Structure of 1034579-02-6
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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. : | 1034579-02-6 |
Formula : | C13H16BNO2S |
M.W : | 261.15 |
SMILES Code : | CC1(C)C(C)(C)OB(C2=CN=C3C(C=CS3)=C2)O1 |
MDL No. : | MFCD12923404 |
InChI Key : | ZFALGGJIXOGZJQ-UHFFFAOYSA-N |
Pubchem ID : | 57416432 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.46 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 76.1 |
TPSA ? Topological Polar Surface Area: Calculated from |
59.59 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.6 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.5 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.0 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.77 |
Solubility | 0.0441 mg/ml ; 0.000169 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.11 |
Solubility | 0.0201 mg/ml ; 0.0000771 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.57 |
Solubility | 0.007 mg/ml ; 0.0000268 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) |
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) |
Yes |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.63 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 |
1.0 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) |
2.94 |
* 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 potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 85.0℃; | A mixture of the product, <strong>[21344-24-1]5-bromothieno[2,3-b]pyridine</strong>I from Part B (1 equiv), bispinacolatodiboron (1.2 equiv), PdCI2dppf (0.1 equiv), and potassium acetate (3 equiv) in dioxane was heated at 85 C until the reaction was deemed complete by TLC, HPLC, or LC-MS analysis. The reaction was allowed to cool to room temperature, filtered through a pad of celite, concentrated to dryness, treated with diethyl ether, filtered through a pad of celite, and then concentrated to afford the desired product, 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thieno[2,3-b]pyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 40.0℃; | A mixture of compound {1 r,4r)-tert-butyl 4-(7-(bis((2- (trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1 ,5-a]pyrimidin-5- yljcyclohexanecarboxylate (1 equiv), boronate (1.75 equiv), palladium catalyst (0.1 equiv), and potassium carbonate (3 equiv) in water and dioxane was stirred at 40 C until the reaction was deemed complete by HPLC, LC-MS, or TLC analysis. The mixture was allowed to cool to room temperature, diluted with water and extracted three times with dichloromethane. The combined organics were dried over sodium sulfate, filtered, concentrated, and purified on silica gel to afford compound (1r,4r)-tert- butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyI)amino)-3-aryl-pyrazolo[1 ,5-a]pyrimidin- 5-yi)cyclohexanecarboxylate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triphenylphosphine; palladium dichloride; silver(l) oxide; at 100.0℃; for 2.0h;Inert atmosphere; | General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with PdCl2 (15.9 mg,0.09 mmol, 15 mol %), PPh3 (314.7 mg, 1.2 mmol, 200mol %), Ag2O (278.1 mg, 1.2 mmol, 200 mol %), aryl (hetero)boronic acid (0.72 mmol, 1.2 equiv) and phosphite ester (0.6 mmol, 1.0 equiv), DMA(3.0 mL, without any purification) was added and the mixture was charged with N2 three times. The reaction mixture was then stirred at 100 C under N2 for 2h. The reaction progress was monitored by TLC. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, and washed with ethyl acetate. The yields of standard reaction were obtained by HPLC. The combined organic solvent was concentratedin vacuo. The residue was purified by silica gel flash chromatography to produce the desired product. |
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