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CAS No. : | 179057-14-8 | MDL No. : | MFCD03012557 |
Formula : | C11H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LFNHUUMUCVZCGY-UHFFFAOYSA-N |
M.W : | 203.19 | Pubchem ID : | 1477779 |
Synonyms : |
|
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 |
---|---|---|
82% | With potassium carbonate In methanol for 3.5h; Heating; | |
81% | With potassium carbonate at 80℃; for 1.5h; | General procedure forthe formation of oxazole as illustrated by the synthesis of 5-(4-methoxyphenyl)oxazole (1) General procedure: To a solution of p-anisaldehyde (1.22 mL, 10.0 mmol) in MeOH (25 mL) were added K2CO3 (1.52 g, 11.0 mmol) and TosMIC (1.08 g, 5.50mmol). The reaction mixture was stirred for 1.5 h at 80° C, cooled down to rt, quenched with H2O, and diluted with EtOAc. After removal of the organic layer, the aqueous layer was extracted with EtOAc. The organic layer was combined, dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (3:1 hexanes/EtOAc) afforded 5-(4-methoxyphenyl)oxazole (1) (955 mg, 99%) as a pale yellow solid |
65% | With potassium carbonate In methanol for 3h; Inert atmosphere; Reflux; |
With sodium carbonate In methanol for 2h; Heating / reflux; | 101 4-Oxazol-5-yl-benzoic acid methyl ester; 4-Formyl-benzoic acid methyl ester (2 g, 11.2 mmol), toluenesulphonylmethyl isocyanide (TOSMIC, 2 g, 10.2 mmol) and anhydrous sodium carbonate (2 g, 18.8 mmol) were brought up in 50 ml_ of anhydrous methanol. The mixture was refluxed for 2 hours, allowed to cool to room temperature, then concentrated in-vacuo. The resulting residue was partitioned between EtOAc and saturated aqueous ammonium chloride. The organic fraction was washed one additional time with ammonium chloride and then once with brine. After drying over MgSO4,the organic fraction was concentrated under vacuum to dryness affording 1.48 g of 4-oxazol-5-yl-benzoic acid methyl ester as a yellow solid.1HNMR (CDCI3): 8.22 (d, J = 8.1 Hz1 2H), 7.97 (s, 1H), 7.74 (d, J = 6 Hz, 2H), 7.48 (s, 1 H), 3.94 (s, 3H). | |
Alkaline conditions; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Referential Example 20 [4-(1,3-Oxazol-5-yl)phenyl]methanol (37) A solution (2.08 mL) of lithium aluminum hydride (2.4 mole) in tetrahydrofuran was added dropwise under ice cooling to a solution of methyl 4-(1,3-oxazol-5-yl)benzoate (1.02 g) in tetrahydrofuran (20 mL), followed by stirring at 0C for 30 minutes. Hydrogen fluoride (840 mg) and water (270 µL) were added to the solution, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through flash column chromatography (n-hexane : ethyl acetate = 3 : 2), followed by concentration under reduced pressure, to thereby yield the title compound (321 mg). 1H-NMR(400MHz,CDCl3)δ:1.92(1H,s)4.73(2H,s)7.34(1H,s), 7.43(2H,d,J=8.3Hz),7.65(2H,d,J=8.3Hz),7.91(1H,s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With [(p-methylphenyl)sulfonylmethyl]isonitrile In acetonitrile at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h 3: toluene / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h 3: toluene / 5 h / Heating 4: NaBH4 / ethanol / a) 50 deg C, 1 h, b) RT, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 5 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 1 h, 2.) CH2Cl2, from -60 deg C to RT, 1 h 3: toluene / 5 h / Heating 4: NaBH4 / ethanol / a) 50 deg C, 1 h, b) RT, 2 h 5: 87 percent / CH2Cl2 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In methanol; ethyl acetate | 37.1 Synthesis of Ethyl 2-({2-[(5-nitro-(2-pyridyl))amino]ethyl}amino)-4-(4-(1,3-oxazol-5-yl)phenyl)pyrimidine-5-carboxylate Step 1: Methyl 4-formylbenzoate (Aldrich Chemical Co., St. Louis, Mo.) (5.0 g, 30.5 mmol), anhydrous potassium carbonate (4.55 g, 33 mmol) and p-toluenesulfonylmethyl isocyanide (TOSMIC, Aldrich Chemical Co.) (6.83 g, 30.5 mmol) were refluxed in methanol (100 ml) for 3.5 hours. The mixture was then concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate, washed twice with water, dried and concentrated in vacuo to give methyl 4-(1,3-oxazol-5-yl)benzoate as a beige solid (4.95 g). (NMR (300 MHz, CDCl3: 8.10 (d, 2H), 7.98 (s, 1H), 7.75 (d, 2H), 7.48 (s, 1H), 3.94 (s, 3H)). | |
