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[ CAS No. 24313-88-0 ]

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Chemical Structure| 24313-88-0
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CAS No. :24313-88-0 MDL No. :MFCD00008393
Formula : C9H13NO3 Boiling Point : 300.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :183.20 g/mol Pubchem ID :32285
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P261 UN#:N/A
Hazard Statements:H315-H335 Packing Group:N/A
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  • Upstream synthesis route of [ 24313-88-0 ]
  • Downstream synthetic route of [ 24313-88-0 ]

[ 24313-88-0 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 24313-88-0 ]
  • [ 71-36-3 ]
  • [ 253-82-7 ]
Reference: [1] Patent: US6017922, 2000, A,
  • 2
  • [ 6307-90-0 ]
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YieldReaction ConditionsOperation in experiment
96.4% With hydrazine hydrate In ethanol for 1 h; Reflux Step B / Intermediate B9: 3,4,5-trimethoxyani.ineTo a solution of 1 ,2,3-trimethoxy-5-nifrobenzene (6.64 g, 31.2 mrnol ) in ethanol (250 mL) was added palladium on carbon (10 percent, 300 mg) and hydrazine hydrate (85 percent, 5.7 mL). After emission of gas has ceased, the reaction mixture was heated at refluxed for 1 hour, cooling to room temperature, filtered and evaporated to afford the product 3,4,5-trimethoxyaniline as a white solid (5.5 g, yield 96.4 percent). H NMR (400 MHz, DMSO-d6) δ ppm 5.86 (s, 2H), 4.82 (br, 2H), 3.64 (s, 6H), 3.50 (s, 3H).
Reference: [1] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 60
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3414 - 3425
[3] Chemische Berichte, 1888, vol. 21, p. 615
[4] Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 467,500
[5] Journal of Pharmacy and Pharmacology, 1958, vol. 10, p. 47,59
[6] Chemische Berichte, 1959, vol. 92, p. 862,866
[7] Acta Chemica Scandinavica (1947-1973), 1963, vol. 17, p. 1151 - 1156
[8] Journal of the Chemical Society, 1963, p. 922 - 927
[9] Journal of Pharmaceutical Sciences, 1973, vol. 62, # 8, p. 1392 - 1394
[10] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 799 - 817
[11] PLoS ONE, 2015, vol. 10, # 6,
[12] Journal of the American Chemical Society, 2015, vol. 137, # 21, p. 6920 - 6931
  • 3
  • [ 115483-29-9 ]
  • [ 24313-88-0 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 51, p. 11925 - 11932
[2] Synlett, 1999, # 9, p. 1413 - 1414
[3] Advanced Synthesis and Catalysis, 2008, vol. 350, # 3, p. 406 - 410
  • 4
  • [ 2675-79-8 ]
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YieldReaction ConditionsOperation in experiment
60% With ammonium hydroxide; ethylenediaminediacetic acid; copper(II) oxide; potassium hydroxide In water at 130℃; for 12 h; Sealed tube 261mg (1mmol) of 3,4,5-trimethoxybromobenzene, 0.35mL aqueous ammonia (25-28percent, 4.655mmol), 8mg (0.1mmol) CuO, 70mg (0.4mmol) ethylenediamine-N,N'-diacetic acid, 112mg (2mmol) KOH, 1mL H2O was added 10mL reaction tube, sealed, under the reaction conditions of 130°C for 12h. After the reaction was stopped, extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, purified by silica gel column chromatography purification, 3,4,5-trimethoxy aniline 110 mg of, yield 60percent.
Reference: [1] Catalysis Communications, 2014, vol. 45, p. 100 - 103
[2] Patent: CN103739417, 2016, B, . Location in patent: Paragraph 0043; 0044
  • 5
  • [ 3086-62-2 ]
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Reference: [1] Organic Preparations and Procedures International, 2013, vol. 45, # 4, p. 321 - 324
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 40 - 42[3] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 46 - 48
[4] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 230
[5] Chemische Berichte, 1959, vol. 92, p. 862,866
[6] Chimica Therapeutica, 1972, vol. 7, p. 466 - 469
  • 6
  • [ 25245-29-8 ]
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YieldReaction ConditionsOperation in experiment
87% With ammonium hydroxide; caesium carbonate In water for 7 h; Reflux General procedure: A mixture of aryl halide (1 mmol), NH4OH(2 mmol),Cs2CO3(1 mmol) and CuO/ZnO/Al2O3 nanocatalyst(0.1 g), in water was stirred at reflux condition. After reactioncompletion, (monitored by TLC), the mixture reactionwas cooled to room temperature and catalyst filtered. Thenthe residue was evaporated to dryness, the residue waspoured into a saturated NaCl solution, extracted with ethylacetate and dried over anhydrous MgSO4.Evaporation of the solvent followed by column chromatography on silicagel gave the pure products in high yields.
