Structure of 364793-57-7
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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. : | 364793-57-7 |
Formula : | C10H4BrClN2 |
M.W : | 267.51 |
SMILES Code : | N#CC1=C(Cl)C2=CC=C(Br)C=C2N=C1 |
MDL No. : | MFCD09261320 |
InChI Key : | SIBDBTCUQDTNQN-UHFFFAOYSA-N |
Pubchem ID : | 23438025 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 59.17 |
TPSA ? Topological Polar Surface Area: Calculated from |
36.68 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.14 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.52 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.7 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.06 |
Solubility | 0.0232 mg/ml ; 0.0000867 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.67 |
Solubility | 0.0568 mg/ml ; 0.000212 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.26 |
Solubility | 0.00148 mg/ml ; 0.00000555 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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 |
-5.64 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<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.79 |
* 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 |
---|---|---|
63% | With sodium; In tetrahydrofuran; | REFERENCE EXAMPLE 6 7-Bromo-4-(2,4-dichloroanilino)-3-quinolinecarbonitrile A mixture of 2,4-dichloroaniline (1.213 g, 7.49 mmol) and sodium hyduide (300 mg of a 60% dispersion in oil, 7.50 mmol) in 50 rnL of tetrahydrofuran was heated at reflux for 15 minutes. The mixture was cooled, <strong>[364793-57-7]7-bromo-4-chloro-3-quinolinecarbonitrile</strong> (1.00 g, 3.75 mmol) was added and the mixture was heated at reflux for 30 minutes. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resultant solid was purified by flash silica gel chromatography eluding with 3:1 hexane: ethyl acetate to provide 927 mg (63% yield) of 7-bromo-4-(2,4-dichloroanilino)-3-quinolinecarbonitrile as a light yellow solid, mp 180-183OC; 1H NMR (DMSO-d6/tiifluoroacetic acid) a 7.53-7.65 (m, 1H), 7.83 (d, J=2 Hz, 1H), 7.93-7.99 (m, 2H), 8.13 (d, J=2 Hz, 1H), 8.53 (d, J=9 Hz, 1H), 8.83 (s, 1H); MS (ES) m/z 392, 394, 396 (M+1). Analysis for C16H8 BrCl2 N3 : Calcd: C, 48.89;H, 2.05; N, 10.69. Found: C, 48.53;H, 2.18; N, 10.61. |
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