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Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
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* Storage: {[proInfo.prStorage]}
CAS No. : | 101023-70-5 | MDL No. : | MFCD09831992 |
Formula : | C9H8ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 213.62 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1,8 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 | UN#: | 2928 |
Hazard Statements: | H301-H311-H314-H331 | Packing Group: | Ⅱ |
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 |
---|---|---|
85% | With copper(ll) sulfate pentahydrate; potassium carbonate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20℃; for 5.0h;Inert atmosphere; | To a solution of <strong>[101023-70-5]methyl 4-(chloro(hydroxyimino)methyl)benzoate</strong> 7 (1.0 g, 0.0046 mol) and 1-ethynyl-4-(pentyloxy)benzene 11 (1.05 g, 0.005 mol ) in t-butanol/water (1:1, 20 mL), potassium carbonate (2.77 g 0.020 mmol), CuSO4.5H2O (50 mg, 5 mol%), sodium ascorbate (250 mg, 25 mol%) were added at rt for 5h. After completion of starting material, reaction mixture was cooled to rt, filtered on celite bed and solvent was evaporated at reduced pressure to obtained the crude product which was dissolved in water (20 mL) and extracted with dichloromethane (2 × 10 mL). The organic layer was separated, washed with brine and dried over Na2SO4. Evaporation of the solvent gave the residue, which was recrystallised in acetonitrile, and dried under vacuum to give 12 as a white solid (1.43 g, 85% of yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-chloro-succinimide; In chloroform; at 20℃; for 4.0h; | To a solution of compound, 37-d, (2.0 g, 1 1 .2 mmol) in chloroform (30 mL) was added N-chlorosuccinimide (NCS, 1 .78 g, 13.4 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with dichloromethane (200 mL), washed with water, dried with anhydrous Na2S04, filtrated and concentrated in vacuo to provide compound, 37-e, (2.30 g, 96%) |
96% | With N-chloro-succinimide; In chloroform-d1; at 20℃; for 4.0h; | Step C: Methyl 4-(chloro(hydroxyimino)methyl)benzoate (37-e) 37-d 37-e To a solution of compound, 37-d, (2.0 g, 1 1.2 mmol) in chloroform (30 mL) was added N-chlorosuccinimide (NCS, 1.78 g, 13.4 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with dichloromethane (200 mL), washed with water, dried with anhydrous Na2S04, filtrated and concentrated in vacuo to provide compound, 37-e, (2.30 g, 96%). |
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 6.0h; | General procedure: To a mixture of aldehyde derivative (8.0 mmol, 1.0 equiv) and hydroxylamine hydrochloride (8.0 mmol, 1.0 equiv) in THF-H2O (20 mL, 1:1v/v) at 0 C, NaOH (8.0 mmol, 1.0 equiv) was added and the mixture and stirred for 10 min. Upon completion of the reaction, the organic phase was removed under vacuum and H2O (10 mL) was added. The aqueous phase was extracted with EtOAc (3 × 10 mL) and the combined organic phase was washed with brine, dried over Na2SO4, and removed under vacuum to afford the crude product, which was directly used for the next step without purification. The crude product was added into a mixture of NCS (8.4 mmol, 1.05 equiv) in DMF (20 mL) at r.t. and the mixture was stirred for 6 h. Upon completion of the reaction, the organic phase was removed under vacuum and H2O (10 mL) was added. The aqueous phase was extracted with EtOAc (3 × 30 mL) and the combined organic phase was washed with brine, dried over Na2SO4, and removed under vacuum to afford the crude product, which was directly used for the next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 2.0h; | Methyl 4-formylbenzoate 5 (0.750 g, 0.004 mol) was added to the solution of hydroxylamine hydrochloride (0.349 g, 0.005 mol) in t-BuOH:H2O (1:1, 28 mL). NaOH (0.201 g, 0.005 mol) was added to the reaction mixture, and stirred for 2h at ambient temperature. TLC analysis indicated oxime formation complete. Chloramine-T trihydrate (1.14 g, 0.005 mmol) was added in small portions over 15 min. followed by CuSO4.5H2O (0.022 g, 0.00009 mol) and cat. copper powder (0.0142 g, 0.00016 moles). 