Structure of 55687-30-4
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CAS No. : | 55687-30-4 |
Formula : | C9H8N2O2 |
M.W : | 176.17 |
SMILES Code : | O=C1NC2=C(C=CC(OC)=C2)N=C1 |
MDL No. : | MFCD15144498 |
InChI Key : | GVERQUMLAYWTMA-UHFFFAOYSA-N |
Pubchem ID : | 491319 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
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 |
* 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 |
---|---|---|
To a solution of 8% aqueous sodium hydroxide (1.32 L) was added 7-methoxy-3,4- dihydroquinoxalin-2(lH)-one (Intermediate 16, 100 g) followed by a solution of 3 wt% hydrogen peroxide in water (1.17 L). The reaction mixture was slowly heated to 80 0C and maintained at this temperature for 4 hours. Then the heating source was removed and acetic acid (150 mL) was added dropwise. The suspension was stirred overnight at room temperature and the precipitated solid was collected by filtration to afford the product as a tan solid (90 g).MS (ESP): 177 (MH+) for C9H8N2O21H-NMR (DMSO-d*) δ: 3.83 (s, 3H); 6.76 (d, IH); 6.90 (dd, IH); 7.67 (d, IH); 7.97 (s,IH); 12.32 (brs, IH). | ||
To a solution of 8% aqueous sodium hydroxide (1.32 L) was added 7-methoxy-3,4- dihydroquinoxalin-2(lH)-one (Intermediate 8, 100 g), followed by a solution of 3 wt% hydrogen peroxide in water (1.17 L). The reaction mixture was slowly heated to 80 0C and maintained at this temperature for 4 hours. The heating source was then removed and acetic acid (150 mL) was added dropwise. The suspension was stirred overnight at room temperature and the precipitated solid was collected by filtration to afford the product as a tan solid (90 g).MS (ES): 177 (MH+) for C9H8N2O21H NMR (DMSO-d.) δ: 3.83 (s, 3H); 6.76 (d, IH); 6.90 (dd, IH); 7.67 (d, IH); 7.97 (s,IH); 12.32 (brs, IH) | ||
2 g | To a stirred solution of Compound 26b (3g,16.85mmol) in 8%NaOH solution(39.6ml) was added 30%H2O2 solution(35.1ml) at RT. The reaction was heated at 80C for 4h afterwhich was added AcOH (4.5ml) dropwise at RT. Upon completion, the filtered solids were given water and diethyl ether washings to afford the required compound (2g) as an off-white solid. |
Intermediate 237-Methoxyquinoxalin-2(lH)-oneTo a solution of 8% aqueous sodium hydroxide (1.32 L) was added 7-methoxy-3,4- dihydroquinoxalin-2(lH)-one (Intermediate 22) (100 g) followed by a solution of 3 wt% hydrogen peroxide in water (1.17 L). The reaction mixture was slowly heated to 80 0C and maintained at this temperature for 4 hours. Then the heating source was removed and acetic acid (150 mL) was added dropwise. The suspension was stirred overnight at room temperature and the precipitated solid was collected by filtration to afford the product as a tan solid (90 g).MS (ESV. 177 (MH+) for C9H8N2O21H-NMR (DMSO-dfi) δ: 3.83 (s, 3H); 6.76 (d, IH); 6.90 (dd, IH); 7.67 (d, IH); 7.97 (s,IH); 12.32 (brs, IH). | ||
