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Chemical Structure| 6942-36-5

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Product Details of [ 6942-36-5 ]

CAS No. :6942-36-5
Formula : C8H6BrNO4
M.W : 260.04
SMILES Code : C1=C(C=CC(=C1C(OC)=O)Br)[N+](=O)[O-]
MDL No. :MFCD00010867
InChI Key :VSEYYEKRZNRECT-UHFFFAOYSA-N
Pubchem ID :245494

Safety of [ 6942-36-5 ]

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

Computational Chemistry of [ 6942-36-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 54.24
TPSA ?

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

72.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.78
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

2.7
Log Po/w (WLOGP)?

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

2.14
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.

1.58
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

0.25
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.69

Water Solubility

Log S (ESOL):?

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

-3.27
Solubility 0.139 mg/ml ; 0.000534 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.

-3.87
Solubility 0.0353 mg/ml ; 0.000136 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

-2.71
Solubility 0.507 mg/ml ; 0.00195 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

Yes
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.

-5.97 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

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<0.0
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)

2.01

Application In Synthesis of [ 6942-36-5 ]

* 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 [ 6942-36-5 ]

[ 6942-36-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 3032-81-3 ]
  • [ 6942-36-5 ]
  • [ 93186-53-9 ]
  • 2
  • [ 6942-36-5 ]
  • [ 133730-34-4 ]
  • [ 1026777-98-9 ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80℃; Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No.1-1-(1)) A mixture of <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (25.0 g, 137 mmol), methyl 2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g, 274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g, 6.85 mmol) was suspended in N,N-dimethylformamide (450 mL), and then the suspension was stirred under argon atmosphere at 80C overnight. After cooling down, ethyl acetate (200 mL), diethylether (400 mL) and water (1000 mL) were added thereto and the mixture was separated into a water phase and an organic layer. The water layer was extracted with a mixed solvent of ethyl acetate (150 mL) - diethylether (150 mL) (twice). The combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound as a brown oil. (Quantitative)
100% With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; Reference Example 1; 5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1)Methyl 2-(2,4-dimethoxyphenyl)-5-nitrobenzoate (Reference Compound No. 1-(1))A mixture of <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (25.0 g, 137 mmol), methyl 2-bromo-5-nitrobenzoate (35.7 g, 137 mmol), cesium carbonate (89.4 g, 274 mmol) and bis(triphenylphosphine)palladium (II) dichloride (4.81 g, 6.85 mmol) was suspended in N,N-dimethylformamide (450 mL), and then the suspension was stirred under argon atmosphere at 80 C. overnight. After cooling down, ethyl acetate (200 mL), diethylether (400 mL) and water (1000 mL) were added thereto and the mixture was separated into a water phase and an organic layer. The water layer was extracted with a mixed solvent of ethyl acetate (150 mL)-diethylether (150 mL) (twice). The combined organic layer was washed with water (500 mL, 3 times) and saturated brine (500 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound as a brown oil. (Quantitative)
40% With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In water; at 150℃; for 0.166667h;Microwave irradiation; Commercially available <strong>[133730-34-4]2,4-dimethoxyphenylboronic acid</strong> (0.182 g, 1.00 mmol), sodium carbonate (0.318 g, 3.00 mmol), aryl bromide 4 (0.261 g, 1.00 mmol), palladium (II) acetate (0.0009 g, 0.004 mmol), tetra-n-butylammonium bromide (0.322 g, 1.00 mmol) and 10 mL of water were added to a microwave vial. The sealed vial was heated in the microwave for 10 min at 150 C. The reaction was then allowed to cool to room temperature, diluted with 100 mL of water, and extracted 2x with ether. Combined ether extracts were then washed with brine and dried with MgSO4. The solvents were removed under reduced pressure. A yellow oil was isolated by column chromatography (0.6318 g, 40%). 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J=2.2 Hz, 1 H), 8.34 (dd, J=8.3, 2.5 Hz, 1 H), 7.49 (d, J=8.5 Hz, 1 H), 7.20 (d, J=8.5 Hz, 1 H), 6.61 (dd, J=8.4, 2.4 Hz, 1 H), 6.49 (d, J=2.2 Hz, 1 H), 3.87 (s, 3 H), 3.76 (s, 3 H), 3.71 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ 166.85, 161.67, 156.92, 146.31, 145.16, 132.90, 132.51, 130.41, 125.82, 124.67, 121.06, 104.82, 98.42, 55.45, 55.18, 52.26. FT-IR (thin film, cm-1): 1734.34, 1609.70, 1523.04, 1349.12. TOF-MS (ESI, [M+H]+) calculated for C16H16NO6 318.0972; found 318.0952
