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Chemical Structure| 13382-61-1 Chemical Structure| 13382-61-1

Structure of 13382-61-1

Chemical Structure| 13382-61-1

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Product Details of [ 13382-61-1 ]

CAS No. :13382-61-1
Formula : C9H6N2O3
M.W : 190.16
SMILES Code : O=[N+](C1=CC=C(C2=COC=N2)C=C1)[O-]
MDL No. :MFCD09032979
InChI Key :STSISQMFQWBGLZ-UHFFFAOYSA-N
Pubchem ID :14567797

Safety of [ 13382-61-1 ]

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

Computational Chemistry of [ 13382-61-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 11
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 50.76
TPSA ?

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

71.85 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.49
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

1.83
Log Po/w (WLOGP)?

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

2.25
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.

0.78
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

0.22
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.31

Water Solubility

Log S (ESOL):?

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

-2.62
Solubility 0.455 mg/ml ; 0.00239 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.

-2.96
Solubility 0.209 mg/ml ; 0.0011 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

-3.14
Solubility 0.138 mg/ml ; 0.000726 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.

-6.16 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)

2.11

Application In Synthesis of [ 13382-61-1 ]

* 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 [ 13382-61-1 ]

[ 13382-61-1 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 20662-89-9 ]
  • [ 13382-61-1 ]
YieldReaction ConditionsOperation in experiment
42% With sulfuric acid; nitric acid; at 0 - 20℃; for 1.16667h; Reference Example 13: 4-(4-Nitrophenyl) oxazole. 4-Phenyloxazole (1 g, 6.89 mmol) was dissolved in concentrated sulfuric acid (5 mL) at 0 0C. A cold solution of nitrating-mixture (prepared by adding 3 mL cone, nitric acid to 5 mL of ice-cold cone, sulfuric acid) was added over 10 minutes. The mixture was allowed to warm to r.t. and stirred for Ih. The resulting solution was poured into ice-cold water giving a white precipitate, which was filtered and washed thoroughly with water. The solid was dissolved in DCM and washed with water then brine. The organic phase was dried over sodium sulfate and concentrated to yield 4-(4- nitro-phenyl)-oxazole (550 mg, 42%) as a white solid.
  • 3
  • [ 13382-61-1 ]
  • [ 1614-12-6 ]
  • [ 125282-23-7 ]
  • 4
  • [ 13382-61-1 ]
  • [ 568556-31-0 ]
YieldReaction ConditionsOperation in experiment
62% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; under 1520.1 Torr; for 16.0h;Inert atmosphere; [00207] A solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (6 mL; 1 : 1 mixture) was added 10% Pd/C (50 mg, 10% wt) under 2 atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford 4-(oxazol-4-yl)aniline as a light brown viscous oil (260 mg, 62%). XH NMR (400 MHz, DMSO-i) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+.
62% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 16.0h;Inert atmosphere; To a solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (3:3 mL) was added 10% Pd/C (50 mg, 10% wt) under nitrogen atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford 4-(oxazol-4-yl)aniline as a light brown viscous oil (260 mg, 62%).1H NMR (400 MHz, DMSO-d6) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+.
62% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 16.0h; To a solution of <strong>[13382-61-1]4-(4-nitrophenyl)oxazole</strong> (500 mg, 2.60 mmol) in MeOH:THF (3:3 mL) was added 10% Pd/C (50 mg, 10% wt) under nitrogen atmosphere at room temperature. The reaction mixture was stirred under hydrogen atmosphere at room temperature for 16h. Then, the reaction mixture was filtered over a pad of celite, and the filtrate was concentrated under vacuum to afford crude compound. The crude compound was purified by FCC (eluent, 30% ethyl acetate in hexane) to afford the title compound 4 as light brown thick liquid (260 mg, 62%).XH NMR (400 MHz, DMSO-i) delta 8.27-8.34 (m, 2H), 7.40-7.46 (m, 2H), 6.56-6.62 (m, 2H), 5.23 (s, 2H). ES-MS m/z 160.95 (M+H)+.
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; under 760.051 Torr; for 12.0h; 5% Palladium-carbon powder was added to a suspension of <strong>[13382-61-1]<strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong>e</strong> in mixture of ethanol and tetrahydrofuran, and the reaction mixture was stirred under 1 atm of hydrogen at ambient temperature for 12 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography, to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS (M)+: 160.
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; for 12.0h; Reference Example 1: 5% Palladium-carbon powder was added to an ethanoltetrahydrofuran mixed suspension of <strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong> and stirred for 12 hours at room temperature in a hydrogen atmosphere. The reaction solution was filtered through Celite and the filtrate was evaporated under reduced pressure. The resulting crude product is purified with a silica gel column chromatography to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS(M)+: 160.
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; ethanol; at 20℃; for 12.0h; 5% Palladium-carbon powder was added to an ethanol-tetrahydrofuran mixed suspension of <strong>[13382-61-1]4-(4-nitrophenyl)-1,3-oxazol</strong> and stirred for 12 hours at room temperature in a hydrogen atmosphere. The reaction solution was filtered through Celite and the filtrate was evaporated under reduced pressure. The resulting crude product is purified with a silica gel column chromatography to obtain [4-(1,3-oxazol-4-yl)phenyl]amine (pale yellow solid). Electron Impact-MS(M)+. 160.
With iron; acetic acid; at 20℃; for 3.0h; [0003431 To a stirred solution of compound 4 (0.7 g, 1 eq) in acetic acid (10 mL), Iron powder (2.063 g) was added in one portion and the reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated to dryness. The residue was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2 X 25 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 30% EtOAc-hexane to afford the title compound 5. LCMS (mlz): 161.00 (M + 1).

