Structure of 95652-81-6
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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. : | 95652-81-6 |
Formula : | C7H6ClNO2 |
M.W : | 171.58 |
SMILES Code : | O=CC1=C(OC)N=C(Cl)C=C1 |
MDL No. : | MFCD11847276 |
InChI Key : | AVBARORPQMEWPR-UHFFFAOYSA-N |
Pubchem ID : | 10855945 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H317-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.13 |
TPSA ? Topological Polar Surface Area: Calculated from |
39.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.86 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.58 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.56 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.53 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.17 |
Solubility | 1.16 mg/ml ; 0.00675 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.01 |
Solubility | 1.66 mg/ml ; 0.00969 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.71 |
Solubility | 0.333 mg/ml ; 0.00194 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 |
-6.22 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 |
2.0 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) |
1.71 |
* 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 palladium diacetate; caesium carbonate; tert-butyl XPhos; In toluene; at 80℃;Inert atmosphere; | Cesium carbonate (223 mg, 0.683 mmol), palladium(ii) acetate (7.67 mg, 0.034 mmol), 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl(t-butyl Xphos) (29 mg, 0.068 mmol), 6-chloro-2-methoxynicotinaldehyde (58.6 mg, 0.341 mmol), and (2-methyl- [l,l'-biphenyl]-3-yl)methanol (88 mg, 0.444 mmol) were combined in a 25 mL round- bottom flask equipped with a stir bar. Toluene (2 mL) was added and the mixture purged with a stream of argon for 5 minutes. The reaction was sealed and heated at 80 C overnight. LC/MS showed 11 peaks of similar intensities. Peaks at 4 minutes had an M+1 of 334 consistent with desired product. The soluble portion of the crude reaction was charged to a 25g silica gel column with dichloromethane. Chromatographed with 0-60% ethyl acetate in hexanes. A fraction containing at least 2 compounds tested positive for an aldehyde using 2,4 dinitrophenyl hydrazine stain. This aldehyde-positive fraction was isolated and used without further purification. |
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