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CAS No. : | 75706-12-6 | MDL No. : | MFCD00867593 |
Formula : | C12H9F3N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VHOGYURTWQBHIL-UHFFFAOYSA-N |
M.W : | 270.21 | Pubchem ID : | 3899 |
Synonyms : |
SU101;HWA486;Leflunomide, Arava, Leflunomidum, HWA-486;HW 486;Arava;RS-34821
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 60.69 |
TPSA : | 55.13 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.18 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 2.49 |
Log Po/w (WLOGP) : | 4.22 |
Log Po/w (MLOGP) : | 2.14 |
Log Po/w (SILICOS-IT) : | 2.97 |
Consensus Log Po/w : | 2.83 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.25 |
Solubility : | 0.153 mg/ml ; 0.000564 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.29 |
Solubility : | 0.138 mg/ml ; 0.00051 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.03 |
Solubility : | 0.00252 mg/ml ; 0.00000933 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.45 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
86% | With sodium hydrogencarbonate In N,N-dimethyl acetamide; toluene | c) 4-Trifluoromethylaniline (5.75 g, 35.7 mm) was dissolved in a mixture of NaHCO3 (3.16 g, 37.6 mm), N,N-dimethylacetamide (0.7 ml, 7.5 mm) and toluene (70 ml). The mixture was warmed to 40° C. and 5-methylisoxazole-4-carboxylic acid chloride (5 g, 34.4 mm) was added dropwise over 20 min. The mixture was stirred at this temperature for another 3 h. and then it was heated to reflux temperature. The hot mixture was washed with water (3*10 ml). The organic phase was allowed to cool to ambient temperature, which induced leflunomide to precipitate as a white powder. The powder was isolated by filtration and then dried at 60° C. to give leflunomide (8.0 g, 86percent) in 99.5percent purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.34% | Stage #1: With thionyl chloride In toluene at 25 - 70℃; for 6 h; Stage #2: at 0 - 30℃; for 6 h; |
N-(4'-trifluoromethyIp)-5-methylisoxazole-4-carboxamide:5-Methylisoxazole~4-carboxylic acid 25.0 g (0.197 mol) was taken in toluene (312.5 ml), heated to reflux arid 62.5 ml toluene was distilled off. The solution was cooled to 25-30 0C. To this solution N, N-Dimethylformamide (0.16 ml) and thionyl chloride 25.68 g (0.216 mol) was added at 25-30 C and heated to 65 to 70 0C for 6 hours. Then the reaction mass was cooled to 0 0C and 4-trifluoromethylaniline 30.07 g (0.199 mol) was added drop wise at this temperature. The resulted reaction mixture was stirred at the same temperature for 2 hours, allowed to come to 25-30 0C and stirred for 4 hours. Water (125 ml) was added to the ' reaction mixture and stirred for 2 hours. The solid was separated out, which was filtered and washed with water (250 ml), dried under vacuum at 80 0C to obtain 40.25 g off white solid which was purified with toluene to give 33.15 g (62.34 percent) leflunomide with 99.9percent HPLC purity and any individual impurity less than 0.1percent. |