Structure of 40360-47-2
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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. : | 40360-47-2 |
Formula : | C5H2Br2ClN |
M.W : | 271.34 |
SMILES Code : | ClC1=NC=C(C=C1Br)Br |
MDL No. : | MFCD00233991 |
InChI Key : | PYSICVOJSJMFKP-UHFFFAOYSA-N |
Pubchem ID : | 817092 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.17 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.2 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.6 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.42 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.93 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.03 |
Solubility | 0.0252 mg/ml ; 0.000093 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.14 |
Solubility | 0.195 mg/ml ; 0.00072 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.34 |
Solubility | 0.0123 mg/ml ; 0.0000452 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.68 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 |
1.0 |
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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.82 |
* 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 |
---|---|---|
44.2% | Amine-L: l-(3,5-dibromopyridin- -yl)piperazineA solution of tert-butyl piperazine-l -carboxylate (279 mg, 1.500 mmol), 3,5-dibromo-2- chloropyridine (407 mg, 1.5 mmol), and DIEA (262 mu^, 1.500 mmol) in NMP was heated at 160- 165 C for 1 h. LCMS showed the desired product is the major peak. After cold down, the solid was treated with 40% TFA in DCM for 2h. Purification in silicon gel column with 5% MeOH/DCM gave l-(3,5-dibromopyridin-2-yl)piperazine (213mg, 0.664 mmol, 44.2 % yield). 500MHz) delta 8.3 1 (1H, s), 8.01 (1H, s), 3.58 (4H,m), 3.38(4H,m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1, the three 100mL flask with a nitrogen apparatus, 40 ml of DMF was added, followed by adding 2.18g (0.02mol) of p-aminophenol and 1.92g (0.02mol) of sodium tert-butoxide (that is, the STB), at room temperature, the reaction was stirred about 1h, and then added 5.43g (0.02mol) 2- chloro-3,5-dibromopyridine, and 2.76g (0.02mol) K2CO3, And stirring was continued at room temperature; reaction progress monitored by TLC, after the end of the reaction, the solvent DMF was distilled off under reduced pressure, dissolved with 50ml of chloroform, and extracted with distilled water, The chloroform layer was dried over anhydrous sodium sulfate, and allowed to stand overnight, filtered concentrated to give a dark brown powder, was added anhydrous ethanol 120mL above dark brown powder, distilled water 24mL, ammonium chloride 9.6g, 6.5g after reduced iron heated to reflux, TLC detection reaction, after about 1h, the raw material point disappears, pumping It was filtered, washed with distilled water and dried to give the product, namely 4- (3,5-dibromo-2-pyridyloxy) aniline; |
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