Structure of 1256945-00-2
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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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CAS No. : | 1256945-00-2 |
Formula : | C7H3BrF3I |
M.W : | 350.90 |
SMILES Code : | FC(C1=CC=C(Br)C=C1I)(F)F |
MDL No. : | MFCD21603817 |
Boiling Point : | No data available |
InChI Key : | PGFPLTAEOHMUKY-UHFFFAOYSA-N |
Pubchem ID : | 49834559 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.15 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
5.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
4.49 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.26 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.93 |
Solubility | 0.00408 mg/ml ; 0.0000116 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.86 |
Solubility | 0.0487 mg/ml ; 0.000139 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.04 |
Solubility | 0.00316 mg/ml ; 0.00000902 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
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) |
Yes |
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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.49 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
1.0 |
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<2.0 |
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 |
---|---|---|
68% | Preparation 12 4-Bromo-2-iodo-1-trifluoromethyl-benzene To a stirred solution of 5-bromo-2-(trifluoromethyl) aniline (300 mg, 1.255 mM) in dry THF (10 mL) was added BF3-etherate (707 mg, 5.02 mM) and tert-butyl nitrite (452 mg, 4.39 mM) at -78 C. Reaction mixture was stirred for 10 min, warmed to room temperature and maintained for 30 min. The reaction mixture was diluted with diethyl ether (30 mL). The solid was filtered off and dried under vacuum. This diazonium salt was added to a mixture of KI (289 mg, 1.746 mM) and iodine (203 mg, 0.876 mM) in acetone taken in an another flask at 0 C. and stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with water (20 mL) and the product was extracted with diethyl ether (2*20 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound as a liquid (230 mg, 68%). 1H NMR (400 MHz, CDCl3) delta 8.19 (s, 1H), 7.59 (d, 1H), 7.50 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium carbonate; triethylamine;palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 80℃; for 16h;Sealed tube; | Preparation 13 3-(5-Bromo-2-trifluoromethyl-phenyl)-acrylic acid methyl ester To a stirred solution of triphenylphosphine (486 mg, 1.857 mM) and Palladium acetate (159.9 mg, 0.714 mM) in dry THF taken in a sealed tube was added triethylamine (0.4 mL, 2.857 mM) at room temperature. Reaction mixture was degassed for 10 min, and then stirred for 15 min. To this 4-Bromo-2-iodo-1-(trifluoromethyl)benzene, methylacrylate (157 mg, 1.57 mM) were added followed by the addition of potassium carbonate (394 mg, 2.887 mM) at RT. Reaction mixture was heated to 80 C. for 16 h. After completion of reaction, reaction mixture was cooled to room temperature and passed through celite bed, washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 0-5% ethyl acetate in pet ether) to afford the title compound as a solid (200 mg, 76%). 1H NMR (400 MHz, CDCl3) delta 7.96 (d, 1H), 7.82 (s, 1H), 7.62 (d, 1H), 7.56 (d, 1H), 6.40 (d, 1H), 3.80 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.5 g | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; In tetrahydrofuran; at -30 - 20℃; for 19h; | Into a glass reaction vessel equipped with a stirrer and a capacity of 200 mL,3.51 g of 4-bromo-2-iodo-1- (trifluoromethyl) benzene(10.0 mmol), 67 mL of dehydrated tetrahydrofuran,8.4 mL (60.0 mmol) of diisopropylamine,701.9 mg (1.0 mmol) of dichlorobis (triphenylphosphine) palladium (II), 190.5 mg (1.0 mmol) of copper (I) iodide) Was added, and while keeping the internal temperature at -30 C., 832 muL of 3-butyn-1-ol(11.0 mmol) were added, followed by reaction at room temperature for 19 hours.The solvent was distilled off under reduced pressure, and a saturated aqueous solution of ammonium chloride was added to the resulting reaction crude productThe mixture was extracted with diethyl ether, dried over magnesium sulfate and the solvent was distilled off under reduced pressure,Silica gel column chromatography (hexane: ethyl acetate = 8: 2)To obtain 2.5 g of compound (C14-e) as a pale yellow solid. |
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