Reference: [1] Chinese Journal of Chemistry, 2014, vol. 32, # 5, p. 396 - 398
[2] Catalysis Letters, 2018, vol. 148, # 12, p. 3750 - 3756
  • 7
  • [ 4521-61-3 ]
  • [ 24313-88-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
[2] Synthesis, 1983, # 1, p. 38 - 40
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 40 - 42[4] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 46 - 48
[5] Chimica Therapeutica, 1972, vol. 7, p. 466 - 469
[6] Chimica Therapeutica, 1972, vol. 7, p. 466 - 469
[7] Organic Preparations and Procedures International, 2013, vol. 45, # 4, p. 321 - 324
  • 8
  • [ 182163-96-8 ]
  • [ 24313-88-0 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2545 - 2553
  • 9
  • [ 118-41-2 ]
  • [ 24313-88-0 ]
Reference: [1] Angewandte Chemie, 1932, vol. 45, p. 536
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1983, p. 40 - 42[4] Khimiya Geterotsiklicheskikh Soedinenii, 1983, vol. 19, # 1, p. 46 - 48
[5] Justus Liebigs Annalen der Chemie, 1905, vol. 340, p. 230
[6] Chemische Berichte, 1959, vol. 92, p. 862,866
[7] Journal of Pharmaceutical Sciences, 1973, vol. 62, # 8, p. 1392 - 1394
[8] Organic Preparations and Procedures International, 2013, vol. 45, # 4, p. 321 - 324
[9] PLoS ONE, 2015, vol. 10, # 6,
[10] Patent: WO2012/92880, 2012, A1,
  • 10
  • [ 42543-45-3 ]
  • [ 24313-88-0 ]
Reference: [1] Monatshefte fuer Chemie, 1967, vol. 98, p. 1962 - 1972
[2] Chimica Therapeutica, 1972, vol. 7, p. 466 - 469
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
[4] Synthesis, 1983, # 1, p. 38 - 40
  • 11
  • [ 15494-44-7 ]
  • [ 616-38-6 ]
  • [ 24313-88-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 81 - 86
  • 12
  • [ 1336-21-6 ]
  • [ 2675-79-8 ]
  • [ 24313-88-0 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 26, p. 4897 - 4901
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  • [ 85657-95-0 ]
  • [ 24313-88-0 ]
Reference: [1] Synthesis, 1983, # 1, p. 38 - 40
  • 14
  • [ 1916-07-0 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 81 - 86
  • 15
  • [ 1016-19-9 ]
  • [ 24313-88-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5864 - 5869
  • 16
  • [ 634-36-6 ]
  • [ 24313-88-0 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 615
[2] Journal of the American Chemical Society, 2015, vol. 137, # 21, p. 6920 - 6931
  • 17
  • [ 372-19-0 ]
  • [ 24313-88-0 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 832 - 834
  • 18
  • [ 24313-88-0 ]
  • [ 25245-29-8 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 21, p. 4477 - 4480
[2] European Journal of Medicinal Chemistry, 2009, vol. 44, # 6, p. 2685 - 2688
[3] Journal of the American Chemical Society, 2008, vol. 130, # 8, p. 2535 - 2545
[4] Chemical Communications, 2017, vol. 53, # 80, p. 11008 - 11011
[5] RSC Advances, 2017, vol. 7, # 86, p. 54881 - 54891
[6] ChemMedChem, 2010, vol. 5, # 12, p. 2016 - 2025
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 13, p. 4627 - 4638
[8] Acta Chemica Scandinavica (1947-1973), 1963, vol. 17, p. 1151 - 1156
[9] Journal of Medicinal Chemistry, 1998, vol. 41, # 6, p. 913 - 918
[10] Organic Letters, 2013, vol. 15, # 11, p. 2742 - 2745
  • 19
  • [ 24313-88-0 ]
  • [ 487-11-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 15, p. 2868 - 2871
  • 20
  • [ 24313-88-0 ]
  • [ 2675-79-8 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 10, p. 2805 - 2811
[2] European Journal of Organic Chemistry, 2003, # 15, p. 2829 - 2839
[3] Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8811 - 8815
[4] Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 705 - 728
[5] Australian Journal of Chemistry, 1992, vol. 45, # 12, p. 1967 - 1982
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  • [ 24313-88-0 ]
  • [ 182163-96-8 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 15, p. 2829 - 2839
[2] Organic Letters, 2013, vol. 15, # 11, p. 2742 - 2745
  • 22
  • [ 575484-83-2 ]
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YieldReaction ConditionsOperation in experiment
91% at 120℃; for 10 h; Inert atmosphere; Large scale Step B:
Preparation of 6-[[5-Fluoro-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4H-pyrido[3,2-b][1,4]oxazin-3-one
6-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]-2,2-dimethyl-4H-pyrido[3,2-b][1,4]oxazin-3-one (Step A) (568 kg, 1.00 mol eq) is mixed with 3,4,5-trimethoxyaniline (402 kg, 1.25 mol eq) in N-methylpyrrolidin-2-one (2835 kg) with stirring under a nitrogen atmosphere.
To this is added water (11 kg) and the mixture heated to about 120° C. and stirred for about 10 hours.
This is then cooled to about 65° C. and the pH adjusted to pH 8.5 with 4percent w/w aqueous sodium hydroxide solution.
The resulting slurry is further cooled to about 20° C., stirred for at least 6 hours and then filtered.
The filtered solid is washed twice with water (2*1440 kg) then twice with acetone (2*1140 kg) and finally dried under vacuum at about 40° C. to give the title compound (754 kg, 91percent) as a colored solid.
1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (s, 6H) 3.59 (s, 3H) 3.66 (s, 6H) 7.04 (s, 2H) 7.32 (d, J=8.5 Hz, 1H) 7.68 (d, J=8.5 Hz, 1H) 8.13 (d, J=3.4 Hz, 1H) 9.10 (br. s, 1H) 9.14 (br. s, 1H) 11.06 (br. s, 1H).
m/z 471 [MH]+.
Reference: [1] Patent: US2015/175639, 2015, A1, . Location in patent: Paragraph 0149; 0150; 0151; 0152
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