsOperation in experiment
75% With sodium methylate; In methanol; EXAMPLE 12 Synthesis of 2-methoxy-3-nitropyridine STR27 2-Chloro-3-nitropyridine (25 g, 0.157 mol) was suspended in methanol (300 ml) and sodium methoxide (17 g, 0.315 mol) was added. The mixture was refluxed for 2 hr and part of the solvent removed under reduced pressure. The reaction mixture was diluted with water (1 litre) and the precipitate collected by filtration. The white solid obtained was washed with more water and dried under vacuum to give the title compound (18.2 g, 75percent). 1 H NMR (CDCl3): 8.42 (dd, J=5, 2 Hz, 1H); 8.28 (dd, J=8, 2 Hz, 1H); 7.06 (dd, J=8, 5 Hz, 1H); 4.13 (s, 3H)
  • 33
  • [ 20265-35-4 ]
  • [ 4214-75-9 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; In water; EXAMPLE 5 Preparation of 3-Nitro-2-aminopyridine One gram (6.5 mmol) of <strong>[20265-35-4]2-methoxy-3-nitropyridine</strong> and 5.0 g (65 mmol) of ammonium acetate were added to a 100 ml round bottom flask. The reaction mixture was heated at 150° C. for approximately 16 hours under an argon atmosphere. An additional 5 g of ammonium acetate was added to the reaction mixture which was allowed to heat for an additional 8 hours. Thin layer chromatography of the mixture indicated that both product and starting material were present. The reaction mixture was cooled and poured into approximately 100 ml of water. The precipitated solid was collected by filtration to provide 209.8 mg of 3-nitro-2-aminopyridine. m/e 139. The NMR spectrum of the collected produot was identical to that of an authentic reference standard. Analysis calculated for C5 H5 N3 O2: Theory: C, 43.17; H, 3.62; N, 30.21; Found: C, 42.89; H, 3.38; N, 30.23.
  • 34
  • [ 67-56-1 ]
  • [ 5470-18-8 ]
  • [ 20265-35-4 ]
  • 35
  • [ 20265-35-4 ]
  • [ 89466-18-2 ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 20265-35-4 ]

Ethers

Chemical Structure| 160590-36-3

A204309 [160590-36-3]

2-Methoxy-3-nitro-4-methylpyridine

Similarity: 0.91

Chemical Structure| 33623-16-4

A233551 [33623-16-4]

2-Methoxy-3-nitropyridin-4-amine

Similarity: 0.91

Chemical Structure| 152684-30-5

A128539 [152684-30-5]

5-Bromo-2-methoxy-3-nitropyridine

Similarity: 0.86

Chemical Structure| 40851-91-0

A150343 [40851-91-0]

6-Chloro-2-methoxy-3-nitropyridine

Similarity: 0.84

Chemical Structure| 1211534-27-8

A376186 [1211534-27-8]

5-Fluoro-2-methoxy-3-nitropyridine

Similarity: 0.84

Nitroes

Chemical Structure| 160590-36-3

A204309 [160590-36-3]

2-Methoxy-3-nitro-4-methylpyridine

Similarity: 0.91

Chemical Structure| 33623-16-4

A233551 [33623-16-4]

2-Methoxy-3-nitropyridin-4-amine

Similarity: 0.91

Chemical Structure| 39745-39-6

A156001 [39745-39-6]

6-Methyl-3-nitropyridin-2-ol

Similarity: 0.88

Chemical Structure| 152684-30-5

A128539 [152684-30-5]

5-Bromo-2-methoxy-3-nitropyridine

Similarity: 0.86

Chemical Structure| 1211534-27-8

A376186 [1211534-27-8]

5-Fluoro-2-methoxy-3-nitropyridine

Similarity: 0.84

Related Parent Nucleus of
[ 20265-35-4 ]

Pyridines

Chemical Structure| 160590-36-3

A204309 [160590-36-3]

2-Methoxy-3-nitro-4-methylpyridine

Similarity: 0.91

Chemical Structure| 33623-16-4

A233551 [33623-16-4]

2-Methoxy-3-nitropyridin-4-amine

Similarity: 0.91

Chemical Structure| 39745-39-6

A156001 [39745-39-6]

6-Methyl-3-nitropyridin-2-ol

Similarity: 0.88

Chemical Structure| 152684-30-5

A128539 [152684-30-5]

5-Bromo-2-methoxy-3-nitropyridine

Similarity: 0.86

Chemical Structure| 1211534-27-8

A376186 [1211534-27-8]

5-Fluoro-2-methoxy-3-nitropyridine

Similarity: 0.84