  • 5
  • [ 99-81-0 ]
  • [ 77287-34-4 ]
  • [ 13382-61-1 ]
YieldReaction ConditionsOperation in experiment
at 130℃; for 1.5h; [000342j A stirred solution of compound 2 (1 g, 1 eq) in formamide 3 (2.55 g, 14.74 eq) was added at 130 C for 1.5 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (2 X 50 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. ?H NMR (400 MHz, CDC13) oe: 8.29 (d, J= 8.8 Hz, 2H), 8.10 (s, 1H), 7.99 (s, 1H), 7.92 (d, J= 8.8 Hz, 2H).
  • 8
  • [ 13382-61-1 ]
  • [ 1003-03-8 ]
  • [ 1552273-94-5 ]
  • 9
  • [ 100-19-6 ]
  • [ 13382-61-1 ]
  • 10
  • [ 13382-61-1 ]
  • 6-(1-methyl-1H-indazol-6-yl)-2-morpholino-N-(4-(oxazol-4-yl)phenyl)pyrimidin-4-amine [ No CAS ]
  • 11
  • [ 13382-61-1 ]
  • 2,4-bis(difluoromethyl)-N-(4-(oxazol-4-yl)phenyl)pyrrolo[1,2-a]pyrimidine-8-carboxamide [ No CAS ]
  • 12
  • [ 13382-61-1 ]
  • 2,4-dimethyl-N-(4-(oxazol-4-yl)phenyl)pyrrolo[1,2-a]pyrimidine-8-carboxamide [ No CAS ]
  • 13
  • [ 13382-61-1 ]
  • 4-hydroxy-2-methyl-N-(4-(oxazol-4-yl)phenyl)pyrrolo[1,2-a]pyrimidine-8-carboxamide [ No CAS ]
  • 14
  • [ 13382-61-1 ]
  • 2,4-dimethyl-N-(4-(oxazol-4-yl)phenyl)imidazo[1,5-a]pyrimidine-8-carboxamide [ No CAS ]
  • 15
  • [ 13382-61-1 ]
  • [ 591-50-4 ]
  • [ 10004-42-9 ]
 

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