Structure of 21190-88-5
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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. : | 21190-88-5 |
Formula : | C8H8BrNO2 |
M.W : | 230.06 |
SMILES Code : | BrC1=CC=CC(=N1)C(=O)OCC |
MDL No. : | MFCD04116913 |
InChI Key : | OONBOXSIWCBAHZ-UHFFFAOYSA-N |
Pubchem ID : | 2758810 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.02 |
TPSA ? Topological Polar Surface Area: Calculated from |
39.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.43 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.4 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.2 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.97 |
Solubility | 0.247 mg/ml ; 0.00107 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.9 |
Solubility | 0.292 mg/ml ; 0.00127 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.37 |
Solubility | 0.099 mg/ml ; 0.000431 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) |
No |
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 |
-5.98 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 |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.03 |
* 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 |
---|---|---|
81% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; caesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 4.5h;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 1.00 eq bromine substrate, 1.00 eq boronic acid, 2.10 eq CsF, 0.05 eq PdCl2(dppf)*DCM and anhydrous DME (2 mL/0.15 mmol bromoarene). The suspension was degassed by vacuum/N2 cycles and stirred at 80 C. As TLC analysis or GC-MS analysis indicated full conversion of the starting material, the reaction mixture was cooled to rt and filtered through a pad of celite, which was rinsed with EtOAc and/or DCM. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography or silica gel filtration yielded the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,2-dimethoxyethane; at 80℃;Schlenk technique; | General procedure: A Schlenk tube was dried under vacuum and charged with 1 0 eq halogenated substrate, 1.1 eq boronic acid, 5 mol% PdCb(dppf), 2.1 eq CsF, and anhydrous DME (~5 mL/100 mg halogenated substrate). The mixture was degassed via three cycles of vacuum/inert gas and was stirred at 80 C (oil-bath) overnight, after which time the reaction mixture was cooled to rt and optionally filtered through a pad of silica get or cotton. Subsequently, the solvent was removed under reduced pressure and final purification via column chromatography yielded the pure product. Reaction control was performed via TLC analysis and/or GC-MS analysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; In 1,2-dimethoxyethane; at 80℃;Schlenk technique; Inert atmosphere; | General procedure: A Schlenk tube was dried under vacuum and charged with 1.0 eq halogenated substrate, 1.1 eq boronic acid, 5 mol% PdCh(dppf), 2.1 eq CsF, and anhydrous DME (~5 mL/100 g halogenated substrate). The mixture was degassed by three cycles of vacuum/inert gas and was stirred at 80 C (oil-bath) overnight, after which time additional 0.3 eq boronic acid and 3 mol% PdCI2(dppf) were added. Subsequently, the reaction mixture was stirred at 80 C (oil-bath) overnight and was then cooled to rt and optionally filtered through a pad of silica gel or cotton. After solvent removal under reduced pressure, the crude product was purified via column chromatography. Reaction control was performed via TLC analysis and/or GC-MS analysis. |
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