Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 72752-80-8 | MDL No. : | MFCD12827780 |
Formula : | C9H7NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FUJBKRLYHYJMNF-UHFFFAOYSA-N |
M.W : | 193.16 | Pubchem ID : | 12564532 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With sodium hydroxide; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In methanol for 0.166667h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water In methanol at 48℃; pH 8.2 (phosphate or carbonate buffer); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In pyridine; at 20℃; for 36h; | Example 11a; ;Step 1 : Methyl 2-oxo-2,3-dihydrobenzo|"d]oxazole-6-carboxylate (129); [0732] A solution of hydroxyaniline 128 (1.085 g, 6.49 mmol) and carbonyl diimidazole(1.409 g, 8.69 mmol) in pyridine (3 mL) was stirred at room temperature for 36 h then diluted with AcOEt, washed with 5% KHSO4 (pH=2), saturated NaHCO3, brine, dried over MgS04, filtered and concentrated to give title compound 129 (1.19 g, 95% yield).[0733] IH NMR (DMSO-d6) delta (ppm): 7.80 to 7.78 (m, IH), 7.74 to 7.73 (m, IH), 7.18 to7.16 (m, IH), 3.83 (s, 3H). |
92% | In tetrahydrofuran; for 3h;Reflux; | EXAMPLE 2The preparation of ethyl {3-[6-(2-dimethylaminoethylcarbamoyl)-2-oxobenzoxazol-3-ylmethyl]phenyl}carbamate (?A29?) is carried out analogously to the following scheme:2.1 9.36 g (0.056 mol) of methyl 3-hydroxy-4-aminobenzoate and 9.85 g of 1,1'-carbonyldiimidazole are dissolved in 125 ml of THF in a 250 ml single-necked flask with reflux condenser and drying tube, and the mixture is refluxed for 3 h. For work-up, the solvent is removed in a rotary evaporator, and the residue is taken up in dichloromethane and washed 3× with 1 N HCl and 1× with water. The organic phase is dried over sodium sulfate and evaporated to dryness in a rotary evaporator; yield 9.92 g (92%) of methyl 2-oxo-2,3-dihydrobenzoxazole-6-carboxylate; ESI: 194 (M+H); HPLC: Rt=2.57 min (method B). |
In tetrahydrofuran; for 24h;Reflux; | To a solution of methyl 4-amino-3-hydroxybenzoate (Intermediate 75, 1 .06 g, 6.34 mmol) in THF (13.5 mL) was added carbonyl diimidazole (1.88 g, 1 1 .6 mmol) and the reaction mixture was heated to reflux temperature for 1 day. After that time, the solvent was removed and the residue was partitioned between CH2CI2 and 1 N aqueous HCI solution. The organic phase was washed with 1 N aqueous HCI solution (2x) and water, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to provide the title compound as white solid (870 mg of a 79% purity, 56% yield). The crude was used in the next step without any further purification.LRMS (m/z): 194 (M+1 )+. |
In tetrahydrofuran; for 24h;Reflux; | Intermediate 76.methyl 2-oxo-2,3-dihydro-1 ,3-benzoxazole-6-carboxylateTo a solution of methyl 4-amino-3-hydroxybenzoate (Intermediate 75, 1 .06 g, 6.34 mmol) in THF (13.5 mL) was added carbonyl diimidazole (1.88 g, 1 1 .6 mmol) and the reaction mixture was heated to reflux temperature for 1 day. After that time, the solvent was removed and the residue was partitioned between CH2CI2 and 1 N aqueous HCI solution. The organic phase was washed with 1 N aqueous HCI solution (2x) and water, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to provide the title compound as white solid (870 mg of a 79% purity, 56% yield). The crude was used in the next step without any further purification.LRMS (m/z): 194 (M+1 )+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Also, the invention provides a compound selected from the group consisting of: ... [3-(4-Benzylpiperidin-1-yl)-2-hydroxypropyl]carbamic acid benzyl ester; {2-(tert-Butyldimethylsilanyloxy)-3-[4-(4-fluorobenzyl)piperidin-1-yl]propyl}carbamic acid benzyl ester; {2-(tert-Butyldimethylsilanyloxy)-3-[4-benzylpiperidin-1-yl]propyl}carbamic acid benzyl ester; {2-(tert-Butyldimethylsilanyloxy)-3-[4-(4-fluorobenzyl)piperidin-1-yl]propylamine; Methyl 2-oxo-2,3-dihydrobenzoxazole-6-carboxylate; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid [3-(4-benzylpiperidin-1-yl)-2-(tert-butyldimethylsilanyloxy)propyl]amide; 2-Oxo-2,3-dihydrobenzoxazole-6-carboxylic acid [3-(4-(4-fluorobenzyl)piperidin-1-yl)-2-(tert-butylimethylsilanyloxy)propyl]amide; ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | The product (1.64 g, 8.47 mmol) from step 1 was dissolved in a mixture of methanol (5 mL) and tetrahydrofuran 5 mL. Potassium hydroxide (1.25 g, 22.28 mmol) in water (6 mL) was added. The reaction mixture was refluxed at 7O0C for 3 days and 800C for 2 days. The solvent was evaporated in vacuo. Water was added and the reaction mixture was acidified with 1N HCI (pH 4~5) and extracted with ethyl acetate. The solvent was evaporated in vacuo to leave 1.43 g (94%) of pure compound. The compound was used for the following reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium carbonate In acetonitrile for 16h; Reflux; | 2.2.2 2.2 1 g (5.2 mmol) of the substance methyl 2-oxo-2,3-dihydrobenzoxazole-6-carboxylate is dissolved in 20 ml of acetonitrile, 2.8 g (20.3 mmol) of potassium carbonate and 1.24 g (5.7 mmol) of m-nitrobenzyl bromide are added, and the mixture is heated under reflux for 16 h. After cooling, 30 ml of dichloromethane are added to reaction mixture, and the mixture is extracted with 2×20 ml of water, the organic phase is dried over sodium sulfate, and the solvent is removed by distillation. The residue is slurried in methanol, filtered off with suction and washed with diethyl ether. The substance is reacted further without further purification; yield: 1.15 g (67%) of methyl 3-(3-nitrobenzyl)-2-oxo-2,3-dihydrobenzoxazole-6-carboxylate; m.p. 149-151° C.; ESI: 329 (M+H); HPLC: Rt=5.12 min (method A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / 48 h / 0 - 20 °C 2: tetrahydrofuran / 24 h / Reflux | ||
Multi-step reaction with 2 steps 1: hydrogenchloride / 0 - 20 °C 2: tetrahydrofuran / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; | 6-(Hydroxymcthyl)benzo[d]oxazol-2(3H)-one (52-2): 1M lithium aluminum hydride in tetrahydrofuran (39 mL, 39 mmol, 1.5 equiv) was added at a rate maintaining the reaction temperature below 5°C to a mixture of compound 52-1 (5 g, 25.6 mmol, 1 equiv) in tetrahydrofuran (120 mL) at 0°C. The reaction was stirred at room temperature for overnight, at which point LC/MS analysis indicated the reaction was complete. The reaction was cooled to 5°C, water (1.5 mL), 4N sodium hydroxide solution (3 mL) and water (6 mL) was added sequentially. The mixture was stirred at room temperature for 30 minutes and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on an Interchim automated chromatography system (220 g Sorbtech silica gel column), eluting with a gradient of 0 to 10% methanol in dichloromethane to give compound 52-2 (1.03 g, 24% yield) as a yellow solid. (CH-QZH-01-021). |
148 mg | With lithium aluminium tetrahydride In tetrahydrofuran at 5 - 20℃; for 1.58333h; Inert atmosphere; | Intermediate 77. 6-(hydroxymethyl)-1 ,3-benzoxazol-2(3H)-one To a solution of methyl 2-oxo-2,3-dihydro-1 ,3-benzoxazole-6-carboxylate (865 mg of 79% purity, 3.51 mmol) in THF (15 mL) was added, under argon atmosphere and at 0 °C, lithium aluminium hydride (400 mg, 10.5 mmol) in portions in order to maintain the internal temperature below 5 °C. After the last addition, the thick suspension was allowed to warm up to room temperature and stirred for 1 .5 hours. Then, water was added (0.4 mL) dropwise followed by addition of 4N sodium hydroxide (0.4 mL) and water (1 .2 mL). The mixture was filtered and the solid residue was washed with EtOH. The ethanolic phase was concentrated to dryness. The brown solid obtained was purified by reverse phase column chromatography over C18 modified silica gel eluting with water:MeOH (from 0 to 100% of MeOH) to give a pure fraction of the title compound (148 mg, 26% yield).LRMS (m/z): 166 (M+1 )+. |
