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Chemical Structure| 190728-25-7 Chemical Structure| 190728-25-7
Chemical Structure| 190728-25-7

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CAS No.: 190728-25-7

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Product Details of 4-(6,7-dimethoxyquinolin-4-yl)oxyaniline

CAS No. :190728-25-7
Formula : C17H16N2O3
M.W : 296.32
SMILES Code : NC1=CC=C(OC2=CC=NC3=CC(OC)=C(OC)C=C23)C=C1
MDL No. :MFCD19685633
InChI Key :VXEQRXJATQUJSN-UHFFFAOYSA-N
Pubchem ID :11594543

Safety of 4-(6,7-dimethoxyquinolin-4-yl)oxyaniline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-(6,7-dimethoxyquinolin-4-yl)oxyaniline

* 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 [ 190728-25-7 ]

[ 190728-25-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 190728-25-7 ]
  • [ 32315-10-9 ]
  • [ 367-34-0 ]
  • [ 144-55-8 ]
  • N-(2,4,5-trifluorophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; In toluene; Example 219 N-(2,4,5-Trifluorophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [255] 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (50 mg) was dissolved in toluene (5 ml) with heat, after the addition of triethylamine (1 ml), triphosgene (55 mg) was added, and the admixture was refluxed with heat for 3 minutes. <strong>[367-34-0]2,4,5-Trifluoroaniline</strong> (75 mg) was added to the reaction mixture, and the admixture was refluxed with heat for 20 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluding with chloroform/acetone (10/1) to obtain 58 mg of the title compound (yield: 73percent). 1 H-NMR (DMSO-d6, 500 MHz): delta 3.94 (s, 3H), 3.95 (s, 3H), 6.45 (d, J=5.5Hz, 1H), 7.24 (d, J=8.6Hz, 2H), 7.40 (s, 1H), 7.52 (s, 1H), 7.59 (d, J=8.6Hz, 2H), 7.62~7.70 (m, 1H), 8.17~8.25 (m, 1H), 8.48 (d, J=4.9Hz, 1H), 8.76 (s, 1H), 9.23 (s, 1H) Mass spectrometry data (FD-MS, m/z): 469 (M+)
  • 2
  • [ 190728-25-7 ]
  • [ 32315-10-9 ]
  • [ 6299-67-8 ]
  • [ 144-55-8 ]
  • N-(2,3-Dimethoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In toluene; Example 232 N-(2,3-Dimethoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [268] 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was dissolved in toluene (5 ml) with heat, after the addition of triethylamine (1 ml), triphosgene (74 mg) was added, and the admixture was refluxed with heat for 3 minutes. 2,3-Dimethoxyaniline (0.05 ml) was added to the reaction mixture, and the admixture was refluxed with heat for 11 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluding with chloroform/acetone (10/1) to obtain 83 mg of the title compound (yield: 100%). 1 H-NMR (CDCl3, 500 MHz): (3.72 (s, 3H), 3.84 (s, 3H), 4.02 (s, 3H), 4.05 (s, 3H), 6.46 (d, J=5.5Hz, 1H), 6.62 (d, J=7.9Hz, 1H), 7.05 (dd, J=8.5, 8.5Hz, 1H), 7.13 (d, J=9.2Hz, 2H), 7.43 (s, 1H), 7.54 (d, J=8.6Hz, 2H), 7.58 (s, 1H), 7.85 (d, J=8.6Hz, 1H), 7.88 (s, 1H), 8.27 (s, 1H), 8.50 (d, J=5.5Hz, 1H) Mass spectrometry data (FD-MS, m/z): 475 (M+)
  • 3
  • [ 190728-25-7 ]
  • [ 32315-10-9 ]
  • [ 32202-61-2 ]
  • [ 144-55-8 ]
