Structure of 5807-30-7
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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. : | 5807-30-7 |
Formula : | C8H6Cl2O2 |
M.W : | 205.04 |
SMILES Code : | C1=C(C=CC(=C1Cl)Cl)CC(O)=O |
MDL No. : | MFCD00004333 |
InChI Key : | ZOUPGSMSNQLUNW-UHFFFAOYSA-N |
Pubchem ID : | 79874 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.01 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.62 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.82 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.83 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.62 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.3 |
Solubility | 0.104 mg/ml ; 0.000506 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.54 |
Solubility | 0.059 mg/ml ; 0.000288 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.41 |
Solubility | 0.079 mg/ml ; 0.000385 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 |
-5.36 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 |
0.56 |
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) |
1.36 |
* 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 |
---|---|---|
95% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 5h; | To an ice-cold solution of 2-(3,4-dichlorophenyl)acetic acid (19.36 g, 94.42 mmol) in THF (200 mL) was added portionwise 97% LiAlH4 (5.54 g, 141.63 mmol). After the addition, the mixture was stirred at room temperature for 5 h. The resulting mixture was poured into ice-water (150 mL), and stirred for 0.5 h. The THF was removed under reduced pressure, then DCM (200 mL) was added. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/hexane = 1/5, V/V) to compound 6 as colourless oil (17.14 mg, 95%). |
89% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h; | A solution of LAH (69 mg, 1.8 mmol) in anhydrous THF was added dropwise to a solution of 2-(3,4-dichlorophenyl)acetic acid (250 mg, 1.2 mmol) in anhydrous THF at 0 C. The reaction mixture was stirred at room temperature for 2 h. Then cooled to 0 C, it was quenched with water and extracted with EA. The residue was dried over sodium sulfate and concentrated in vacuo. The desired compound (207 mg) was obtained. (yield : 89 %)1H NMR (400 MHz, CDCl3) delta 7.40 (d, J = 8.0 Hz, 1H), 7.37 (s, 1H), 7.10 (dd, J = 8.0, 2.0 Hz, 1H), 3.89 (t, J = 6.4 Hz, 2H), 2.85 (t, J = 6.4 Hz, 2H). |
With lithium aluminium tetrahydride; In diethyl ether; for 12h;Heating / reflux; | 3,4-Dichlorophenethyl alcohol: To a solution of lithium aluminum hydride (7.79 g, 195 mmol) in anhydrous diethyl ether (435 mL) was added slowly as a powder, via a solid dropping funnel, 3,4-dichlorophenyl acetic acid (27.20 g, 130 mmol). When the addition was completed, the reaction mixture was refluxed for 12 hours. The reaction was quenched by cautious addition of saturated sodium sulfate aqueous solution (20 mL), the resulting insoluble was then filtered off and the filtrate was concentrated in vacuo to yield 25.09 g of the desired alcohol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: [0445] Certain compounds disclosed herein with an amide moiety, without a triazole moiety, were synthesized according to the above scheme, over two steps. In the first step, <strong>[62037-46-1]1- amino-3-chloropropan-2-ol hydrochloride</strong> was combined with R-COOH, 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl), hydroxybenzotriazole hydrate (HOBt.H2O), triethylamine (Et3N), and dichloromethane (DCM), and the mixture stirred at room temperature for 18 h. In the second step, the product from the first step was reacted with NaOH (1N) and acetone at room temperature for 30 minutes to produce the final compound comprising an amide moiety, without a triazole. |
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