Structure of 67878-76-6
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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. : | 67878-76-6 |
Formula : | C12H9BrO2 |
M.W : | 265.10 |
SMILES Code : | O=C(OC)C1=CC=C2C(Br)=CC=CC2=C1 |
MDL No. : | MFCD08275021 |
Boiling Point : | No data available |
InChI Key : | KNUWUXJWMBRWJM-UHFFFAOYSA-N |
Pubchem ID : | 13477022 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 62.93 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.72 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.59 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.5 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.19 |
Solubility | 0.0172 mg/ml ; 0.0000648 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.96 |
Solubility | 0.0288 mg/ml ; 0.000109 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.0 |
Solubility | 0.00263 mg/ml ; 0.00000993 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.28 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 |
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) |
1.38 |
* 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 |
---|---|---|
97% | With sulfuric acid; for 2.0h;Cooling with ice; Reflux; | Disperse 5-bromo-2naphthoic acid (0.75 g, 3 mmol) in 10 mL of methanol and cool in an ice bath.Slowly add 1 mL of concentrated sulfuric acid to the reaction solution, and react at reflux for 2 h.20 mL of water was added and extracted with DCM. The organic phase was washed successively with a saturated sodium bicarbonate solution and a saturated saline solution.Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain methyl 5-bromo-2naphthoate,Yield: 97%. |
69% | With thionyl chloride; at 25 - 30℃; for 3.25h;Heating / reflux; | Preparation of 5-Bromo-2-naphthalenecarboxylic acid, Methyl Ester. [0110] 5-Bromo-2-naphthoic acid (17.33 g, 69 mmol) and 250 mL of MeOH were combined in a flask under N2 atmosphere. Thionyl chloride (5.84 mL, 80 mmol) was added dropwise over 15 minutes at a temperature of 25-30 C., resulting in a pale yellow mixture. The mixture was heated at reflux for 3 ¼ hours. The resulting yellow solution was concentrated in vacuo to 137.4 g of solution then placed in a freezer overnight. The resulting thick mixture was filtered and the solid was washed with 100 mL of cold MeOH. The solid was dried in vacuo at 50 C. to give 11.39 g of the intermediate title compound as white crystals. A second crop was filtered and washed with 100 mL of cold MeOH. The solid was dried to 1.31 g of white crystals. Yield: 69%, 2 crops. |
With sulfuric acid; at 80℃; for 16.0h;Inert atmosphere; | Sulfuric acid (0.2 mL) was added to the solution of <strong>[1013-83-8]5-bromo-2-naphthoic acid</strong> (1.0 g, 3.98 mmol, 1.0 eq) in MeOH (10 mL) at room temperature and the solution was stirred under nitrogen atmosphere, at 80 C for 16 h. After complete consumption of starting material, the reaction mixture was evaporated under reduced pressure, diluted ethyl acetate and washed with saturated aqueous sodium bicarbonate. The aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2504, filtered and solvents evaporated from the filtrate under reduced pressure to afford methyl 5- bromo-2-naphthoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With methanol; thionyl chloride; at 25℃; for 4.0h;Heating / reflux; | 5-Bromo-2-naphthoic acid (17.33 g, 69 mmol) and 250 mL of MeOH were combined in a flask under N2 atmosphere. Thionyl chloride (5.84 mL, 80 mmol) was added dropwise over 15 minutes at a temperature of 25-30 C. resulting in a pale yellow mixture. The mixture was heated at reflux for 3? hours. The resulting yellow solution was concentrated in vacuo to 137.4 g of solution then placed in the freezer overnight. The resulting thick mixture was filtered and the solid was washed with 100 mL of cold MeOH. The solid was dried in vacuo at 50 C. to give 11.39 g of intermediate title compound as white crystals. A second crop was filtered and washed with 100 mL of cold MeOH. The solid was dried to 1.31 g of white crystals. Yield: 69percent, 2 crops. |
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