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CAS No. : | 886497-85-4 | MDL No. : | MFCD04115887 |
Formula : | C8H4F4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CSMVUVGPLMTFIZ-UHFFFAOYSA-N |
M.W : | 224.11 | Pubchem ID : | 3852520 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.04 |
TPSA : | 46.53 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) : | -5.43 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 3.15 |
Log Po/w (WLOGP) : | 4.1 |
Log Po/w (MLOGP) : | 2.21 |
Log Po/w (SILICOS-IT) : | 2.27 |
Consensus Log Po/w : | 2.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.31 |
Solubility : | 0.109 mg/ml ; 0.000488 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.8 |
Solubility : | 0.0358 mg/ml ; 0.00016 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.69 |
Solubility : | 0.463 mg/ml ; 0.00207 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
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 |
---|---|---|
65% | With triethylamine; HATU; In dichloromethane; at 20℃; | Example 6 Preparation of 2-fluoro-N-(2-oxo-1,2-dihydropyridin-4-yl)-5-(trifluoromethoxy)benzamide A solution of <strong>[886497-85-4]2-fluoro-5-(trifluoromethoxy)benzoic acid</strong> (5.3 g, 23.47 mmol), HATU (8.92 g, 23.47 mmol), 2-methoxypyridin-4-amine (2.9 g, 23.47 mmol) and Et3N (13.09 mL, 93.88 mmol) in dichloromethane (47.4 mL) was stirred at room temperature overnight. The crude mixture was purified by column chromatography eluting with a gradient of ethyl acetate in hexanes (0-50%) to yield 2-fluoro-N-(2-methoxy-4-pyridyl)-5-(trifluoromethoxy)benzamide (5.03 g, 65%) as a white solid. ESI-MS m/z calc. 330.06, found 331.1 (M+1)+; Retention time: 1.48 minutes (3 minutes run). 1H NMR (400 MHz, DMSO-d6) delta 10.90 (s, 1H), 8.10 (m, 1H), 7.73 (dd, J=5.1, 3.2 Hz, 1H), 7.66 (m, 1H), 7.55 (t, J=9.2 Hz, 1H), 7.21 (dd, J=3.7, 1.8 Hz, 2H), 3.84 (s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine; HATU; In dichloromethane; at 20℃; for 2.0h; | (R)-Benzyl-2-(2-fluoro-5-(trifluoromethoxy)benzamido)-3-methylbutanoate To a suspension of <strong>[886497-85-4]2-fluoro-5-(trifluoromethoxy)benzoic acid</strong> (30 g, 134 mmol) in dichloromethane (400 mL) was added (ft)-benzyl-2-amino-3-methylbutanoate hydrochloride (34 g, 147 mmol), 1 - [bis(dimethylamino)methylene]-1 A7-1 ,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate (HATU) (76 g, 201 mmol) and triethylamine (27.1 g, 268 mmol). The resulting mixture was stirred for 2 hours at room temperature before the reaction was quenched with ice-water (500 mL). The mixture was extracted with ethyl acetate (3 chi 300 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate : petroleum ether = 1 :1 to afford (R)-benzyl-2-(2-fluoro-5- (trifluoromethoxy)benzamido)-3-methylbutanoate as a white solid (54 g, 97%). LCMS (ESI): m/z = 414.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; hexane; toluene; at 0 - 20℃; for 3.0h; | Preparation of methyl 2-fluoro-5-(trifluoromethoxy) benzoate: to a solution of <strong>[886497-85-4]2-fluoro-5-(trifluoromethoxy)benzoic acid</strong> (1 g ,4.464 mmol,l eq) in MeOH: Toluene(l : l) (10 mL) added TMS diazomethane (2M in Hexane) (2.63 mL, 5.35 mmol, 1.2 eq) at 0 C and stirred at RT for 3 h. After completion, the solvent was evaporated under reduced pressure to get methyl 2-fluoro-5-(trifluoromethoxy) benzoate (1 g crude) as a pale yellow liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | 1A: N-((5-Bromo-2-methylpyridin-3-yl)methyl)-2-fluoro-5-(trifluoromethoxy)benzamide : A mixture of (5-bromo-2-methylpyridin-3-yl)methanamine (100 mg, 0.497 mmol), BOP (330 mg, 0.746 mmol) <strong>[886497-85-4]2-fluoro-5-(trifluoromethoxy)benzoic acid</strong> (123 mg, 0.547 mmol) and Hunig's Base (0.434 mL, 2.487 mmol) in DMF (3 mL) was stirred at rt ON. The reaction mixture was diluted to 75 mL with ethyl acetate, then washed 10% aqueous LiCl and brine. The organics were dried over anhydrous sodium sulfate, filtered and concentrated. The crude residue was purified by column chomatography on the Isco system (24 g, 0-100% EtO Ac/Hex) to afford N-((5-bromo-2-methylpyridin-3-yl)methyl)-2-fluoi-5-(trifluoromethoxy)benzamide (184 mg, 0.429 mmol, 86 % yield). MSESI m/z 407.0 (M+H) |
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