CAS 151767-02-1 | Montelukast Sodium

Properties

Appearance white to tan powder
Melting point:115 °C(dec.)
storage temp. 2-8°C
solubility DMSO: ≥8mg/mL at 60°C
optical activity[α]/D +90 to +106° in methanol (c=1)

 

Application:

    Montelukast sodium, [R - (E)] -1-ff [1- [3- [2- [7-chloro-2-quinoline) vinyl] phenyl-3- [2- (1-hydroxy-1-methylethyl) phenyl] propyl] thio] methyl] cyclopropane sodium acetate, molecular formula: C35H35CINNaO3S. Montelukast can effectively slow down or even prevent dementia in the elderly. Montelukast can increase the growth rate of nerve cells in young mice by 50%.

Application Area	Description
Asthma	Maintenance Treatment: Used for the prevention and chronic treatment of asthma in adults and pediatric patients (as young as 12 months old).Exercise-Induced Bronchoconstriction: Used to prevent bronchoconstriction induced by exercise.
Allergic Rhinitis	Hay Fever: Relieves symptoms such as nasal congestion, runny nose, and sneezing caused by seasonal or perennial allergies.
Pediatrics	Available in chewable tablets and oral granules, making it suitable for young children who cannot swallow regular tablets.

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Related Intermediate Chemicals

The synthesis of Montelukast involves the coupling of three main fragments: a quinoline moiety, an ethanol side chain, and a mercaptobenzothiophene group.

Here are the critical intermediates involved in the synthesis:

Intermediate Name	CAS Number	Role in Synthesis
(R)-1-[(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propanol	151767-03-2	The Free Alcohol (Montelukast Alcohol). This is the immediate precursor to the final drug. It is converted to the mesylate (or tosylate) and then reacted with thiol.
6-Acetyl-2-mercaptobenzo[b]thiophene	1128-00-9	The Thiol Source. This is the source of the benzothiophene ring and the sulfur atom that forms the thioether linkage in the final product.
(E)-1-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-1-propanone	136760-02-8	The Quinoline Ketone. A mian intermediate in the construction of the left-hand side (quinoline) fragment.
7-Chloro-2-trifluoromethanesulfonyloxyquinoline	151550-08-2	A triflate intermediate used in the synthesis of the quinoline ring system via palladium-catalyzed coupling reactions.
2-(2-Bromoethyl)acetophenone	18366-82-4	A building block used in the synthesis of the central propanol chain and the isopropyl phenyl group.

Summary of the Synthetic Route

A typical synthetic route involves:

Fragment A (Quinoline): Synthesis of the 7-chloroquinoline derivative with a vinyl group attached to a phenyl ring.

Fragment B (Chain): Synthesis of the chiral propanol chain containing the isopropyl phenyl group.

Coupling (A+B): Fragment A and Fragment B are coupled, often via a Grignard reaction, to form the Montelukast Alcohol (the tertiary alcohol intermediate).

Activation: The alcohol group is activated (e.g., converted to a mesylate).

Thiol Coupling: The activated alcohol is reacted with 6-Acetyl-2-mercaptobenzo[b]thiophene to form the thioether bond.

Salt Formation: The resulting free acid (after hydrolysis of the acetyl group) is neutralized with sodium hydroxide to form Montelukast Sodium.

 

 

Synonyms:

151767-02-1

Singulair

Montelukast sodium salt

MK-476

Montelukast monosodium salt

sodium (R,E)-2-(1-(((1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)thio)methyl)cyclopropyl)acetate

Montelukast sodium hydrate

151767-02-1 (sodium)

Cyclopropaneacetic acid, 1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)-, sodium salt, (R-(E))-

Cyclopropaneacetic acid, 1-[[[(1R)-1-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-, sodium salt (1:1)

 

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