Structure of 1193-54-0
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 1193-54-0 |
Formula : | C4HCl2NO2 |
M.W : | 165.96 |
SMILES Code : | O=C(C(Cl)=C1Cl)NC1=O |
MDL No. : | MFCD01716135 |
InChI Key : | KVBAKSQRUXXHCK-UHFFFAOYSA-N |
Pubchem ID : | 14513 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 35.46 |
TPSA ? Topological Polar Surface Area: Calculated from |
46.17 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.97 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.05 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.2 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.61 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.48 |
Solubility | 5.49 mg/ml ; 0.0331 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.53 |
Solubility | 4.93 mg/ml ; 0.0297 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.01 |
Solubility | 1.61 mg/ml ; 0.00971 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 |
No |
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 |
-6.62 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 |
2.0 |
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) |
2.03 |
* 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 |
---|---|---|
71% | With sodium thiosulfate; In methanol; water; at 65℃; for 1h; | A solution of 6.64 g [0.04 mol] of dichloromaleimide (VI-2) in 40 ml of methanol is introduced at 65 C. and, over the course of about 10 minutes, a solution, likewise heated at 65 C., of 13.89 g [0.056 mol] of sodium thiosulfate pentahydrate in 40 ml of water is added dropwise. After the end of the addition, the mixture is stirred for hour more at 65 C. Thereafter the reaction mixture is cooled to 15 C., 10 and of water are added, and it is stirred for 15 minutes. Thereafter the solid is isolated by filtration with suction, washed with 30 ml of water and then 15 ml of MODEL and dried. This gives 3.6 g of dark-green solid, which according to HPLC analysis is composed to an extent of 99.6 area-% of the compound (I-2), corresponding to a yield of 71% of theory. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In acetic acid; at 108℃; for 1.5h; | General procedure: To suspension of 16.7 g (0.1 mol) of dichloromaleic anhydride in 60 g of glacial acetic acid was added dropwise 0.1 mol of the corresponding amine. The mixture was stirred for 30 min at 85 and for 90 min at 108. Then the mixture was cooled while stirred to 10, the precipitate was filtered off, washed with water, and dried in a vacuum at 60. |