Structure of 719282-11-8
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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.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
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| CAS No. : | 719282-11-8 |
| Formula : | C9H8ClNO3 |
| M.W : | 213.62 |
| SMILES Code : | O=C(O)C1=CC(NC(C)=O)=CC=C1Cl |
| English Name : | 5-Acetamido-2-chlorobenzoic acid |
| MDL No. : | MFCD00466845 |
| InChI Key : | AMOFQIUOTAJRKS-UHFFFAOYSA-N |
| Pubchem ID : | 680956 |
| Num. heavy atoms | 14 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.11 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 3.0 |
| Num. H-bond donors | 2.0 |
| Molar Refractivity | 52.72 |
| TPSA ? Topological Polar Surface Area: Calculated from |
66.4 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.17 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.37 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.81 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.68 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.45 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.49 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.15 |
| Solubility | 1.52 mg/ml ; 0.00713 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.37 |
| Solubility | 0.917 mg/ml ; 0.00429 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.78 |
| Solubility | 0.353 mg/ml ; 0.00165 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 |
-6.63 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) |
1.5 |
* 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 sodium methylate; copper |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| bei der Oxydation; | ||
| With potassium permanganate; magnesium sulfate at 80 - 85℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride at 150 - 160℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With nitric acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pentan-1-ol; copper; potassium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pentan-1-ol; copper; potassium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pentan-1-ol; copper; potassium carbonate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium acetate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 27% | With triethylamine In dichloromethane at 20℃; for 2h; | 111 EXAMPLE 111. Synthesis of S-Aeety.amino^-Chloro-Benzoic Acid (Intermediate 57)57[0315] To a solution of 5-amino-2-chloro-benzoic acid (0.50 g, 2.9 mmol) in DCM (15 mL) was added acetyl chloride (0.30 mL, 4.2 mmol) followed by triethylamine (1.2 mL, 8.6 mmol). The mixture was stirred at RT for 2 h and poured into water. The mixture was extracted with ethyl acetate and the combined organic layers washed with water, brine, dried over Na2SO4 and filtered. The filtrate was concentrated and afforded the title compound (0.17 g, 27%) as a brown solid. |

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