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[ CAS No. 53164-05-9 ]

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Chemical Structure| 53164-05-9
Chemical Structure| 53164-05-9
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Product Details of [ 53164-05-9 ]

CAS No. :53164-05-9 MDL No. :MFCD00151473
Formula : C21H18ClNO6 Boiling Point : 565.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :415.82 g/mol Pubchem ID :1981
Synonyms :

1. Acemetacin

Safety of [ 53164-05-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P280-P284-P301+P310-P302+P350 UN#:2811
Hazard Statements:H300-H310-H330 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53164-05-9 ]

  • Upstream synthesis route of [ 53164-05-9 ]
  • Downstream synthetic route of [ 53164-05-9 ]

[ 53164-05-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 53164-04-8 ]
  • [ 53164-05-9 ]
YieldReaction ConditionsOperation in experiment
97.8% With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 80℃; for 24 h; a synthetic method of acemetacin, the steps of which are
A. 100 g (0.198 mol) of acesulfame benzyl ester was dissolved in 400 mL of dichloromethane, and then 250 mL of N,N-dimethylaniline was added to obtain a solution A.
B. 100 mL of dichloromethane was added to 79.2 g (0.594 mol of 1) of A1C13, and solution A was slowly added at zero.
C. After the addition is completed, the reaction is raised to room temperature for 55 or 58 or 60 or 63 or 65 minutes. After the reaction is completed, the reaction mixture is poured into ice water, stirred for 28 or 29 or 30 or 31 or 32 minutes, and then filtered to obtain a crude product. acematecin
D. The crude acemetacin obtained in the step C is recrystallized from acetone and water (volume ratio of 2:1), decolorized by adding activated carbon, and the crystals are dried at 80 ° C for 24 hours to obtain 80.4 g of pure Asi. Mesin, the yield is 97.8percent. The purity was determined by HPLC to be greater than 99.8percent.
The other steps are the same as in the first embodiment.
Reference: [1] Patent: CN108440374, 2018, A, . Location in patent: Paragraph 0023-0028; 0030-0035; 0037-0042; 0044-0049; 0051-0
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3348 - 3353
[3] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
  • 2
  • [ 75302-98-6 ]
  • [ 53164-05-9 ]
YieldReaction ConditionsOperation in experiment
80% With trifluoroacetic acid In dichloromethane at 20℃; for 48 h; 55b.
2-(2-(1-((4-Chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetyloxy)acetic Acid
The product of Example 55a (6.12 g, 13 mmol) was dissolved in CH2Cl2 (50 mL) and TFA (15 mL) was added.
The reaction mixture was stirred at room temperature for 2 days.
The solvent and TFA were evaporated in vacuo and the residue obtained was dissolved in EtOAc (50 mL) and the solvent evaporated again to remove traces of trifluoroacetic acid.
The residue obtained was recrystallized from EtOAc:hexane (1:4) to give the title compound (4.3 g, 80percent yield) as a gray colored solid.
Mp 137-138° C. 1H NMR (300 MHz, CDCl3) δ 8.93 (br s, 1H), 7.65 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 6.96 (d, J=2.3 Hz, 1H), 6.87 (d, J=9.0 Hz, 1H), 6.6 (dd, J=9.0 and 2.4 Hz, 1H), 4.67 (s, 2H), 3.81 (s, 3H), 3.78 (s, 2H), 2.36 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 172.6, 170.3, 168.4, 155.9, 139.2, 136.1, 133.7, 131.1 (2*C), 130.7, 130.4, 129.1 (2*C), 114.9, 111.8, 111.7, 101.2, 60.5, 55.6, 29.6, 13.4; LRMS (APIMS) m/z 416 (MH+).
Reference: [1] Patent: US2004/24057, 2004, A1, . Location in patent: Page/Page column 52
  • 3
  • [ 75302-98-6 ]
  • [ 53-86-1 ]
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YieldReaction ConditionsOperation in experiment
66% With iodine; aluminium In acetonitrile at 20℃; for 6 h; To a suspension of AlI3 (2.0 mmol) in acetonitrile (20 mL) was charged ester 20 (0.943 g, 2.0 mmol). The mixture was stirred for 6h at 20 oC. After quenchingwith 2 M HCl (10 mL), the mixture was extracted by EA (50 mL × 3). The combined organic phase was washed with saturated aqueous Na2S2O3 (10 mL) to remove elementiodine. After evaporation of organic solvents, the residue was purified by flash column chromatography (PE/EA 3:2, EA was acidified with 1percent formic acid) to afford indometacin22 (0.209 g, 30percent) as a minor product, and 24 (0.554 g, 66percent) as a yellow solid
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 15, p. 1469 - 1472
  • 4
  • [ 1601-20-3 ]
  • [ 64-19-7 ]
  • [ 53164-05-9 ]
YieldReaction ConditionsOperation in experiment
98.8% at 60℃; for 5 h; Large scale 50 kg of acetic acid into the reaction tank,Stirring into the hydrogen chloride,The content of hydrogen chloride (w / w) was 16percent.Adding aluminum trichloride 2.0 Kg,Acemetacin t-butyl 100KG,The temperature was stirred at 60 ° C for 5 hours,Cooling to 20 ,Standing for 2 hours to complete crystallization, filtration, washing the top, 80 deg.] C and drying, to obtain 82.1 kg acemetacin, yield 93.19percent. The crude product dissolved in 360 kg of toluene, heated to dissolve, put into the activated carbon 1 kg, stirring for 20 minutes, pumping, cooling to room temperature, standing for 2 hours to complete crystallization, filtration, a small amount of toluene washing, dry,It was 80.5 kg acemetacin Competitive product .The yield of the solution was 98.8percent.
Reference: [1] Patent: CN106316921, 2017, A, . Location in patent: Paragraph 0008; 0009; 0010; 0011; 0012; 0013; 0014-0016
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  • [ 19501-58-7 ]
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Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
  • 6
  • [ 53164-08-2 ]
  • [ 53164-05-9 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
  • 7
  • [ 53-86-1 ]
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Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
  • 8
  • [ 53164-03-7 ]
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Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325
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