Structure of 886365-25-9
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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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CAS No. : | 886365-25-9 |
Formula : | C8H8BrNO3 |
M.W : | 246.06 |
SMILES Code : | O=C(OC)C1=C(Br)C=NC(OC)=C1 |
MDL No. : | MFCD07375112 |
InChI Key : | HSPQMLCPRUPXSD-UHFFFAOYSA-N |
Pubchem ID : | 46311225 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 49.71 |
TPSA ? Topological Polar Surface Area: Calculated from |
48.42 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.7 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.64 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.22 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.89 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.72 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.58 |
Solubility | 0.647 mg/ml ; 0.00263 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.33 |
Solubility | 1.15 mg/ml ; 0.00465 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.09 |
Solubility | 0.201 mg/ml ; 0.000818 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 |
-6.59 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) |
2.1 |
* 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 |
---|---|---|
77% | With silver (II) carbonate In toluene at 50℃; for 15 h; | To a solution of methyl 5-bromo-2-hydroxy-pyridine-4-carboxylate (20.0 g, 86.2 mmol) in toluene (200 mL) was added silver carbonate (30.9 g, 112.1 mmol) and iodomethane (18.4 g, 129.3 mmol). The reaction mixture was stirred at 50 °C for 15 h and filtered. The filtrate was concentrated under reduced pressure. The residue was purified bycolumn chromatography (silica gel, 100-200 mesh, 0 to 30percent ethyl acetate in petroleum ether) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (16.4g, 77percent) as a white solid, used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.9 g | at 0℃; for 1 h; | To a solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (23.5 g, 108.8 mmol) in MeOH (100 mL) were successively added a solution of I2 (35.9 mg, 141.4 mmol) in MeOH (75 mL) and a solution of KOH (15.9 g, 282.8 mmol) in MeOH (75 mL) at 0 °C. The resulting mixture was stirred for 1 hr at 0 °C and the reaction was quenched with saturated aqueous NaHS03. The resulting mixture was diluted with DCM (400 mL). The separated organic phase was washed with H20 (150 mL) and brine (150 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column (eluting with PE:EA=20: 1, v:v) to give methyl 5-bromo-2-methoxy-pyridine-4-carboxylate (14.9 g) as a light yellow solid. |
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