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ablukast

Product Name
ablukast
CAS No.
96566-25-5
Chemical Name
ablukast
Synonyms
ablukast;Ablukastum;Ro-23-3544;Unii-000tkm5bbq;Ablukast (Ro23-3544);Ablukastum [inn-latin];Inhibitor,Leukotriene Receptor,Ablukast,LTC4,bronchoconstriction,inhibit;6-Acetyl-7-((5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl)oxy)chromane-2-carboxylic acid;6-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid;2H-1-Benzopyran-2-carboxylic acid, 6-acetyl-7-((5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl)oxy)-3,4-dihydro-, (+-)-
CBNumber
CB41386369
Molecular Formula
C28H34O8
Formula Weight
498.57
MOL File
96566-25-5.mol
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ablukast Property

Melting point:
113-115 °C
Boiling point:
730.8±60.0 °C(Predicted)
Density 
1.219±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMSO : 100 mg/mL (200.58 mM; Need ultrasonic)
pka
2.92±0.20(Predicted)
form 
Solid
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0025760
Product name
ABLUKAST
Purity
95.00%
Packaging
5MG
Price
$496.29
Updated
2021/12/16
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ablukast Chemical Properties,Usage,Production

Originator

Ulpax,Roche

Uses

Anti-asthmatic (leukotriene antagonist).

