Structure of 17178-10-8
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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. : | 17178-10-8 |
Formula : | C10H14O4S |
M.W : | 230.28 |
SMILES Code : | COCCOS(=O)(=O)C1=CC=C(C)C=C1 |
MDL No. : | MFCD00025910 |
InChI Key : | TZXJJSAQSRHKCZ-UHFFFAOYSA-N |
Pubchem ID : | 86977 |
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 | 0.4 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 56.29 |
TPSA ? Topological Polar Surface Area: Calculated from |
60.98 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.43 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.38 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.83 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.05 |
Solubility | 2.04 mg/ml ; 0.00886 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.18 |
Solubility | 1.52 mg/ml ; 0.00659 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.4 |
Solubility | 0.0927 mg/ml ; 0.000403 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) |
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 |
-6.78 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 |
1.0 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) |
2.67 |
* 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 |
---|---|---|
In toluene; | a. Preparation of the intermediate A solution comprising 595 g (4.4 moles) of 2,3,6-trimethylaniline in 1 liter of toluene is heated to boiling 503 g (2.2 moles) of p-toluenesulfonic-acid-(2-methoxyethyl)-ester is dropped thereto within 6 hrs. The reaction mixture is cooled, poured into 2 liter of isopropylethylether and the solid residue filtered off and washed with diethylether. The combined filtrates are evaporated. After distillation in vacuo 301 g (i.e. 71% theoretical amount) of N-(2-methoxyethyl)-2,3,6-trimethylaniline are obtained, b-p. 141-144 C/14 Torr. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.3% | With tetrabutylammomium bromide; potassium carbonate; In acetone; for 6h;Reflux; | To a stirred solution of <strong>[22717-55-1]methyl 4-chloro-2-hydroxybenzoate</strong> (2.0 g, 10.718 mmol, 1.05 eq) in acetone (50 mL) was added 2-methoxyethyl4-methylbenzenesulfonate (4.93 g, 21.437mmol, 2.0 eq) followed by potassium carbonate (7.40 g, 53.59 mmol, 5.0 eq) and TBAB(0.690 g, 2.143 mmol, 0.2 eq). The reaction mixture was refluxed for 6 hours. TLC indicatedstarting material was consumed and the desired product was observed. After completion ofthe reaction (monitored by TLC), the reaction mixture was evaporated under reduced10 pressure, diluted with water (200 mL) and extracted with ethyl acetate (2xl00 mL). Thecombined organic extracts were washed with water (50 mL), brine solution (20 mL), driedover sodium sulfate, filtered and evaporated under reduced pressure. The residue was purifiedby silica gel column chromatography by using 40% ethyl acetate in hexanes as an eluent toobtain the title compound (2.0 g, yield: 76.3%) as a liquid. 1H NMR (300 MHz, CDCh): 815 ppm 7.83-7.74 (m, lH), 6.99-6.95 (m, 2H), 4.17 (t, J = 4.8 Hz, 2H), 3.87 (s, 3H), 3.80 (t, J =4.5 Hz, 2H), 3.47 (s, 3H); ESI-MS: m/z 266.93 (M+Nat. |
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