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CAS No. : | 206055-91-6 | MDL No. : | MFCD06656791 |
Formula : | C10H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CBTFIJPSRUYXHW-UHFFFAOYSA-N |
M.W : | 254.08 | Pubchem ID : | 11032412 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.77 |
TPSA : | 46.26 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) : | -6.52 cm/s |
Log Po/w (iLOGP) : | 2.38 |
Log Po/w (XLOGP3) : | 1.87 |
Log Po/w (WLOGP) : | 2.44 |
Log Po/w (MLOGP) : | 1.59 |
Log Po/w (SILICOS-IT) : | 2.92 |
Consensus Log Po/w : | 2.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.04 |
Solubility : | 0.23 mg/ml ; 0.000906 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.875 mg/ml ; 0.00344 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.44 |
Solubility : | 0.00918 mg/ml ; 0.0000361 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
69% | With triethylamine In dichloromethane at 20℃; for 1.5 h; | -bromo-N-hydroxybenzimidoyl chloride (3.5 g, 14.9 mmol) synthesized in Step 2 of Preparation Example 6, propargyl alcohol (2.74 mL, 45 mmol) and triethylamine (Et3N, 7.7 mL) were added to methylene chloride (50 mL) and the reactants were stirred at room temperature for 1.5 hours. After completion of the reaction was confirmed by TLC, extraction was done with water (200 mL) and methylene chloride (500 mL). The organic layer was washed with water (100 mL.x.2) and brine (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound (3-(4-bromophenyl)isoxazol-5-yl)methanol (11e). Yield: 69percent.1H NMR (CDCl3, 400 MHz): 7.66 (d, 2H, J=2.4 Hz), 7.64 (d, 2H, J=1.6 Hz), 6.53 (s, 1H), and 4.81 (s, 2H). |
69% | With triethylamine In dichloromethane at 20℃; for 5 h; | Step 1: Preparation of (3-(4-bromophenyI)isoxazol-5-vI)methanoI (lie)4-bromo-N-hydroxybenzimidoyl chloride (3.5 g, 14.9 mmol) synthesized in Step 2 ofPreparation Example 6, propargyl alcohol (2.74 mL, 45 mmol) and triethylamine (Et3N, 7.7 rnL) were added to methylene chloride (50 rnL) and the reactants were stirred at room temperature for 1.5 hours. After completion of the reaction was confirmed by TLC, extraction was done with water (200 mL) and methylene chloride (500 mL). The organic layer was washed with water (100 mL X 2) and brine (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound (3-(4-bromophenyl)isoxazol-5- yl)methanol (1 Ie). Yield: 69percent.1H NMR(CDCl3, 400MHz): 7.66(d, 2H, J=2.4Hz), 7.64(d, 2H, J=I.6Hz), 6.53(s, IH)5 and 4.81(s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethylamine In dichloromethane at 0 - 20℃; for 12 h; | To a stirred solution of Z (500 mg, 2.132 mmol) in CH2CI2 (10 ml) was added propargyl alcohol (120 mg, 2.132 mmol) and followed by Et3N (0.34 ml 2.345 mmol) at 0 °C under inert atmosphere. The resulting reaction mixture was stirred for 12 h at RT. Progress of the reaction was monitored by TLC. The reaction mixture was then diluted with water and extracted with CH2CI2 (3x30 mL). The combined organic layer was washed with water, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude. The crude material was purified by silica gel column chromatography eluting with 15-20percent EtOAc/hexane as eluent to afford AA (400 mg, 1.57 mmol, 73percent) as a white solid. *H NMR (500 MHz, CDC13): 5 7.67 (d, / = 8.5 Hz, 2H), 7.59 (d, / = 8.5 Hz, 2H), 6.54 (s , 1H), 4.83 (d, / = 4.5 Hz, 2H), 2.13 (bs, 1H). LC-MS: m/z 252 [M-2] " at 3.28 min (95.08percent purity). |
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