CID 521843

Base Information

• Chemical Name: CID 521843
• CAS No.: 596-51-0
• Molecular Formula: C19H28BrNO3
• Molecular Weight: 398.34
• Hs Code.: 29339900
• Mol file: 596-51-0.mol

Synonyms:

Chemical Property of CID 521843

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 193 - 194.5oC
• Refractive Index: 1.6200 (estimate)
• PSA: 46.53000
• Density: 1.3222 (rough estimate)
• LogP: -0.58090
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: ≥24mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 397.12526
• Heavy Atom Count: 24
• Complexity: 430

Purity/Quality:

99%+ ^*data from raw suppliers

Glycopyrronium bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
• Description: Glycopyrrolate is an antagonist of muscarinic acetylcholine receptors (mAChRs; Kis = 0.42, 1.77, 0.52, 0.78, and 1.29 nM for the M1-M5 receptors, respectively). It induces relaxation of precontracted isolated human bronchi when used at concentrations of 0.01, 0.1, or 1 μM. Glycopyrrolate reduces post-prandial gastric antral motility in dogs when administered at a dose of 0.01 mg/kg. It inhibits salivation in a rat model of sialorrhea induced by pilocarpine with an ED50 value of 0.74 μg/kg. Formulations containing glycopyrrolate have been used in the treatment of sialorrhea, peptic ulcers, and chronic obstructive pulmonary disease (COPD).
• Uses: Inhaled glycopyrrolate?of is used ?to treat air flow blockage and prevent worsening of chronic obstructive ?pulmonary disease (COPD), including chronic bronchitis and emphysema. COPD is a long-term lung disease that causes bronchospasm (difficulty with breathing). For use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubat A synthetic, quaternary ammonium anticholinergic. Antispasmodic; preanesthetic medicant.
• Therapeutic Function: Spasmolytic
• Clinical Use: Glycopyrrolate is used as an adjunct in the management of pepticulcer and other GI ailments associated with hyperacidity,hypermotility, and spasm. In common with other anticholinergics,its use does not preclude dietary restrictions or use ofantacids and sedatives if these are indicated.

Technology Process of CID 521843

There total 14 articles about CID 521843 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

C17H22Br2O3 + dimethyl amine (124-40-3) → glycopyrronium bromide (596-51-0,129784-12-9,201667-20-1,53808-86-9,58493-54-2)

Guidance literature:

With potassium carbonate; In methanol; at 65 ℃;

Reference yield: 63.0%

methyl bromide (74-83-9) + 1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate 5-nitroisophthalic acid → (3RS)-3-[(2SR)-(2-cyclopentyl-2-hydroxy-2-phenyl-acetyl)oxy]-1,1-dimethylpyrrolidinium bromide (596-51-0,129784-12-9,201667-20-1,53808-86-9,58493-54-2)

Guidance literature:

1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate 5-nitroisophthalic acid; With potassium carbonate; In Isopropyl acetate; water; for 0.25h; Industrial scale;

methyl bromide; In ethyl acetate; at 0 - 20 ℃; for 5h; Industrial scale;

Reference yield: 22.0%

methyl bromide (74-83-9) + 3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine (13118-11-1) → glycopyrronium bromide (596-51-0,129784-12-9,201667-20-1,53808-86-9,58493-54-2)

Guidance literature:

In butanone; at 20 ℃; Cooling with ice;

DOI:10.1002/cmdc.201700189

upstream raw materials:

methyl bromide

3-(2-cyclopentyl-2-hydroxy-2-phenylacetyloxy)-1-methylpyrrolidine

1-methyl-3-pyrrolidinol

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Downstream raw materials:

(1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate mono(4-methylbenzenesulfonate)

3-hydroxy-1,1-dimethyl pyrrolidinium bromide

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium benzoate

Refernces

• 1、 -. "Glycopyrronium bromide intermediate as well as preparation method and application thereof". Paragraph 0078-0100. . Retrieved 2022/01/10.
• 2、 -. "PROCESS FOR SYNTHESIS OF GLYCOPYRRONIUM BROMIDE". Page/Page column 5-6. . Retrieved 2018/09/26.