[ CAS No. 53164-05-9 ] {[proInfo.proName]}

Name: 53164-05-9|2-(2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetoxy)acetic acid|98%
Brand: Ambeed
SKU: A374323
Price: 5.0 USD
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Quality Control of [ 53164-05-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 53164-05-9 ]

SDS Specification

Alternatived Products of [ 53164-05-9 ]

Product Details of [ 53164-05-9 ]

CAS No. :	53164-05-9	MDL No. :	MFCD00151473
Formula :	C₂₁H₁₈ClNO₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FSQKKOOTNAMONP-UHFFFAOYSA-N
M.W :	415.82	Pubchem ID :	1981
Synonyms :	TVX 1322	Chemical Name :	2-(2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetoxy)acetic acid

Calculated chemistry of [ 53164-05-9 ]

Physicochemical Properties

Num. heavy atoms :	29
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.19
Num. rotatable bonds :	8
Num. H-bond acceptors :	6.0
Num. H-bond donors :	1.0
Molar Refractivity :	107.02
TPSA :	94.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.88
Log Po/w (XLOGP3) :	4.19
Log Po/w (WLOGP) :	3.47
Log Po/w (MLOGP) :	2.86
Log Po/w (SILICOS-IT) :	3.8
Consensus Log Po/w :	3.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.91
Solubility :	0.00509 mg/ml ; 0.0000122 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.89
Solubility :	0.000535 mg/ml ; 0.00000129 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.83
Solubility :	0.000608 mg/ml ; 0.00000146 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.89

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:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 53164-05-9 ]

* 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.

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 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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 (2C), 130.7, 130.4, 129.1 (2C), 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 ]
[ 53164-05-9 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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

5
[ 19501-58-7 ]
[ 53164-05-9 ]

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 ]
[ 53164-05-9 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325

8
[ 53164-03-7 ]
[ 53164-05-9 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325

[ 53164-05-9 ] Synthesis Path-Downstream 1~33

1
[ 53164-05-9 ]
2-(4-Chlorphenyl)-6-methoxy-4H-3.1-benzoxazinon-4 [ No CAS ]
N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure [ No CAS ]

Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 127 - 134

2
[ 53164-05-9 ]
2-Acetyl-N-(4-chlor-benzoyl)-4-methoxy-anilin [ No CAS ]
N-(4-Chlor-benzoyl)-5-methoxy-anthranilsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-essigsaeuremethylester [ No CAS ]
<2-(4-Chlor-benzoylamino)-5-methoxy>-benzoyl-2-acetoxy-essigsaeure [ No CAS ]

Reference： [1]Archiv der Pharmazie,1985,vol. 318,p. 127 - 134

3
[ 53164-04-8 ]
[ 53164-05-9 ]

Yield	Reaction Conditions	Operation in experiment
97.8%	With aluminum (III) chloride; In dichloromethane; N,N-dimethyl-formamide; at 80℃; for 24.0h;	a synthetic method of acemetacin, the steps of which areA. 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. acematecinD. 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 97.8%. The purity was determined by HPLC to be greater than 99.8%.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,p. 3348 - 3353
[3]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 1314 - 1325

