Structure of 893444-21-8
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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. : | 893444-21-8 |
Formula : | C6H4F3N3O2 |
M.W : | 207.11 |
SMILES Code : | NC1=NC(=CC=C1[N+]([O-])=O)C(F)(F)F |
MDL No. : | MFCD11847683 |
InChI Key : | YSMYCFONKCAXBB-UHFFFAOYSA-N |
Pubchem ID : | 53404040 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.17 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.47 |
TPSA ? Topological Polar Surface Area: Calculated from |
84.73 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.8 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.75 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.23 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.39 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.07 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.44 |
Solubility | 0.746 mg/ml ; 0.0036 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.2 |
Solubility | 0.131 mg/ml ; 0.000633 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.94 |
Solubility | 2.38 mg/ml ; 0.0115 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 |
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) |
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 |
-6.29 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) |
2.1 |
* 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 |
---|---|---|
100% | With ammonia; In ethanol; at 20.0℃; for 15.0h; | A pressure vessel was charged with compound 5.1 (126 mg, 0.56 mmol) and a saturated solution of ammonia in ethanol (10 mL). The vessel was sealed and the reaction mixture was stirred at room temperature for 15 hours, whereupon the reaction mixture was concentrated. Compound 5.2 (138 mg, >100%) was isolated as a yellow solid, contaminated with inorganic salts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; at 20.0℃; for 1.5h; | To compound 5.2 (138 mg, <0.67 mmol) in methanol / ethyl acetate (10 mL, 1:1) at room temperature was added palladium on carbon (36 mg, 10%, wet) and the reaction mixture was placed under an atmosphere of hydrogen(balloon). After 1.5 hours, the reaction mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate and methanol. The solvent was removed under reduced pressure to afford diamine 5.3 (149 mg, >100%) as a yellow film, which was used without further purification. |
With hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; for 1.5h; | Step 2: To a solution of 3-nitro-6-(trifLuoromethyl)pyridin-2-amine (838mg, 4.05mmol) in methanol (30mL) was added 10% palladium on carbon (400mg). The mixture was hydrogenated on a Parr shaker at 40 psi for 90 min. The catalyst was filtered and the solvent was evaporated to give 6~(trifluoromethyl)pyridine-2,3-diamine as a yellow solid. LC-MS (M+H) = 178 |
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