Structure of 5462-30-6
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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. : | 5462-30-6 |
Formula : | C8H6Cl2N2O3 |
M.W : | 249.05 |
SMILES Code : | CC(NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O)=O |
MDL No. : | MFCD00024301 |
InChI Key : | ZEGRPTYRAGSSBH-UHFFFAOYSA-N |
Pubchem ID : | 226498 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 59.6 |
TPSA ? Topological Polar Surface Area: Calculated from |
74.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.75 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.41 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.67 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.59 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.57 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.8 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.0 |
Solubility | 0.249 mg/ml ; 0.000999 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.63 |
Solubility | 0.059 mg/ml ; 0.000237 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.4 |
Solubility | 0.0985 mg/ml ; 0.000395 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 |
-6.11 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 |
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 |
2.0 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) |
2.22 |
* 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 |
---|---|---|
95.23% | at 3 - 13℃; for 6.5 h; | 3,4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3,4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3,4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4,5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4,5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | at 3 - 13℃; for 6.5 h; | Experiment 3: 3,4-Dichloroacetanilide (II) (150 g, 0.735 moles), sulfuric acid (156.0 g, 99percent w/w, 1.576 moles), oleum (260.5 g, 31.1percent w/w, 2.844 moles), and nitric acid (51 g, 98percent w/w, 0.79 moles) were used. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3,4-Dichloroacetanilide (II) to the resultant sulfuric acid in the mixture was 1:6. The reaction conditions, and product yield and purity are summarized in Table 1. (0074) 177 g of 2-nitro-4,5-dichloroacetanilide (I) was obtained (yield = 92percent and HPLC purity of 92percent). HPLC analysis of product showed the presence of 6percent of III. 3,4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3,4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3,4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4,5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4,5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III. |
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