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CAS No. : | 178747-50-7 | MDL No. : | MFCD11846403 |
Formula : | C7H3ClFNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NXXMYNTVLHIRDD-UHFFFAOYSA-N |
M.W : | 171.56 | Pubchem ID : | 15453973 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 38.98 |
TPSA : | 26.03 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) : | -5.38 cm/s |
Log Po/w (iLOGP) : | 2.11 |
Log Po/w (XLOGP3) : | 2.77 |
Log Po/w (WLOGP) : | 3.04 |
Log Po/w (MLOGP) : | 2.42 |
Log Po/w (SILICOS-IT) : | 2.96 |
Consensus Log Po/w : | 2.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.25 |
Solubility : | 0.0955 mg/ml ; 0.000557 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.97 |
Solubility : | 0.183 mg/ml ; 0.00107 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.8 |
Solubility : | 0.0269 mg/ml ; 0.000157 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.48 |
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 |
---|---|---|
43% | With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 110.0℃; for 18.0h; | (Octahydro-quinazolin-3-yl)-methanol (5.42 g, 26.2 mmol), 1, 8-diazobicyclo [5.4. 0] - undec-7-ene (12.9 ML, 85 mmol), and <strong>[178747-50-7]3-chloro-5-fluoro-benzo[d]isoxazole</strong> (5.54 g, 32.3 MMOL) were dissolved in pyridine (16 ML), and then heated (110C) with stirring for 18 hours. 10% aqueous sodium bicarbonate and methylene chloride (250 ml of each) were added, and the mixture was vigorously stirred. The aqueous phase was then re-extracted with three 100 ml portions of fresh methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate) and concentrated in vacuo to an amorphous solid (4.88 g). Flash chromatography of the entire sample (silica gel, 47-61 micron mesh; elution with methanol/methylene chloride = 6.94 in volume) afforded the title compound (3.46 g, 43% yield) as an amorphous solid. MS m/z 306 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | (a) 3-Chloro-5-fluoro-1,2-benzisoxazole. To a solution of 5-fluoro-3-hydroxyisoxazole (1.0 g) in pyridine (0.53 ml) was added phosphorus oxychloride (0.89 ml) and the mixture was refluxed for 8 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and the combined extracts were washed with saturated salt water and dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography, to give the title compound (0.85 g, 77%) as a colorless oil. | |
52% | Step 4 3-Chloro-5-fluoro-benzo[d]isoxazole To a mixture of the Step 3 title compound (1.68 g, 11 mmol) and phosphous oxychloride (2.46 ml, 26 mmol), pyridine (979 mul) was added. The resulting reaction mixture was heated at 100 C. for 18 hours. Cooled to ambient temperature, the mixture was cautiously added to water (15 ml). After 5 minutes of stirring, a solid precipitate formed, which was filtered. The filter cake was washed with water (5 ml and dried in vacuo, affording the title compound as a tan amorphous solid (973 mg, 52% yield). 1H NMR (400 MHz, CD3OD) delta7.50 (m, 2H), 7.72 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In pyridine; diethyl ether; dichloromethane; ethyl acetate; | The Step 4 title compound (dihydrochloride salt; 125 mg, 0.31 mmol), 1,8-diazabicyclo[5.4.0]-undec-7-ene (153 mul, 1.0 mmol), and <strong>[178747-50-7]3-chloro-5-fluoro-benzo[d]isoxazole</strong> (66 mg, 0.39 mmol) were dissolved in pyridine (150 mul). The reaction was heated at 90 C. for 18 hours. 10% aqueous sodium bicarbonate and methylene chloride (15 ml of each) were added to the well-stirred mixture. The aqueous phase was then re-extracted with three 15 ml portions of fresh methylene chloride. The combined organic extracts were dried (anhydrous sodium sulfate) and the solvent was removed in vacuo. Purification of the oily semi-solid residue (150 mg) by flash chromatography (silica gel, 47-61 micron mesh; elution with methanol/methylene chloride=7.5:92.5 in volume) afforded the tile compound (free base) as a colorless amorphous solid (57 mg. 36% yield). Dissolution of the entire sample in ethyl acetate/methylene chloride (1.0 ml of each), addition of a saturated diethyl ether solution of anhydrous hydrogen chloride (3 ml); and finally, solvent removal in vacuo afforded the title compound dihydrochloride as an amorphous solid. Free base data: 13C NMR (75 MHz, CDCl3) delta161.62, 160.91, 159.45, 158.45, 141.54, 129.55, 121.70, 118.44, 116.88, 115.28, 113.35, 111.73, 107.76, 71.26, 61.21, 60.55, 59.20, 54.68, 54.60, 54.12, 48.71, 36.88, 29.43, 27.37, 23.90 ppm; MS m/z 465 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In N-methyl-acetamide; | (b) 3-(2-(N-t-Butoxycarbonylamino)ethylthio)-5-fluoro-1,2-benzisoxazole. To a solution of <strong>[178747-50-7]3-chloro-5-fluoro-1,2-benzisoxazole</strong> (0.83 g) in dimethylformamide (8 ml) was added 2-t-butoxycarbonylaminoethanethiol (0.86 g) and potassium carbonate (0.67 g) with stirring under nitrogen atmosphere, and the mixture was then stirred at 80 C. for 3 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate and the combined extracts were washed with brine and dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography, to give the title compound (1.21 g, 80%) as a colorless powder. NMR spectrum(CDCl3)deltappm: 1.44(9H,s), 3.41(2H,t,J=6.2 Hz), 3.58(2H,td,J=6.2 Hz,J=6.2 Hz), 4.98(1H,brs), 7.21-7.51(3H,m). |
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