With potassium carbonate In methanol; ethyl acetate | 37.1 Step 1 Step 1 Methyl 4-formylbenzoate (Aldrich Chemical Co., St Louis, Mo.) (5.0 g, 30.5 mmol), anhydrous potassium carbonate (4.55 g, 33 mmol) and p-toluenesulfonylmethyl isocyanide (TOSMIC, Aldrich Chemical Co.) (6.83 g, 30.5 mmol) were refluxed in methanol (100 ml) for 3.5 hours. The mixture was then concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate, washed twice with water, dried and concentrated in vacuo to give methyl 4-(1,3-oxazol-5-yl)benzoate as a beige solid (4.95 g). (NMR (300 MHz, CDCl3: 8.10 (d, 2H), 7.98 (s, 1H), 7.75 (d, 2H), 7.48 (s, 1H), 3.94 (s, 3H)). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | Stage #1: ((R)-4-benzoyl-2-methylpiperazin-1-yl)acetonitrile; 4-oxazol-5-ylbenzoic acid methyl ester With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2 - 5h; Stage #2: With sodium hypochlorite; water In tetrahydrofuran for 0.0833333 - 0.166667h; | 101 Example 101: 1-((R)-4-Benzoyl-2-methyl-piperazin-1-yl)-2-(4-oxazol-5-yl- phenvθ-ethane-1 ,2-dione; ((R)-4-Benzoyl-2-methyl-piperazin-1-yl)-acetonitrile (182 mg, 0.896 mmol) and 4-oxazol-5-yl-benzoic acid methyl ester (245 mg, 1 mmol) were dissolved in 10 mL of anhydrous THF. N-Sodium hexamethyldisilazane (NaHMDS, 500 mg, 2.7 mmol) was then added directly to the solution in portions while stirring at ambient temperature. The resulting mixture was allowed to stir for 2 to 5 hours. Bleach (10 mL) was then added in one portion and the resulting biphasic emulsion stirred or shaken rapidly for 5 to 10 minutes. 30 mL of EtOAc was added and the resulting organic layer washed once with an equal volume of saturated aqueous sodium sulfite. The organic fraction was then washed with two portions of saturated ammonium chloride and then brine. After drying over MgSO-J, the organic fraction was concentrated in-vacuo to give 265 mg of a brown residue that was subjected to purification by reverse- phase HPLC ultimately affording 49 mg of pure 1-((R)-4-benzoyl-2-methyl- piperazin-1 -yl)-2-(4-oxazol~5-yl-phenyl)-ethane-1 ,2-dione as light yellow syrup (13 %, isolated yield). MS: Calculated for C23H2IN3O4- H+: 403.15. Found: 404.5. 1HNMR (CDCI3): 8.07-8.00 (m, 3H), 7.82 (d, J= 5.7 Hz, 2H), 7.57 (s, 1H)1 7.5-7.35 (br. m, 5H), 5.2-2.9 (br. m, 7H), 1.3 (br. s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: ((R)-4-[methoxyimino]-phenyl-methyl}-2-methyl-piperazin-1-yl)-acetonitrile; 4-oxazol-5-ylbenzoic acid methyl ester With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2 - 5h; Stage #2: With sodium hypochlorite; water In tetrahydrofuran for 0.0833333 - 0.166667h; | 106 Example 106: 1-((R)-4-friVIethoxyimino1-phenyl-methyl|-2-methyl- piperazin-1 -yl)-2-(4-oxazol-5-yl-phenyl)-ethane-1 ,2-dione; ((R)-4-Benzoyl-2-methyUpiperazin-1-yI)-acetonitrile (245 mg, 0.9 mmol) and 4- oxazol-5-yl-benzoic acid methyl ester (182 mg, 0.9 mmol) were dissolved in 10 mL of anhydrous THF. N-Sodium hexamethyldisilazane (NaHMDS, 500 mg, 2.7 mmol) was then added directly to the solution in portions while stirring at ambient temperature. The resulting mixture was allowed to stir for 2 to 5 hours. Bleach (10 ml_) was then added in one portion and the resulting biphasic emulsion stirred or shaken rapidly for 5 to 10 minutes. 