208 mg | To a solution of 8% aqueous sodium hydroxide (4.5 mL) was added 3 (340 mg) followed by a solution of 30 wt % hydrogen peroxide in water (1.97 mL). The reaction mixture was slowly heated to 80 C and maintained at this temperature for 4 ii. The mixturewas cooled down to room temperature, and acetic acid (510 iL) was added dropwise. The suspension was stirred overnight at room temperature and the precipitated solid was collected by filtration to afford 4 as a tan solid (208 mg, 51% for two steps). ‘H NMR (DMSO-d6) : 3.83 (s, 3H); 676 (d, IH); 6.89-6.93 (dd, IH); 7.67-7.70 (d, IH); 7.97 (s, 1EI); 12.30 (hrs, 1Ff). (See Reck. F.; et al., J. Med. Chem. 2011, 54. 7834.) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; toluene; at 20℃;Reflux; | Step A: 7-Methoxyquinoxalin-2(1H)-one and 6-methoxyquinoxalin-2(1H)-one A 50% solution of ethyl 2-oxoacetate (18.47 mL, 93 mmol) in toluene was added to a solution of 4-methoxybenzene-1,2-diamine (10.73 g, 78 mmol) in ethanol (100 mL) at ambient temperature and the reaction was refluxed for 2 h. The reaction was concentrated in vacuo and crystallized from ethanol to afford a mixture of 6-methoxyquinoxalin-2(1H)-one and 7-methoxyquinoxalin-2(1H)-one (5.73 g, 32.50 mmol, 42% yield). MS (LC/MS) R.T.=0.68; [M+H]+=177.10. | |
In ethanol;Reflux; | To a solution of 4-methoxybenzene-1,2-diamine (5 g, 36.2 mmol) in ethanol (50 ml) was added ethyl 2-oxoacetate (4.06 g, 39.8 mmol)). The reaction mass was heated at reflux for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate and then evaporated to dryness to get the crude compound. The crude compound was washed with pet ether to get crude compound (5.1 g, 80% yield) as a mixture of regioisomers (black solid). This crude compound was taken to the next step without separation of isomers.1H NMR (400 MHz, DMSO-d6): δ ppm 8.17 (s, 1H), 7.98 (s, 1H), 7.70-7.68 (d, J=8 Hz, 1H), 7.31-7.30 (d, J=4 Hz, 1H), 7.27-7.20 (m, 2H), 6.93-6.90 (m, 1H), 6.77-6.76 (d, J=4 Hz, 1H), 3.84 (s, 3H), 3.83 (s, 3H); MS: MS m/z 177.0 (M++1). | |
In toluene; at 20℃; for 2h;Reflux; | 50% solution of ethyl2-oxoacetate (18.47 ml., 93mmol) in toluene was added to a solution of 4-methoxybenzene-I,2-diamine (10.73 g, 78 mmol) in ethanol (100 mL) at ambient temperature and the reaction was ref/uxed for 2 h.The reaction was concentrated in vacuo and crystallized fromethanol to afford a mixture of 6-methoxyquinoxalin-2(1H)oneand 7-methoxyquinoxalin-2(1H)-one (5.73 g, 32.50mmol, 42% yield). |
In ethanol; toluene; at 0 - 20℃; for 2h; | Intermediate 149: 2-Chloro-7-methoxyquinoxalineA solution of 4-methoxybenzene-l,2-diamine (16.8 g, 0.12 mmol) in ethanol (250 mL) was treated with a solution of ethyl oxoacetate (50 wt % in toluene, 50 mL, 0.23 mmol) dropwise with cooling in an ice bath. The reaction was allowed to warm to room temperature and after 2 hours, a precipitate was collected by filtration giving 15 g of a brown solid as a 2:1 mixture of 6-methoxyquinoxalin-2(lH)-one to 7-methoxyquinoxalin-2(lH)-one. These EPO <DP n="135"/>isomers were inseparable by TLC. The mixture was suspended in phosphorus oxychloride (150 niL) and heated to reflux for 1 hour. The reaction was cooled to room temperature and was quenched on ice. The pH of the mixture was adjusted to pH 8 with solid sodium carbonate, it was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated to dryness to give 10.4 g of a crude mixture of 2-chloro-6- methoxyquinoxaline and the desired 2-chloro-7-methoxyquinoxaline. Chromatography on silica gel with 5% ethyl acetate in hexanes afforded 0.77 g of the product as a colorless solid. MS (ESt: 195 (MH+) for C9H7ClN2O1H NMR (CDCht δ 3.96 (s, 3H); 7.29 (d, IH); 7.41 (dd, IH); 7.97 (d, IH); 8.63 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.6% | In ethyl acetate; trichlorophosphate; | Step 2: Preparation of 2-chloro-6-methoxyquinoxaline and 3-chloro-6-methoxyquinoxaline A solution of 6-methoxyquinoxalin-2(1H)-one & <strong>[55687-30-4]7-methoxyquinoxalin-2(1H)-one</strong> (3 g, 18.28 mmol) in POCl3 (20 ml) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to afford mixture of regioisomers (3.7 g). 