Structure of 937602-15-8
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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. : | 937602-15-8 |
Formula : | C7H7F3N2 |
M.W : | 176.14 |
SMILES Code : | FC(C1=CN=C(NC)C=C1)(F)F |
MDL No. : | MFCD08689790 |
InChI Key : | ALRNMRIFTCZDDH-UHFFFAOYSA-N |
Pubchem ID : | 18526206 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.29 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
24.92 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.61 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.1 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.02 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.09 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.46 |
Solubility | 0.609 mg/ml ; 0.00345 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.2 |
Solubility | 1.11 mg/ml ; 0.00628 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.35 |
Solubility | 0.0792 mg/ml ; 0.00045 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) |
No |
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 |
-5.92 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 |
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 |
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) |
1.8 |
* 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 |
---|---|---|
In 1-methyl-pyrrolidin-2-one; water; at 20℃; for 3h; | Reference Production Example 6; To a mixture of 18.2 of 2-chloro-5- trifluoromethylpyridine and 100 ml of N- methylpyrrolidone was added 23.3 g of a 40% methylamine aqueous solution, and the mixture was stirred for 3 hours at room temperature. Water was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 17.3 g of N-methyl-(5- trifluoromethylpyridine-2-yl) -amine .Me1H-NMR (CDCl3) delta: 8.34 (s, IH), 7.60 (dd, J=8.8, 2.4Hz, IH), 6.40 (d, J=8.8Hz, IH), 4.89(br s, IH), 2.97 (d, J=5.1Hz, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; at 80℃; for 2h; | Into a mixture of 17.3 g of N-methyl(5- trifluoromethylpyridin-2-yl) -amine and 100 ml of sulfuric acid was dropped 12.3 g of nitric acid, then, the mixture was stirred for 2 hours while heating at 800C. After cooling down to room temperature, water was poured into the reaction mixture, and the deposited precipitate was filtrated, then, washed with water, then, dried under reduced pressure to obtain 18.8 g of N-methyl (3-nitro-5-trifluoromethylpyridin-2-yl) -amine.1H-NMR (CDCl3 ) delta: 8.66-8.64 (m, 2H) , 8.43 (br s, IH) , 3.23 (d, J=4.9Hz, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.18 g | With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃; for 3h; | Production Example 15 [0734] A mixture of 0.35 g of <strong>[937602-15-8]2-methylamino-5-trifluoromethylpyridine</strong>, 0.50 g of 3-ethylsulfanyl-5-trifluoromethylpicolinic acid, 0.46 g of EDCI hydrochloride, 0.02 g of HOBt and 3 mL of pyridine was stirred at room temperature for 3 hours. A saturated aqueous sodium bicarbonate solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.18 g of 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluorome thylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 24). Compound of Present Invention 24 [0735] 1H-NMR(CDCl3)delta: 8.54-8.47(2H, m), 7.89-7.81(2H, m), 7.61(1H, s), 3.55(3H, s), 3.02(2H, q), 1.35(3H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 3h;Cooling with ice; | Example 1-1 (0142) Production Method of 2-fluoro-N-methyl-4-(trifluoromethyl)-N-(5-(trifluoromethyl)pyridin-2-yl)benzamide (0143) 2-Fluoro-4-trifluoromethyl benzoyl chloride (409 mg) and a THF (1 mL) solution were added to a mixture of <strong>[937602-15-8]N-methyl-5-(trifluoromethyl)pyridin-2-amine</strong> (264 mg), THF (4 mL) and triethylamine (1 mL) under ice cooling. After heating to room temperature, N,N-dimethyl aminopyridine (50 mg) was added, and the resulting mixture was stirred for 3 hours. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was dried over anhydrous magnesium sulfate and then concentrated in vacuo. The resulting residue was subjected to column chromatography to give the desired compound (260 mg, yield: 47%). |
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