Structure of 51792-34-8
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 51792-34-8 |
Formula : | C6H8O2S |
M.W : | 144.19 |
SMILES Code : | COC1=CSC=C1OC |
MDL No. : | MFCD01096546 |
InChI Key : | ZUDCKLVMBAXBIF-UHFFFAOYSA-N |
Pubchem ID : | 3613501 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P264-P270-P301+P312-P330-P501 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 37.3 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.7 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.16 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.77 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.45 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.68 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.98 |
Solubility | 1.5 mg/ml ; 0.0104 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.13 |
Solubility | 1.07 mg/ml ; 0.00741 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.9 |
Solubility | 1.82 mg/ml ; 0.0126 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 |
-6.09 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) |
2.58 |
* 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 |
---|---|---|
copper; In dimethyl sulfoxide; at 20 - 120℃; for 7.5h; | [0034] 3,4-Dimethoxy-2,5-thiophenedicarboxylic acid (232 g) and copper powder (23 g) were added to DMSO (650 g) at room temperature. The reaction mixture was stirred under oxygen atmosphere for 30 minutes at room temperature and then heated at 120° C. for 7 hours. The reaction mixture was then poured into ice water (500 mL), and the crude product was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was removed by evaporation. The residue was vacuum-distilled at 50 mmHg to give 127 g of 3,4-ethylenedioxythiophene in high purity (96percent or higher). The purity was confirmed by gas chromatographic analysis. The chemical structure was confirmed by mass analysis and 1H-NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.5% | With copper(I) bromide; In methanol; at 70 - 97℃;Inert atmosphere; | 21 g of sodium methoxide and 72 g of methanol were added to a 100 ml four-necked flask (the concentration of sodium methoxide relative to the methanol solvent was 22.6percent by weight based on the total amount of sodium methoxide before the reaction) and dissolved at 70 under an argon atmosphere.After addition of 0.83 g of cuprous bromide, 15 g of 3,4-dibromothiophene was added dropwise, and the reaction solution became colorless transparent to black. After completion of the dropwise addition, 50 g of methanol was distilled off (sodium methoxide to methanol solvent The concentration was 48.8 wtpercent based on the total amount of sodium methoxide before the reaction)The reaction was heated to reflux at 97 .When the reaction was traced by gas chromatography, 3,4-dibromothiophene and 3-bromo-4-methoxythiophene were found to be below the detection limit at the reflux starting time of 5 hours.After water was added to the reaction mixture and the mixture was filtered, the crude product was extracted from toluene, and the toluene layer was washed with water, and then the toluene layer was dried with magnesium sulfate.After the magnesium sulfate was removed by filtration, the toluene layer was concentrated by a rotary evaporator and then subjected to vacuum distillation to obtain 7.28 g (yield: 81.5percent) of 3,4-dimethoxythiophene. The purity of its 3,4-dimethoxythiophene was 98.01percent by gas chromatography.The purity (concentration) by gas chromatography in the present invention was indicated by the area ratio of the peak area obtained by the detection device by FID using Agilent 6890N network GC manufactured by Aglient Technologies. |
60% | With copper(l) iodide; In methanol; at 80℃; for 72h; | Step 3: 3,4-dibromothiophene (10 g, 41.2 mmol) is added to 30 g of a methanol-sodium methoxide solution with a mass percent of 30percent and stirred. Then CuI (1.96 g, 10.3 mmol) is added quickly, and refluxed at 80° C. for 72 hrs. The mixture is cooled to room temperature, to which a saturated NaCl solution is added. The mixture is extracted with ethyl acetate several times, and dried over anhydrous sodium sulfate to remove solvents. The crude is passed through a separation column, to give a oily liquid, 3,4-dimethoxythiophene (compound 3), yield 60percent, purity 95percent. |