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CAS No. : | 1374258-43-1 | MDL No. : | MFCD21602947 |
Formula : | C8H4BrF3N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YLMFTTBYMVQLMH-UHFFFAOYSA-N |
M.W : | 265.03 | Pubchem ID : | 67491372 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.8 |
TPSA : | 28.68 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) : | -5.69 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 3.13 |
Log Po/w (WLOGP) : | 4.5 |
Log Po/w (MLOGP) : | 2.9 |
Log Po/w (SILICOS-IT) : | 3.65 |
Consensus Log Po/w : | 3.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.86 |
Solubility : | 0.0362 mg/ml ; 0.000137 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.4 |
Solubility : | 0.105 mg/ml ; 0.000397 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.65 |
Solubility : | 0.00592 mg/ml ; 0.0000223 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.9 |
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 |
---|---|---|
57.5% | Stage #1: With potassium acetate; acetic anhydride In chloroform at 0 - 20℃; for 1 h; Stage #2: With tert.-butylnitrite In chloroform at 60℃; |
To a mixture of 133-S2(700 mg, 2.77 mmol) and potassium acetate (325.8 mg, 3.32 mmol) in CHC13 (20 mL) was addeddropwise acetic anhydride (846.6 mg, 8.30 mmol) at 0 °C. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was heated to 60 °C and tert-butyl nitrite (570.6 mg, 5.54 mmol) was added. After stirring overnight at 60 °C, the mixture was diluted with water and extracted with DCM twice. The combined organic layers were washed with brine, dried overanhydrous Na2SO4, and concentrated under reduced pressure. The remaining residue was dissolved in MeOH (5 mL) and 6 N HC1 (5 mL). The mixture was stirred at room temperature for 4 hours, basified with 10 N aqueous NaOH solution, and extracted with DCM twice. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel (PE/EtOAc= 10:1 to 3:1) to afford 133-S3 (420 mg, 57.5percent yield) as a yellow oil. LC/MS (ESI) m/z: 265 (M+H). |
52% | Stage #1: With potassium acetate; acetic acid In toluene for 0.25 h; Stage #2: With isopentyl nitrite In toluene at 20℃; for 18 h; |
To a solution of 4-bromo-2-methyl-6-(trifluoromethyl)aniline (3.3 g, 13 mmol) in toluene (65 mL) and glacial acetic acid (11.2 mL, 195 mmol) was added potassium acetate (10.2 g, 104 mmol) portionwise. After 15 minutes a large amount of precipitate had formed, hindering stirring of the reaction. The reaction was diluted with acetic acid (10 mL). Isoamyl nitrite (1.92 mL, 14.3 mmol) was then added dropwise and the reaction was stirred at room temperature for 3 hours. Additional isoamyl nitrite (0.5 mL, 3.7 mmol) was added and the reaction was left stirring for 15 hours. The reaction was diluted with water (100 mL) and stirred for 1.5 hours. The solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The layers were separated and the organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (5-50percent ethyl acetate/heptanes) gave the title compound (1.78 g, 52percent) as a yellow powder. -ESI (M-H+1) 264.9; 1H NMR (400 MHz, CDCl3, δ): 8.13 (s, 1 H), 8.09-8.11 (m, 1H), 7.76 (dd, J=1.66, 0.88 Hz, 1H). |
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