Yield	Reaction Conditions	Operation in experiment
97.1%		EXAMPLE 5 The t-butyl ester of acemetacin (201 mg) was dissolved in 3.5 ml of formic acid and the resultant solution was stirred at room temperature for 3 hours. Formic acid was caused to evaporate under reduced pressure. The residue was taken up in 400 ml of a 1:5 liquid mixture of acetone and benzene and insoluble material was removed by filtration. The solvent was then driven off from the filtrate. The residue was recrystallized from benzene to obtain 172 mg of acemetacin as pale yellowish crystals (yield: 97.1%).
86-91%		EXAMPLE 4 Acemetacin 0.003 mole of tetrakis-triphenylphosphine-palladium-(O) is added to 0.03 mole of acemetacin allyl ester in 50 ml of tetrahydrofuran, under nitrogen. 0.3 mole of piperidine is added dropwise at 20-25 C., with stirring, and stirring is then continued for 2 hours at room temperature (check by thin layer chromatography). 200 ml of half-concentrated hydrochloric acid are added dropwise with cooling, the phases are separated off, the aqueous phase is extracted twice with methylene chloride and the combined organic phases are evaporated in vacuo. The residue is recrystallized from toluene. Yield: 86-91% of theory; melting point: 150 C.
		EXAMPLE 5 (ACEMETACIN) 0.4 g of p-toluenesulphonic acid is added to 9.6 g of tert.-butyl ester of acemetacin according to example 1 in 30 ml of acetic acid, and the mixture is stirred at 100 C. for 4 to 5 hours. After the mixture has cooled down to room temperature, 50 ml of water are added. Acemetacin precipitates, is filtered off with suction and is recrystallized from acetone/water. Yield: 8.0 g=90.6% of theory of pure product.

		EXAMPLE 14 (solution) Polyisobutylene of molecular weight 400,000: 40.00 g Thinly liquid paraffin: 50.00 g Polyterpene resin from alpha-pinene: 10.00 g Acemetacin: 17.65 g Release: about 12% after 6 hours.
		Preparation of acemetacin Splitting of the protective group of acemetacin derivative according to the invention The 4-methoxybenzyl ester (5.35 g=0.01 mol) prepared as described above is dissolved in 5.4 g (0.05 mol) of anisole, and 0.73 g (0.02 mol) of glacial acetic acid/HCl (75.9 mg of HCl/ml) is added while stirring and in the absence of moisture. After a reaction time of 5 hours, the conversion is quantitative. 1.8 g (0.023 mol) of ammonium acetate are added to the reaction mixture, the mixture is stirred for 10 minutes, 20 ml of water are added, and stirring is continued for a further 10 minutes. Thereafter, the mixture is extracted with 40 ml of toluene, the organic phase is washed neutral and dried over Na2 SO4, and the solvent is distilled off. The residue is stirred throughly with 200 ml of petroleum ether. Crystals are formed, and are filtered off under suction, washed with petroleum ether and dried. The substance is purified by dissolving it in methylene chloride, adding 80 ml of carbon tetrachloride and distilling off the methylene chloride at 70 C. Acemetacin crystallises at room temperature. Recrystallisation from toluene gave the pure substance in a yield of 2.8 g=67.3% of theory, with a melting point of 150-151 C.
		EXAMPLE 7 Acemetacin 31.9 g of acemetacin allyl ester, 100 ml of toluene, 2.3 g of triphenylphosphine and 0.75 g of palladium on charcoal (5% strength) are taken as an initial charge, under nitrogen. 11.9 g of piperidine are added dropwise, with stirring, and the mixture is then stirred for a further 3 hours at 90 C. It is filtered hot and the catalyst is rinsed with hot toluene. The filtrate is evaporated, the residue is taken up in methylene chloride (about 300 ml) and this solution is washed with half-concentrated hydrochloric acid (100 ml) and then with water. After removal of the solvent in vacuo, the residue is recrystallized from toluene. Yield: 27.3 g=94% of theory; melting point: 150

6
[ 53164-05-9 ]
5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester [ No CAS ]
[ 74-11-3 ]

Reference： [1]Journal of Pharmaceutical Sciences,2001,vol. 90,p. 298 - 309
[2]Journal of Pharmaceutical Sciences,2001,vol. 90,p. 298 - 309
[3]Journal of Organic Chemistry,2006,vol. 71,p. 3718 - 3726

7
[ 53164-05-9 ]
[ 2882-15-7 ]
[ 53-86-1 ]
5-methoxy-2-methylindol-3-yl acetic acid carboxymethyl ester [ No CAS ]
[ 74-11-3 ]

Reference： [1]Carbohydrate research,2002,vol. 337,p. 1387 - 1395

8
[ 53164-05-9 ]
[ 1613-88-3 ]