  • N-(5-Indanyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% In toluene; Example 114 N-(5-Indanyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [197] 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (51 mg) was suspended in toluene (5 ml), triphosgene (54 mg) was added, and the admixture was refluxed with heat for 12 minutes. <strong>[32202-61-2]4-Aminoindan</strong> (36 mg) was added, and the admixture was refluxed with heat for 36 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation and the resulting residue was purified by column chromatography on silica gel eluding with chloroform/acetone (10/1) to obtain 13 mg of the title compound (yield: 16percent). 1 H-NMR (CDCl3, 500 MHz): delta 2.04 (m, 2H), 2.82~2.86 (m, 4H), 4.01 (s, 3H), 4.03 (s, 3H), 6.40 (d, J=5.5 Hz, 1H), 7.03 (m, 1H), 7.08 (d, J=8.5 Hz, 2H), 7.13 (m, 1H), 7.32 (s, 1H), 7.40~7.57 (m, 6H), 8.44 (d, J=4.9 Hz, 1H) Mass spectrometry data (FD-MS, m/z): 455 (M+)
  • 4
  • [ 190728-25-7 ]
  • [ 32315-10-9 ]
  • [ 120121-01-9 ]
  • 1-(3-Chlorophenyl)ethyl N-{4-((6,7-dimethoxy-4-quinazolinyl)oxy)phenyl}carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; In methanol; dichloromethane; chloroform; water; toluene; Example 3 1-(3-Chlorophenyl)ethyl N-{4-((6,7-dimethoxy-4-quinazolinyl)oxy)phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (72 mg) was added to toluene/triethylamine = 10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (109 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-chloro-alpha-methylbenzyl alcohol (46 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed tocool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (88 mg, yield 70%). 1H-NMR (CDCl3, 400 MHz): 8.44 - 8.50 (1H, m), 8.14 (1H, s), 7.58 - 7.64 (3H, m), 7.26 - 7.42 (4H, m), 7.15 - 7.19 (2H, m), 6.86 (1H, s), 6.67 (1H, d, J = 6.6), 5.88 (1H, q, J = 6.6), 4.16
  • 5
  • [ 190728-25-7 ]
  • [ 54-60-4 ]
  • [ 1207980-99-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; 4-(6,7-Dimethoxyquinolin-4-yloxy)benzenamine (60 mg, 202 μmol), 2-(4- fluorophenylamino)benzoic acid (56 mg, 243 μmol), and HATU (108 mg, 283 μmol) were combined in a resealable tube. DCM (1012 μl, 202 μmol) and N-ethyl-N- isopropylpropan-2-amine (71 μl, 405 μmol) were added, and the reaction mixture in the tube was allowed to stir at RT. Upon completion (as judged by LCMS), the reaction mixture was concentrated in vacuo, dissolved in minimal DMSO and purified by preparative HPLC {15-85% (0.1% TFA in CH3CN) in H2O over 20 min}. Fractions containing pure product were combined and neutralized with saturated aqueous NaHCO3 then extracted with EtOAc, dried over MgSO4, filtered, and concentrated in vacuo to afford pure N-(4-(6,7-dimethoxyquinolin-4-yloxy)phenyl)-2-(4- fluorophenylamino)benzamide as a off-white solid. MS Calcd for C3oH24FN3θ4: [M]+ = 509. Found: [M+H]+= 510.
  • 6
  • [ 190728-25-7 ]
  • [ 6914-71-2 ]
  • methyl 1-((4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)carbamoyl)cyclopropane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.5% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2h; 4 - ((6. 7 -methoxy -4 - 1 -based) phenoxy) aniline 100 ml 5 2h (11.4g 0.039 muM, 1.0 1 8.6g 0.055 muM 1.4 100 ml 0 C 2 M 0.2 muMAt the end of the reaction, a purified unitz 800 ml stirred crystallization 5~6h, was added. Filter, filter cake, and 20 ml washing, gave 1 - ((4 - ((6, 7 -dimethoxyquinoline -4 -yloxy) phenyl) carbamoyl) cyclopropanecarboxylic acid methyl 14.7g, Bunit_ID, and purity Kunitz. 90.5%. 'unitz 99.8%'.
  • 7
  • [ 190728-25-7 ]
  • [ 22902-86-9 ]
  • 2-(4-chloro-3-(trifluoromethyl)phenyl)-N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)phenyl)acetamide [ No CAS ]
 

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