Structure of 6942-36-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
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 |
72.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.14 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.58 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.25 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.27 |
Solubility | 0.139 mg/ml ; 0.000534 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.87 |
Solubility | 0.0353 mg/ml ; 0.000136 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.71 |
Solubility | 0.507 mg/ml ; 0.00195 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.97 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.01 |
* 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.
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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)+. |
Yield | Reaction Conditions | Operation 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) |
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