Structure of 76535-75-6
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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. : | 76535-75-6 |
Formula : | C14H26N2O4 |
M.W : | 286.37 |
SMILES Code : | O=C(N1CCN(C(OC(C)(C)C)=O)CC1)OC(C)(C)C |
MDL No. : | MFCD01435774 |
InChI Key : | YROXEBCFDJQGOH-UHFFFAOYSA-N |
Pubchem ID : | 545824 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 20 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.86 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 84.34 |
TPSA ? Topological Polar Surface Area: Calculated from |
59.08 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.77 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.8 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.86 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.33 |
Solubility | 1.33 mg/ml ; 0.00463 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.63 |
Solubility | 0.673 mg/ml ; 0.00235 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.46 |
Solubility | 10.0 mg/ml ; 0.035 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) |
No |
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 |
-6.79 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) |
2.68 |
* 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 |
---|---|---|
95% | With iron oxide In ethanol at 20℃; for 0.416667 h; Green chemistry | General procedure: A round-bottom flask (10 mL), which contains EtOH(5 mL), was charged with a solution of diboc (1–2 mmol),nano-Fe3O4 (3 molpercent, 0.007 g) and the amine (1 mmol). The mixture was stirred at room temperature for the appropriate time (Table 3). After completion of the reaction, the catalyst was collected by a magnet and separated from the solution of product and the remaining starting materials.After drying and evaporation of the solvent, the resulting solid was recrystallized from n-hexane or ethyl acetate(5 mL) to give the pure product. The recovered catalyst was washed with EtOH, dried and reused for the next run. The catalyst was recovered and reused for six times without any significant changes in the yield and the reaction time. |
93% | Stage #1: With C12H24KO6(1+)*Br3H(1-) In ethanol at 20℃; for 0.0166667 h; Stage #2: at 20℃; for 0.0166667 h; |
For the N-boc protection of amines, to solution of diboc (1 mmol) in ethanol (5 ml) was added {K*18-crown-6]Br3}n (0.001 mmol). The solution was stirred at room temperature for 1 min. The amine (1 mmol) was then added and solution as stirred at room temperature for an appropriate time (table 1). After completion of the reaction, the solvent was removed by water bath distillation. To the residue was added ethyl acetate (5 ml) and the mixture was filtered (the catalyst is insoluble in n-hexane and ethyl acetate). The solid was washed with ethyl acetate ()10 ml*2) amd combined filtrates were reduced to dryness to yield the pure products. |
87% | With copper In neat (no solvent) at 20℃; for 0.25 h; | General procedure: To a mixture of amine (1.0 mmol) and (Boc)2O (1.2 mmol), copper nano particles (0.1 mmol) was added with vigorous stirring at room temperature or 70 oC for the appropriate time (Scheme 2 and Table 2) until disappearance of the precursor amine was observed in the TLC. After completion, the reaction mixture was diluted with dry ether (5 mL) and catalyst was separated by filtration and the residue was washed with ether. The combined filtrate was evaporated to dryness and dried under vacuum. The N-Boc product is essentially pure on TLC but for getting analytical data the sample was passed through silica-gel (100-200 mesh) column using 10-30percent ethyl acetate in hexane as eluent. The physical data (m.p., FTIR, NMR) of the known compounds were found to be identical with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 0℃; for 1 h; | To a cold methylene chloride solution (10 ml) of piperazine (30.23 mmol, 2.60 g) was added methylene chloride solution (10 ml) of BOC anhydride (1.50 mmol) and the mixture was stirred at 0°C for 1 hour. After the reaction is complete, water is added and the aqueous K2CO3 solution is added to make the reaction mixture basic. All of the reaction mixture was extracted with methylene chloride and the product was isolated by column chromatography. |
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