1-ethynyl-4-(pentyloxy)benzene 11 (0.945 g, 0.005 mol) was added to this reaction mixture. pH of the reaction was adjusted to 7.5 by addition of a few drops of 1M NaOH and further stirred for 16h. The reaction mixture was poured into ice cold water (50 mL) and aq. NH4OH (10 mL). Obtained copper salts were filtered on celite bed and washed with dichloromethane (100 mL). The layers were separated and the aq. layer was extracted with dichloromethane (3 x 100 mL), washed with brine (1 x 25 mL),dried over anhy. Na2SO4 and filtered. Evaporation of solvent under reduced pressure gave the crude product, which was dissolved in DCM (50 mL) and added to (400 mL) of Hexane, while stirring for 15 min. Solid obtained was filtered, washed with hexane (300 mL) and dried to furnish methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate 12 as off-white solid (0.830 g, 50% yield). 1H NMR (400 MHz, CDCl3); delta 8.16 (d, J = 8.4 Hz, 2H, H-3 & H-3?), 7.95 (d, J = 8.4 Hz, 2H, H-4 & H-4?), 7.78 (d, J = 8.4 Hz, 2H, H-10 & H-10?), 7.0 (d, J = 8.8 Hz, 2H, H-11 & H-11?), 6.75 (s, 1H, H-7), 4.03 (t, J = 6.8 Hz, 2H, H-13), 3.96 (s, 3H, H-18), 1.85-1.80 (m, 2H, H-14), 1.50-1.38 (m, 4H, H-15 & H-16), 0.96 (t, J = 7.2 Hz, 3H, H-17); 13C NMR (100 MHz, CDCl3); delta 170.9 (C-1), 166.5 (C-8), 162.0 (C-6), 160.9 (C-12), 133.5 (C-5), 131.2 (C-2), 130.1 (C-3 & C-3?), 127.4 (C-4 & C-4?), 126.7 (C-10 & C-10?), 119.7 (C-9), 114.9 (C-11 & C-11?), 96.0 (C-7), 68.2 (C-18), 52.2 (C-13), 28.8 (C-14), 28.1 (C-15), 22.4 (C-16), 13.9 (C-17); Mass (ESI) m/z = 366.2 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With triethylamine; In tetrahydrofuran; at 20℃; | To a mixture of compound 37-e (517 mg, 2.43 mmol), compound 37-j (700 mg,2.21 mmol) in THF (5 mL) was added triethylamine (335 mg, 3.31 mmol) dropwise. The mixture was stirred overnight at room temperature. The residue obtained from removal of the solvent was purified by flash chromatography (PE:EA = 1 :2) to afford compound 37-k (420 mg, 38%) as a yellow solid. 1H NMR (300 MHz, CDCI3) delta 8.786 (s, 1H), 8.753-8.731 (d, J= 6.6 Hz, 1H), 8.172-8.144 (d, J= 8.4 Hz, 2H), 8.004-7.976 (d, J= 8.4 Hz, 2H), 7.838-7.806 (m, 1H ), 7.645 (s, 1H), 7.615 (s, 1H), 7.495-7.470 (s, 1H), 6.875-6.846 (d, J= 8.7 Hz, 2H), 6.697-6.668 (d, J= 8.7 Hz, 2H), 5.786 (s, 2H), 3.960 (s, 3H), 3.723 (s, 3H), LC-MS (ESI): 495 [M+H]+. |
38% | With triethylamine; In tetrahydrofuran; at 20℃; | Step H: Methyl 4-(5-(4-(4-methoxybenzyloxy -2-(pyridin-2-ynpyrimidin-5-yl)isoxazol-3- yPbenzoate (37-k) To a mixture of compound 37-e (517 mg, 2.43 mmol), compound 37-j (700 mg, 2.21 mmol) in THF (5 mL) was added triethylamine (335 mg, 3.31 mmol) dropwise. The mixture was stirred overnight at room temperature. The residue obtained from removal of the solvent was purified by flash chromatography (PE:EA = 1 :2) to afford compound 37-k (420 mg, 38%) as a yellow solid. NMR (300 MHz, CDCI3) delta 8.786 (s, 1H), 8.753-8.731 (d, J= 6.6 Hz, 1H), 8.172-8.144 (d, J= 8.4 Hz, 2H), 8.004-7.976 (d, J= 8.4 Hz, 2H), 7.838-7.806 (m, 1H ), 7.645 (s, 1H), 7.615 (s, 1H), 7.495-7.470 (s, 1H), 6.875-6.846 (d, J= 8.7 Hz, 2H), 6.697-6.668 (d, J= 8.7 Hz, 2H), 5.786 (s, 2H), 3.960 (s, 3H), 3.723 (s, 3H), LC-MS (ESI): 495 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
780 mg | With triethylamine; In tetrahydrofuran; at 20℃; for 12.0h; | A mixture of compound 38-e (750 mg, 2.8 mmol), compound 37-j (820 mg, 2.6 mmol) and triethylamine (780 mg, 7.8 mmol) in THF (20 mL) was stirred at room temperature for 12 h. Tthe resulting mixture was concentrated under reduce pressure, purified by column chromatography on silica gel (DCM:MeOH=30: l) to give compound 38-f (780 mg ). LC-MS 543[M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine; In dichloromethane; at 0 - 20℃; for 12.0h; | General procedure: To a solution of hydroximoyl chloride 8aeg (0.21 mmol) andartemisitene 7 (0.2 mmol) in CH2Cl2 (3 mL) was added Et3N(0.25 mmol) at 0 C. The resulting mixture was stirred at roomtemperature for 