Structure of 5162-82-3
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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. : | 5162-82-3 |
Formula : | C8H7ClO2 |
M.W : | 170.59 |
SMILES Code : | O=C(O)C1=CC=C(C)C(Cl)=C1 |
MDL No. : | MFCD00045841 |
InChI Key : | SDKUOEOJAXGCLU-UHFFFAOYSA-N |
Pubchem ID : | 78840 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.38 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.65 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.35 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.31 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.39 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.21 |
Solubility | 0.104 mg/ml ; 0.000612 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.59 |
Solubility | 0.0436 mg/ml ; 0.000255 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.77 |
Solubility | 0.29 mg/ml ; 0.0017 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) |
No |
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 |
-5.11 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 |
0.56 |
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) |
1.25 |
* 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 |
---|---|---|
With cetyltrimethylammonim bromide; chlorine; In water; at 60℃; for 8h; | Add in a glass reactor equipped with a thermometer, a stirring paddle and a condenser200 g of p-toluic acid and 800 ml of water, and 2 g of cetyltrimethylammonium bromide,After heating to 60 C, chlorine gas was introduced and the reaction was monitored using a chromatogram.When the product yield is greater than 98%, the reaction is stopped and the reaction is carried out for 8 hours.The reaction solution was added to a Buchner funnel, filtered, and washed with 1500 ml of water.The obtained filter cake was vacuum dried at 80 C to a constant weight.Quantitative analysis by liquid chromatography,A purity of 98% 3-chloro-4-methylbenzoic acid was obtained.The other 2% is p-toluic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.8% | With copper(l) iodide; copper; potassium carbonate; at 230℃; for 48h; | To a solution of 68 (15.0 g, 87.9 mmol), 69 (77.3 mL, 87.9 mmol),Cu-powder (2.79 g, 43.9 mmol), CuI (8.37 g, 43.9 mmol) and K2CO3(24.3 g, 175 mmol) were mixed in a steel vessel and stirred for 2 days at230 C. Progress of the reaction mixture was monitored by TLC andLCMS. The resulting mixture was diluted with EtOAc (250 mL), 1 NNaOH (500 mL) and stirred for 1 h at room temperature. The aqueouslayer was extracted with EtOAc (3 × 250 mL) and then acidified with1 N HCl solution (pH 2) and extracted with EtOAc (3 × 250 mL). Theorganic layer was washed with brine solution (1 × 250 mL), dried withanhydrous sodium sulphate and then concentrated under vacuo to give58 (8.0 g, 39.8%) as a white solid. 1H NMR (400 MHz; DMSO-d6): 12.96(s, 1H), 7.64 (d, 1H), 7.46-7.38 (m, 3H), 7.30 (s, 1H), 7.15 (t, 1H), 6.97(d, 2H), 2.27 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 3h; | Example 80A 4-Bromomethyl-3-chloro-benzoic acid A 50 mL round bottom flask was charged with <strong>[5162-82-3]3-chloro-4-methyl-benzoic acid</strong> (1 g, 5.9 mmol), NBS (1.043 g, 5.9 mmol), AIBN (97 mg, 0.59 mmol) and CCl4 (20 mL). The mixture was completed after refluxing at 80 C. for 3 hours, then quenched with water, diluted with CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with brine, dried over Na2SO4, concentrated to provide the crude mixtures. Then preparative reverse-phase HPLC was used to provide the pure title compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 4.79(s, 2H), 7.75(d, 1H, J=7.93), 7.89(d, 1H, J=7.93), 7.94 (s, 1H), 13.35(s, br, 1H); MS (ESI) m/e 246.6 (M-H)+. |
A180061 [39652-34-1]
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