Structure of 6294-93-5
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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. : | 6294-93-5 |
Formula : | C7H4ClF3O |
M.W : | 196.55 |
SMILES Code : | OC1=CC=C(Cl)C(C(F)(F)F)=C1 |
MDL No. : | MFCD00042525 |
InChI Key : | ZLFPIEUWXNRPNM-UHFFFAOYSA-N |
Pubchem ID : | 80520 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.48 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.7 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.8 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.22 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.15 |
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 |
3.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.76 |
Solubility | 0.0344 mg/ml ; 0.000175 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.92 |
Solubility | 0.0237 mg/ml ; 0.00012 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.33 |
Solubility | 0.0921 mg/ml ; 0.000469 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 |
-4.8 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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.24 |
* 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 hydroxide; In dimethyl sulfoxide; | EXAMPLE 13 Approximately 20 parts of <strong>[89634-75-3]2-chloro-5-fluorobenzotrifluoride</strong> is reacted with 14 parts of powdered potassium hydroxide (85%) in dimethylsulfoxide solvent at a temperature of about 60-70 C. for 12 to 16 hours to form 4-chloro-3-trifluoromethylphenolate. The reaction mixture is cooled, poured into iced water, and acidified with concentrated hydrochloric acid. The aqueous mixture is then extracted with methylene chloride and the organic layer dried and concentrated to recover 4-chloro-3-trifluoromethylphenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20℃; for 24.0h; | Example P37: Preparation of 2-(4-Chloro-3-trifluoromethyl-phenoxy)-6-methyl-5.nitro- nicotinonitrile:Error. Objects cannot be created from editing field codes.In a 50 ml single-necked round-bottomed flask, 990 mg 4-chloro-3-trifluoromethyl-phenol is dissolved in 5.00 ml of dry dioxane. Afterwards, 1.73 ml of Hnig's base is added under stirring, followed by 1.00 g of <strong>[26820-34-8]2-chloro-6-methyl-5-nitro-nicotinonitrile</strong> and stirring continued at an ambient temperature for 24 hours (dark violet suspension). Afterwards, the mixture is filtered through a pad of silica gel on a sintered glass filter disk, followed by washing with dichloromethane. The combined organic phases are concentrated in vacuo to give 2.32 g of a dark violet gum. After purification by chromatography [silica gel cartridge (50 g, 150 ml), eluent: hexanes/ ethyl acetate 4:1 (v:v)], 1.53 g of the title compound are obtained in the form of a orange solid (MP: 110-1 110C).1H NMR (400MHz, CDCI3): delta 2.77 (s, 3H), 7.34 (dd, 1 H), 7.60 (m, 2H), 8.72 (s, 1 H). LC: UV Detection: 220 nm; R1 = 2.08 min. <n="90"/>TLC: Plates: Merck DC-Plates, silica gel F254, saturated atmosphere in developing tank, UV detection, eluent: heptane/ ethyl acetate 2:1 (v:v); Rf of title compound = 0.54, Rf of starting material = 0.52. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 18h; | To a stirred solution of <strong>[1354961-13-9]tert-butyl 5-chloro-2,4-difluorobenzoate</strong> (Preparation 51, 200 mg, 0.80 mmol) in DMSO (4 mL) was added K2CO3 (333 mg, 2.41 mmol) followed by 4-chloro-3-(trifluoromethyl)phenol (190 mg, 0.97 mmol) and the reaction stirred at room temperature for 18 h. Water (10 mL) and EtOAc (15 mL) were added and the layers separated. The aqueous layer was extracted with EtOAc (15 mL). The combined organic extracts were washed with brine (15 mL), dried (MgSO4) filtered and the solvent removed under reduced pressure to give the title compound (245 mg, 72%) as a solid.1H NMR (CDCl3, 400 MHz): δ 1.58 (9H, s), 6.66 (1H, d), 7.14 (1H, dd), 7.36 (1H, d), 7.54 (1H, d) and 8.00 (1H, d). |
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