148 mg | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; | Intermediate 77. 6-(hydroxymethyl)-1 ,3-benzoxazol-2(3H)-one Intermediate 77. 6-(hydroxymethyl)-1 ,3-benzoxazol-2(3H)-oneTo a solution of methyl 2-oxo-2,3-dihydro-1 ,3-benzoxazole-6-carboxylate (865 mg of 79% purity, 3.51 mmol) in THF (15 mL) was added, under argon atmosphere and at 0 °C, lithium aluminium hydride (400 mg, 10.5 mmol) in portions in order to maintain the internal temperature below 5 °C. After the last addition, the thick suspension was allowed to warm up to room temperature and stirred for 1 .5 hours. Then, water was added (0.4 mL) dropwise followed by addition of 4N sodium hydroxide (0.4 mL) and water (1 .2 mL). The mixture was filtered and the solid residue was washed with EtOH. The ethanolic phase was concentrated to dryness. The brown solid obtained was purified by reverse phase column chromatography over C18 modified silica gel eluting with water:MeOH (from 0 to 100% of MeOH) to give a pure fraction of the title compound (148 mg, 26% yield).LRMS (m/z): 166 (M+1 )+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.58 h / 5 - 20 °C / Inert atmosphere 2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.58 h / 5 - 20 °C / Inert atmosphere 2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube | ||
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere 2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 4 h / 120 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; | Methyl 3-(2-((7-methoxyquinolin-4-yl)oxy)ethyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate (11d) General procedure: The crude product above (2.0mmol) was dissolved in DMF (20mL). The corresponding benzo[d]oxazol-2(3H)-one (2.4mmol) and Cs2CO3 (782mg, 2.4mmol) was added to the solution. The reaction mixture was stirred at 50°C for 5h and then cooled to room temperature. The mixture was diluted with water (40mL) and then was extracted with ethyl acetate (20mL×3). The combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 11. White solid (17%, 4 steps). 1H NMR (300MHz, CDCl3) δ 8.65 (d, J=5.3Hz, 1H), 8.03 (dd, J=8.2, 1.5Hz, 1H), 7.89 (d, J=1.4Hz, 1H), 7.82 (d, J=9.2Hz, 1H), 7.33 (d, J=2.4Hz, 1H), 7.24 (d, J=8.3Hz, 1H), 7.08 (dd, J=9.2, 2.6Hz, 1H), 6.61 (d, J=5.3Hz, 1H), 4.53 (t, J=4.9Hz, 2H), 4.41 (t, J=4.9Hz, 2H), 3.94 (d, J=3.3Hz, 3H), 3.92 (s, 3H). 13C NMR (101MHz, CDCl3) δ 167.52 (s), 162.53 (s), 162.10 (s), 155.76 (s), 152.92 (s), 152.55 (s), 143.68 (s), 136.64 (s), 127.88 (s), 126.60 (s), 124.11 (s), 120.18 (s), 116.81 (s), 112.93 (s), 109.33 (s), 108.55 (s), 100.63 (s), 66.75 (s), 56.91 (s), 53.85 (s), 43.28 (s). MS (ESI): 395.1 [M+H]+. Purity: >95% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2: zinc(II) iodide / tetrahydrofuran / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2.1: zinc(II) iodide / tetrahydrofuran / 3 h / 70 °C 3.1: potassium <i>tert</i>-butylate / 1,2-dimethoxyethane / 1 h / 0 °C 3.2: 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2.1: zinc(II) iodide / tetrahydrofuran / 3 h / 70 °C 3.1: potassium <i>tert</i>-butylate / 1,2-dimethoxyethane / 1 h / 0 °C 3.2: 48 h / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 20 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2.1: zinc(II) iodide / tetrahydrofuran / 3 h / 70 °C 3.1: potassium <i>tert</i>-butylate / 1,2-dimethoxyethane / 1 h / 0 °C 3.2: 48 h / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 20 h / 100 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 70 °C |
[ 54903-16-1 ]
2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid
Similarity: 0.98
[ 65422-70-0 ]
Methyl 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.97
[ 65422-72-2 ]
2-Oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylic acid
Similarity: 0.95
[ 1221792-78-4 ]
Methyl 7-methoxy-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.94
[ 195140-52-4 ]
Benzyl 4-(((2,5-dimethoxyphenyl)carbamoyl)oxy)benzoate
Similarity: 0.94
[ 65422-70-0 ]
Methyl 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.97
[ 1221792-78-4 ]
Methyl 7-methoxy-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.94
[ 139284-98-3 ]
Ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.94
[ 195140-52-4 ]
Benzyl 4-(((2,5-dimethoxyphenyl)carbamoyl)oxy)benzoate
Similarity: 0.94
[ 100246-04-6 ]
Methyl 2-oxo-2,3-dihydrobenzo[d]oxazole-4-carboxylate
Similarity: 0.93
[ 54903-16-1 ]
2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid
Similarity: 0.98
[ 65422-70-0 ]
Methyl 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.97
[ 65422-72-2 ]
2-Oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylic acid
Similarity: 0.95
[ 1221792-78-4 ]
Methyl 7-methoxy-2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.94
[ 139284-98-3 ]
Ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate
Similarity: 0.94