Structure of 400-74-8
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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. : | 400-74-8 |
Formula : | C7H3F4NO2 |
M.W : | 209.10 |
SMILES Code : | FC(C1=CC([N+]([O-])=O)=CC=C1F)(F)F |
MDL No. : | MFCD00024576 |
InChI Key : | DNTHMWUMRGOJRY-UHFFFAOYSA-N |
Pubchem ID : | 94954 |
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 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.33 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.38 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.17 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.41 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.0 |
Solubility | 0.207 mg/ml ; 0.000992 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.28 |
Solubility | 0.109 mg/ml ; 0.00052 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.95 |
Solubility | 0.235 mg/ml ; 0.00112 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 |
-5.68 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) |
1.84 |
* 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 |
---|---|---|
With potassium carbonate; In acetonitrile; at 80.0℃; | 1-Fluoro-4-nitro-2- (trifluoromethyl) benzene(300 mg, 1.4 mmol), (R) - (+) - 3-dimethylaminopyrrolidine dihydrochloride(261 mg, 1.4 mmol) was dissolved in acetonitrile (20 mL) and potassium carbonate (387 mg, 2.8 mmol) was added. The reaction system at 80 C overnight, then allowed to cool. The reaction mixture was poured into water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The organic phase is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude title compound (320 mg) was used as a yellow solid for the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h; | A solution of 1-fluoro-4-nitro-2-(trifluoromethyl)benzene (5.3 mL, 38 mmol) and <strong>[74420-02-3]1H-pyrrolo[2,3-b]pyridin-4-ol</strong> (CAS No. [74420-02-3]; 4.67 g, 34.8 mmol) in DMSO (110 mL) was treated withpotassium carbonate (19.2 g, 139 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with two times with 20 mL water and brine (20 mL), dried with sodium sulfate and concentrated in vacuo. The resulting residue was purified via a Biotage chromatography system (bOg snap KP-Silcolumn, hexane I 20 ? 100percent ethyl acetate) to obtain 4.62 g (96 percent purity, 39 percent yield) of thedesired title compound.1HNMR (400 MHz, DMSO-d6) delta [ppm]: 6.11 (d, 1H), 6.92 (d, 1H), 7.25 (d, 1H), 7.48 (d, 1H),8.28 (d, 1 H), 8.46 (dd, 1 H), 8.58 (d, 1 H), 12.05 (br s, 1 H). |
39% | With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h; | A solution of 1 -fluoro-4-nitro-2-(trifluoromethyl)benzene (5.3 mL, 38 mmol) and 1 /-/-pyrrolo[2,3- b]pyridin-4-ol (CAS No. [74420-02-3]; 4.67 g, 34.8 mmol) in DMSO (1 10 mL) was treated with potassium carbonate (19.2 g, 139 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with two times with 20 mL water and brine (20 mL), dried with sodium sulfate and concentrated in vacuo. The resulting residue was purified via a Biotage chromatography system (100g snap KP-Sil column, hexane / 20 - 100percent ethyl acetate) to obtain 4.62 g (96 percent purity, 39 percent yield) of the desired title compound. 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 6.1 1 (d, 1 H), 6.92 (d, 1 H), 7.25 (d, 1 H), 7.48 (d, 1 H), 8.28 (d, 1 H), 8.46 (dd, 1 H), 8.58 (d, 1 H), 12.05 (br s, 1 H). |
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