Home Cart Sign in  
Chemical Structure| 337463-88-4 Chemical Structure| 337463-88-4
Chemical Structure| 337463-88-4

6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

CAS No.: 337463-88-4

4.5 *For Research Use Only !

Cat. No.: A203706 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg ł§ď¶ÊÊ Inquiry Inquiry
250mg łÿ˶ÊÊ Inquiry Inquiry
1g łÇÊó¶ÊÊ Inquiry Inquiry
5g łÿ§ó¶ÊÊ Inquiry Inquiry
10g łÇÊďÿ¶ÊÊ Inquiry Inquiry

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

  • 100mg

    ł§ď¶ÊÊ

  • 250mg

    łÿ˶ÊÊ

  • 1g

    łÇÊó¶ÊÊ

  • 5g

    łÿ§ó¶ÊÊ

  • 10g

    łÇÊďÿ¶ÊÊ

In Stock

- +

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 337463-88-4 ]

CAS No. :337463-88-4
Formula : C7H5BrN2O2
M.W : 229.03
SMILES Code : BrC1=CC=C2OCC(=O)NC2=N1
MDL No. :MFCD11101028
InChI Key :GDVHYNCHZKTTSQ-UHFFFAOYSA-N
Pubchem ID :21873772

Safety of [ 337463-88-4 ]

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

Calculated chemistry of [ 337463-88-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 48.76
TPSA ?

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

51.22 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.69
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

1.16
Log Po/w (WLOGP)?

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

0.6
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.

0.51
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

1.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.13

Water Solubility

Log S (ESOL):?

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

-2.36
Solubility 0.998 mg/ml ; 0.00436 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.

-1.83
Solubility 3.38 mg/ml ; 0.0148 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

-3.12
Solubility 0.175 mg/ml ; 0.000766 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.

-6.87 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.

0.55

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)

2.36

Application In Synthesis of [ 337463-88-4 ]

* 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 [ 337463-88-4 ]

[ 337463-88-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 337463-88-4 ]
  • [ 959992-62-2 ]
YieldReaction ConditionsOperation in experiment
100% Step 4 To a solution of Compound (9) (3.12 g, 13.7 mmol) in tetrahydrofuran (50 mL), borane-tetrahydrofuran complex (33 mL, 33.0 mmol) was added at room temperature. The solution was then stirred at 90C for 1.5 hours. Methanol (2.0 mL) was added to the reaction solution, and then the mixture was stirred at 90C for 20 minutes. The reaction solution was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, dried with anhydrous magnesium sulfate, and then concentrated in vacuo to yield subject compound (10) (3.17 g, 100%) as a yellow powder.1H-NMR (DMSO-d6) 57.04 (1H, br s), 6.69 (1H, d, J = 7.8 Hz), 6.40 (1H, d, J = 7.8 Hz), 3.91 (2H, t, J = 4.2Hz), 3.19-3.23 (2H, m) LC/MS (Method A): 1.44 min, [M+H]+ = 215.2.
99% With diborane; In tetrahydrofuran; for 1h;Cooling with ice; Reflux; Under ice bath conditions, Borane in tetrahydrofuran (5.5 mL, 5.5 mmol, 1.0 M) Add dropwise to compound 3.2 (500 mg, 2.19 mmol) In a solution of tetrahydrofuran (25 mL), The reaction system was stirred under reflux with heating for 1 hour. The reaction was then carefully quenched with methanol (10 drops) under reflux. The mixture was cooled to room temperature and concentrated under reduced pressure to remove solvent. The residue was chromatographed on silica gel ( petroleum ether / ethyl acetate = 5/1) Purification afforded compound 23.1 (470 mg, yield: 99%) It is a white solid.
87% With dimethylsulfide borane complex; potassium carbonate; In tetrahydrofuran; at 70℃; for 0.25h;Inert atmosphere; Part IV- Synthesis of 6-Bromo-3,4-dihydro-2H-pyrido[3,2-b] [1,4]oxazine; 6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (1.35 g, 5.89 mmol) was dissolved inTHF (40 mL). Boranedimethylsulphide complex (2.0 Min THF, 5.89 mL, 11.79 mmol) wasadded and the resulting mixture heated to 70 C under nitrogen for 15 minutes. Next, thereaction mixture was cooled to room temperature, quenched with methanol ( ~5 mL ), and then dried under vacuum to obtain a white solid. The crude material was dissolved indichloromethane and washed with H20. The aqueous phase was discarded and the organicphase was dried under vacuum to give 6-bromo-3,4-dihydro-2H-pyrido[3,2-b ][1,4]oxazine.Yield: 1.1 g (87%). LCMS (ESI): calc. C7H7BrN20 = 214, 216; obs. M+H = 215, 217.
  • 2
  • [ 337463-88-4 ]
  • [ 201230-82-2 ]
  • [ 20348-09-8 ]
  • [ 443956-11-4 ]
  • 3
  • [ 337463-88-4 ]
  • [ 955368-90-8 ]
  • C16H14N6O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; Compound 3.2 (1.9 g, 8.29 mmol),<strong>[955368-90-8]2-allyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one</strong> (1.84 g, 8.29 mmol),Cuprous iodide (1.5 g, 8.29 mmol),Anhydrous potassium carbonate (2.35 g, 17 mmol)And N,N-dimethylethylenediamine (0.73g, 8.29mmol)Add to 1,4-dioxane (30 mL),The reaction system was stirred at 100 C overnight.Cool to room temperature,Filter the reaction solution,The filtrate is concentrated,The residue was purified by silica gel column chromatography (EtOAc /EtOAcCompound 3-1 (1.56 g, yield: 51%) was obtained as a yellow solid.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 337463-88-4 ]

Bromides

Chemical Structure| 959992-62-2

A298409 [959992-62-2]

6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Similarity: 0.88

Chemical Structure| 122450-96-8

A196227 [122450-96-8]

7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.82

Chemical Structure| 916737-77-4

A484454 [916737-77-4]

6-Bromo-3-methoxypyridin-2-amine

Similarity: 0.75

Chemical Structure| 894852-01-8

A105591 [894852-01-8]

7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.72

Chemical Structure| 25218-99-9

A102367 [25218-99-9]

N-(6-Bromopyridin-2-yl)acetamide

Similarity: 0.71

Amides

Chemical Structure| 20348-09-8

A120892 [20348-09-8]

2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.86

Chemical Structure| 122450-96-8

A196227 [122450-96-8]

7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.82

Chemical Structure| 31354-48-0

A131327 [31354-48-0]

N-(3-Hydroxypyridin-2-yl)acetamide

Similarity: 0.73

Chemical Structure| 894852-01-8

A105591 [894852-01-8]

7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.72

Chemical Structure| 25218-99-9

A102367 [25218-99-9]

N-(6-Bromopyridin-2-yl)acetamide

Similarity: 0.71

Related Parent Nucleus of
[ 337463-88-4 ]

Other Aromatic Heterocycles

Chemical Structure| 959992-62-2

A298409 [959992-62-2]

6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Similarity: 0.88

Chemical Structure| 20348-09-8

A120892 [20348-09-8]

2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.86

Chemical Structure| 122450-96-8

A196227 [122450-96-8]

7-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.82

Chemical Structure| 20348-23-6

A310395 [20348-23-6]

3,4-Dihydro-2H-pyrido[3,2-b]-1,4-oxazine

Similarity: 0.74

Chemical Structure| 894852-01-8

A105591 [894852-01-8]

7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

Similarity: 0.72