2 g of the above mixture was separated by SFC purification to afford 2-chloro-7-methoxyquinoxaline (0.7 g, 34.7%) and 2-chloro-7-methoxyquinoxaline (0.9 g, 44.6%) as off white solid. 2-chloro-6-methoxyquinoxaline: 1H NMR (400 MHz, DMSO-d6): δ ppm 1H NMR (400 MHz, CDCl3): δ ppm 8.71 (s, 1H), 7.91-7.89 (d, J=8 Hz, 1H), 7.46-7.38 (m, 2H), 3.97 (s, 3H); MS: MS m/z 194.9(M++1). |
With trichlorophosphate; for 1h;Heating / reflux; | Intermediate 149: 2-Chloro-7-methoxyquinoxalineA solution of 4-methoxybenzene-l,2-diamine (16.8 g, 0.12 mmol) in ethanol (250 mL) was treated with a solution of ethyl oxoacetate (50 wt % in toluene, 50 mL, 0.23 mmol) dropwise with cooling in an ice bath. The reaction was allowed to warm to room temperature and after 2 hours, a precipitate was collected by filtration giving 15 g of a brown solid as a 2:1 mixture of 6-methoxyquinoxalin-2(lH)-one to 7-methoxyquinoxalin-2(lH)-one. These EPO <DP n="135"/>isomers were inseparable by TLC. The mixture was suspended in phosphorus oxychloride (150 niL) and heated to reflux for 1 hour. The reaction was cooled to room temperature and was quenched on ice. The pH of the mixture was adjusted to pH 8 with solid sodium carbonate, it was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated to dryness to give 10.4 g of a crude mixture of 2-chloro-6- methoxyquinoxaline and the desired 2-chloro-7-methoxyquinoxaline. Chromatography on silica gel with 5% ethyl acetate in hexanes afforded 0.77 g of the product as a colorless solid. MS (ESt: 195 (MH+) for C9H7ClN2O1H NMR (CDCht δ 3.96 (s, 3H); 7.29 (d, IH); 7.41 (dd, IH); 7.97 (d, IH); 8.63 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | A solution of 7-methoxyquinoxalin-2(lH)-one (Intermediate 15, 320 mg, 1.79 mmol) in dry DMF (10 mL) was cooled in an ice bath under nitrogen and treated with sodium hydride (60% in oil, 86 mg, 2.15 mmol). The reaction was stirred at room temperature for ~90 min. The reaction was again cooled in an ice bath and treated with a solution of 2-{{2>S,AR)-A-[{tert- butoxycarbonyl)amino]-3-methoxypiperidin-l-yl}ethyl methanesulfonate in dry DMF (Intermediate 33, -0.20 mmol/mL, 1.97 mmol). The reaction was stirred at room temperature overnight, then concentrated to dryness under reduced pressure. The residue was <n="99"/>partitioned between ethyl acetate and water. The aqueous phase was re-extracted 2x with ethyl acetate. The combined organic layers were dried over magnesium sulfate. Chromatography on silica gel with a gradient of 15-25% acetone in hexanes gave 420 mg (55%) of the product as a colorless solid. MS (ESP): 433 (MH+) for C22H32N4O51H NMR (DMSO-d*) δ: 1.38 (s, 9H); 1.43-1.51 (m, IH); 1.57-1.72 (m, IH); 2.20-2.40 (m, 2H); 2.55-2.66 (m, 2H); 2.67-2.78 (m, IH); 2.80-2.93 (m, IH); 3.18 (s, 3H); 3.29 (s, IH); 3.51-3.65 (m, IH); 3.92 (s, 3H); 4.24-4.43 (m, 2H); 6.40 (d, IH); 6.96-7.05 (m, 2H); 7.75 (d, IH); 8.04 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 mL of an N,N-dimethylformamide solution containing 1.0 g of <strong>[55687-30-4]7-methoxyquinoxalin-2(1H)-one</strong> was subjected to azeotropic dehydration with toluene, then 0.24 g of 60% sodium hydride was added thereto at room temperature, and the mixture was stirred at 60C for 30 minutes. Thereto was added 2 mL of an N,N-dimethylformamide solution containing 2.3 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate, and the mixture was stirred at the same temperature for 6 hours and then left to stand for 13 hours. Thereto was further added 0.12 g of 60% sodium hydride, and the mixture was stirred for 1 hour. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane : ethyl acetate 2:1] to obtain 0.60 g of a yellow oily substance, 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate. 1H-NMR (DMSO-d6) δ: 1.06 (3H, t, J=7.1 Hz), 1.20-1.36 (2H, m), 1.37 (9H, s), 1.48-1.65 (4H, m), 1.86-1.95 (2H, m), 2.71-2.87 (2H, m), 3.64-3.74 (2H, m), 3.91 (3H, s), 4.01 (2H, q, J=7.1 Hz), 4.13-4.21 (2H, m), 6.97 (1H, d, J=2.4 Hz), 7.01 (1H, dd, J=8.8, 2.4 Hz), 7.76 (1H, d, J=8.8 Hz), 8.03 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With caesium carbonate; In dimethyl sulfoxide; at 70℃; for 72h; | 7-Methoxyquinoxalin-2(lH)-one (Intermediate 10, 20 g, 114 mmol), 2-bromo-l,l- diethoxyethane (25.6 mL, 170 mmol), and cesium carbonate (55.5 g, 170 mmol) were combined in 200 mL of dry DMSO and heated to 70 0C for 72 hours. The reaction mixture was cooled to room temperature, diluted with water (1000 mL), and extracted with ethyl acetate (3x500 mL). The combined organic layers were washed with water followed by brine. The combined organic phases were dried over sodium sulfate, filtered, and concentrated to dryness giving 39.1 g of a maroon oil. This was subjected to flash chromatography (330g of silica) eluting with 15-50% ethyl acetate/hexanes. Combining the more polar spot gave 17 g (51%) of the desired product as an oil which solidified upon standing.MS (ESV 293 (MH+) for Ci5H20N2O41H NMR (DMSO-d≤) δ ppm 1.00 (t, 6H); 3.38 - 3.53 (m, 2H); 3.58 - 3.75 (m, 2H); 3.90 (s, 3H); 4.34 (d, 2H); 4.77 (t, IH); 6.99 (dd, IH); 7.16 (d, IH); 7.73 (d, IH); 8.07 (s, IH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67 - 78% | 7-Methoxyquinoxalin-2(lH)-one (Intermediate 10, 0.52 g, 2.95 mmol), 2-{4-[(tert- butoxycarbonyl)amino]-3-fluoropiperidin-l-yl} ethyl methanesulfonate, trans enantiomer A(Intermediate 22, -0.38 mmol/mL, 3.82 mmol), and sodium hydride (60% in oil, 153 mg,3.82 mmol) were reacted using a procedure similar to the one described for the synthesis ofIntermediate 23. Chromatography on silica gel with a gradient of 10-50% acetone in hexanes gave 0.83 g (67%) of the product as an off white solid.1H NMR fPMSO-d/) δ ppm: 1.23-1.45 (m, HH); 1.64-1.80 (m, IH); 2.04-2.19 (m, 2H); 2.61-2.71 (m, 2H); 2.84 (d, IH); 3.25-3.33 (m, IH); 3.92 (s, 3H); 4.27-4.43 (m, 2H); 4.28 (m, IH);16.94-7.05 (m, 3H); 7.75 (d, IH); 8.04 (s, IH).MS (ESP): 421 (MH+) for C2IH29FN4O4; Intermediate 34 tert-Butyl (3-fluoro-l-[2-(7-methoxy-2-oxoquinoxalin-l(2H)-yl)ethyl]piperidin-4- ylj carbamate, trans enantiomer B7-Methoxyquinoxalin-2(lH)-one (Intermediate 