Structure of 33863-76-2
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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. : | 33863-76-2 |
Formula : | C6H3BrClF |
M.W : | 209.44 |
SMILES Code : | FC1=CC(Cl)=CC(Br)=C1 |
MDL No. : | MFCD00070747 |
InChI Key : | GGMDFPMASIXEIR-UHFFFAOYSA-N |
Pubchem ID : | 2736223 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 39.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.3 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.34 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.06 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.6 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.39 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.74 |
Solubility | 0.0385 mg/ml ; 0.000184 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.02 |
Solubility | 0.201 mg/ml ; 0.000961 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.15 |
Solubility | 0.0148 mg/ml ; 0.0000706 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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 |
-5.21 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 |
1.0 |
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 |
0.0 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) |
1.77 |
* 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 |
---|---|---|
66% | A mixture of 1-bromo-3-chloro-5-fluorobenzene (8Og, 480mmol), zinc cyanide (33.65g, 290mmol) and zinc dust (0.94g, 14.46mmol) in DMF (34OmL) was stirred at rt for 5 min. Dichloro[1 ,1 '- EPO <DP n="34"/>bis(diphenylphosphino)ferrocene] palladium(ll) (4.99g, 16mmol) was then added and the mixture was heated under reflux for 50 min. The reaction mixture was cooled to rt and filtered through Arbocel, washing through with diethyl etherpentane (50:50, 7 x 10OmL). The phases were separated and the organic phase was diluted with water (10OmL) and extracted with further diethyl ethe?pentane (50:50, 3 x 10OmL). The combined organic solutions were then washed with water, dried over magnesium sulfate and concentrated in vacuo. Distillation of the residue under reduced pressure afforded the title compound as a colourless solid in 66% yield, 48.5g. LRMS: m/z APCI 155 [MH+] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydride; In N,N-dimethyl-formamide; at 120℃; for 8h; | 5H-benzo [4,5] thieno [3,2-c] carbazole 15 g (54.94 mmol) of 1-bromo-3-chloro-5-fluorobenzene 22.9 g (109.89 mmol) of sodium hydride, 3.2 g (82.41 mmol) of sodium hydride and 200 mL of DMF were placed and reacted at 120 DEG C for 8 hours. room After cooling down, it was extracted with distilled water and dichloromethane. Then, it was dissolved in dichloromethane and silica gel and prolyl And the solvent was removed to obtain 17 g (76%) of the target compound 4-2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Reflux; | To a 2 L round-bottom flask were added 50 g (238.73 mmol, 1 eq) of 1-bromo-3-chloro-5-fluorobenzene and 84.6 g (238.73 mmol, 1 eq) of 2-triphenylenylpinacolborane, 13.8 g (11.94 mmol, 0.05 eq) of Pd(PPh3)4, 99.0 g (716.20 mmol, 3 eq) of K2CO3 were added and 600 ml / 120 ml / 120 ml of toluene / ethanol (EtOH) / H2O were added and stirred under reflux. After the reaction was completed, the reaction mixture was extracted with CH2Cl2 / H2O and the CH2Cl2 layer was dried over MgSO4. Thereafter, the silica-gel column was purified to obtain 62.0 g of Compound 1-1 in a yield of 73%. |
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