Structure of 4489-34-3
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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.
Synonyms: 4,6-Dichloro-2-methylsulfonyl pyrimidine
4.5
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Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 4489-34-3 |
Formula : | C5H4Cl2N2O2S |
M.W : | 227.07 |
SMILES Code : | C1=C(N=C([S](C)(=O)=O)N=C1Cl)Cl |
Synonyms : |
4,6-Dichloro-2-methylsulfonyl pyrimidine
|
MDL No. : | MFCD00672147 |
InChI Key : | DROUVIKCNOHKBA-UHFFFAOYSA-N |
Pubchem ID : | 239685 |
GHS Pictogram: |
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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 | 0.2 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 45.15 |
TPSA ? Topological Polar Surface Area: Calculated from |
68.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.36 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.27 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.33 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.59 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.45 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.62 |
Solubility | 0.541 mg/ml ; 0.00238 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.75 |
Solubility | 0.404 mg/ml ; 0.00178 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.21 |
Solubility | 0.142 mg/ml ; 0.000624 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 |
-6.48 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 |
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) |
2.0 |
* 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 |
---|---|---|
28% | With caesium carbonate; In acetonitrile; at 20℃; for 8h; | A 250 mL 2-neck round-bottomed equipped with stir bar was charged with 4,6-dichloro-2-(methylsulfonyl)pyrimidine (5.0 g, 22.12 mmol, 1.0 eq.), ethyl 1H- pyrazole-3-carboxylate (3.10 g, 22.12 mmol, 1.0 eq.) and cesium carbonate (7.28 g, 22.12 mmol,1.0 eq.) in acetonitrile (50 mL) stirred at ft for 8 h. Progress of the reaction was monitored by TLC. Reaction mass diluted with water (80 mL), extracted with ethyl acetate (2 x 40 mL) and the combined organic layer was washed with water (50 ml), brine (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by CombiFlash by using with 15percent ethyl acetate in hexane as eluent. The desired fractions were evaporated under reduced pressure to afford ethyl 1-(4,6- dichloropyrimidin-2-yl)- 1 H-pyrazole-3 -carboxylate (off-white solid) (1.8 g, 6.26 mmol, 28percent) MS (M+H): mlz=287.10. |
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