Structure of 1644-88-8
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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. : | 1644-88-8 |
Formula : | C7H4F3NO3 |
M.W : | 207.11 |
SMILES Code : | [O-][N+](=O)C1=C(OC(F)(F)F)C=CC=C1 |
MDL No. : | MFCD00041010 |
InChI Key : | YTWBYJAWWKTPOV-UHFFFAOYSA-N |
Pubchem ID : | 12513085 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.95 |
TPSA ? Topological Polar Surface Area: Calculated from |
55.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.83 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.94 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.75 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.92 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.29 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.15 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.1 |
Solubility | 0.166 mg/ml ; 0.000803 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.76 |
Solubility | 0.0361 mg/ml ; 0.000175 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.41 |
Solubility | 0.804 mg/ml ; 0.00388 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) |
Yes |
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 |
-5.48 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) |
1.98 |
* 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 |
---|---|---|
62% | antimonypentachloride; In tetrachloromethane; | nitrophenyl trifluoromethyl ether Using the same reactor setup as in Example 1, the reactor is charged with 3-nitrophenol (13.9 g, 0.1 mol), anhydrous carbon tetrachloride (38 ml, 0.39 mol), anhydrous antimony trifluoride (53.6 g, 0.3 mol) and a catalytic amount of antimony pentachloride (1 ml, 7.7 mmol). The reactor is then sealed and heated at 150 C (internal) with vigorous stirring for 5.5 hours. Subsequently, the reactor is opened and the contents neutralized with saturated NaHC03 The product is separated by steam distillation, and a 62 percent yield of the product is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | antimonypentachloride; In tetrachloromethane; | nitrophenyl trifluoromethyl ether A 300 cc Parr reactor (steel) equipped with a sealed mechanical stirrer and an internal thermocouple is dried, flushed with nitrogen and charged with 4-nitrophenol (1.4 g, 10 mmol), anhydrous carbon tetrachloride (4 ml, 41.4 mmol), anhydrous antimony trifluoride (5.5 g, 30.8 mmol), and a catalytic amount of antimony pentachloride (0.1 ml, 0.77 mmol). The reactor is then sealed and heated at 150 C (internal) with vigorous stirring for 6.5 hours. Subsequently, the reaction vessel is opened and the contents partitioned between ether and saturated NaHCO3. Concentration of the organic extract, and flash chromatography of the concentrate produces a 29 percent yield of the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 22: Step a3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid. | ||
Intermediate 30: Step a 3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid. | ||
Intermediate 62: Step a 3-Nitro-4-trifluoromethoxy-benzenesulfonamide To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid. |
To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid. | ||
To chlorosulfonic acid (11.3 mL, 170 mmol) was slowly added commercially available <strong>[1644-88-8]2-trifluoromethoxy-nitrobenzene</strong> (8 g, 38.6 mmol). The reaction mixture was heated at 120 C. for 4 h and then cooled down. The above crude mixture was added to a stirred solution of conc. aq. NH4OH (34.7 mL, 514 mmol, 14.8 M) in iPrOH (100 mL) at -45 C. dropwise over 30 min. The reaction mixture was stirred at -45 C. for 1 h, and 2 N HCl was added to acidify the mixture. Concentration to remove iPrOH was followed by suspension in water, and filtration of the solid. The solid was washed successively with 1 N HCl and water, then air dried to yield the title compound as a white solid. |
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