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CAS No. : | 99455-15-9 | MDL No. : | MFCD06738671 |
Formula : | C9H5BrClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MOEWRAKNXMILKB-UHFFFAOYSA-N |
M.W : | 242.50 | Pubchem ID : | 14221034 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.45 |
TPSA : | 12.89 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) : | -5.05 cm/s |
Log Po/w (iLOGP) : | 2.4 |
Log Po/w (XLOGP3) : | 3.84 |
Log Po/w (WLOGP) : | 3.65 |
Log Po/w (MLOGP) : | 3.12 |
Log Po/w (SILICOS-IT) : | 3.76 |
Consensus Log Po/w : | 3.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.38 |
Solubility : | 0.0101 mg/ml ; 0.0000417 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.81 |
Solubility : | 0.0378 mg/ml ; 0.000156 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.17 |
Solubility : | 0.00162 mg/ml ; 0.00000668 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.79 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
78.8% | Stage #1: With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 2 h; Heating / reflux |
Example 6 Preparation of Compound of Formula (VIII): 7-Bromo-2-chloroquinoline. An inerted reactor equipped with a mechanical stirrer, a reflux condenser, an addition funnel and caustic scrubber was charged with 7-bromo-2-hydroxyquinoline (1.22 Kg, 5.45 mole), dichloromethane (9.706 Kg), and dimethylformamide (0.276 Kg) followed by a slow addition of thionyl chloride (0.973 Kg, 8.17 mole, 1.5 equiv.). The reaction mixture was then gradually heated to reflux. The reflux was continued until solution is achieved (about 2 hours). The reaction mixture was then cooled to 20 to 25°C, and USP purified water (3.663 Kg) was added and stirred. Then to the reactor was gradually added with stirring a solution of potassium carbonate (0.828 Kg) in USP purified water (0.828 Kg). After 15 minutes, the stirring was stopped and the layers were allowed to separate. The pH of aqueous layer was confirmed greater than 7. The dichloromethane solution was separated and washed with USP purified water (3.663 Kg). USP purified water (7.326 Kg) was then added to the dichloromethane solution, and the dichloromethane was distilled off until the product precipitated out of the aqueous layer. The reactor was cooled to 20 to 25°C. The product was filtered and washed USP purified water (2 x 1.22 Kg). The product was dried in a vacuum oven at 40 to 5O0C to obtain 1.154 Kg of desired product. Yield: 78.8percent. NMR: Compatible with product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | for 16 h; Reflux | This compound was prepared from 7-bromo-2-chloroquinoline(2) in 98percent yield as described for compound 1; Mp 68-69 °C; 1HNMR (300 MHz, CDCl3): δ 8.05 (d, 1H, 1.8 Hz), 7.93 (d, 1H, 8.7 Hz),7.57 (d, 1H, 9.0 Hz), 7.47 (dd, 1H, 8.7 Hz and 1.8 Hz), 6.91 (d, 1H,9.0 Hz), 4.00 (s, 3H); MS (APCI, pos. 30 V) m/z: [M+H]+, 239.06. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydrogenchloride In 1,4-dioxane; water for 2 h; Reflux | A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) was heated at reflux for 2 h. The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93percent). 1H NMR (400 MHz, DMSO-d6): δ 11.80 (s, 1H), 7.91 (d, 1H), 7.63 (d, 1H), 7.48 (d, 1H), 7.34 (dd, 1H), 6.53 (d, 1H). |
93% | With hydrogenchloride In 1,4-dioxane; water for 2 h; Reflux | A stirred solution mixture of 7-bromo-2-chloroquinoline (5.0 g, 20.6 mmol) in 5 M aqueous hydrochloric acid (133 mL) and 1,4-dioxane (14 mL) was heated at reflux for 2 h. The reaction was cooled and the resulting precipitate was collected by filtration and washed with water to afford the subtitled compound as a colourless solid (4.3 g, 93percent). 1H NMR (400 MHz, DMSO-d6): δ 11.80 (s, 1H), 7.91 (d, 1H), 7.63 (d, 1H), 7.48 (d, 1H), 7.34 (dd, 1H), 6.53 (d, 1H). |
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