Structure of 85100-77-2
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 85100-77-2 |
Formula : | C8H15BrN2 |
M.W : | 219.12 |
SMILES Code : | CN1C=C[N+](CCCC)=C1.[Br-] |
MDL No. : | MFCD03427611 |
InChI Key : | KYCQOKLOSUBEJK-UHFFFAOYSA-M |
Pubchem ID : | 2734236 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.62 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
8.81 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-2.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.3 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-1.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.89 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.79 |
Solubility | 0.359 mg/ml ; 0.00164 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.12 |
Solubility | 1.65 mg/ml ; 0.00753 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.55 |
Solubility | 6.2 mg/ml ; 0.0283 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
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 |
-6.0 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.6 |
* 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 |
---|---|---|
In acetone; at 20℃; for 24h; | General procedure: To a solution of the crude 1-butyl-3-methylimidazoliumbromide, obtained from the above reactions,in acetone (70 mL) was added hexafluorophosphoric acid (10.90 g,100.0 mmol). The reaction mixture was stirred for 24 h at room temperature. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding 1-Butyl-3-methylimidazolium hexafluorophosphate. Same procedure was used except that trifluoro methane sulphonic acid (15.08 g,100.0 mmol) was used instead of hexafluorophosphoric acid. The resulting mixture was filtered. Evaporation of the solvent under reduced pressure afforded the corresponding imidazolium trifluromethanesulphonate.1-Butyl-3-methylimidazolium tetrafluoroborate was also prepared using the same procedure as above except that tetrafluoro boric acid (15.08 g, 100.0 mmol) was used in place of hexafluorophosphoric acid. Progress of the reaction was measured by TLC. Completion of the reaction was confirmed by 1HNMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.382 g | In neat (no solvent); at 100℃; for 0.333333h;Microwave irradiation; | General procedure: a mixture of 1-methylimidazole (0.4105 g, 5 mmol), 1-bromobutane (0.6850 g, 5 mmol) was heated under microwave irradiation (or conventional heating) in a 10 mL pressurized glass tube fitted with a Teflon-coated septum at 80 C for 20 min. Then, LiOTf (0.78 g, 5 mmol) was added and the mixture was irradiated at 100 C for 20 min. After cooling, the mixture was diluted with MeCN (5 mL), and after removal of the precipitated salt LiBr, the filtrate was then filtered through Celite. The crude product was washed with Et2O and concentrated to give a colorless to pale yellow liquid (1.382 g, 96 % yield). The [BMIM]OTf was dried under reduced pressure. The purity and authenticity of the ionic liquids were confirmed by 1H and 13C NMR spectroscopy. |
In acetone; acetonitrile; at 60℃; for 24h; | 1-Butyl-3-methylimidazolium bromide was dissolved in acetone/acetonitrile (50:50) and an equimolar amount of LiTfO in acetone was added. The mixture was stirred for 1 day at 60 C and then filtered. The solvent was removed under reduced pressure and the crude product dissolved in CH2Cl2. Upon cooling to 5 C most of the Li halide precipitated and the precipitate was filtered off. The remaining solution was washed halide-free with deionized water (AgNO3 test) and filtered over a column filled with neutral Al2O3 and activated charcoal. The residual organic phase was freed from solvent under reduced pressure and dried under dynamic vacuum for 1-2 days at 80-90 C. |