10, 0.52 g, 2.95 mmol), 2-{4-[(tert- butoxycarbonyl)ammo]-3-fluoropiperidin-l-yl}ethyl methanesulfonate, trans enantiomer B(Intermediate 27, -0.38 mrnol/mL, 3.82 mmol), and sodium hydride (60% in oil, 153 mg,3.82 mmol) were reacted using a procedure similar to the one described for the synthesis ofIntermediate 23. Chromatography on silica gel with a gradient of 10-50% acetone in hexanes gave 0.93 g (78%) of the title product as an off white solid.MS (ESP): 421 (MH+) for C2JH29FN4O41H NMR (DMSO-d≤) δ ppm: 1.23-1.45 (m, HH); 1.64-1.80 (m, IH); 2.04-2.19 (m, 2H); 2.61-2.71 (m, 2H); 2.84 (d, IH); 3.25-3.33 (m, IH); 3.92 (s, 3H); 4.27-4.43 (m, 2H); 4.28 (m, IH);16.94-7.05 (m, 3H); 7.75 (d, IH); 8.04 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | Step B: 2-Chloro-6-methoxyquinoxaline A mixture of 6-methoxyquinoxalin-2(1H)-one and <strong>[55687-30-4]7-methoxyquinoxalin-2(1H)-one</strong> (5.67 g, 32.20 mmol) was refluxed in phosphorus oxychloride (120 mL) for 1 h. The reaction was concentrated and quenched by addition of ice, then basified with sodium carbonate, and extracted with ethyl acetate (3×200 mL). The organic layers were combined and concentrated in vacuo. The crude product was absorbed onto sodium sulfate and purified by column chromatography (0 to 5% ethyl acetate/hexanes) to afford 2-chloro-6-methoxyquinoxaline (2.21 g, 11.36 mmol, 35% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.69 (s, 1H), 7.88 (d, J=9.32 Hz, 1H), 7.43 (dd, J=9.32, 2.77 Hz, 1H), 7.37 (d, J=2.77 Hz, 1H), 3.95 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | To a solution of 7-methoxyquinoxalin-2(lH)-one (prepared according to the procedure described in PCT Pub. No.WO08/071961; 397 mg, 2.26 mmol) in dry DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil; 113 mg, 2.82 mmol) with stirring under nitrogen. After 30 minutes a solution of trans-te/t-butyl 4-(l-(2-nitrophenylsulfonyl)aziridin-2-yl)- cyclohexylcarbamate (Intermediate 11, 800 mg, 1.88 mmol) in dry DMF (3 mL) was added and the mixture was stirred at room temperature for 15 hours. The mixture was quenched with potassium phosphate buffer pH 7 (IM, 2 mL). The reaction mixture was partitioned between ethyl acetate and water, the layers were separated and the aqueous phase was back-extracted once with ethyl acetate. The combined organic phases were washed with water (3x), followed by brine (Ix), dried over sodium sulfate and concentrated under reduced pressure. The residue was triturated with hot toluene and the solid was collected by filtration to give 570 mg of the title product. The filtrate was concentrated in vacuo and the resulting crude material subjected to chromatography on silica gel eluting with 10-50% acetone in hexanes to give an additional 153 mg (64% total yield) of product as a racemic mixture in the form of an off white solid. MS (ES): 602 (MH+) for C28H35N5O8S1H NMR (DMSO-J6) δ: ppm 0.98 - 1.18 (m, 4H); 1.37 (s, 9H); 1.45 - 1.58 (m, IH); 1.72 - 1.92 (m, 4H); 3.10 (brs, IH); 3.73 (brs, IH); 3.92 (s, 3H); 4.13 - 4.31 (m, 2H); 6.61 - 6.71 (m, IH); 6.86 (dd, IH); 7.04 (s, IH); 7.46 - 7.68 (m, 5H); 7.86 - 7.97 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h; | Trans-{4-[(lR)-l-hydroxy-2-(7-methoxy-2-oxo-2H-quinoxalin-l-yl)-ethyl]- cyclohexylj-carbamic acid