Manufacturing Process

A solution of 109.8 g (0.75 mol) of diethyl oxalate and 65 g (0.427 mol) of 2',4'-dihydroxyacetophenone in 100 mL of EtOH was added slowly under Ar, with cooling, to a stirred solution of NaOEt (from 40 g of Na and 550 mL of EtOH). The mixture was stirred at 50°C for 3 h, cooled to room temperature, and poured into a separatory funnel containing 500 mL of 2 N HCl. It was extracted with CH2CH2 washed with 500 mL of saturated NaHCO3, dried and evaporated to give a red oil, which was dissolved in 250 mL of EtOH and 10 mL of conc. HCl. The mixture was boiled under reflux for 1 h, cooled to ca. 10°C and the product was collected by filtration. It was washed with some EtOH followed by hexane to give 86.0 g (86% yield) of ethyl 7-hydroxy-4-oxo- 4H-1-benzopyran-2-carboxylate: m.p. 218-223°C. Crystallization of a portion from hot AcOH gave an analytical sample: m.p. 221-223°C.
A solution of 80 g (0.34 mol) of ethyl 7-hydroxy-4-oxo-4H-1-benzopyran-2- carboxylate in 60 mL of AcOH and 275 mL of THF was hydrogenated over 4.0 g of 10% Pd on charcoal at 45°C and 65 psi. After hydrogen absorption ceased, the catalyst was removed by filtration and the solvents were evaporated under reduced pressure. Crystallization from CCl4 gave 65 g (85%) of ethyl (R,S)-3,4-dihydro-7-hydroxy-2H-1-benzopyran-2-carboxylate: m.p. 80-82°C.
A stirred mixture of 65 g (0.293 mol) of ethyl (R,S)-3,4-dihydro-7-hydroxy- 2H-1-benzopyran-2-carboxylate in 650 mL of AcOH, 1.5 mL of acetic anhydride, and 65 mL of BF3·OEt2 was heated at reflux for 18 h and evaporated. To the residue was added 700 mL of water, and the mixture was stirred at room temperature for 1.0 h. The product was collected by filtration and washed with hexane. It was then dissolved in 900 mL of MeOH, treated with 6.6 g of p-toluenesulfonic acid, boiled under reflux for 18 h, and cooled to 0°C. The product was collected by filtration to give 52 g (70% yield) of ethyl (R,S)-3,4-dihydro-7-hydroxy-2H-1-benzopyran-2-carboxylate: m.p. 140- 142°C.
A 1 L, 3-necked, round-bottomed flask equipped with a mechanical stirrer and an Ar bubbler was charged with 37.5 g (0.179 moles) of 5-bromo-1-pentanyl acetate, 350 mL of anhyd. DMSO, 40.7 g (0.163 mol) of ethyl (R,S)-3,4- dihydro-7-hydroxy-2H-1-benzopyran-2-carboxylate, and 51.0 g (0.369 mol) of powdered potassium carbonate. The mixture was stirred at room temperature for 18 h, poured into 1.0 L of water and extracted into EtOAc (2*1 L). The extract was washed with 1 L of brine, dried and evaporated. The residue was dissolved in 200 mL of ether, cooled to 57°C and, with stirring, diluted with petroleum ether. The product was collected by filtration, washed with a little 1:1 ether-petroleum ether (b.p. 40-60°C) and dried to give 60.0 g (97%) of methyl (R,S)-6-acetyl-3,4-dihydro-7-((5-acetoxypentyl)oxy-2H-1-benzopyran- 2-carboxylate: m.p.51-53°C.
A solution of 72.08 g (0.19 mol) of 5-bromo-1-pentanyl acetate in 1.4 L of MeOH was treated with 38 mL of a 1.0 molar solution of tetrabutylammonium hydroxide and the mixture was stirred at room temperature for 3.0 h, 3.0 mL of AcOH was added and the solution was evaporated at 35°C. The residue was dissolved in 400 mL of EtOAc and the solution was washed with saturated NaHCO3, brine, dried, and evaporated to give 60.45 g (94% yield) of the intermediate hydroxy ester (an analytical sample may be obtained by crystallization from 70% EtOAc in hexane, m.p. 58-61°C. A stirred solution of 60.25 g of the hydroxyester in 700 mL of EtOAc was cooled to 5°C and treated with 75.5 mL (3 equiv.) of triethylamine and 32.6 mL (2.35 equiv.) of methanesulfonyl chloride. The mixture was stirred at 6°C for 2.0 h, transferred to a separatory funnel and washed sequentially with water, 2 N HCl, and brine. Concentration of the EtOAc to ca. 300 mL and dilution cooled to 0°C and treated with 75.5 mL (3 equiv.) of triethylamine and 32.6 mL (2.35 equiv.) of methanesulfonyl chloride. The mixture was stirred at 6°C for 2.0 h transferred to a separatory funnel and washed sequentially with water, 2 N HCl, and brine. Concentration of the EtOAc to ca. 300 mL and dilution with 250 mL of hexane led to crystallization (0°C, 18 h). The product was collected by filtration and washed with some cold hexane - EtOAc (1:1) to give 66 g (84% yield) of methyl (R,S)-6-acetyl-3,4-dihydro-7-[5- [(methylsufonyl)oxy]pentyloxy]-2H-1-benzopyran-2-carboxylate: m.p. 73- 76°C.
A mixture of 66.13 g (0.159 mol) of methyl (R,S)-6-acetyl-3,4-dihydro-7-[5- [(methylsufonyl)oxy]pentyloxy]-2H-1-benzopyran-2-carboxylate, 30.99 g (0.159 mol) of 1-[2,4-dihydroxy-3-propylphenyl)ethanone, 33.07 g (0.239 mol) of pulverized potassium carbonate, 5.16 g (15.9 mmol) of tris(3,6- dioxahepyl)amine in 900 mL of toluene was stirred under Ar at reflux for 6 h and then at room temperature overnight. The mixture was poured into 300 mL of water and the organic phase was separated, washed with brine, dried and evaporated to give 84.3 g of methyl (R,S)-6-acetyl-7-[5-(4-acetyl-3- hydroxy-2-propylphenoxy)pentoxy]-3,4-dihydro-2H-1-benzopyran-2- carboxilate. Crystallization from MeOH (0°C, 18 h) gave 66 g (81% yield), m.p. 77-80°C.
A stirred solution of 55.82 g (0.109 mol) of methyl (R,S)-6-acetyl-7-[5-(4- acetyl-3-hydroxy-2-propylphenoxy)pentoxy]-3,4-dihydro-2H-1-benzopyran-2- carboxylate in 725 mL of MeOH was treated with 4.45 g (0.111 mol) of NaOH in 20 mL of water and the mixture was stirred at reflux for 1.25 h. It was cooled, concentrated to a volume of ca 360 mL, diluted with 310 mL of ether and left at 0°C overnight. The product was collected by filtration, dried in to give 45.76 g of (R,S)-6-acetyl-7-[[5-(4-acetyl-3-hydroxy-2- propylphenoxy)pentyl]oxy]-3,4-dihydro-2H-H-benzopyran-2-carboxylic acid sodium salt (Ablukast) as the monohydrate. A further 12.27 g of product was obtained from the mother liquor to give a total yield of 99%.

Therapeutic Function

Antiallergic, Anti-asthmatic

ablukast Preparation Products And Raw materials

Raw materials

Preparation Products

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ablukast Suppliers

TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32161
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
52924
Advantage
58

96566-25-5, ablukastRelated Search:


  • ablukast
  • 6-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
  • Ro-23-3544
  • 2H-1-Benzopyran-2-carboxylic acid, 6-acetyl-7-((5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl)oxy)-3,4-dihydro-, (+-)-
  • Ablukastum
  • Ablukastum [inn-latin]
  • Unii-000tkm5bbq
  • Ablukast (Ro23-3544)
  • Inhibitor,Leukotriene Receptor,Ablukast,LTC4,bronchoconstriction,inhibit
  • 6-Acetyl-7-((5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl)oxy)chromane-2-carboxylic acid
  • 96566-25-5