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Chemical Structure| 55687-30-4

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Product Details of [ 55687-30-4 ]

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

Safety of [ 55687-30-4 ]

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

Application In Synthesis of [ 55687-30-4 ]

* 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.

  • Downstream synthetic route of [ 55687-30-4 ]

[ 55687-30-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 55687-30-4 ]
  • [ 55686-93-6 ]
  • 2
  • [ 55687-29-1 ]
  • [ 55687-30-4 ]
YieldReaction ConditionsOperation 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.)

  • 4
  • [ 298-12-4 ]
  • [ 102-51-2 ]
  • [ 55687-30-4 ]
  • [ 91192-32-4 ]
  • 5
  • [ 55687-30-4 ]
  • [ 2746-25-0 ]
  • 7-methoxy-2-(4-methoxy-benzyloxy)-quinoxaline [ No CAS ]
  • [ 357637-41-3 ]
  • 6
  • [ 55687-30-4 ]
  • [ 824-94-2 ]
  • [ 357637-41-3 ]
  • 7
  • [ 924-44-7 ]
  • [ 102-51-2 ]
  • [ 55687-30-4 ]
  • [ 91192-32-4 ]
YieldReaction ConditionsOperation 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).

  • 10
  • [ 55687-30-4 ]
  • 4-chloro-7-methoxy-imidazo[1,5-<i>a</i>]quinoxaline [ No CAS ]
  • 11
  • [ 55687-30-4 ]
  • N-(2-Chloro-6-methylphenyl)-7-methoxyimidazo[1,5-a]quinoxalin-4-amine [ No CAS ]
  • 13
  • [ 55687-30-4 ]
  • (7-methoxy-quinoxalin-2-yl)-(3-piperidino-propyl)-amine [ No CAS ]
  • 15
  • [ 55687-30-4 ]
  • [ 91192-32-4 ]
  • [ 55686-93-6 ]
  • [ 55687-11-1 ]
YieldReaction ConditionsOperation 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).
  • 16
  • [ 55687-30-4 ]
  • [ 1033748-15-0 ]
  • [ 1033748-14-9 ]
YieldReaction ConditionsOperation 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).
  • 17
  • [ 55687-30-4 ]
  • [ 917833-15-9 ]
  • [ 917834-19-6 ]
YieldReaction ConditionsOperation 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)
  • 18
  • [ 55687-30-4 ]
  • [ 2032-35-1 ]
  • [ 1095275-82-3 ]
YieldReaction ConditionsOperation 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)
  • 19
  • [ 55687-30-4 ]
  • 2-{4-[(tert-butoxycarbonyl)amino]-3-fluoropiperidin-1-yl}-ethyl methanesulfonate [ No CAS ]
  • tert-butyl {3-fluoro-1-[2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 20
  • [ 55687-30-4 ]
  • [ 91192-32-4 ]
  • [ 55687-11-1 ]
YieldReaction ConditionsOperation 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).
  • 21
  • [ 55687-30-4 ]
  • trans-tert-butyl 4-(1-(2-nitrophenylsulfonyl)aziridin-2-yl)-cyclohexylcarbamate [ No CAS ]
  • trans-tert-butyl 4-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)-1-(2-nitrophenylsulfonamido)ethyl)-cyclohexylcarbamate [ No CAS ]
YieldReaction ConditionsOperation 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)
  • 22
  • [ 55687-30-4 ]
  • [ 1198355-18-8 ]
  • [ 1251610-89-5 ]
YieldReaction ConditionsOperation 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.
  • 23
  • [ 55687-30-4 ]
  • [ 917341-20-9 ]
  • [ 917343-39-6 ]
YieldReaction ConditionsOperation 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).
  • 24
  • [ 55687-30-4 ]
  • 1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-7-methoxyquinoxalin-2(1H)-one bis-(hydrochloride) [ No CAS ]
  • 25
  • [ 55687-30-4 ]
  • C24H27N5O4 [ No CAS ]
  • 26
  • [ 55687-30-4 ]
  • [ 917343-38-5 ]
  • 28
  • [ 55687-30-4 ]
  • trans-(R)-(4-oxiranyl-cyclohexyl)-carbamic acid tert-butyl ester [ No CAS ]
  • trans-{4-[(1R)-1-hydroxy-2-(7-methoxy-2-oxo-2H-quinoxalin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 29
  • [ 55687-30-4 ]
  • 2-(cis(+/-))-(4-azido-3-[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)ethyl methanesulfonate [ No CAS ]
  • C23H36N6O3Si [ No CAS ]
  • 30
  • [ 55687-30-4 ]
  • 2-(trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-[tert-butyl-(dimethyl)silyl]oxy}piperidin-1-yl)ethyl methanesulfonate [ No CAS ]
  • tert-butyl {trans(+/-)-3-[tert-butyl(dimethyl)silyl]oxy}-1-[2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate [ No CAS ]
  • 31
  • [ 55687-30-4 ]
  • 2-{trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-methoxypiperidin-1-yl}ethyl methanesulfonate [ No CAS ]
  • tert-butyl {3-methoxy-1-[2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate [ No CAS ]
  • 32
  • [ 55687-30-4 ]
  • cis(+/-)-2-{4-[(tert-butoxycarbonyl)amino]-3-fluoropiperidin-1-yl}ethyl methanesulfonate [ No CAS ]
  • cis(+/-)-tert-butyl {3-fluoro-1-[2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate [ No CAS ]
  • 33
  • [ 55687-30-4 ]
  • tert-butyl (2-fluoro-3-iodopropoxy)diphenylsilane [ No CAS ]
  • 1-(3-[tert-butyl(diphenyl)silyl]oxy}-2-fluoropropyl)-7-methoxyquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 34
  • [ 55687-30-4 ]
  • 6-[(4S)-4-[3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one [ No CAS ]
  • 35
  • [ 55687-30-4 ]
  • 1-(4-[tert-butyl(diphenyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 55687-30-4 ]

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