Structure of 244193-50-8
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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. : | 244193-50-8 |
Formula : | C10H19BF4N2 |
M.W : | 254.08 |
SMILES Code : | C[N+]1=CN(CCCCCC)C=C1.F[B-](F)(F)F |
MDL No. : | MFCD03095459 |
InChI Key : | MFXLOVLEQJRXFP-UHFFFAOYSA-N |
Pubchem ID : | 2734179 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.7 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 63.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
8.81 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 |
4.63 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.2 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.6 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.66 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.22 |
Solubility | 0.0153 mg/ml ; 0.0000603 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.54 |
Solubility | 0.00731 mg/ml ; 0.0000288 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.38 |
Solubility | 1.06 mg/ml ; 0.00418 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) |
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) |
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 |
-4.56 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 |
2.0 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) |
1.89 |
* 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 ammonium tetrafluoroborate; In acetonitrile; for 24h;Reflux; | General procedure: The second step of synthesis of [C4mim][BF4] is the substitution of the bromide ion with the BF4- ion. Tetrafluoroborate salt was synthesized by metathesis reactions from the corresponding bromide. [C4mim][Br] (0.1 mol) was dissolved in acetonitrile (50 mL), and ammonium tertrafluoroborate (0.11 mol) was added. The mixture was refluxed for at least 24 h. When it was cooled to room temperature, NH4Br precipitate was removed by filtration. Any remaining precipitate was removed by further filtration at this step. The remaining acetonitrile was removed by rotary evaporation to get crude 1-butyl-3-methylimidazolium tetrafluorobarate. Crude [C4mim][BF4] was dissolved in dichloromethane (50 mL) and cooled below 278 K. Deionized water and a separation funnel were also cooled to below 278 K. The dichloromethane solution was washed with cooled deionized water (30 mL) five times until the aqueous solution did not form any precipitate with 0.1 mol L-1 AgNO3 solution. The solvent dichloromethane was removed by rotary evaporation, and the [C4mim][BF4] was dried under high vacuum at (323-333)K for at least 6 h (Scheme 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium tetrafluoroborate; at 70℃; for 336h; | In einen 1 I Schlenkkolben werden 126,0 g (1,53 mol) 1-Methylimidazol, 370,2 g (3,07 mol) Hexylchlorid und 251,8 g (2,30 mol) Natriumtetrafluoroborat gegeben und bei 70C ca. 2 Wochen geruehrt. Der entstandene weisse Feststoff wird ueber eine Schutzgasfritte abfiltriert und die sich gebildeten zwei Phasen voneinander mit Hilfe eines Scheidetrichters getrennt. Die untere gelbliche Phase wird ueber Nacht bei 60C im HV getrocknet. Man erhaelt 1-Hexyl-3-methylimidazoliumtetrafluoroborat in 91 %iger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 ml des Produktes mit ca. 5 ml Wasser versetzt und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Niederschlags spricht fuer die komplette Abwesenheit von Chloridresten. 1H-NMR (300 MHz, CDCl3):delta=9.9 ppm (s,1H,Ha); delta=7.26 ppm (d,1H,Hc); delta=7.24 ppm (d,1H,Hd); delta=4.1 ppm (t,2H,He); delta=3.9 ppm (s,2H,Hb); delta=1.6 ppm (m,2H,Hf); delta=1.2 ppm (m,6H,Hg,h,i); delta=0.8 ppm (t,3H,HJ). 13C-NMR (75 MHz, CDCl3):delta=137 ppm (C1); delta=124-122 ppm (C3,C4); delta=48 ppm (C5); delta=35 ppm (C2); delta=29-24 ppm (C6-C8); delta=20 ppm (C9); delta=13 ppm (C10). 19F-NMR (281 MHz, CDCl3):delta= -151,3 ppm (d, 1J(BF)= 22 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
, wherein said salt is selected from the group consisting of: ... 4-methyl-N-hexylpyridinium chloride, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-pentyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-heptyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium tetrafluoroborate, 1-nonyl-3-methylimidazolium tetrafluoroborate, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20℃; for 24h; | General procedure: Another anion exchange reaction was carried out to achieve IL with boron tetrafluorides as a counter anion (IL-BF4) by metathesis reaction as per reported literature with minor modifications (Scheme 2). A demonstrative example for the synthesis of [RMIM]BF4 (i.e., [EMIM]BF4, [BMIM]BF4, [HMIM]BF4, [OMIM]BF4, [DMIM]BF4) and [RBZMIM]BF4 (i.e., [EBZMIM]BF4, [BBZMIM]BF4, [HBZMIM]BF4, [OBZMIM]BF4, [DBZMIM]BF4) in Scheme 2 (step-3) derivatives are as follows: 1:2 ratio of the 1-methyl-3-alkylimidazolium bromide or 1-methyl-3-alkylbenzimidazolium bromide ([RBZMIM]Br) and NaBF4 were added distinctly in to the round bottom flask containing 25mL of methanol and stirred at room temperature for 24h. Afterward, the salt was removed by filtering the reaction mixture using Whatman filter paper. Further, the filtrate was centrifuged for 10min at 3000rpm to isolate the residual salts. Solvent was evaporated under reduced pressure, vacuum dried and characterized (using 1H and 13C NMR and mass spectroscopy). The spectral details of the synthesized ILs are provided in the supplementary information Figs. S1 to S30. |