Structure of 29874-83-7
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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. : | 29874-83-7 |
Formula : | C14H9ClN2 |
M.W : | 240.69 |
SMILES Code : | ClC1=NC(C2=CC=CC=C2)=C3C=CC=CC3=N1 |
MDL No. : | MFCD01152724 |
InChI Key : | SFKMVPQJJGJCMI-UHFFFAOYSA-N |
Pubchem ID : | 3123582 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 16 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
25.78 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.78 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.95 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.02 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.11 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.62 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.65 |
Solubility | 0.00543 mg/ml ; 0.0000226 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.51 |
Solubility | 0.00738 mg/ml ; 0.0000307 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.47 |
Solubility | 0.0000821 mg/ml ; 0.000000341 mol/l |
Class? Solubility class: Log S scale |
Poorly 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 |
-4.74 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 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.95 |
* 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 |
---|---|---|
71% | With palladium diacetate; caesium carbonate; XPhos; In ethanol; water; toluene; at 110℃; for 3h;Inert atmosphere; | Under a nitrogen stream A13 2.7 g (7.5 mmol), 2.7 g (11.3 mmol) of 2-chloro-4-phenylquinazoline, 0.1 g (5 mol%) of Pd (OAc) 2, xphos, 3.6 g (7.5 mmol) 4.9 g (15.0 mmol) of cesium carbonate and 90 ml / 30 ml / 30 ml of toluene / H2O / ethanol were added and stirred at 110 C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO4. After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound R81 (2.3 g, 5.3 mmol, yield 71%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 5h; | In the reaction flask, add 7-bromo-benzocarbazole 29.5g (100mmol), 2-chloro-4-phenylquinazoline 16.5g (110mmol), DMF 500mL and potassium carbonate 43.3g (314mmol), at 140 C reaction 5h; the reaction was stopped after the reaction was completed, and the reaction was cooled to room temperature, filtered with water, the resulting solid was purified by toluene recrystallization, to obtain a white powder M1; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydride; In N,N-dimethyl-formamide; | Dissolve 9-bromo-7H-benzo[C]carbazole (10.0g, 33.78mmol) in 500ml of DMF, then add sodium hydride (2.7g, 67.56mmol), then add 2-chloro-4-benzene Quinazoline (9.76 g, 40.54 mmol) was stirred at room temperature overnight. After the reaction was completed, distilled water was added to precipitate a solid, which was filtered to obtain the solid, and washed with distilled water and ethanol in turn to obtain a gray solid intermediate A (15 g, yield 89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 3h;Reflux; | Combine S2 (30mmol), 2-chloro-4-phenylquinazoline (60mmol), potassium carbonate (45mmol), dioxane (200mL), tetrakis (triphenylphosphine) palladium (0.3mmol), water 50mL Add to the reaction flask, heat to reflux and react for 3 hours. TLC monitors the completion of the reaction. The reaction solution is poured into water and filtered. After extraction with dichloromethane, it is concentrated and recrystallized with toluene to obtain Intermediate A. |
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