Structure of 52670-38-9
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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. : | 52670-38-9 |
Formula : | C8H7N |
M.W : | 117.15 |
SMILES Code : | NC1=CC=CC=C1C#C |
MDL No. : | MFCD00168862 |
InChI Key : | ALQPJHSFIXARGX-UHFFFAOYSA-N |
Pubchem ID : | 4153905 |
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 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.02 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 |
1.49 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.05 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.75 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.0 |
Solubility | 1.18 mg/ml ; 0.01 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.64 |
Solubility | 2.66 mg/ml ; 0.0227 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.07 |
Solubility | 1.0 mg/ml ; 0.00855 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 |
-5.96 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 |
2.0 |
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) |
1.24 |
* 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 |
---|---|---|
87.45% | With palladium 10% on activated carbon; hydrazine hydrate; In ethanol;Heating; | To a solution of compound 6k (1.5 g, 10.19 mmol) in ethanol(20 mL), 80% hydrazine monohydrate (1.8 g, 20.39 mmol) and 10%Pd/C (20 mg) were successively added. The reaction mixture was stirred under reflux at 80 C for 2-3 h and the reaction was monitored by TLC. After completion of the reaction, the solution was filtered to remove the Pd/C and the solvent was removed under vacuum. Then water and ethyl acetate were added to the residue and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give pure 2-ethynylaniline as light yellow oil liquid, yield: 87.45%. 3-ethynylaniline (7l) and 4-ethynylaniline (7m) were prepared withthe same method and the corresponding compounds 6l and 6m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; | General procedure: Under the protection of nitrogen, a THF solution (20 mL) containing Et3N (15 mmol) and o-ethynylaniline (6 mmol) was added to a flask containing amide (5 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.1 mmol) and CuI (0.05 mmol). The mixture was stirred overnight at room temperature (monitored by TLC). Then the solvent was removed under vacuum. The obtained residue was treated with a mixture of chloroform (30 mL) and water (30 mL). The separated organic layer was washed with brine (15 mL), dried with anhydrous MgSO4. After filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (EtOAc-PE, 1:2) to give N-[2-[(2-Aminophenyl)ethynyl]phenyl]amide. |
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