12 h. The solvent was evaporated in vacuo and theresidue was purified via silica column chromatography with petroleumether/ethyl acetate (3:1) as eluent to provide compounds9a-g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40%; 43% | With sodium hydrogencarbonate; In ethyl acetate; for 72.0h; | General procedure: To a solution of alkene (±)-10 (500 mg, 2.18 mmol) in EtOAc (10 mL) was added chloro oximes 11-13 (930 mg, 4.36 mmol) and solid NaHCO3 (916 mg, 10.9 mmol). The mixture was vigorously stirred for 72 h and the progress of the reaction was followed by TLC (cyclohexane/EtOAc 85:15). Water was added and the organic phase was separated, dried over anhydrous Na2SO4 and evaporated. The crude material obtained was purified by column chromatography on silica gel to separate the diastereoisomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With copper(l) iodide; potassium carbonate; In diethyl ether; at 20℃; for 6.0h; | General procedure: A mixture of 1-iodo-2-(prop-2-yn-1-yloxy)benzene derivative 7 (0.5 mmol, 1.0 equiv), N-hydroxy-4-methylbenzimidoyl chloride derivative 8 (0.525 mmol, 1.05 equiv), CuI (0.01 mmol, 2% equiv), and potassium carbonate (1.0 mmol, 2.0 equiv) in Et2O (1 mL) was stirred at r.t. for 6 h. Upon completion of the reaction, the organic phase was removed under vacuum and H2O (10 mL) was added. The aqueous phase was extracted with EtOAc (3 × 3 mL) and the combined organic phase was washed with brine, dried over Na2SO4, and removed under vacuum. The residue was purified by column chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; for 16h;Reflux; | General procedure: N-Chlorosuccinimide (1.10 g, 8.26 mmol) was added to a mixture of compound 4a (1.41 g, 7.87 mmol) in DMF (35 mL) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water at room temperature and extracted with Et2O. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. Triethylamine (0.96 g, 9.44 mmol) was addedto a mixture of the residue and <strong>[934664-41-2]tert-butyl 3-methyleneazetidine-1-carboxylate</strong> (1.59 g, 9.39 mmol) in THF (30 mL) at room temperature.The mixture was refluxed for 16 h. The mixture wasquenched with saturated aqueous NaHCO3 solution at room temperatureand extracted with AcOEt. The organic layer was separated,washed with water and brine, dried over MgSO4 andconcentrated under reduced pressure. The residue was purifiedby silica gel column chromatography (hexane/AcOEt = 75/25 to20/80) to give a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-chloro-succinimide; In N,N-dimethyl-formamide; at 20℃; for 1.0h; | General procedure: N-Chlorosuccinimide (1.10 g, 8.26 mmol) was added to a mixture of compound 4a (1.41 g, 7.87 mmol) in DMF (35 mL) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water at room temperature and extracted with Et2O. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. |
Tags: 101023-70-5 synthesis path| 101023-70-5 SDS| 101023-70-5 COA| 101023-70-5 purity| 101023-70-5 application| 101023-70-5 NMR| 101023-70-5 COA| 101023-70-5 structure
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Code | Phrase |
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P378 | |
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P391 | Collect spillage. Hazardous to the aquatic environment |
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Code | Phrase |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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Health hazards | |
Code | Phrase |
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H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
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H305 | May be harmful if swallowed and enters airways |
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H311 | Toxic in contact with skin |
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H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
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H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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