Structure of 1350643-72-9
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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. : | 1350643-72-9 |
Formula : | C17H15ClN2O |
M.W : | 298.77 |
SMILES Code : | O=C1N(C2=CC=CC=C2)C([C@@H](N)C)=CC3=C1C(Cl)=CC=C3 |
MDL No. : | MFCD23166427 |
InChI Key : | MZINZXIFJMLTOK-NSHDSACASA-N |
Pubchem ID : | 66607319 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 21 |
Num. arom. heavy atoms | 16 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 87.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
48.02 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.97 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.47 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.19 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.0 |
Solubility | 0.0302 mg/ml ; 0.000101 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.64 |
Solubility | 0.0682 mg/ml ; 0.000228 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.98 |
Solubility | 0.000311 mg/ml ; 0.00000104 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) |
Yes |
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 |
-6.01 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) |
2.93 |
* 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 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In N,N-dimethyl acetamide; water; at 120℃; for 16h;Sealed tube; | 0740] To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 1 (1.41 g, 4.72 mmol) and <strong>[628692-15-9](2-methoxypyrimidin-5-yl)boronic acid</strong> (1.09 g, 7.08 mmol) in anhydrous DMA (20 mL) in a sealed tube, PdCl2(dppf) (309 mg, 0.38 mmol) and aqueous Na2CO3 solution (1 M, 14.2 mL, 14.2 mmol) were added and the resulting mixture was stirred at 120° C. for 16 h. The reaction mixture was allowed to cool to RT, quenched with water, and then extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was slurried in ether for 10 min. The solid was collected by filtration, rinsed with ether and dried in vacuo to afford a first amount of product 2. The filtrate was concentrated in vacuo and the residue was further purified by ISCO column chromatography using a silica gel cartridge and eluting with 0-8percent MeOH-DCM to afford a second amount of product 2. |
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