30 mL of EtOAc was added and the resulting organic layer washed once with an equal5 volume of saturated aqueous sodium sulfite.. The organic fraction was then washed with two portions of saturated ammonium chloride and then brine. After drying over MgSO4, the organic fraction was concentrated in-vacuo to give 200 mg of a brown residue that was subjected to purification by reverse- phase HPLC ultimately affording 49 mg of 1-((R)-4-[(E)-methoxyimino]- i o phenyl-methyl}-2-methyl-piperazin-1 -yl)-2-(4-oxazol-5-yl-phenyl)-ethane-1 ,2- dione. MS: Calculated for C24H24N4O4 H+: 432.18. Found: 433.4. 1HNMR (CDCI3): 8.09-7.99 (m, 3H), 7.82-7.65 (m, 2H)1 7.57 (s, 1H), 7.5-7.3 (m, 5H), 5.3-2.8 (m, 10H), 1.42-1.37 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | Stage #1: ((R)-4-benzoyl-2-methylpiperazin-1-yl)acetonitrile; 4-oxazol-5-ylbenzoic acid methyl ester With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; Stage #2: With sodium hypochlorite In tetrahydrofuran; water Stage #3: trifluoroacetic acid In water; acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With copper diacetate; Trimethylacetic acid In 1,3,5-trimethyl-benzene at 170℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With trimethylaluminum In toluene at 80℃; for 4h; | 109 Example 109:Methyl 2,2-dimethyl-4-(5-(4-(4-(oxazol-5-yl)benzamido)phenyl)thiazol-2-yl) butanoateTo a solution of the compound of example 86 (150 mg) and methyl 4-(oxazol-5- yl)benzoate (120 mg) in toluene (12 mL) was added a solution of trimethyl aluminium (0.38 mL, 2M solution in toluene). The mixture was sealed and heated at 80 °C for 4 h. The reaction mixture was cooled to room temperature, water was added and the reaction mixture was neutralized with saturated aqueous solution of sodium carbonate. The reaction mixture was extracted with ethyl acetate and the layers were separated. The organic layer was washed with brine solution, dried over anhydrous sodium sulphate and the solvent was evaporated to obtain a residue, which was purified by column chromatography (silicagel, ethyl acetate in petroleum ether) to yield a solid. The solid was crystallized in chloroform in petroleum ether to afford the title compound. Yield: 184 mg (78 %); 1 H NMR (DMSO-d6, 300MHz): δ 10.44 (s, 1 H), 8.5 (s, 1 H), 8.1 (d, 2H), 8.0 (s, 1 H), 7.91 - 7.85 (ddd, 5H), 7.64 (d, 2H), 3.62 (s, 3H), 2.92 (m, 2H), 1 .98 (m, 2H), 1 .2 (s, 6H); MS: m/z 476 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper diacetate; Trimethylacetic acid In 1,3,5-trimethyl-benzene at 165℃; for 4h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide; In methanol; water; at 20℃; for 24h; | A solution of methyl 4-(oxazol-5-yl)benzoate (10)(20.0 mg, 0.098 mmol) in MeOH (570 L) was treated with a aqueous NaOH solution(1 N, 160 L). The reaction mixture was stirred for 24 h at rt and acidified topH 3 with a aqueous HCl solution (1 N). The resulting mixture was extractedwith a mixtue of CHCl3 : MeOH (5 : 1). The organic layer wascombined, dried over Na2SO4, filtered, and concentrated in vacuo to afford 4-(oxazol-5-yl)benzoic acid (11) (18.5 mg, quant.) as a white solid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With pyridine; copper diacetate; Trimethylacetic acid In o-xylene at 150℃; for 4h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper diacetate; Trimethylacetic acid In o-xylene at 150℃; for 20h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / water; methanol / 1.5 h / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 6 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol / 1.5 h / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With copper(II) acetate monohydrate In o-xylene at 130℃; for 22h; Inert atmosphere; |
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