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CAS No. : | 28910-83-0 | MDL No. : | MFCD06659048 |
Formula : | C13H8ClF2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DUMGVPIXKALANS-UHFFFAOYSA-N |
M.W : | 267.66 | Pubchem ID : | 15563835 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 65.65 |
TPSA : | 43.09 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) : | -5.12 cm/s |
Log Po/w (iLOGP) : | 2.03 |
Log Po/w (XLOGP3) : | 3.96 |
Log Po/w (WLOGP) : | 4.28 |
Log Po/w (MLOGP) : | 3.66 |
Log Po/w (SILICOS-IT) : | 4.11 |
Consensus Log Po/w : | 3.61 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.36 |
Solubility : | 0.0118 mg/ml ; 0.0000441 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.57 |
Solubility : | 0.00728 mg/ml ; 0.0000272 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.68 |
Solubility : | 0.000559 mg/ml ; 0.00000209 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.03 |
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 |
---|---|---|
100% | Stage #1: With trifluoroacetic acid In dichloromethane for 1 h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate |
The N-Boc-aminobenzophenone was dissolved in dry CH2Cl2 (50 mL) and trifluoroacetic acid (50 mL) was added. After stirring for 1 h, the solution was evaporated to dryness in vacuo. The resulting residue was dissolved in EtOAc (100 mL) and water (100 mL) containing NaHCO3. The organic portion was washed with a saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated to dryness in vacuo to provide, quantitatively, 1aa MS m/z=268 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water; ethyl acetate at 0 - 5℃; for 0.833333 h; Stage #2: With iodine; potassium iodide In water; ethyl acetate at 20℃; for 1 h; |
(5-Chloro-2-iodo-phenyl)-(2,6-difluoro-phenyl)-methanone (2aa) Method G: (2-Amino-5-chloro-phenyl)-(2,6-difluoro-phenyl)-methanone (1aa) (2.6 g, 9.7 mmol) was dissolved in acetic acid (10 mL) and concentrated HCl (4 mL) and the solution was cooled to 0° C. A solution of NaNO2 (0.7 g, 10.7 mmol) in H2O (6 mL) was added dropwise so as to maintain a temperature of between 0-5° C. Following this addition, the reaction mixture was stirred at 0° C. for 30 min. Cold EtOAc (20 mL) was added dropwise and the solution was stirred for 20 min. Iodine (1.5 g, 5.8 mmol) and potassium iodide (1.9 g, 11.6 mmol) in H2O (10 mL) were added dropwise and the mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with EtOAc (200 mL) and washed with saturated aqueous sodium thiosulfate (4.x.100 mL). The combined aqueous portions were extracted with EtOAc (3.x.50 mL). The combined organic portions were then washed with a saturated aqueous NaHCO3 solution (3.x.50 mL), H2O (2.x.50 mL), dried over Na2SO4, filtered and evaporated in vacuo to afford 2aa (3.3 g, 90percent) as a light yellow solid. |
80% | Stage #1: With hydrogenchloride In water; acetic acid at 20 - 25℃; for 0.5 h; Stage #2: With sodium nitrite In water; acetic acid at 0 - 5℃; for 1 h; Stage #3: With potassium iodide In Isopropyl acetate; water; acetic acid at 0 - 25℃; for 3 h; |
(5-chloro-2-iodophenyl) (2 ,6-difluorophen Dmethanone (2)[0147] Into a reactor at room temperature was added (2-amino-5-chlorophenyl)(2,6- difluorophenyl)methanone (1, 60.0kg, 224mol) and acetic acid (427L). The mixture was stirred until all solids fully dissolved, filtered and washed with acetic acid (9.47L). Concentrated HC1 (156L) was added over a minimum of 30 minutes at 20 to 25 °C and the resulting mixture was cooled to 0 to 5 °C. A solution of sodium nitrite (18.6kg, 269mol) in water (88.0L) was added while maintaining the reaction temperature between 0 and 5 °C. The mixture was stirred for lh at 0 to 5 °C. Water (270L) and isopropyl acetate (717L) were then added at 0 to 5 °C. A solution of potassium iodide (50.2kg, 303mol) in water (133L) was added over 1 h at 0 to 5 °C. The reaction mixture was stirred for 30min and warmed to 20 to 25 °C over 1.5h. The layers were separated and the organic phase was washed with a dilute brine solution (22kg NaCl in 200L water) and a sodium carbonate solution (175kg Na2CC>3 in 523L water). The resulting organic layer was washed twice with a sodium ascorbate solution (15.8kg in 188L water for each wash) followed by water (200L). The organic phase was concentrated using a maximum 50 °C jacket temperature until 430L of solvent was removed. Heptane (400L) was added and the mixture was concentrated using a 50 °C jacket temperature until 395L of solvent were removed. 2- Butanol (398L) was added and the mixture was concentrated using a maximum 60 °C jacket temperature until 322L of solvent were removed. An additional portion of 2-butanol (398L) was added and the mixture was concentrated using a 70 °C jacket temperature until 390L of solvent were removed. The reaction mixture was cooled to -5 to -8 °C, stirred for 2h, filtered and washed with 2-butanol (2 x 84.2L) at -5 to 0 °C. The resulting wet cake was dried at 40 to 50 °C under vacuum to provide 67.6kg (80percent yield) of 2. NMR (300 MHz, CDCL) δ 7.89 (d, J=8.2 Hz, IH), 7.51 (m, IH), 7.44 (d, J=2.3 Hz, IH), 7.18 (dd, J=2.3, 8.2 Hz, IH), 7.00 (m, 2H); Elemental Anal. Calcd. for C13H6ClF2IO: C, 41.25; H, 1.60; CI, 9.37; F, 10.04; I, 33.52; O, 4.23. Found: C,41.36; H, 1.65; CI, 9.51; F, 10.03; 1, 33.41; 0, 4.04. |
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