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CAS No. : | 22235-25-2 | MDL No. : | MFCD00625827 |
Formula : | C9H8F3NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UOVPHHSFTNRQHJ-UHFFFAOYSA-N |
M.W : | 219.16 | Pubchem ID : | 4026781 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.13 |
TPSA : | 52.32 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) : | -6.23 cm/s |
Log Po/w (iLOGP) : | 1.87 |
Log Po/w (XLOGP3) : | 1.98 |
Log Po/w (WLOGP) : | 3.23 |
Log Po/w (MLOGP) : | 2.36 |
Log Po/w (SILICOS-IT) : | 2.05 |
Consensus Log Po/w : | 2.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.54 |
Solubility : | 0.626 mg/ml ; 0.00286 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.7 |
Solubility : | 0.433 mg/ml ; 0.00197 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.01 |
Solubility : | 0.215 mg/ml ; 0.000979 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
98% | With tin(II) chloride dihdyrate; water In methanol at 70℃; for 2 h; | To a mixture of methyl 3-nitro-5- (trifluoromethyl)benzoate (350 mg, 1.40 mmol) and tin(II) chloride dihydrate (1.58 g, 7.02 mmol) in methanol (20 mL) was added water (1 mL) and the resulting mixture was stirred at 70 °C for 2 h. After cooling to room temperature, the reaction mixture was concentrated and was quenched by the addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (3X). The combined organic portion was dried over magnesium sulfate, was filtered and was concentrated to give methyl 3-amino-5- (trifluoromethyl)benzoate (300 mg, 98percent yield) as a colorless solid. XH NMR (400 MHz,CDCI3): δ 7.65 (s, 1H), 7.48 (s, 1H), 7.05 (s, 1H), 3.99 (br s, 2H), 3.91 (s, 3H). |
96% | With hydrogen In methanol at 20℃; for 3 h; | To a solution of methyl 3-nitro-5-(trifluoromethyl) benzoate (1.50 g, 6.02 mmol) in methanol (20 . mL) was added palladium carbon (50percent water-containing product,15 mg) , and the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hr. The reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure and dried to give the title compound(1.27 g, 96percent) as a white solid.1H-NMR (DMSO-d6, 300 MHz) δ 3.85 (3H, s) , 5.94 (2H, s) , 7.08 (IH, s), 7.26 (IH, s), 7.42 (IH, s) . |
95% | With hydrogen In ethanol at 20℃; for 1 h; | Reference Example 28 Methyl 3-amino-5-(trifluoromethyl)benzoate A solution of methyl 3-nitro-5-(trifluoromethyl)benzoate (Reference Example 27, 24.6 g, 98.9 mmol) in ethanol (1500 mL) was sparged in a Parr bottle with nitrogen for 10 min. After this time, 10 wt percent Pd/C (5.0 g, 5.0 mmol) was added and the reaction mixture was subjected to 40 psi of hydrogen on Parr shaker at room temperature for 1 h. After this time, the reaction mixture was filtered through a pad of celite and concentrated under reduced pressure to provide Methyl 3-amino-5-(trifluoromethyl)benzoate (20.6 g, 95percent) as a light purple oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.92 (s, 3H), 4.02 (br s, 2H), 7.05 (s, 1H), 7.48 (s, 1H), 7.64 (s, 1H). |
86% | With hydrogen In methanol | Methyl 3-amino-5-(trifluoromethyl)benzoate. Methyl 3-nitro-5-(trifluoromethyl)benzoate (9.0 g, 36.1 mmol) in methanol (30 mL) was flushed with nitrogen, and treated with palladium (10percent on charcoal, 0.90 g). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Flash chromatography on silica gel (30percent ethyl acetate/hexanes) afforded 6.8 g (86percent). 1H-NMR (CDCl3, 500 MHz) δ 7.64 (s, H), 7.49 (s, 1H), 7.05 (s, 1H), 3.91 (s, 3H). Mass spec.: 220.05 (MH)+. |
74% | Stage #1: With tin(ll) chloride In ethanol at 60℃; for 4 h; |
A solution of 3-nitro-5-trifluoromethyl-benzoic acid methyl ester (8.6 mmol, 2.15 g) and tin chloride dihydrate (25.8 mmol, 5.82 in ethanol (40 ml) is allowed to warm to 60 0C and stir for 4 hours. The mixture is cooled to room temperature, then concentrated under reduced pressure. The obtained residue is neutralized with saturated aq. NaHCO3. The mixture is filtered and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give 3-amino-5- trifluoromethyl-benzoic acid methyl ester (74percent, 1.4 g); ESI-MS m/z: 220 [M+1]\\ Retention time 1.81 min (condition A). |
0.85 g | With 10% palladium on activated charcoal; hydrogen In methanol at 20℃; for 3 h; | (Reference Example 28) Synthesis of methyl 3-amino-5-(trifluoromethyl)benzoate: A solution of 3-nitro-5-(trifluoromethyl)benzoic acid (1.0 g, 4.2 mmol) and p-toluenesulfonic acid (0.05 g) in methanol was stirred while heating under reflux for eight hours. The obtained solution was returned to room temperature and then concentrated under vacuum. The obtained residue was dissolved in methanol, palladium (5.0percent by weight) on carbon (containing 50percent water by weight, 0.2 g) was added thereto, and the obtained solution was stirred at room temperature for three hours under hydrogen atmosphere. The reaction mixture was filtered through Celite® and the filtrate was concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1, Rf = 0.47) to obtain the title compound (0.85 g, 91percent) (hereinafter referred to as the compound of Reference Example 28) as an oily substance. MS(ESI) [M + H]+: 220. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.85 g | Stage #1: for 15 h; Reflux Stage #2: With 10% palladium on activated carbon; Degussa type; hydrogen In methanol; water for 1 h; |
To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (1.0 g, 4.25 mmol) in methanol, a catalyst amount of p-toluenesulfonic acid was added, and the obtained solution was heated under reflux for 15 hours. The obtained reaction liquid was returned to room temperature and then concentrated to the half of the original volume. Palladium (10percent by weight) on carbon (containing 50percent water by weight, 0.062 g) was added to the reaction liquid, and the obtained solution was stirred for one hour under hydrogen atmosphere. The reaction liquid was filtered through Celite®, the filtrate was concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent; hexane:ethyl acetate = 90:10 → 60:40) to obtain the title compound (0.85 g). MS(ESI) [M + H]+: 221. |
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