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CAS No. : | 24522-30-3 | MDL No. : | MFCD05669245 |
Formula : | C10H7F3N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JBNCFFDGYDZEEN-UHFFFAOYSA-N |
M.W : | 228.17 | Pubchem ID : | 3823803 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.31 |
TPSA : | 52.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.59 cm/s |
Log Po/w (iLOGP) : | 1.23 |
Log Po/w (XLOGP3) : | 2.96 |
Log Po/w (WLOGP) : | 3.52 |
Log Po/w (MLOGP) : | 1.88 |
Log Po/w (SILICOS-IT) : | 2.33 |
Consensus Log Po/w : | 2.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.13 |
Solubility : | 0.168 mg/ml ; 0.000736 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.73 |
Solubility : | 0.0421 mg/ml ; 0.000185 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.78 |
Solubility : | 0.0376 mg/ml ; 0.000165 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
95% | Stage #1: With 4-methyl-morpholine In tetrahydrofuran at 0 - 10℃; for 1 h; Industry scale Stage #2: With isopropyl chloroformate In tetrahydrofuran at 0 - 10℃; for 2 - 3 h; Industry scale |
Example 1 Preparation of 4-trifluoromethyl cyanoacetoanilide (compound (IV)) In 700 L of tetrahydrofuran, 63.4 kg of cyanoacetic acid was dissolved with stirring in nitrogen atmosphere at room temperature. This solution was cooled to 0 to 10°C, and then N-methylmorpholine was added dropwise with stirring at the same temperature in about an hour. Then, 100.0 kg of 4-trifluoromethylaniline was added dropwise. To this reaction mixture, 91.3kg of isopropyl chlorocarbonate was added dropwise with stirring at the same temperature in about an hour. Further, the stirring was continued for 1 to 2 hours. After the reaction was finished, 200 L of water was added to the reaction mixture, which was stirred and then allowed to stand for separation. An organic layer (upper layer) was washed with 16.7 percent brine, and then 400 L of isopropyl alcohol was added thereto, which was concentrated under reduced pressure until the liquid amount became 400 L. To the condensed solution, 400 L of isopropyl alcohol was added, which was concentrated again under reduced pressure until the liquid amount became 400 L. To the condensed solution, 100 L of isopropyl alcohol was added at 20 to 30°C with stirring, and then 500 L of water was added dropwise in about an hour. Then, the stirring was further continued for an hour at the same temperature. This mixture was cooled to 0 to 10°C with stirring, and then stirred at the same temperature for an hour. Precipitated crystals were collected by filtration and dried, to give 134.5 kg of the title compound (IV) in a yield of 95.0 percent. |
88.15% | With dicyclohexyl-carbodiimide In ethyl acetate at 25 - 30℃; for 2 h; Inert atmosphere | In a 500-ml., four-necked, round-bottomed flask fitted with a mechanical stirrer, a 125-ml dropping funnel, and a thermometer were placed 8.34g. (0.098 moles) of cyanoacetic acid (7) and 165- ml., of ethyl acetate and the mixture was stirred for 10 minutes under nitrogen atmosphere and then added 10.0 g. ( 0.62 moles) of 4-trifluoromethyl aniline (3). From a clean dropping funnel 14.1 g. (0.068 moles, dissolved in ethyl acetate 85mL) of dicyclohexylcarbodiimide was added dropwise over a period of about 1 hour at the same temperature. The reaction mixture was stirred for additional 1.0 hour at 25-30°C. After completion of the reaction precipitated urea was filtered and slurry washed successively with two 50-ml. portions of ethyl acetate and filtered. The organic extracts were combined and washed successively with two 50-ml. portions of 5percent sodium bicarbonate solution, 25-ml.of 5percent hydrochloric acid solution, and again with 50-ml. of 5percent sodium chloride solution. Separated organic layer was evaporated under reduced pressure to yield solid material. To the solid 170-ml isopropyl alcohol was added and the mixture was heated to70-75°C, obtained clear solution and filtered. The filtrate was concentrated to 10 volumes and cooled to 15-20°C. The separated product was filtered and dried in a vacuum oven. Yield =12.5. g (88.15percent), HPLC Purity: 99.6percent |
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