Structure of 26274-35-1
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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. : | 26274-35-1 |
Formula : | C17H13N |
M.W : | 231.29 |
SMILES Code : | C1(C2=CC=CC=C2)=NC=CC(C3=CC=CC=C3)=C1 |
MDL No. : | MFCD00972966 |
InChI Key : | YASXBDJBCBUIHT-UHFFFAOYSA-N |
Pubchem ID : | 42014 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 18 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 75.11 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.14 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.42 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.46 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.59 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.49 |
Solubility | 0.00748 mg/ml ; 0.0000323 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.12 |
Solubility | 0.0176 mg/ml ; 0.0000762 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.07 |
Solubility | 0.0000199 mg/ml ; 0.0000000859 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
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 |
-4.77 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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.92 |
* 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 |
---|---|---|
57% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 14h;Inert atmosphere; | General procedure: Reactions were carried out with Phenylboronic acid (146 mg,1.2 mmol), 2-bromo-pyridine derivatives (234 mg, 1.0 mmol, <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> for 18a; 172 mg, 1.0 mmol, 2-bromo-4-methylpyridine for 18b; 192 mg, 1.0 mmol, 2-bromo-4-chloropyridine for 18c; 183 mg, 1.0 mmol, 2-bromoisonicotinonitrilefor 18d; 186 mg, 1.0 mmol, 2-bromoisonicotinaldehyde for 18e;176 mg, 1.0 mmol, 2-bromo-5-fluoropyridine for 18j; 192 mg,1.0 mmol, 2-bromo-5-chloropyridine for 18k; 183 mg, 1.0 mmol, 6-bromonicotinonitrile for 18m; 186 mg, 1.0 mmol, 6-bromonicotinaldehyde for 18n; 236 mg, 1.0 mmol, 2-bromo-5-(methylsulfonyl)pyridine for 18o, 200 mg, 1.0 mmol, 1-(6-bromopyridin-3-yl)ethan-1-one for 18p, 234 mg, 1.0 mmol, 2-bromo-5-phenylpyridine for 18r; 263 mg, 1.0 mmol, N-benzyl-6-bromopyridin-3-amine for 18s), Pd(PPh3)2Cl2 (3.5 mg, 0.5 mol %),K2CO3 (387 mg, 2.8 mmol) in DME/H2O (8 mL, 3:1) under nitrogenatmosphere. The mixture was stirred at 80 C for about 14 h and thecompletion of the reaction was monitored by TLC. After cooling toroomtemperature, themixturewas extracted with ethyl acetate. Thecombined organic layers were washed with brine and the organicphase was dried with anhydrous sodium sulfate and concentrated invacuo. The crude compound was purified by silica gel column chromatographyto give corresponding intermediates. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13%; 9%; 37% | With palladium(II) trifluoroacetate; triphenylphosphine; potassium hydroxide; In acetonitrile; at 30℃; for 24h;Inert atmosphere; | General procedure: 2,5-dibromopyridine (0.12 g, 0.50 mmol), phenylboronic acid (67 mg, 0.55 mmol), K2CO3 (0.14 g, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol %), PPh3 (26 mg, 10 mol %) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at 50 C under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10 mL). The solution was washed with water (10 mL*3) and brine (10 mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 400:1) to give the desired product 3a (114 mg, 97%) as a white solid. |