Structure of 81565-19-7
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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. : | 81565-19-7 |
Formula : | C6H3ClF3N |
M.W : | 181.54 |
SMILES Code : | FC(F)(F)C1=C(Cl)C=NC=C1 |
MDL No. : | MFCD07368053 |
InChI Key : | YNYROPYZSZBORI-UHFFFAOYSA-N |
Pubchem ID : | 12140226 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 34.25 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.89 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.68 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.36 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.91 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.18 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.01 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.63 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.79 |
Solubility | 0.294 mg/ml ; 0.00162 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.27 |
Solubility | 0.973 mg/ml ; 0.00536 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.53 |
Solubility | 0.0541 mg/ml ; 0.000298 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 |
-5.73 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 |
2.0 |
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 |
0.0 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) |
1.38 |
* 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 |
---|---|---|
(2) 3-Chloro-4-trifluoromethylpyridine was obtained from 3- chloro-4-iodopgammaridine by the method described in Eur. J. Org. Chem., (2004), 3793. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(3) The title compound was obtained from 3-chloro-4- trifluoromethylpyridine by the method described in Eur . J . Org . Chem., (2004), 3793. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With dihydrogen peroxide; acetic acid; at 80℃; | Step A. 3-Chloro-4-(trifluoromethyl)pyridine 1-oxide A mixture of <strong>[81565-19-7]3-chloro-4-(trifluoromethyl)pyridine</strong> (2.00 g, 11.0 mmol) and H2O2 (3.2 mL, 31 mmol) in AcOH (6 mL) was stirred at 80 C. overnight. The reaction mixture was allowed to cool to ambient temperature and quenched with NaHSO3 solution. The mixture was concentrated under reduced pressure and the residue was added saturated NaHCO3 solution (30 mL). The resulting mixture was extracted with DCM (3 times). The combined organic phases were washed with aq. NaHCO3, water and brine, dried over Na2SO4 and concentrated under reduced pressure to give 2.11 g (97% yield) of the sub-title compound as a pink solid. LCMS calc. for C6H4ClF3NO (M+H)+: m/z=198.0. found: 198.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In toluene; at 50 - 80℃; for 3h; | In a 250 ml four-necked flask equipped with a reflux condenser, a thermometer and a dropping funnel, 30.0 g (0.157 mol) of 4-(trifluoromethyl)nicotinic acid, 100 ml of toluene, heated to 50-60 C, and dripped 28.0 g (0.235 mol) of thionyl chloride was added, and the addition was completed in about 1 hour. After the dropwise addition was completed, the temperature was raised to 80 C for 2 hours, and the reaction was completed to obtain a 4-(trifluoromethyl)nicotinyl chloride solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In water; toluene; at 10 - 30℃; for 5h; | In a 1000 ml four-necked flask equipped with a thermometer and a dropping funnel, 33.3 g (0.314 mol) of sodium carbonate and 133.2 g of tap water were charged, and after stirring for 10 minutes, 120 ml of toluene was added, and aminoacetonitrile hydrochloride was 21.79 g (0.235). Mol), then the temperature is lowered to 10 C under stirring, and the dropwise addition of <strong>[81565-19-7]4-(trifluoromethyl)nicotinyl chloride</strong> solution is started. The addition is completed in about 3 hours, the temperature is maintained at 10-15 C, and the addition is completed. After incubation at 30 C for 2 hours, the reaction was completed, filtered, and the product was washed with 30 ml of water to obtain a white solid product, N-cyanomethyl-4-(trifluoromethyl)nicotinamide.The purity was 99.8%, and the yield was 93.2% based on 4-(trifluoromethyl)nicotinic acid. |
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