Structure of 1215205-50-7
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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. : | 1215205-50-7 |
Formula : | C12H13BrO2 |
M.W : | 269.13 |
SMILES Code : | O=C(C1(C2=CC=C(Br)C=C2)CC1)OCC |
MDL No. : | MFCD15143548 |
InChI Key : | KCCISTCYYRKGFF-UHFFFAOYSA-N |
Pubchem ID : | 53216840 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.42 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 62.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.21 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.5 |
Solubility | 0.0851 mg/ml ; 0.000316 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.33 |
Solubility | 0.126 mg/ml ; 0.000467 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.55 |
Solubility | 0.00759 mg/ml ; 0.0000282 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) |
Yes |
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 |
-5.73 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.92 |
* 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 |
---|---|---|
80% | With thionyl chloride In methanol at 0 - 70℃; | To a 50 mL round-bottom flask was added l-(4-bromophenyl)cyclopropane-1- carboxylic acid 149a (2 g, 8.30 mmol, 1.00 equiv.) and methanol (20 mL). Thionyl chloride(2.96 g, 24.88 mmol, 3.00 equiv.) was added drop·wise with stirring at 0°C. The resultingmixture was stined at 70 °C ovemight. After cooling to room temperature, the reaction wasquenched by the addition of water/ice. The aqueous mixture was extracted with ethyl acetate5 (50 mL x 2). The combined organic extracts were vvashed with brine (50 rnL x 2, dried overanhydrous sodium sulfate, and concentrated under vacuum. The crude product was purifiedby Flash-Prep-HPLC eluting with EA/PE (from 0percent to 10percent '.vithin 20 rnin) to give methyl1-(4-bromophenyl)cyclopropa.ne-l-carboxyate 149b (l.7g, 80percent;) as colorless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12 h; | General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetates 3 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.) and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture was added DBU (456 mg, 3 mmol, 3.0 equiv.). The mixture was stirred for 12 hours at room temperature till the reaction was complete. To the resulting mixture was added saturated ammonium chloride solution (25 mL), and the mixture was then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 4 was purified using column chromatography on silica gel using an appropriate eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; | Example 14A Ethyl 1-(4-bromophenyl)cyclopropanecarboxylate 1.45 g (36.2 mmol) of sodium hydride in mineral oil (60percent pure) were initially charged in 100 ml of DMF. A mixture of 4.0 g (16.5 mmol) of ethyl (4-bromophenyl)acetate and 6.5 g (34.6 mmol) of 1,2-dibromoethane was dissolved in 50 ml of THF and slowly added dropwise. The mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 μm, 250 mm*40 mm (30percent methanol/70percent water to 100percent methanol) over a run time of 25 min]. After HPLC control, the product-containing fractions were combined and concentrated. This gave 1.15 g (26percent of theory) of a liquid. GC-MS [Method 5]: Rt=5.45 min; MS(ESIpos): m/z=268/270 (M+) 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.09 (t, 3H), 1.16-1.20 (m, 2H), 1.46-1.50 (m, 2H), 4.02 (q, 2H), 7.26-7.31 (m, 2H), 7.47-7.51 (m, 2H) |
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