Structure of 766473-89-6
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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. : | 766473-89-6 |
Formula : | C8H4F3IO2 |
M.W : | 316.02 |
SMILES Code : | O=C(O)C1=CC=CC(C(F)(F)F)=C1I |
MDL No. : | MFCD08059374 |
InChI Key : | DNGSEJLGVHIEEZ-UHFFFAOYSA-N |
Pubchem ID : | 14612544 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 51.12 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.58 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.98 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.16 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.52 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.23 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.1 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.86 |
Solubility | 0.0434 mg/ml ; 0.000137 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.43 |
Solubility | 0.118 mg/ml ; 0.000374 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.59 |
Solubility | 0.0814 mg/ml ; 0.000258 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 |
-6.11 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 |
0.56 |
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) |
1.94 |
* 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 |
---|---|---|
Oakwood Products, Inc., 1741 Old Dunbar Road, West Columbia, S.C. 29172, USA. TCI America, 9211 N. Harborgate Street, Portland, Oreg. 97203, USA ... 5-fluoro-2-(trifluoromethyl)benzoic acid; 2-hydroxy-3-isopropyl-benzoic acid; 3-iodobenzoic acid; 5-iodosalicylic acid; 2-iodo-3-(trifluoromethyl)benzoic acid; 4-methyl-2-chlorobenzoic acid; 2-methyl-3-nitrobenzoic acid; 2-methyl-4-nitro-benzoic acid; ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; for 2h;Heating / reflux; | Step B: Preparation of 2-lodo-3-(trifluoromethyl)benzoyl chloride; [0424] 2-lodo-3-(trifluoromethyl)benzoic acid (10.0 g, 31.6 mmol) was stirred in thionyl chloride (100 mL, 31.6 mmol) at reflux for 2 hours. The mixture was then cooled to room temperature. The thionyl chloride was removed under vacuum, and the residue was azeotroped with dry toluene to give the product as a yellow-orange semi-solid (10.51 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A: Preparation of 2-lodo-3-(trifluoromethyl)benzoic acid; [0422] 30% H2SO4 (30 mL) was added to a solution of 3-(trifluoromethyl)anthranilic acid (10.0 g, 48.8 mmol) in DMSO (10 mL) at room temperature. The mixture was cooled to O0C, and a solution of sodium nitrite (5.05 g, 73.2 mmol) in water (10 mL) was added dropwise over 5 minutes. The mixture was stirred for 1 hour at 00C, and a solution of KI in water (10 mL) was added dropwise over 5 minutes. The ice bath was removed, and the mixture was stirred for 1 hour. EtOAc was added, and the solution was washed with 2N sodium nitrite twice, brine once, and dried over MgSO4. The solvent was then removed under vacuum to give the product as an off-white solid (12.6 g). [M- H]- = 315.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | 2-Iodo-3-trifluoromethylacetic acidrefPreviewPlaceHolder30 (228 mg, 0.72 mmol) in DMF (2.5 mL) was mixed with EDC (138 mg, 0.72 mmol) and 1-hydroxy-7-azabenzotriazole (97 mg, 0.72 mmol), then stirred at room temperature for 30 min. To this mixture, a solution of 1refPreviewPlaceHolder18 (127 mg, 0.55 mmol) and triethylamine 430 (199 mul, 1.43 mmol) in DMF (2.5 mL) was added and stirred further for 3 h. The reaction mixture was added aqueous NaHCO3 and ethyl acetate. The organic layer was separated and washed by brine, dried with Na2SO4, and evaporated to dryness. The crude product was chromatographed on silica gel with hexane/EtOAc = 1:2 to provide 2 (205 mg, 0.388 mmol, 71%) as a white solid. 1H NMR (300 MHz CDCl3) delta 7.67 (d, J = 7.6 Hz, 1H), 7.48 (t, J = 7.4 Hz, 1H), 7.42-7.28 (m, 6H), 5.78-5.65 (m, 1H), 5.12 (d, J = Hz, 16.8 Hz), 5.09 (d, J = Hz, 9.3 Hz), 4.96 (d, J = 6.6 Hz, 9.3 Hz), 3.33-3.18 (m, 2H), 3.05-2.98 (m, 1H), 2.87-2.79 (m, 1H), 2.62-2.53 (m, 1H), 1.85-1.73 (m, 1H), 1.56-1.28 (m, 5H), = +16.2 (c = 1.0; CHCl3)}, MS (FAB) m/z: 529 (M+). |
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