Structure of 50786-37-3
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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.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 50786-37-3 |
Formula : | C5H4Br2N2 |
M.W : | 251.91 |
SMILES Code : | NC1=C(Br)C=C(Br)N=C1 |
MDL No. : | MFCD01646058 |
InChI Key : | ZGOYBMZUFFEHSP-UHFFFAOYSA-N |
Pubchem ID : | 824582 |
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 | 1.0 |
Molar Refractivity | 44.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
38.91 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.71 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.89 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.36 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.06 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.84 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.09 |
Solubility | 0.207 mg/ml ; 0.000821 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.33 |
Solubility | 1.18 mg/ml ; 0.00468 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.38 |
Solubility | 0.106 mg/ml ; 0.000422 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 |
-6.49 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.07 |
* 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 |
---|---|---|
With acetic anhydride; at 0 - 20℃; | To a stirred solution of compound 208.1 (350 mg) in formic acid (2.2 ml) was added acetic anhydride (1.2 ml) at 0 C and stirred at room temperature for 5 hr. After completion of the starting material (by TLC), the reaction mixture was concentrated under reduced pressure to afford compound 208.2 (250 mg, 64%) of a white solid which was used immediately in the next step without further purification. H-NMR (CDCl3, 500 MHz) delta 9.37 (s, 1H), 8.52 (s, 1H), 7.73 (s, 1H), 7.25 (bs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred solution of compound D.I (500 mg, 1.77 mmol) in AcOH (20 ml), was added iron powder (400 mg, 7.27 mmol). The reaction mixture was heated at 60 C for 2 hr. After completion of the starting material (by TLC), the reaction mixture was filtered on celite bed and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the crude material was diluted with NaHCO3 solution (100 ml) and extracted with ethyl acetate (3x 20 ml). The combined organic extracts was washed with water and dried over anhydrous sodium sulphate, concentrated under reduced pressure to afford compound 208.1 (350 mg, 78.47%, crude) as brown solid, which was used for the next step any further purification. 1H-NMR (CDCl3, 500 MHz) delta 7.94 (s, 1H), 7.54 (s, H), 7.26 (s, 1H), 3.50 (bs, 2H); LCMS m/z = 259 [M+l]. [00268] Synthesis of Compound 208.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.0 g | 4,6-Dibromopyridine-3-amine (40.9 g, 164 mmol) was dissolved in CH2C12 (200 ml), and triethylamine (49.3 g, 487 mmol) was added. The mixture was stirred at room temperature for 10 mm, and the solution of the acid chloride was then added slowly. The reaction mixture was stirred at room temperature for 16 h, the solvent was removed under reduced pressure and the residue was separated chromatographically by column chromatography on silica gel (gradient: ethyl acetate/petroleum ether 50:50-75:25). This gave 20.0 g (34% yield) of N-(4,6-dibromo-3-pyridyl)pyridine-3-carboxamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium bromate; sulfuric acid; sodium bromide; In water; acetonitrile; at 0 - 5℃; for 1.5h; | At 0-5 C., a solution of sodium bromide (21.87 g, 212.4 mmol) and sodium bromate (63.76 g, 425.0 mmol) in water (400 ml) was added to a solution of pyridine-3-amine (20.0 g, 0.213 mol) in acetonitrile (200 ml). With cooling, sulphuric acid (prepared from concentrated sulphuric acid 20.84 g, 212.5 mmol and 200 ml of water) was then added over 30 mm. The mixture was stirred at 5 C. for 1 h and filtered and the residue was washed with a saturated NaHCO3 solution (200 ml) and water (200 ml) and dried under reduced pressure. This gave 40.0 g (quantitative) of crude product, which was reacted in the next step without further purification. |