  • 3
  • [ 1002309-48-9 ]
  • [ 6942-36-5 ]
  • methyl 2-(1-cyclobutyl-1H-pyrazol-4-yl)-5-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With dichlorobis(triphenylphosphine)palladium(II); potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 2h;Inert atmosphere; <strong>[1002309-48-9]1-cyclobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (1.5 g, 6.0 mmol) and methyl 2-bromo-5-nitrobenzoate (1.66 g, 6.0 mmol) in DME (30 mL) and water (15 mL) was degassed with nitrogen for 5 minutes. Bis(triphenylphosphine)-palladium(ll) dichloride (127 mg, 0.18 mmol) and potassium carbonate (2.5 g, 18.1 mmol) were added and the reaction heated with stirring at 100 C for 2 hours. The reaction mixture was cooled to room temperature, diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine (2 x 30 mL), dried (Na2S04), filtered and concentrated at reduced pressure. The residue was purified by Biotage Isolera chromatography (silica gel; using a gradient of eluents; 0-50% EtOAc in heptane) to give the title compound (1.72 g, 72% yield) as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta [ppm] 8.43 (d, J = 2.5 Hz, 1 H), 8.33 (dd, J = 8.7, 2.6 Hz, 1 H), 8.20 (s, 1 H), 7.83 (d, J = 8.7 Hz, 1 H), 7.72 (s, 1 H), 4.97 - 4.81 (m, 1 H), 3.85 (s, 3H), 2.45 -2.33 (m, 2H), 1.87 - 1.76 (m, 2H). LCMS (Analytical Method A): R t= 1.19 mins, MS (ESIPos): m/z = 302 (M+H)
72% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 2h;Inert atmosphere; 1-Cyclobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g, 6.0 mmol) and methyl 2-bromo-5-nitrobenzoate (1.66 g, 6.0 mmol) in DME (30 mL) and water (15 mL) was degassed with nitrogen for 5 minutes. Pd(PPh3)2Cl2 (127 mg, 0.18 mmol) and K2CO3 (2.5 g, 18.1 mmol) were then added and the reaction was heated to 100 C. for 2 hours. The reaction was then cooled to RT and diluted with water (30 mL) and extracted with EE (50 mL). The organic layer was then washed with brine (2*30 mL), dried (Na2SO4), filtered and concentrated at reduced pressure. The residue was purified by Biotage Isolera chromatography (using a gradient of eluents; 0-50% EE in heptane) to afford the title compound (1.72 g, 72% yield) as a yellow oil. 1H NMR (500 MHz, DMSO-d6) delta 8.43 (d, J=2.5 Hz, 1H), 8.33 (dd, J=8.7, 2.6 Hz, 1H), 8.20 (s, 1H), 7.83 (d, J=8.7 Hz, 1H), 7.72 (s, 1H), 4.97-4.81 (m, 1H), 3.85 (s, 3H), 2.45-2.33 (m, 4H), 1.87-1.76 (m, 2H). LCMS (Analytical Method A): Rt=1.19 min; MS (ESIPos) m/z=302 (M+H)+.
  • 4
  • [ 1151802-22-0 ]
  • [ 6942-36-5 ]
  • 2-(1-cyclopropyl-1H-pyrazol-4-yl)-5-nitrobenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% A mixture of <strong>[1151802-22-0]1-<strong>[1151802-22-0]cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong></strong> (1 .00 g, 4.27 mmol), methyl 2-bromo-5-nitrobenzoate (1 .01 g, 3.88 mmol), dichlorobis(triphenylphosphine)palladium(ll) (51 mg, 0.07 mmol) and potassium carbonate (1 .77 g, 12.82 mmol) were dissolved in dimethoxyethane (13 mL) and water (6.5 mL) then degassed via bubbling nitrogen gas through the solution for 10 minutes. The mixture was then heated at 100 C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with EtOAc (50 mL) and washed with 2M aq. lithium hydroxide solution (20 mL), 2M aqueous hydrogen chloride solution (30 mL), saturated aqueous sodium chloride solution (20 mL), dried (MgS04), filtered and concentrated at reduced pressure giving the title compound (0.9 g, 77% yield) as a yellow solid. 1H NMR (250 MHz, DMSO-d6) delta [ppm] 13.67 (s, 1 H), 8.38 (d, J = 2.5 Hz, 1 H), 8.30 (dd, J = 8.6, 2.6 Hz, 1 H), 8.20 (s, 1 H), 7.80 (d, J = 8.6 Hz, 1 H), 7.72 (d, J = 0.6 Hz, 1 H), 3.89 - 3.72 (m, 1 H), 1.13 - 0.96 (m, 4H). LCMS (Analytical Method A): Rt = 1.03 mins; MS (ESIPos) m/z = 273.95 (M+H)
  • 5
  • [ 1151802-22-0 ]
  • [ 6942-36-5 ]
  • methyl 2-(1-cyclopropyl-1H-pyrazol-4-yl)-5-nitrobenzoate [ No CAS ]
 

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