Structure of 118289-16-0
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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. : | 118289-16-0 |
Formula : | C6H6BrNO |
M.W : | 188.02 |
SMILES Code : | BrC1=NC=CC(=C1)CO |
MDL No. : | MFCD04039313 |
InChI Key : | IQNUGAFIKDRYRP-UHFFFAOYSA-N |
Pubchem ID : | 14512957 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.06 |
TPSA ? Topological Polar Surface Area: Calculated from |
33.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.99 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.65 |
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 |
1.24 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.06 |
Solubility | 1.65 mg/ml ; 0.00877 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.27 |
Solubility | 10.0 mg/ml ; 0.0532 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.71 |
Solubility | 0.368 mg/ml ; 0.00196 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) |
No |
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 |
-6.74 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.62 |
* 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 manganese(IV) oxide; In dichloromethane; at 20℃; for 54h; | 149 g (1714 mmol) of manganese dioxide is added in measured quantities to 28.0 g (148.9 mmol) of 2-bromo-4-hydroxymethyl-pyridine in 500 ml of dichloromethane within 6 hours. Then, stirring is continued at room temperature for 48 hours. It is suctioned off over Celite and concentrated by evaporation. 16.4 g of solidifying white oil accumulates. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 1h;Inert atmosphere; | To a solution of <strong>[118289-17-1]2-bromopyridine-4-carbaldehyde</strong> (20 g, 107.52 mmol) in MeOH (150 mL) was added portion wise sodium borohydride (12.0 g, 322.56 mmol) at 0° C. under inert atmosphere. The mixture was stirred at RT for 1 h. Saturated NH4Cl solution was added followed by extraction with EtOAc (3*200 mL). The combined organic layers were dried (Na2SO4) and evaporated in vacuo to obtain i (18.0 g, 90percent). 1H NMR (DMSO-d6, 400 MHz): delta 8.30 (d, J=4.8 Hz, 1H), 7.54 (s, 1H), 7.35 (d, J=4.8 Hz, 1H), 5.55 (t, J=6.0 Hz, 1H) and 4.53-4.54 (d, J=5.6 Hz, 2H). |
With sodium tetrahydroborate; In methanol; at 0 - 25℃;Inert atmosphere; | In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), <strong>[118289-17-1]2-bromo-pyridine-4-carbaldehyde</strong> (904 mg, 4.86 mmol) was dissolved in MeOH (10 mL). NaBH4 (236 mg, 5.99 mmol) was added portionwise at 0 0C and the reaction mixture stirred at rt for 1 h. Water (10 mL) was added and the mixture extracted <n="85"/>with EA (3 x 20 ml_). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid. TLC: rf (1 :1 hept-EA) = 0.22. LC-MS-conditions 02: tR = 0.63 min; [M+H]+ = 188.33. |
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