tert-butyl ester: To a solution of the compound of Preparation C (1.58 g, 6.55 mmol) in DMF (33 rnL) was added 7-methoxy-lH-quinoxalin-2-one (1.18 g, 1.02 eq.) and Cs2CO3 (4.27 g, 2 eq.). The reaction mixture was stirred at 800C for 4 h. The solvent was removed under reduced pressure, and the residue was partitioned between water (50 mL) and EA (50 mL). The aq. layer was extracted once more with EA (50 mL). The org. layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by CC (DCM-MeOH 99-1 then 95-5) to afford the title compound as a yellow solid (0.800 g, 29% yield). MS (ESI, m/z): 418.1 [M+Η+] for C22H31N3O5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.05 g | To a stirred solution of Compound 26c (0.2g,1.13mmol) in DMF(2ml) at 0C was added NaH(0.054g,2.3mmol). The reaction was slowly brought to ambient temperature and stirred for lh. Then Compound 26e (0.5g,1.36mmol) in DMF(2ml) was added at RT and stirred for 16h. Upon completion, the reaction was quenched with chilled water and extracted into ethylacetate. The combined layers were dried over Na2SC>4 and concentrated under reduced pressure. The obtained crude was purified by (100-200mesh) silicagel column chromatography eluting the required compound with 5%MeOH-CH2Cl2 as red colored viscous material (0.05g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h; | 7.i. Trans-{4-[(1R)-1-hydroxy-2-(7-methoxy-2-oxo-2H-quinoxalin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester To a solution of the compound of Preparation C (1.58 g, 6.55 mmol) in DMF (33 mL) was added 7-methoxy-1H-quinoxalin-2-one (1.18 g, 1.02 eq.) and Cs2CO3 (4.27 g, 2 eq.). The reaction mixture was stirred at 80 C. for 4 h. The solvent was removed under reduced pressure, and the residue was partitioned between water (50 mL) and EA (50 mL). The aq. layer was extracted once more with EA (50 mL). The org. layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by CC (DCM-MeOH 99-1 then 95-5) to afford the title compound as a yellow solid (0.800 g, 29% yield). MS (ESI, m/z): 418.1 [M+H+] for C22H31N3O5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; | 7-Methoxyquinoxalin-2(1H)-one (synthesized with Reference to WO2009/1126; 1.50 g, 8.50 mmol) and tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilane (Reference Example 29; 5.64 mmol, 12.75 mmol) were dissolved in N,N-dimethylformamide (60 ml). Cesium carbonate (3.88 g, 11.90 mmol) was added to the solution, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 690 mg (17%) of the title compound in the form of a light brown solid. 1H-NMR(400MHz,CDCl3)δ:1.12(9H,s),3.86(3H,s),3.91-4.10(2H,m),4.57-4.69(2H,m),4.87-5.01(1H,m),6.92-6.96(1H,m),6.98(1H,brs),7.38-7.48(6H,m),7.67-7.73(4H,m),7.78(1H,d,J=8.8Hz),8.14(1H,s). |
Tags: 55687-30-4 synthesis path| 55687-30-4 SDS| 55687-30-4 COA| 55687-30-4 purity| 55687-30-4 application| 55687-30-4 NMR| 55687-30-4 COA| 55687-30-4 structure
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P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
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 |
H361 | Suspected of damaging fertility or the unborn child |
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 |
Sorry,this product has been discontinued.
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