Structure of 76228-06-3
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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. : | 76228-06-3 |
Formula : | C9H8BrNO |
M.W : | 226.07 |
SMILES Code : | BrC2=CC=C1NCCC(C1=C2)=O |
MDL No. : | MFCD00600620 |
InChI Key : | WAFBCQPOMZIGTJ-UHFFFAOYSA-N |
Pubchem ID : | 759447 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 54.46 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.1 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.85 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.08 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.76 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.07 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.92 |
Solubility | 0.271 mg/ml ; 0.0012 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.32 |
Solubility | 1.08 mg/ml ; 0.00478 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.03 |
Solubility | 0.0212 mg/ml ; 0.000094 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) |
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 |
-6.2 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) |
1.73 |
* 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 |
---|---|---|
58% | at 90℃; | a) 6-Bromo-2,3 -dihydro- 1 H-quinolin-4-one4-Bromoaniline (2.Og, 11.6 mmol) and acrylic acid (0.95 mL, 13.9 mmol) were stirred in toluene (15 mL) at 1000C for 3 days. After cooling, the reaction mixture was extracted with IN NaOH (150 mL). The aqueous layer was acidified with 2N HCl (pH~3) and subsequently extracted with ethylacetate (2x100 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford N-(4-bromophenyl)-3- aminopropionic acid (1.65g, 58percent). A mixture of the carboxylic acid (1.64g, 6.72 mmol) in polyphosphoric acid (30g) was stirred at 9O0C overnight. The reaction was allowed to cool and ice-water was added. The mixture was then extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with IN NaOH, water and brine respectively. Drying (Na2SO4) and concentration afforded the cyclized product (0.88g, 58percent). 1H NMR (d-chloroform) δ (ppm): 2.67 (t, 2H), 3.54 (t, 2H), 6.57 (d, IH), 7.33 (dd, IH), 7.92 (s, IH). |
3% | at 55℃; | Crude 3-((4-bromophenyl)amino)propanoic acid (4.1 mmol based on theoretical yield)was dissolved in Eaton’s reagent (12.3 g) at a ratio of 3 g Eaton’s reagent per mmol ofS41carboxylic acid. The solution was heated to 55 °C overnight. After cooling to roomtemperature, the reaction was quenched over ice. The product was extracted with ethyl acetate(3 × 25 mL), washed with brine, dried over Na2SO4. Purification using flash chromatography(silica gel, hexanes: ethyl acetate, 83:17 to 0:100) afforded pure 6-bromo-2,3-dihydroquinolin-4(1H)-one (0.029 g, 0.130 mmol, 3 percent yield). |
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