Structure of 6342-63-8
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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. : | 6342-63-8 |
Formula : | C9H9BrO2 |
M.W : | 229.07 |
SMILES Code : | COC1=CC(C(C)=O)=C(Br)C=C1 |
MDL No. : | MFCD02683853 |
InChI Key : | YOUSWNMOPSGTSG-UHFFFAOYSA-N |
Pubchem ID : | 240433 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.22 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 50.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 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 |
2.58 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.66 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.16 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.84 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.48 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.12 |
Solubility | 0.172 mg/ml ; 0.000752 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.78 |
Solubility | 0.379 mg/ml ; 0.00166 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.72 |
Solubility | 0.0436 mg/ml ; 0.000191 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 |
-5.87 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) |
1.55 |
* 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 |
---|---|---|
75% | With potassium tert-butylate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 80℃; for 2h;Schlenk technique; Inert atmosphere; | General procedure: In an oven dried Schlenk tube under nitrogen atmosphere, were added aryliodides 2a-2f (0.50 mmol), ortho-bromoacetophenone 1a-1c (0.55mmol), Pd(OAc)2 (2 mol%), xantphos (4 mol%) and tBuOK (0.65 mmol) followed by addition of dry toluene (4 mL). The resulted reaction mixture was stirred at 80 C for 45 min to 3 h. Progress of the reaction was monitored by TLC till the reaction is completed. The reaction mixture was then quenched with saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (3 20 mL). The combined organic layers were dried (Na2SO4) and concentrated under in vacuo. The crude product 3ac-3cf was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃;Inert atmosphere; | To a 2L reaction flask in a nitrogen atmosphere was added 1- (2-bromo-5-methoxyphenyl) ethanone, 68 g (190.86 mmol) of the compound [6-1] and 410 ml of 1,4-dioxane are introduced and the temperature is raised.4.24 g (3.64 mmol) of tetrakis (triphenylphosphine) palladium (0) and 75.4 g (545.33 mmol) of potassium carbonate dissolved in distilled water were added at 60 C and stirred overnight under reflux.When the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate,Extracted with distilled water, and the organic layer is treated with anhydrous magnesium sulfate and filtered.The filtrate was concentrated under reduced pressure, separated and purified by silica gel chromatography,64.7 g (94%) of an intermediate compound [6-2] in a clear oil state was prepared. |
64.3 g | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 60℃; for 15h;Reflux; | 40 g (174.59 mmol) of 1- (2-bromo-5-methoxyphenyl) ethanone and 65.3 g (183.32 mmol) of the compound [41-1] were placed in a 2 L reaction flask, 400 ml of 1,4-dioxane is added and the temperature is raised. 4.03 g (3.4918 mmol) of tetrakis (triphenylphosphine) palladium (0) was added at 60 C, 72.39 g (523.77 mmol) of potassium carbonate dissolved in distilled water was added, and the mixture was refluxed and stirred for 15 hours.When the reaction is completed, the reaction mixture is cooled to room temperature, extracted with ethyl acetate / distilled water, and treated with anhydrous magnesium sulfate. The reaction mixture is distilled under reduced pressure. The crude product was separated and purified by silica gel chromatography to obtain 64.3 g (97 wt%) of an intermediate compound [41-2] in a clear oil state |
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