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CAS No. : | 857061-44-0 | MDL No. : | MFCD08459291 |
Formula : | C7H3BrClF3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XPIQQGXRDHXMGQ-UHFFFAOYSA-N |
M.W : | 259.45 | Pubchem ID : | 20269851 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.15 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.95 cm/s |
Log Po/w (iLOGP) : | 2.3 |
Log Po/w (XLOGP3) : | 4.13 |
Log Po/w (WLOGP) : | 5.27 |
Log Po/w (MLOGP) : | 4.66 |
Log Po/w (SILICOS-IT) : | 4.17 |
Consensus Log Po/w : | 4.1 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.35 |
Solubility : | 0.0115 mg/ml ; 0.0000442 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.84 |
Solubility : | 0.0378 mg/ml ; 0.000146 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.75 |
Solubility : | 0.00456 mg/ml ; 0.0000176 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.56 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 hydrogenchloride; CO2; carbon dioxide; magnesium; In tetrahydrofuran; | EXAMPLE 3 3-Chloro-2-trifluoromethylbenzoic acid 1.03 g (42.4 mmol) of magnesium turnings were dissolved in THF. 2 drops of 1,2-dibromomethane were added, and the reaction mixture was, after the exothermal reaction had set in, stirred at 32-35 C. with ice-cooling. 10.0 g (38.5 mmol) of <strong>[857061-44-0]1-bromo-3-chloro-2-trifluoromethylbenzene</strong> in THF were then added dropwise such that the temperature did not exceed 32 C. The mixture was stirred for another 30 min and cooled to 0 C., and carbon dioxide was introduced over a period of 2 h. The mixture was then warmed to room temperature, and CO2 was introduced for a further hour. The solution was poured into a mixture of 1 M hydrochloric acid and ice and extracted with methyl tert-butyl ether. The organic phase was then extracted with 1 M NaOH and the aqueous phase was acidified with concentrated hydrochloric acid and extracted with methylene chloride. Drying and distillative removal of the solvent gave 7.7 g (84% of theory) of the title compound as colorless crystals (m.p. 110 C.). In addition to the above compounds, further heteroaroyl derivatives of the formula III and heteroaroyl-substituted phenylalanineamides of the formula I which were prepared or are preparable in a manner similar to the processes described above are listed in Tables 2, 3, 4 and 5 below. | |
With hydrogenchloride; CO2; carbon dioxide; magnesium; In tetrahydrofuran; | EXAMPLE 3 3-Chloro-2-trifluoromethylbenzoic acid 1.03 g (42.4 mmol) of magnesium turnings were dissolved in THF. 2 drops of 1,2-dibromomethane were added, and the reaction mixture was, after the exothermal reaction had set in, stirred at 32-35 C. with ice cooling. 10.0 g (38.5 mmol) of <strong>[857061-44-0]1-bromo-3-chloro-2-trifluoromethylbenzene</strong> in THF were then added dropwise such that the temperature did not exceed 32 C. The mixture was stirred for another 30 min and cooled to 0 C., and carbon dioxide was introduced for 2 h. The mixture was then warmed to room temperature, and CO2 was introduced for another hour. The solution was poured into a mixture of 1M hydrochloric acid and ice and extracted with methyl tert-butyl ether. The organic phase was then extracted with 1M NaOH and the aqueous phase was acidified with conc. hydrochloric acid and extracted with methylene chloride. Drying and distillative removal of the solvent gave 7.7 g (84% of theory) of the title compound as colorless crystals (m.p. 110 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tert-pentoxide;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90℃; for 17h;Product distribution / selectivity; | Example 1B; Preparation of 7-(4-{4-[3-chloro-2-(trifluoromethyl)phenyl]piperazin-1-yl}butoxy)-[1,8]-naphthyridin-2(1H)-one; 1-(3-Chloro-2-trifluoromethyl-phenyl)-piperazine hydrochloride; To a degassed solution of toluene (200 mL) containing racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (490 mg, 0.77 mmoles), Pd2(dba)3 (291.09 mg, 0.308 mmoles). N-Boc piperazine (28.71 g, 154.17 mmoles) and sodium tert-amylate (20.4 g, 185 mmoles) was added aryl bromide (40.0 g, 154.17 mmoles). The reaction was heated to 90 C. and stirred at that temperature for 17 hours. The reaction was cooled to approximately room temperature and washed with water (100 mL). To the organic layer was added hydrogen chloride (1.5 equiv; 231.26 mmoles; 17.52 mL; 19.27 g) and the reaction was heated to 80 C. (approximately 3 hours). The reaction was equipped with a Dean-Stark apparatus and water removed by atmospheric distillation until <0.1% water remained. The reaction was cooled to room temperature and stirred for two days. The resultant slurry was filtered, and the wet cake washed with toluene to provide 52.6 g (113% crude yield) of the product, which was sufficiently pure to use without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | A flask was charged with l-bromo-3-chloro-2-(trifluorom ethyl )benzene (500 mg, 1.94 mmol, 1.00 equiv) and THF (20 mL) under nitrogen. -Butyllithium (0.93 mL, 2.32 mmol, 1.20 equiv, 2.5M in hexane) was added dropwise at -78 C. The resulting solution was stirred for 2 h at - 78 C. DMF (10 mL) was added. The resulting solution was stirred for 2 h at -78 C and quenched with water (20 mL). The mixture was extracted with EtOAc (3 x 20 mL) and the organic layers were combined, washed with brine (2 x 25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 130 mg (32% yield) of 3-chloro-2-(trifluoromethyl)benzaldehyde as a yellow oil. LCMS (ESI, m/z): 209 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; | 1-Bromo-3-chloro-2-(trifluoromethyl)benzene (1.0 g, 3.85 mmol),Methylboronic acid (231 mg, 3.85 mmol) andK2CO3 (1.6 g, 11.58 mmol) was dispersed in 1,4-dioxane/water (16 mL / 4 mL).After replacing the nitrogen, Pd(dppf)Cl2 (145 mg, 0.2 mmol) was added.After replacing the nitrogen three times, the reaction was warmed to 90 C and allowed to react overnight.The reaction system was used directly for the next reaction. |
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