Structure of 50270-27-4
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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. : | 50270-27-4 |
Formula : | C5HCl3N2O |
M.W : | 211.43 |
SMILES Code : | ClC1=NC(=C(C(=N1)Cl)C=O)Cl |
MDL No. : | MFCD02257700 |
InChI Key : | KVJIRFGNHAAUNQ-UHFFFAOYSA-N |
Pubchem ID : | 10932746 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 42.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.85 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.34 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.55 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.25 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.79 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.05 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.1 |
Solubility | 0.17 mg/ml ; 0.000803 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.1 |
Solubility | 0.169 mg/ml ; 0.000799 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.46 |
Solubility | 0.074 mg/ml ; 0.00035 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 |
-5.78 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 |
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) |
1.61 |
* 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 |
---|---|---|
92% | Step 2. 2,4,6-trichloropyrimidin-5-formonitrile 2,4,6-trichloropyrimidin-5-carboxaldehyde (10 g, 47.4 mmol), hydroxylamine hydrochloride (3.3 g, 47.5 mmol), glacial acetic acid (100 mL), and H2O (5 mL) were added to a 150-mL round-bottom flask, and heated to 60 C. to react for 1 hour. After the completion of the reaction, the reaction solution was poured into crushed ice, and was extracted with CH2Cl2. The resultant organic phases were combined, washed with a saturated NaCl solution, dried with anhydrous Na2SO4, and then filtered and concentrated. The obtained substance was dissolved in SOCl2 (60 mL), reacted at room temperature for 10 minutes, and then heated for a reflux reaction for 2 hours. After the completion of the reaction, the resultant mixture was subjected to reduced pressure distillation to remove SOCl2 to give a residue, which was then dissolved in EtOAc and washed with H2O. The resultant organic phase was dried with anhydrous Na2SO4, filtered, and concentrated to obtain an oily substance of 9 g. The yield was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; water; at -78 - -10℃; for 2.5h;Inert atmosphere; | To a solution of 2,4,6-trichloropyrimidine-5-carbaldehyde (3.9 g, 18.5 mmol) in tetrahydrofuran (100 mL) was added dropwise a solution of ethyl 3-hydrazinobenzoate hydrochloride (4.0 g, 18.5 mmol) in tetrahydrofuran/ water (50 mL, v: v = 9: 1) at -78 C under nitrogen atmosphere. Then triethylamine (7.7 mL, 55.4 mmol) was added dropwise and the mixture was stirred at -78 C for 30 minutes under nitrogen atmosphere. Then the mixture was warmed to -10 C and stirred for further 2 h. Upon completion of the reaction, the solvent was removed in vacuo. The residue was purified with silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to give 1.01 g of the product (batch contained impurities) as a light yellow solid. MS (ESIpos): m/z = 337 (M+H)+ |
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